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Molbank, Volume 2024, Issue 1 (March 2024) – 45 articles

Cover Story (view full-size image): Stille coupling of 5,5'-dibromo-4,4'-diphenyl-2,2'-bithiazole with 9-(2-ethylhexyl)-3-(tributylstannyl)-9H-carbazole and Pd(Ph3P)2Cl2 in PhMe, at ca. 110 °C, for 2 h, provided 5,5'-bis[9-(2-ethylhexyl)-9H-carbazol-3-yl]-4,4'-diphenyl-2,2'-bithiazole in 85% yield. The 2,2’-bithiazoles are non-natural heterocyclic systems studied as electron acceptors with potential applications in materials sciences. View this paper
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8 pages, 723 KiB  
Communication
Three-Step Synthesis of N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide from 4,7-Dichloroquinoline
by Deiby F. Aparicio Acevedo, Marlyn C. Ortiz Villamizar and Vladimir V. Kouznetsov
Molbank 2024, 2024(1), M1796; https://doi.org/10.3390/M1796 - 21 Mar 2024
Viewed by 902
Abstract
The quinoline derivative, N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide, was synthesized in a conventional three-step procedure from 4,7-dichloroquinoline using a N-oxidation reaction/C2-amide formation reaction/C4 SNAr reaction sequence. The structure of the compound was fully characterized by FT-IR, 1H-, 13C-NMR, DEPT-135°, and ESI-MS [...] Read more.
The quinoline derivative, N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide, was synthesized in a conventional three-step procedure from 4,7-dichloroquinoline using a N-oxidation reaction/C2-amide formation reaction/C4 SNAr reaction sequence. The structure of the compound was fully characterized by FT-IR, 1H-, 13C-NMR, DEPT-135°, and ESI-MS techniques. Its physicochemical parameters (Lipinski’s descriptors) were also calculated using the online SwissADME database. Such derivatives are relevant therapeutic agents exhibiting potent anticancer, antibacterial, antifungal, and antiparasitic properties. Full article
(This article belongs to the Section Organic Synthesis)
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8 pages, 1779 KiB  
Communication
Structural Characterization of 4-(4-Nitrophenyl)thiomorpholine, a Precursor in Medicinal Chemistry
by Paul R. Palme, Richard Goddard, Peter Imming and Rüdiger W. Seidel
Molbank 2024, 2024(1), M1795; https://doi.org/10.3390/M1795 - 20 Mar 2024
Viewed by 913
Abstract
4-(4-nitrophenyl)thiomorpholine, the title compound, has been used as a precursor for the corresponding 4-thiomorpholinoaniline, which is a useful building block in medicinal chemistry. The crystal and molecular structures of the title compound, however, have not been described thus far. We synthesized the title [...] Read more.
4-(4-nitrophenyl)thiomorpholine, the title compound, has been used as a precursor for the corresponding 4-thiomorpholinoaniline, which is a useful building block in medicinal chemistry. The crystal and molecular structures of the title compound, however, have not been described thus far. We synthesized the title compound by means of a nucleophilic aromatic substitution reaction of 4-fluoronitrobenzene and thiomorpholine and structurally characterized it by X-ray crystallography, DFT calculations, and Hirshfeld surface analysis. In the crystal, the molecule exhibits an approximately CS-symmetric structure, with the nitrogen-bound 4-nitrophenyl group in a quasi axial position on the six-membered thiomorpholine ring in a low-energy chair conformation. The solid-state structure of the title compound is markedly different from that of its morpholine analogue. This can be ascribed to the formation of centrosymmetric dimers through intermolecular C–H···O weak hydrogen bonds involving the methylene groups adjacent to the sulfur atom and face-to-face aromatic stacking. Full article
(This article belongs to the Section Structure Determination)
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10 pages, 1899 KiB  
Communication
Butyl (2,2-Dibutoxybutanoyl)-ʟ-Tryptophanate
by Diego Quiroga and Ericsson Coy-Barrera
Molbank 2024, 2024(1), M1794; https://doi.org/10.3390/M1794 - 19 Mar 2024
Viewed by 883
Abstract
The multicomponent reaction between ʟ-tryptophan 1, 2-oxobutanoic acid 2, and 1-butanol in the presence of SiMe3Cl was studied using microwave irradiation conditions. The main product was identified as an unreported acetal-containing compound, namely, butyl (2,2-dibutoxybutanoyl)-ʟ-tryptophanate (3), yielding [...] Read more.
The multicomponent reaction between ʟ-tryptophan 1, 2-oxobutanoic acid 2, and 1-butanol in the presence of SiMe3Cl was studied using microwave irradiation conditions. The main product was identified as an unreported acetal-containing compound, namely, butyl (2,2-dibutoxybutanoyl)-ʟ-tryptophanate (3), yielding 89%. NMR experiments demonstrated that the adjacent methylene protons of the acetal group appeared as two signals exhibiting their behavior as diastereotopic protons. DFT/B3LYP calculations revealed an asymmetric molecular structure with specific angles, leading to an explanation of the NMR results. The calculated chemical shifts showed slight differences with the experimental values and suggested magnetic anisotropy and inductive deprotection around the methylene hydrogen atoms in the acetal location. The reaction mechanism was proposed in which SiMe3Cl plays a crucial role by promoting water removal through key steps. Full article
(This article belongs to the Section Organic Synthesis)
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8 pages, 973 KiB  
Communication
Synthesis and In Vitro Antibacterial Evaluation of Mannich Base Nitrothiazole Derivatives
by Phelelisiwe S. Dube, Dylan Hart, Lesetja J. Legoabe, Audrey Jordaan, Digby F. Warner and Richard M. Beteck
Molbank 2024, 2024(1), M1793; https://doi.org/10.3390/M1793 - 18 Mar 2024
Viewed by 927
Abstract
Nitrothiazole derivatives have been reported to exhibit activity against aerobic, anaerobic, and microaerophilic bacteria. This activity profile makes the nitrothiazole compound class an ideal lead source against Mycobacterium tuberculosis, which flourishes in varied environments with different oxygen concentrations. In this work, we [...] Read more.
Nitrothiazole derivatives have been reported to exhibit activity against aerobic, anaerobic, and microaerophilic bacteria. This activity profile makes the nitrothiazole compound class an ideal lead source against Mycobacterium tuberculosis, which flourishes in varied environments with different oxygen concentrations. In this work, we investigated six nitrothiazole derivatives for antitubercular activity. The compounds exhibited potent activity, with compounds 9 and 10 possessing an equipotent MIC90 value of 0.24 µM. The compounds were investigated for cytotoxicity against HEK293 cells and hemolysis against red blood cells, and they demonstrated no cytotoxicity nor hemolytic effects, suggesting they possess inherent antitubercular activity. Full article
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4 pages, 338 KiB  
Short Note
5-(9-(p-Tolyl)-2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazol-6-yl)thiophene-2-carbaldehyde
by Nikita S. Gudim, Ekaterina A. Knyazeva and Oleg A. Rakitin
Molbank 2024, 2024(1), M1792; https://doi.org/10.3390/M1792 - 14 Mar 2024
Viewed by 870
Abstract
Donor–π spacer–acceptor (D–π–A) dyes are among the most attractive structures for the design of organic dye-sensitized solar cells (DSSCs). Typically, the key intermediates for these sensitizers are D–π compounds containing an aldehyde group to which an anchor acceptor group is attached via the [...] Read more.
Donor–π spacer–acceptor (D–π–A) dyes are among the most attractive structures for the design of organic dye-sensitized solar cells (DSSCs). Typically, the key intermediates for these sensitizers are D–π compounds containing an aldehyde group to which an anchor acceptor group is attached via the Knoevenagel reaction. In this communication, 5-(9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazol-6-yl)thiophene-2-carbaldehyde was prepared via the Suzuki cross-coupling reaction. The structure of the newly synthesized compound was established by means of high-resolution mass spectrometry, 1H NMR, 13C NMR, IR, and UV–Vis spectroscopy. The title compound would be used in the synthesis of sensitizers for DSSCs. Full article
(This article belongs to the Section Organic Synthesis)
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6 pages, 688 KiB  
Short Note
1-(3,4-Dimethoxyphenyl)-3-(4-methoxyphenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one
by Anna Nacher-Luis and Isidro M. Pastor
Molbank 2024, 2024(1), M1791; https://doi.org/10.3390/M1791 - 12 Mar 2024
Viewed by 880
Abstract
The study of new catalytic protocols for the synthesis of organic compounds with a more sustainable perspective is of interest. The use of ionic organic solids, such as 1,3-bis(carboxymethyl)imidazolium chloride as a catalyst has allowed the Michael addition of N-heterocycles to chalcones. This [...] Read more.
The study of new catalytic protocols for the synthesis of organic compounds with a more sustainable perspective is of interest. The use of ionic organic solids, such as 1,3-bis(carboxymethyl)imidazolium chloride as a catalyst has allowed the Michael addition of N-heterocycles to chalcones. This methodology has been applied to the unique preparation of the potential bioactive compound 1-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one with moderate yield, due to the retro-Michael reaction. Both synthetic reactions (i.e., preparation of chalcone and triazole Michael-addition to chalcone) have good green metrics. Full article
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6 pages, 1119 KiB  
Short Note
(E)-1-(1-(Benzofuran-2-yl)ethylidene)-2-(2,4,6-trichlorophenyl)hydrazine
by Bakr F. Abdel-Wahab, Hanan A. Mohamed, Benson M. Kariuki and Gamal A. El-Hiti
Molbank 2024, 2024(1), M1790; https://doi.org/10.3390/M1790 - 11 Mar 2024
Viewed by 901
Abstract
The reaction of a mixture of equimolar quantities of 2-acetylbenzofuran and (2,4,6-trichlorophenyl)hydrazine in ethanol containing concentrated hydrochloric acid (0.2 mL; 37%) as a catalyst under reflux for two hours yielded 1-(1-(benzofuran-2-yl)ethylidene)-2-(2,4,6-trichlorophenyl)hydrazine. The crude product was purified by crystallization using dimethylformamide to provide the [...] Read more.
The reaction of a mixture of equimolar quantities of 2-acetylbenzofuran and (2,4,6-trichlorophenyl)hydrazine in ethanol containing concentrated hydrochloric acid (0.2 mL; 37%) as a catalyst under reflux for two hours yielded 1-(1-(benzofuran-2-yl)ethylidene)-2-(2,4,6-trichlorophenyl)hydrazine. The crude product was purified by crystallization using dimethylformamide to provide the title heterocycle in a 90% yield. The structure of the new heterocycle was confirmed through X-ray diffraction and spectral analyses. Full article
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Graphical abstract

6 pages, 1080 KiB  
Short Note
1-(2,4-Dinitrophenyl)-2-((Z)-2-((E)-4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine
by Bakr F. Abdel-Wahab, Hanan A. Mohamed, Benson M. Kariuki and Gamal A. El-Hiti
Molbank 2024, 2024(1), M1789; https://doi.org/10.3390/M1789 - 11 Mar 2024
Viewed by 899
Abstract
The reaction of (E)-2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one and (2,4-dinitrophenyl)hydrazine in boiling ethanol containing hydrochloric acid (0.2 mL; 37%) for 1.5 h gave 1-(2,4-dinitrophenyl)-2-(2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine in a 90% yield. Various spectral analyses, including NMR, and X-ray crystallography established the structure of the newly synthesized hydrazone. Full article
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4 pages, 327 KiB  
Communication
Bis(2,2,6,6-tetramethyl-1-(λ1-oxidaneyl)piperidin-4-yl) 3,3′-((2-hydroxyethyl)azanediyl)dipropionate
by Roman P. Kustin, Oleg V. Levin, Sofia S. Filippova and Elena V. Alekseeva
Molbank 2024, 2024(1), M1788; https://doi.org/10.3390/M1788 - 8 Mar 2024
Viewed by 885
Abstract
TEMPO-containing conductive polymers are used in organic electronics due to their electrochemical properties. One of significant limitations in developing such materials is the structural modification by several TEMPO moieties. Here, we report a synthesis of the first-generation dendrimer containing two TEMPO fragments, bis(2,2,6,6-tetramethyl-1-(λ [...] Read more.
TEMPO-containing conductive polymers are used in organic electronics due to their electrochemical properties. One of significant limitations in developing such materials is the structural modification by several TEMPO moieties. Here, we report a synthesis of the first-generation dendrimer containing two TEMPO fragments, bis(2,2,6,6-tetramethyl-1-(λ1-oxidaneyl)piperidin-4-yl) 3,3′-((2-hydroxyethyl)azanediyl)dipropionate, that can be implemented into a conductive polymer structure. The resulting product was characterized using 1H and 13C nuclear magnetic resonance spectroscopy (NMR) and high-resolution mass spectroscopy (HRMS). Full article
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7 pages, 1573 KiB  
Communication
Synthesis and Monoamine Oxidase Inhibition Properties of 4-(2-Methyloxazol-4-yl)benzenesulfonamide
by Anton A. Shetnev, Julia A. Efimova, Mikhail K. Korsakov, Anél Petzer and Jacobus P. Petzer
Molbank 2024, 2024(1), M1787; https://doi.org/10.3390/M1787 - 6 Mar 2024
Viewed by 896
Abstract
4-(2-Methyloxazol-4-yl)benzenesulfonamide was synthesized by the reaction of 4-(2-bromoacetyl)benzenesulfonamide with an excess of acetamide. The compound was evaluated as a potential inhibitor of human monoamine oxidase (MAO) A and B and was found to inhibit these enzymes with IC50 values of 43.3 and [...] Read more.
4-(2-Methyloxazol-4-yl)benzenesulfonamide was synthesized by the reaction of 4-(2-bromoacetyl)benzenesulfonamide with an excess of acetamide. The compound was evaluated as a potential inhibitor of human monoamine oxidase (MAO) A and B and was found to inhibit these enzymes with IC50 values of 43.3 and 3.47 μM, respectively. The potential binding orientation and interactions of the inhibitor with MAO-B were examined by molecular docking, and it was found that the sulfonamide group binds and interacts with residues of the substrate cavity. 4-(2-Methyloxazol-4-yl)benzenesulfonamide showed no cytotoxic effect against human stromal bone cell line (HS-5) in the concentration range of 1–100 µmol. Thus, the new selective MAO-B inhibitor was identified, which may be used as the lead compound for the development of antiparkinsonian agents. Full article
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5 pages, 1111 KiB  
Short Note
Bis(N-tert-butylacetamido)(dimethylamido)(chloro)titanium
by Dennis M. Seth, Jr. and Rory Waterman
Molbank 2024, 2024(1), M1786; https://doi.org/10.3390/M1786 - 6 Mar 2024
Viewed by 939
Abstract
The titanium amidate compound bis(N-tert-butylacetamido)(dimethylamido)(chloro)titanium was synthesized by the protonolysis of tris(dimethylamido)(chloro)titanium and structurally characterized by 1H and 13C NMR spectroscopy as well as X-ray diffraction. The compound does not appear to react cleanly nor readily with routine alkylating [...] Read more.
The titanium amidate compound bis(N-tert-butylacetamido)(dimethylamido)(chloro)titanium was synthesized by the protonolysis of tris(dimethylamido)(chloro)titanium and structurally characterized by 1H and 13C NMR spectroscopy as well as X-ray diffraction. The compound does not appear to react cleanly nor readily with routine alkylating agents such as sec-butyllithium, benzyl potassium, or trimethylsilyl methyllithium. Full article
(This article belongs to the Section Structure Determination)
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7 pages, 558 KiB  
Short Note
2-((5-(3-(2-Fluorophenyl)acryloyl)-4-methylthiazol-2-yl)amino)isoindoline-1,3-dione
by Olha-Maria Fedusevych, Andrii Lozynskyi, Marta Sulyma and Roman Lesyk
Molbank 2024, 2024(1), M1785; https://doi.org/10.3390/M1785 - 6 Mar 2024
Viewed by 963
Abstract
In this work, the title compound was synthesized via the Claisen–Schmidt condensation of a 2-((5-acetyl-4-methylthiazol-2-yl)amino)isoindoline-1,3-dione with 2-fluorobenzaldehyde. The structure of the synthesized compound (yield 62%) was confirmed by 1H, 13C NMR, and LC–MS spectra. According to US NCI protocols, the compound [...] Read more.
In this work, the title compound was synthesized via the Claisen–Schmidt condensation of a 2-((5-acetyl-4-methylthiazol-2-yl)amino)isoindoline-1,3-dione with 2-fluorobenzaldehyde. The structure of the synthesized compound (yield 62%) was confirmed by 1H, 13C NMR, and LC–MS spectra. According to US NCI protocols, the compound displayed a high level of antimitotic activity against tested human tumor cells, with mean GI50/TGI values of 15.72/50.68 μM. The drug-like properties of the synthesized compound were evaluated using SwissAdme, revealing satisfactory drug-like parameters, and it presents interest for the design of new synthetic agents with biological activity. Full article
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5 pages, 620 KiB  
Short Note
(10E,15Z)-12-(Dimethylsulfonio)-9,13-dihydroxyoctadeca-10,15-dienoate
by Haruka Nishino, Bo-Tao Zhang, Hajime Uchida, Michiya Kamio, Hiroshi Nagai and Masayuki Satake
Molbank 2024, 2024(1), M1784; https://doi.org/10.3390/M1784 - 3 Mar 2024
Viewed by 1245
Abstract
A novel oxylipin, okeanoate (1), was isolated from the Okinawan cyanobacterium Okeania hirsuta. The structure of 1 was elucidated based on spectroscopic data including 1D and 2D NMR, as well as high-resolution mass spectrometry. This is the first oxylipin with [...] Read more.
A novel oxylipin, okeanoate (1), was isolated from the Okinawan cyanobacterium Okeania hirsuta. The structure of 1 was elucidated based on spectroscopic data including 1D and 2D NMR, as well as high-resolution mass spectrometry. This is the first oxylipin with a dimethylsulfonium moiety in the middle of the hydrocarbon chain. Full article
(This article belongs to the Section Natural Products)
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9 pages, 3101 KiB  
Communication
Synthesis of (Z)-3-Allyl-5-(4-nitrobenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one and Determination of Its Crystal Structure
by Bastien Moreno, Isabelle Jourdain, Michael Knorr, Sarra Boudriga, Carsten Strohmann and Tobias Schrimpf
Molbank 2024, 2024(1), M1783; https://doi.org/10.3390/M1783 - 1 Mar 2024
Viewed by 1101
Abstract
To extend the existing library of arylidenerhodanines which display a potential biological activity, 3-N-allylrhodanine 1 was condensed under Knoevenagel conditions with p-nitrobenzaldehyde in acetic acid to afford the π-conjugated heterocyclic compound 3-allyl-5-(4-nitrobenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one 2. Compound 2 was characterized by IR [...] Read more.
To extend the existing library of arylidenerhodanines which display a potential biological activity, 3-N-allylrhodanine 1 was condensed under Knoevenagel conditions with p-nitrobenzaldehyde in acetic acid to afford the π-conjugated heterocyclic compound 3-allyl-5-(4-nitrobenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one 2. Compound 2 was characterized by IR and NMR spectroscopy, and its UV-vis spectrum was compared with that of compound 3-allyl-5-(4-methoxybenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one 3. The molecular structure is ascertained by a single-crystal X-ray diffraction study performed at 100 K. Full article
(This article belongs to the Section Organic Synthesis)
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5 pages, 561 KiB  
Short Note
3-(2-Chloroethoxy)-1-(4-methoxyphenyl)-1H-pyrazole-4-carbaldehyde
by Gabrielė Varvuolytė, Aurimas Bieliauskas, Neringa Kleizienė, Asta Žukauskaitė and Algirdas Šačkus
Molbank 2024, 2024(1), M1782; https://doi.org/10.3390/M1782 - 1 Mar 2024
Viewed by 1078
Abstract
Herein, we describe the synthesis of 3-(2-chloroethoxy)-1-(4-methoxyphenyl)-1H-pyrazole-4-carbaldehyde via the Vilsmeier-Haack reaction. The structure of this previously unreported compound is thoroughly elucidated through NMR, FT-IR spectroscopy and HRMS spectrometry. Full article
(This article belongs to the Section Organic Synthesis)
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6 pages, 1230 KiB  
Short Note
(N,N′-Di-tert-butyl-S-phenylsulfinimidamidato-κNN′)-chlorogermanium-κGe-chloro(η2,η2-cycloocta-1,5-diene)rhodium
by Narimi Hosoda, Akihiko Ishii and Norio Nakata
Molbank 2024, 2024(1), M1781; https://doi.org/10.3390/M1781 - 28 Feb 2024
Viewed by 1133
Abstract
The title complex [{PhS(tBuN)2}(Cl)Ge:→RhCl(cod)] (2) was synthesized by the reaction of three-coordinated chlorogermylene, [PhS(tBuN)2]GeCl (1), supported by a diimidosulfinate ligand with a half equivalent of [RhCl(cod)]2 in benzene. The molecular [...] Read more.
The title complex [{PhS(tBuN)2}(Cl)Ge:→RhCl(cod)] (2) was synthesized by the reaction of three-coordinated chlorogermylene, [PhS(tBuN)2]GeCl (1), supported by a diimidosulfinate ligand with a half equivalent of [RhCl(cod)]2 in benzene. The molecular structure of 2 was determined by 1H and 13C NMR spectroscopies and single-crystal X-ray diffraction (SCXRD) analysis. The electronic property of germylene 1 was assessed by determining the Tolman electronic parameter of the corresponding cis-dicarbonyl Rh(I) complex, [{PhS(tBuN)2}(Cl)Ge:→RhCl(CO)2] (3), that was prepared by the treatment of 2 with carbon monoxide. Full article
(This article belongs to the Section Structure Determination)
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5 pages, 2358 KiB  
Short Note
1,4-Bis(2-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl)piperazine
by Nikolai S. Li-Zhulanov, Artem D. Rogachev, Yuri V. Gatilov, Konstantin P. Volcho and Nariman F. Salakhutdinov
Molbank 2024, 2024(1), M1780; https://doi.org/10.3390/M1780 - 28 Feb 2024
Viewed by 981
Abstract
The reaction of (−)-nopol mesylate with piperazine in acetonitrile under reflux, afforded symmetric 1,4-bis(2-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl)piperazine in a good yield. The compound was fully characterized and its structure was confirmed using X-ray diffraction analysis. Full article
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12 pages, 1766 KiB  
Communication
5-Fluorouracil/Coumarin and 5-Fluorouracil/Chromone Hybrids: Synthesis and Drug-Likeness Modeling
by Laura Giraldo-Arroyave, Andrés F. Yepes and Wilson Cardona-Galeano
Molbank 2024, 2024(1), M1779; https://doi.org/10.3390/M1779 - 28 Feb 2024
Viewed by 1021
Abstract
A series of 5-fluorouracil/coumarin and 5-fluorouracil/chromone hybrids were synthesized with good yields using click chemistry as the key step. The structures of these compounds and all intermediates were elucidated by spectroscopic analysis. Furthermore, pharmacokinetic and drug-like computations taken together indicated that the novel [...] Read more.
A series of 5-fluorouracil/coumarin and 5-fluorouracil/chromone hybrids were synthesized with good yields using click chemistry as the key step. The structures of these compounds and all intermediates were elucidated by spectroscopic analysis. Furthermore, pharmacokinetic and drug-like computations taken together indicated that the novel hybrids have a strong possibility to advance to further biological studies. Full article
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5 pages, 764 KiB  
Short Note
2-Methyl-4-Oxo-4,5-Dihydro-1H-Pyrrole-3-Carboxylic Acid Phenylamide
by Plamen Angelov and Pavel Yanev
Molbank 2024, 2024(1), M1778; https://doi.org/10.3390/M1778 - 28 Feb 2024
Viewed by 957
Abstract
2-Methyl-4-oxo-4,5-dihydro-1H-pyrrole-3-carboxylic acid phenylamide was obtained as a single product in an experiment on the cyclization modes of a glycine-derived enamino amide. High yield and operational simplicity are the main features of the presented synthetic procedure. Additionally, this result extends our previous [...] Read more.
2-Methyl-4-oxo-4,5-dihydro-1H-pyrrole-3-carboxylic acid phenylamide was obtained as a single product in an experiment on the cyclization modes of a glycine-derived enamino amide. High yield and operational simplicity are the main features of the presented synthetic procedure. Additionally, this result extends our previous observations on the cyclization reactions of similarly functionalized enamines, by revealing the preferred cyclization pathway under Boc-deprotection conditions. Full article
(This article belongs to the Section Organic Synthesis)
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5 pages, 1296 KiB  
Short Note
2,3,5,6-Tetrafluoro-[N-(3-aminopropyl)-ε-caprolactam]-4-pyridine
by Chadron M. Friesen, Nathan J. Weeks and Scott T. Iacono
Molbank 2024, 2024(1), M1777; https://doi.org/10.3390/M1777 - 22 Feb 2024
Viewed by 984
Abstract
The title compound was synthesized at a near-quantitative yield using the nucleophilic aromatic substitution of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with perfluoropyridine (PFP). The purity and structure were determined by NMR (1H, 13C, 19F), GC-EIMS, and single-crystal X-ray crystallography. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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6 pages, 1438 KiB  
Short Note
4,5-Dimethylfuro[3,4-d]pyridazin-1(2H)-one
by Kirill A. Gomonov, Vasilii V. Pelipko, Igor A. Litvinov, Ruslan I. Baichurin and Sergey V. Makarenko
Molbank 2024, 2024(1), M1776; https://doi.org/10.3390/M1776 - 20 Feb 2024
Viewed by 2162
Abstract
The synthesis of previously unknown 4,5-dimethylfuro[3,4-d]pyridazin-1(2H)-one has been proposed and structurally characterized via a single-crystal X-ray diffraction analysis, 1H, 13C–{1H}, 1H–13C HMQC, and 1H–13C HMBC NMR spectroscopy, and IR spectroscopy. Full article
(This article belongs to the Section Structure Determination)
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6 pages, 1027 KiB  
Short Note
N-(2,2-Diphenylethyl)-4-nitrobenzamide
by Diyana Dimitrova, Stanimir Manolov, Iliyan Ivanov, Dimitar Bojilov, Lyusi Kasamova and Paraskev Nedialkov
Molbank 2024, 2024(1), M1775; https://doi.org/10.3390/M1775 - 12 Feb 2024
Viewed by 1842
Abstract
In this study, we outline the eco-friendly mechanosynthesis of N-(2,2-diphenylethyl)-4-nitrobenzamide by reacting 2,2-diphenylethan-1-amine with 4-nitrobenzoyl chloride. The resulting bio-functional hybrid compound was meticulously characterized through the analysis of 1H-, 13C-NMR, UV, and detailed mass spectral analysis. Full article
(This article belongs to the Section Structure Determination)
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6 pages, 1964 KiB  
Short Note
2-Benzoyl-4-phenyl-1,2,5-thiadiazol-3(2H)-one 1,1-Dioxide
by Emmanouil Broumidis, Samuel B. H. Patterson, Georgina M. Rosair, Panayiotis A. Koutentis and Andreas S. Kalogirou
Molbank 2024, 2024(1), M1774; https://doi.org/10.3390/M1774 - 12 Feb 2024
Viewed by 1192
Abstract
3,5-Diphenyl-4H-1,2,6-thiadiazin-4-one treated with meta-chloroperoxybenzoic acid undergoes an oxidative ring contraction to give 2-benzoyl-4-phenyl-1,2,5-thiadiazol-3(2H)-one 1,1-dioxide in a 29% yield, the structure of which is supported by single-crystal X-ray diffraction analysis and the available spectroscopic data. Full article
(This article belongs to the Section Organic Synthesis)
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5 pages, 392 KiB  
Communication
Four-Step Synthesis of 3-Allyl-2-(allyloxy)-5-bromoaniline from 2-Allylphenol
by Enrique B. Aparicio, Stephen R. Isbel and Alejandro Bugarin
Molbank 2024, 2024(1), M1773; https://doi.org/10.3390/M1773 - 7 Feb 2024
Viewed by 1114
Abstract
This communication reports a four-step protocol to produce 3-allyl-2-(allyloxy)-5-bromoaniline 5 from commercially available 2-allylphenol. The synthetic steps used were nitration, selective bromination, allylation, and reduction of the nitro group. Full article
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9 pages, 2545 KiB  
Communication
Synthesis and Anti-Inflammatory Activity of (Z)-4-(2-(3-Oxopiperazin-2-ylidene)acetyl)benzoic Acid
by Maksim V. Dmitriev, Ekaterina E. Khramtsova, Danila Y. Apuskin, Alexander I. Andreev, Ilya I. Kovalenko, Irina V. Mashevskaya and Andrey N. Maslivets
Molbank 2024, 2024(1), M1772; https://doi.org/10.3390/M1772 - 5 Feb 2024
Viewed by 1101
Abstract
Non-steroidal anti-inflammatory drugs (NSAIDs) are an important class of medications; however, they have some drawbacks. We are developing a new NSAID with pronounced anti-inflammatory and analgesic activities and a very low toxicity—(Z)-3-(2-oxo-2-(p-tolyl)ethylidene)piperazin-2-one (piron). In this work, we describe the synthesis of [...] Read more.
Non-steroidal anti-inflammatory drugs (NSAIDs) are an important class of medications; however, they have some drawbacks. We are developing a new NSAID with pronounced anti-inflammatory and analgesic activities and a very low toxicity—(Z)-3-(2-oxo-2-(p-tolyl)ethylidene)piperazin-2-one (piron). In this work, we describe the synthesis of the main metabolite of piron—(Z)-4-(2-(3-oxopiperazin-2-ylidene)acetyl)benzoic acid. The anti-inflammatory activity of the synthesized metabolite was determined in vivo. Full article
(This article belongs to the Collection Heterocycle Reactions)
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7 pages, 2421 KiB  
Short Note
N-(2,4-Difluorophenyl)-2-fluorobenzamide
by Niall Hehir and John F. Gallagher
Molbank 2024, 2024(1), M1771; https://doi.org/10.3390/M1771 - 4 Feb 2024
Viewed by 1137
Abstract
The title compound N-(2,4-difluorophenyl)-2-fluorobenzamide (Fo24) was synthesized in high yield (1.09 g; 87%) using standard synthetic procedures from the condensation reaction of 2-fluorobenzoyl chloride with 2,4-difluoroaniline. Crystals of Fo24 were grown from CH2Cl2 at room temperature. The [...] Read more.
The title compound N-(2,4-difluorophenyl)-2-fluorobenzamide (Fo24) was synthesized in high yield (1.09 g; 87%) using standard synthetic procedures from the condensation reaction of 2-fluorobenzoyl chloride with 2,4-difluoroaniline. Crystals of Fo24 were grown from CH2Cl2 at room temperature. The Fo24 crystal structure was determined using single-crystal X-ray diffraction methods at 294 (1) K in space group Pn (No. 7). Fo24 is the second regular tri-fluorinated benzamide with the formula C13H8F3N1O1 to be reported and contrasts with the more common difluorinated and tetra-fluorinated analogues. In Fo24, both aromatic rings are effectively coplanar with an interplanar angle of 0.7(2)°. The central amide group plane is oriented by 23.04(18)° and 23.69(17)° from both aromatic rings, forming an intramolecular contact with an ortho-F12 atom with H1⋯F12 = 2.12(4) Å. The primary hydrogen bonds are 1D amide–amide interactions that form along the b-axis direction. In addition, weaker C-H⋯F/O interactions are noted: a R22(12) synthon involving two C-H, a N-H and two C-F groups, with C-F⋯C ring–ring stacking contacts completing the interactions. Full article
(This article belongs to the Section Structure Determination)
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7 pages, 651 KiB  
Communication
Chlorido-pentamethylcyclopentadienyl-[2-(2-pyridyl-кN)-ferrocenyl-кC]-iridium(III)
by Stefan Weigand and Karlheinz Sünkel
Molbank 2024, 2024(1), M1770; https://doi.org/10.3390/M1770 - 2 Feb 2024
Viewed by 943
Abstract
Treatment of 2-pyridyl-ferrocene wit [Cp*IrCl2]2 in the presence of NaOAc produces the title compound Cp*ClIr[(C5H3C5H4N-кN,кC)Fe(C5H5)] (2) in low yield. A crystal structure determination shows the (SpSIr/RpRIr)-2 enantiomeric pair of diastereomers. Full article
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6 pages, 1447 KiB  
Short Note
(E)-5-[Bromo(phenyl)methylene]-4-phenyl-2-(p-tolyl)-4,5-dihydrooxazole
by Nobuyoshi Morita, Saki Kurami, Naho Ishii, Kosaku Tanaka III, Yoshimitsu Hashimoto and Osamu Tamura
Molbank 2024, 2024(1), M1769; https://doi.org/10.3390/M1769 - 2 Feb 2024
Viewed by 1122
Abstract
One-pot synthesis of (E)-5-[bromo(phenyl)methylene]-4-phenyl-2-(p-tolyl)-4,5-dihydrooxazole (9) from propargylic alcohol 5 and p-toluamide (6) was achieved via gold(III)-catalyzed propargylic substitution, followed by gold(III)-catalyzed bromocyclization. The structure of 9 was confirmed by an X-ray crystallographic analysis. Full article
(This article belongs to the Section Organic Synthesis)
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5 pages, 341 KiB  
Short Note
9-Vinyl-9H-carbazole-3,6-dicarbonitrile
by Kristina Svetlova, Alexander Kazantsev, Oleg Levin, Sofia Filippova and Elena Alekseeva
Molbank 2024, 2024(1), M1768; https://doi.org/10.3390/M1768 - 2 Feb 2024
Viewed by 1148
Abstract
Carbazole polymers attract significant attention as promising luminophores, organic electronic and photovoltaic materials, photo/electrocatalysts, energy storage materials, redox mediators and catalysts. However, the oxidation potential of the commercially available poly(vinylcarbazole) is insufficient for some applications such as high-voltage Li-Ion batteries. We have proposed [...] Read more.
Carbazole polymers attract significant attention as promising luminophores, organic electronic and photovoltaic materials, photo/electrocatalysts, energy storage materials, redox mediators and catalysts. However, the oxidation potential of the commercially available poly(vinylcarbazole) is insufficient for some applications such as high-voltage Li-Ion batteries. We have proposed a monomer for the novel polycarbazole with an increased oxidation potential, which will be compatible with high-voltage cathode materials for Li-Ion. In addition, the proposed polymer is an interesting substrate for the further carbonization to obtain N-doped carbons with a high electrocatalytic activity level. Full article
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5 pages, 887 KiB  
Communication
Synthesis of a Novel Tetracyclic Isoxazole by Intramolecular Nitrile Oxide Cycloaddition
by Gavin R. Hoffman and Allen M. Schoffstall
Molbank 2024, 2024(1), M1767; https://doi.org/10.3390/M1767 - 1 Feb 2024
Viewed by 1188
Abstract
Intramolecular cycloadditions have the great advantage of forming two rings simultaneously. We report the use of intramolecular [3 + 2] cycloaddition of the nitrile oxide derived from an N-propargylbenzimidazole oxime in the synthesis of a hitherto unreported tetracyclic isoxazole-containing ring system bearing [...] Read more.
Intramolecular cycloadditions have the great advantage of forming two rings simultaneously. We report the use of intramolecular [3 + 2] cycloaddition of the nitrile oxide derived from an N-propargylbenzimidazole oxime in the synthesis of a hitherto unreported tetracyclic isoxazole-containing ring system bearing “6-5-5-5”-membered ring fusions. The initial condensation was achieved through reaction of o-phenylenediamine with ethyl diethoxyacetate, followed by alkylation with propargyl bromide, deprotection of the acetal to the aldehyde, formation of an aldoxime, and intramolecular nitrile oxide cycloaddition (INOC). Characterization of the aldoxime and tetracyclic isoxazole is included herein. Full article
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