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Molbank, Volume 2017, Issue 4 (December 2017) – 14 articles

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2478 KiB  
Short Note
1,3-Bis[(E)-(3-bromobenzylidene)amino]propan-2-ol
by Ismail Warad, Huda Abedalrazeq, Nisreen Amer, Mohammmed Al-Nuri, Anas Al Ali, Nabil Al-Zaqri and Naveen Shivalingegowda
Molbank 2017, 2017(4), M971; https://doi.org/10.3390/M971 - 19 Dec 2017
Cited by 2 | Viewed by 3666
Abstract
1,3-Bis[(E)-(3-bromobenzylidene)amino]propan-2-ol Schiff base was synthesized in an acceptable yield by condensation of 3-bromobenzaldehyde with 1,3-diaminopropan-2-ol in methanol. The structure of the desired Schiff base compound was spectroscopically analyzed by EI-MS, CHN-elemental analysis, FT-IR, UV-visible, and 1H and 13C-NMR. The [...] Read more.
1,3-Bis[(E)-(3-bromobenzylidene)amino]propan-2-ol Schiff base was synthesized in an acceptable yield by condensation of 3-bromobenzaldehyde with 1,3-diaminopropan-2-ol in methanol. The structure of the desired Schiff base compound was spectroscopically analyzed by EI-MS, CHN-elemental analysis, FT-IR, UV-visible, and 1H and 13C-NMR. The structure was also computed by DFT-optimization, MEP, Mulliken, NPA, IR- B3LYP/6-311++G(d), and SCF-TD-DFT. Full article
(This article belongs to the Special Issue Heterocycles)
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465 KiB  
Short Note
4-Phenethylthio-2-phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one
by Sergey A. Smolnikov, Ekaterina V. Gorgopina, Vera R. Lezhnyova, Gwyneth En-Tian Ong, Wai-Keung Chui and Anton V. Dolzhenko
Molbank 2017, 2017(4), M970; https://doi.org/10.3390/M970 - 15 Dec 2017
Cited by 7 | Viewed by 3088
Abstract
Exploring the pharmacologically important pyrazolo[1,5-a][1,3,5]triazin-7(6H)-one scaffold for the construction of new bioactive compounds, we developed a synthesis of 4-phenethylthio-2-phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one (4) via S-alkylation of 2-phenyl-4-thioxopyrazolo[1,5-a][1,3,5]triazine-7(6H)-one (3), prepared [...] Read more.
Exploring the pharmacologically important pyrazolo[1,5-a][1,3,5]triazin-7(6H)-one scaffold for the construction of new bioactive compounds, we developed a synthesis of 4-phenethylthio-2-phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one (4) via S-alkylation of 2-phenyl-4-thioxopyrazolo[1,5-a][1,3,5]triazine-7(6H)-one (3), prepared by the double ring closure of pyrazole and triazine rings upon the treatment of 1-cyanoacetyl-4-benzoylthiosemicarbazide (2) with alkali. The antiproliferative activity of 4 against human lung cancer (A549) and human breast cancer (MDA-MB231) cell lines was investigated. Compound 4 was found to be more active against lung cancer cells than breast cancer cells. Full article
(This article belongs to the Special Issue Heterocycles)
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881 KiB  
Communication
A Novel PCC-Catalyzed Process Involving the Oxidative Cleavage of an α-Bromomethyl-tetrahydrofuran Bond. Synthesis of (2S,3R)-2-{(R)-Bromo[(2R,3R,5S,6R)-3,5-dibromo-6-ethyltetrahydro-2H-pyran-2-yl]methyl}-5-oxotetrahydrofuran-3-yl Benzoate
by Vincenzo Piccialli
Molbank 2017, 2017(4), M969; https://doi.org/10.3390/M969 - 13 Dec 2017
Cited by 1 | Viewed by 3418
Abstract
In this note, we report the discovery of a novel pyridinium chlorochroamte-catalyzed process in which an α-bromomethyl-tetrahydrofuran bond was oxidatively cleaved to give a γ-lactone functionality. The title compound was synthesized from a C15 polybrominated acetogenin compound, isolated from the marine sponge Mycale [...] Read more.
In this note, we report the discovery of a novel pyridinium chlorochroamte-catalyzed process in which an α-bromomethyl-tetrahydrofuran bond was oxidatively cleaved to give a γ-lactone functionality. The title compound was synthesized from a C15 polybrominated acetogenin compound, isolated from the marine sponge Mycale rotalis, by benzoylation followed by pyridinium chlorochromate-catalyzed oxidation. This new degraded derivative was fully characterized by 1H-NMR, 13C-NMR, FTIR (Fourier transform infrared), EIMS (Electron impact mass spectrometry) and HRESIMS (High-resolution electrospray ionisation mass spectrometry). Full article
(This article belongs to the Section Organic Synthesis)
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468 KiB  
Short Note
1,3-Bis(1,2,4-triazol-1-yl)adamantane
by Roman Marchenko and Andrei Potapov
Molbank 2017, 2017(4), M968; https://doi.org/10.3390/M968 - 12 Dec 2017
Cited by 5 | Viewed by 3086
Abstract
Functional adamantane derivatives are interesting as active pharmaceutical ingredients, building blocks for supramolecular ensembles, and ligands in light of the coordination chemistry of functional materials. In this communication, synthesis of two isomeric 1,3-bis(1,2,4-triazolyl)adamantanes by the reaction of 1,3-dibromoadamantane with 1,2,4-triazole in the absence [...] Read more.
Functional adamantane derivatives are interesting as active pharmaceutical ingredients, building blocks for supramolecular ensembles, and ligands in light of the coordination chemistry of functional materials. In this communication, synthesis of two isomeric 1,3-bis(1,2,4-triazolyl)adamantanes by the reaction of 1,3-dibromoadamantane with 1,2,4-triazole in the absence of solvent is reported. The products, namely 1,3-bis(1,2,4-triazol-1-yl)adamantane and 1-(1,2,4-triazol-1-yl)-3-(1,2,4-triazol-4-yl)adamantane were separated by column chromatography and identified by NMR and mass-spectrometry. Full article
(This article belongs to the Section Organic Synthesis)
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656 KiB  
Short Note
N1-(5-Fluoro-2,4-dinitrophenyl)-N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine
by Georgia A. Zissimou and Panayiotis A. Koutentis
Molbank 2017, 2017(4), M967; https://doi.org/10.3390/M967 - 2 Dec 2017
Viewed by 3555
Abstract
Treating 1,5-difluoro-2,4-dinitrobenzene (1) with N1-phenyl-5-(trifluoromethyl)benzene-1,2-diamine (4) and N,N-diisopropylethylamine in EtOH at ca. 0 °C for 4 h affords a mixture of N1-(5-ethoxy-2,4-dinitrophenyl)-N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine (5) (38%) and N [...] Read more.
Treating 1,5-difluoro-2,4-dinitrobenzene (1) with N1-phenyl-5-(trifluoromethyl)benzene-1,2-diamine (4) and N,N-diisopropylethylamine in EtOH at ca. 0 °C for 4 h affords a mixture of N1-(5-ethoxy-2,4-dinitrophenyl)-N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine (5) (38%) and N1-(5-fluoro-2,4-dinitrophenyl)-N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine (6) (51%) that can be separated by chromatography. Repeating the reaction in dichloromethane led to the sole formation of N1-(5-fluoro-2,4-dinitrophenyl)-N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine (6) in 96% yield. Full article
(This article belongs to the Section Organic Synthesis)
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339 KiB  
Short Note
(±)-Methyl 1,1a,2,7b-Tetrahydro-2-oxocyclopropa[c] Chromene-1a-carboxylate
by Sunyoung Choi and Sung-Gon Kim
Molbank 2017, 2017(4), M966; https://doi.org/10.3390/M966 - 18 Nov 2017
Cited by 2 | Viewed by 2676
Abstract
A novel method for the preparation of (±)-methyl 1,1a,2,7b-tetrahydro-2-oxocyclopropa[c]chromene-1a-carboxylate has been developed. The cyclopropanation of methyl coumarin-3-carboxylate provided title compound in moderate yield by dropwise treatment with 1.5 equiv. of dimethylsulfoxonium methylide over 6 h. The structure of the newly synthesized [...] Read more.
A novel method for the preparation of (±)-methyl 1,1a,2,7b-tetrahydro-2-oxocyclopropa[c]chromene-1a-carboxylate has been developed. The cyclopropanation of methyl coumarin-3-carboxylate provided title compound in moderate yield by dropwise treatment with 1.5 equiv. of dimethylsulfoxonium methylide over 6 h. The structure of the newly synthesized compound was determined using 1H-, 13C-NMR, IR and mass spectral data. Full article
(This article belongs to the Section Organic Synthesis)
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1878 KiB  
Communication
Heterobimetallic 3d-4f (Zn/La) {6,6′-Dimethoxy-2,2′-[naphthalene-2,3-diylbis(nitrilomethylidyne)]diphenolato}-pyridylzinc(II)-tris(nitrato-O,O′)lanthanum(III) Monohydrate
by Calliope Bee Sue Linden, Nikita Chaudhary, Matthias Zeller and Evan R. Trivedi
Molbank 2017, 2017(4), M965; https://doi.org/10.3390/M965 - 18 Nov 2017
Cited by 1 | Viewed by 3875
Abstract
Herein, we report the synthesis and structural characterization of a complex with extended aromaticity based on a naphthalene-bridged Schiff base complex with two metal binding pockets. In a first step, the Zn(II) complex (ZnL), {6,6′-dimethoxy-2,2′-[naphthalene-2,3-diylbis(nitrilomethylidyne)]diphenolato}a-pyridylzinc(II) was isolated followed by refluxing with lanthanum(III) nitrate [...] Read more.
Herein, we report the synthesis and structural characterization of a complex with extended aromaticity based on a naphthalene-bridged Schiff base complex with two metal binding pockets. In a first step, the Zn(II) complex (ZnL), {6,6′-dimethoxy-2,2′-[naphthalene-2,3-diylbis(nitrilomethylidyne)]diphenolato}a-pyridylzinc(II) was isolated followed by refluxing with lanthanum(III) nitrate to produce the heterobimetallic complex {ZnL[La(NO3)3·H2O]}. Crystals suitable for X-ray diffraction were grown by vapor diffusion of THF into a pyridine solution of the complex. The monoclinic unit cell (P21/n) is commensurately modulated along the c-axis direction and contains four crystallographically independent molecules with pseudo-translational symmetry being broken by slightly differing orientations of included pyridine and THF solvate molecules. The zinc atom adopts a distorted square pyramidal geometry and sits slightly above the ligand plane, whereas the lanthanum atom adopts an all-face capped trigonal prismatic geometry and sits below the ligand plane. Structural characterization of this diamagnetic complex lays the groundwork for applying these synthetic techniques to the near-infrared emitting lanthanides for practical application. Full article
(This article belongs to the Section Structure Determination)
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2957 KiB  
Communication
(S)-2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrobenzo[e]pyrazino[1,2-a][1,4]diazepine-6,12(11H,12aH)-dione—Synthesis and Crystallographic Studies
by Adam Mieczkowski, Damian Trzybiński, Marcin Wilczek, Mateusz Psurski, Maciej Bagiński, Bartosz Bieszczad, Magdalena Mroczkowska and Krzysztof Woźniak
Molbank 2017, 2017(4), M964; https://doi.org/10.3390/M964 - 27 Oct 2017
Cited by 10 | Viewed by 3703
Abstract
(S)-2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrobenzo[e]pyrazino[1,2-a][1,4]diazepine-6,12(11H,12aH)-dione was obtained in a three-step, one-pot synthesis, starting from optically pure (S)-2-piperazine carboxylic acid dihydrochloride. Selective acylation of the β-nitrogen atom followed by condensation with isatoic anhydride and cyclization [...] Read more.
(S)-2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrobenzo[e]pyrazino[1,2-a][1,4]diazepine-6,12(11H,12aH)-dione was obtained in a three-step, one-pot synthesis, starting from optically pure (S)-2-piperazine carboxylic acid dihydrochloride. Selective acylation of the β-nitrogen atom followed by condensation with isatoic anhydride and cyclization with HATU/DIPEA to a seven-member benzodiazepine ring, led to the tricyclic benzodiazepine derivative. Crystallographic studies and initial biological screening were performed for the title compound. Full article
(This article belongs to the Special Issue Heterocycles)
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363 KiB  
Short Note
N-{4-[(2E)-3-(2H-1,3-Benzodioxol-5-yl)prop-2-enoyl]phenyl}quinoline-3-carboxamide
by Efrain Polo, Jorge Trilleras and Margarita Gutiérrez Cabrera
Molbank 2017, 2017(4), M960; https://doi.org/10.3390/M960 - 18 Oct 2017
Cited by 3 | Viewed by 2861
Abstract
An amide chalconehas been synthesized in a two-step reaction. First, N-(4-acetylphenyl)quinoline-3-carboxamide 2 was synthesized by the reaction of quinoline-3-carboxylic acid 1 and thionyl chloride (SOCl2), following the addition of 4-aminoacetophenone. Then, a typical Claisen–Schmidtreactionwas made between 2 and piperonal using [...] Read more.
An amide chalconehas been synthesized in a two-step reaction. First, N-(4-acetylphenyl)quinoline-3-carboxamide 2 was synthesized by the reaction of quinoline-3-carboxylic acid 1 and thionyl chloride (SOCl2), following the addition of 4-aminoacetophenone. Then, a typical Claisen–Schmidtreactionwas made between 2 and piperonal using KOH solution as a catalystin ethanol, under ultrasonic irradiation. The structure of the target compound was established by FTIR (Fourier-transform infrared spectroscopy), HRMS, 1H and 13C-NMR. Full article
(This article belongs to the Section Organic Synthesis)
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1066 KiB  
Short Note
1,8-bis(2-hydroxy-3,5-di-tert-butylbenzyl)-4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane
by Ane I. Aranburu Leiva, Mandeep Kaur, Sophie L. Benjamin, Alan M. Jones, Stuart K. Langley and Ryan E. Mewis
Molbank 2017, 2017(4), M963; https://doi.org/10.3390/M963 - 13 Oct 2017
Cited by 2 | Viewed by 3469
Abstract
A cyclam (1,4,8,11-tetraazacyclotetradecane)-based macrocycle bearing two benzyl and two 2-hydroxy-3,5-di-tert-butylbenzyl pendent arms was synthesized and characterized using spectroscopic techniques and single crystal X-ray diffraction. The macrocycle crystallizes in the triclinic space group P-1, with the asymmetric unit containing one-half of [...] Read more.
A cyclam (1,4,8,11-tetraazacyclotetradecane)-based macrocycle bearing two benzyl and two 2-hydroxy-3,5-di-tert-butylbenzyl pendent arms was synthesized and characterized using spectroscopic techniques and single crystal X-ray diffraction. The macrocycle crystallizes in the triclinic space group P-1, with the asymmetric unit containing one-half of the molecule. The structure is stabilized by hydrogen-bonding which exists between the phenolic protons and the nitrogen atoms of the macrocyclic ring. The presence of this hydrogen bonding is observed in the 1H-NMR due to the deshielded nature of the phenolic OH peak (δ 9.99). Cyclic voltammetry of the ligand revealed a single quasi-reversible peak at −0.58 V (Epc = −0.48 V and Epa = −0.68 V), which is due to the electrochemical oxidation of the phenol to the phenoxyl radical. Full article
(This article belongs to the Section Structure Determination)
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1331 KiB  
Short Note
1,3-Bis(2,6-diisopropylphenyl)-2-trichloromethylimidazolidine
by Darcie L. Stack and Jason D. Masuda
Molbank 2017, 2017(4), M962; https://doi.org/10.3390/M962 - 12 Oct 2017
Cited by 1 | Viewed by 3644
Abstract
A new chloroform adduct of the N-heterocyclic carbene (NHC) 1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene (SIPr) has been prepared via C–H bond activation of the chloroform at the carbene carbon. This redox product was crystallized and was characterized by 1H and 13C-NMR spectroscopy, elemental analysis [...] Read more.
A new chloroform adduct of the N-heterocyclic carbene (NHC) 1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene (SIPr) has been prepared via C–H bond activation of the chloroform at the carbene carbon. This redox product was crystallized and was characterized by 1H and 13C-NMR spectroscopy, elemental analysis (EA), and single-crystal X-ray diffraction. The 1H and 13C-NMR spectroscopic data are in agreement with the crystal structure. Density functional theory (DFT) calculations were performed as a means for comparison to experimental data and the computational results are in agreement with those obtained experimentally. Full article
(This article belongs to the Section Structure Determination)
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562 KiB  
Short Note
5,9,11-Trihydroxy-10-(2″-hydroxy-3″-methylbut-3″-en-1-yl)-2,2-dimethyl-3-(2′-methylbut-3′-en-2′-yl)-2H,12H-pyrano[2,3-a]xanthen-12-one from Calophyllum pseudomole
by Mulyadi Tanjung, Ratih Dewi Saputri and Tjitjik Srie Tjahjandarie
Molbank 2017, 2017(4), M961; https://doi.org/10.3390/M961 - 30 Sep 2017
Viewed by 2576
Abstract
A new pyranocoumarin, namely 5,9,11-trihydroxy-10-(2″-hydroxy-3″-methylbut- 3″en-1-yl)-2,2-dimethyl-3-(2′-methylbut-3′-en-2′-yl)-2H,12H-pyrano[2,3-a]xanthen-12-one 1, was isolated from the stem barkof Calophyllum pesudomole. The structure of compound 1 was elucidated based on its ultaraviolet (UV); infrared (IR); high resolution electro spray ionization mass spectrometry (HRESIMS); [...] Read more.
A new pyranocoumarin, namely 5,9,11-trihydroxy-10-(2″-hydroxy-3″-methylbut- 3″en-1-yl)-2,2-dimethyl-3-(2′-methylbut-3′-en-2′-yl)-2H,12H-pyrano[2,3-a]xanthen-12-one 1, was isolated from the stem barkof Calophyllum pesudomole. The structure of compound 1 was elucidated based on its ultaraviolet (UV); infrared (IR); high resolution electro spray ionization mass spectrometry (HRESIMS); 1D and 2D nuclear magnetic resonance (NMR) spectral data. Full article
(This article belongs to the Section Natural Products)
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932 KiB  
Short Note
(2-Deoxy-2-{[2-(2-pyridinyl-κN)-4-thiazolecarbonyl-κN3]amino}-α-d-glucopyranose)dichloropalladium(II) Methanol Solvate
by Shintaro Kodama, Akihiro Nomoto, Yuta Sakai, Shouhei Katao, Kiyomi Kakiuchi, Shigenobu Yano and Akiya Ogawa
Molbank 2017, 2017(4), M959; https://doi.org/10.3390/M959 - 25 Sep 2017
Viewed by 2646
Abstract
A novel palladium(II) complex with a glycoconjugated 2-(2-pyridyl)thiazole ligand was synthesized. Single-crystal X-ray analysis revealed a packing structure that may be stabilized by hydrogen bonding between sugar moieties and between methanol (crystal solvent) and a sugar moiety. Full article
(This article belongs to the Section Structure Determination)
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2058 KiB  
Short Note
Methyl N-[1-(Benzoylamino)-2-methoxy-2-oxoethyl]-tryptophanate
by Oumaima Karai, Maha El Hamdani, Hassane Faraj, Anouar Alami, Mohammed Rachid Kabbour, Abdelilah El Hallaoui, Mohammed Bouksaim and Younas Aouine
Molbank 2017, 2017(4), M958; https://doi.org/10.3390/M958 - 22 Sep 2017
Cited by 1 | Viewed by 2867
Abstract
The title compound, methyl N-[1-(benzoylamino)-2-methoxy-2-oxoethyl]tryptophanate 2, was synthesized in high yield, via N-alkylation reaction of methyl 2-azido-2-benzamidoacetate with methyl 2-amino-3-(1H-indol-3-yl)propanoate in acetone, with the presence of diisopropylethylamine as a base. The structure of the prepared compound was characterized [...] Read more.
The title compound, methyl N-[1-(benzoylamino)-2-methoxy-2-oxoethyl]tryptophanate 2, was synthesized in high yield, via N-alkylation reaction of methyl 2-azido-2-benzamidoacetate with methyl 2-amino-3-(1H-indol-3-yl)propanoate in acetone, with the presence of diisopropylethylamine as a base. The structure of the prepared compound was characterized by 1H, 13C NMR in addition to MS, X-Ray diffraction data, and elemental analysis. This compound was tested in vitro for its antibacterial activity against Gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus, and Gram-negative bacteria, Escherichia coli, Pseudomonas aeruginosa, and Salmonella enteric. The MIC values showed that the synthesized compound had a bactericidal effect against the strains tested. Full article
(This article belongs to the Section Organic Synthesis)
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