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Molecules, Volume 11, Issue 11 (November 2006) – 9 articles , Pages 827-939

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91 KiB  
Article
Reactivity of 4-tert-Butyldimethylsiloxy-1,2,3,6-tetrahydropyridines with Hydrazines
by Javier Figueroa, Esther Caballero, Pilar Puebla, Fernando Tomé and Manuel Medarde
Molecules 2006, 11(11), 929-939; https://doi.org/10.3390/11110929 - 30 Nov 2006
Cited by 5 | Viewed by 9932
Abstract
The reactivity of 6-(nitrophenyl or trimethoxyphenyl)-4-tert-butyldimethyl- siloxy-1,2,3,6-tetrahydropyridine derivatives with hydrazines under acid conditions is described. The structure of the products isolated − hydrazones, pyrazolines or pyridazinones − depended on the conditions used. In addition, a systematic study of the reaction outcomes was carried [...] Read more.
The reactivity of 6-(nitrophenyl or trimethoxyphenyl)-4-tert-butyldimethyl- siloxy-1,2,3,6-tetrahydropyridine derivatives with hydrazines under acid conditions is described. The structure of the products isolated − hydrazones, pyrazolines or pyridazinones − depended on the conditions used. In addition, a systematic study of the reaction outcomes was carried out by introducing variations on the substituents of the tetrahydropyridine ring. Full article
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100 KiB  
Article
Improving the Quality of Published Chemical Names with Nomenclature Software
by Gernot A. Eller
Molecules 2006, 11(11), 915-928; https://doi.org/10.3390/11110915 - 29 Nov 2006
Cited by 40 | Viewed by 12007
Abstract
This work deals with the use of organic systematic nomenclature in scientific literature, its quality, and computerized methods for its improvement. Criteria for classification of systematic names in terms of quality/correctness are discussed and applied to a sample set of several hundred names [...] Read more.
This work deals with the use of organic systematic nomenclature in scientific literature, its quality, and computerized methods for its improvement. Criteria for classification of systematic names in terms of quality/correctness are discussed and applied to a sample set of several hundred names extracted from the literature. The same structures are named with three popular state-of-the-art nomenclature programs – AutoNom 2000, ChemDraw 10.0, and ACD/Name 9.0. When comparing the results, all nomenclature tools show a significantly better performance than 'average chemists'. One program allows the generation not only of IUPAC names but also of CAS-like index names that are compared with the officially registered names. The scope and limitations of nomenclature software are discussed and a comparison of the programs' actual capabilities is given. Full article
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163 KiB  
Article
Copper(II) Complexes with Ligands Derived from 4-Amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one: Synthesis and Biological Activity
by Tudor Rosu, Simona Pasculescu, Veronica Lazar, Carmen Chifiriuc and Raluca Cernat
Molecules 2006, 11(11), 904-914; https://doi.org/10.3390/11110904 - 17 Nov 2006
Cited by 82 | Viewed by 10664
Abstract
The synthesis of Cu(II) complexes derived from Schiff base ligands obtainedby the condensation of 2-hydroxybenzaldehyde or terephtalic aldehyde with 4-amino-antipyrine (4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one) is presented. The newlyprepared compounds were characterized by 1H-NMR, UV-VIS, IR and ESRspectroscopy. The determination of the antimicrobial activity of the [...] Read more.
The synthesis of Cu(II) complexes derived from Schiff base ligands obtainedby the condensation of 2-hydroxybenzaldehyde or terephtalic aldehyde with 4-amino-antipyrine (4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one) is presented. The newlyprepared compounds were characterized by 1H-NMR, UV-VIS, IR and ESRspectroscopy. The determination of the antimicrobial activity of the ligands and of thecomplexes was carried out on samples of Escherichia coli, Klebsiella pneumoniae,Acinetobacter boumanii, Pseudomonas aeruginosa, Staphylococcus aureus and Candidasp. The qualitative and quantitative antimicrobial activity test results proved that all theprepared complexes are very active, especially against samples of Ps. aeruginosa, A.Boumanii, E. coli and S. aureus. Full article
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145 KiB  
Article
Facile Synthesis of 5, 6, 7, 8-Tetrahydropyrimido [4, 5-b]-quinoline Derivatives
by Yehya Mahmud Elkholy and Mohamed Abdelhamed Morsy
Molecules 2006, 11(11), 890-903; https://doi.org/10.3390/11110890 - 17 Nov 2006
Cited by 49 | Viewed by 10158
Abstract
2–Amino–4-phenyl–5,6,7,8–tetrahydroquinoline–3–carbonitrile (3) was synthesized by treating cyclohexanone (1) with 2–benzylidenemalononitrile (2) in the presence of ammonium acetate. The reactivity of compound 3 towards dimethylformamide dimethyl acetal (DMF-DMA), carbon disulfide, urea, thiourea, formamide, formic acid, acetyl chloride and isothiocyanate were studied. In addition, the [...] Read more.
2–Amino–4-phenyl–5,6,7,8–tetrahydroquinoline–3–carbonitrile (3) was synthesized by treating cyclohexanone (1) with 2–benzylidenemalononitrile (2) in the presence of ammonium acetate. The reactivity of compound 3 towards dimethylformamide dimethyl acetal (DMF-DMA), carbon disulfide, urea, thiourea, formamide, formic acid, acetyl chloride and isothiocyanate were studied. In addition, the antimicrobial activity of some selected derivatives is reported. Full article
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171 KiB  
Article
Synthesis and Structural Characterization of 1- and 2-Substituted Indazoles: Ester and Carboxylic Acid Derivatives
by Fátima C. Teixeira, Hélène Ramos, Inês F. Antunes, M. João M. Curto, M. Teresa Duarte and Isabel Bento
Molecules 2006, 11(11), 867-889; https://doi.org/10.3390/11110867 - 14 Nov 2006
Cited by 32 | Viewed by 13140
Abstract
A series of indazoles substituted at the N-1 and N-2 positions with ester-containing side chains -(CH2)nCO2R of different lengths (n = 0-6, 9, 10) are described.Nucleophilic substitution reactions on halo esters (X(CH2)nCO2 [...] Read more.
A series of indazoles substituted at the N-1 and N-2 positions with ester-containing side chains -(CH2)nCO2R of different lengths (n = 0-6, 9, 10) are described.Nucleophilic substitution reactions on halo esters (X(CH2)nCO2R) by 1H-indazole inalkaline solution lead to mixtures of N-1 and N-2 isomers, in which the N-1 isomerpredominates. Basic hydrolysis of the ester derivatives allowed the synthesis of thecorresponding indazole carboxylic acids. All compounds were fully characterised bymultinuclear NMR and IR spectroscopies, MS spectrometry and elemental analysis; theNMR spectroscopic data were used for structural assignment of the N-1 and N-2 isomers.The molecular structure of indazol-2-yl-acetic acid (5b) was determined by X-raydiffraction, which shows a supramolecular architecture involving O2-H...N1intermolecular hydrogen bonds. Full article
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65 KiB  
Article
Revisiting the Reaction Between Diaminomaleonitrile and Aromatic Aldehydes: a Green Chemistry Approach
by Augusto Rivera, Jaime Ríos-Motta Ríos-Motta and Francisco León
Molecules 2006, 11(11), 858-866; https://doi.org/10.3390/11110858 - 11 Nov 2006
Cited by 18 | Viewed by 11910
Abstract
The reaction between diaminomaleonitrile (DAMN) and aldehydes and the resulting monoimines are well known. Since the standard reaction conditions involve the use of toxic solvents (typically methanol), we have sought to apply green chemistry principles to this reaction by either using water as [...] Read more.
The reaction between diaminomaleonitrile (DAMN) and aldehydes and the resulting monoimines are well known. Since the standard reaction conditions involve the use of toxic solvents (typically methanol), we have sought to apply green chemistry principles to this reaction by either using water as the solvent without any catalysts or employing “solvent-free” conditions. The monoimines derived from DAMN are of interest as precursors for obtaining different heterocyclic systems and linear polymers. The methodologies used have significant advantages with regards to cost and environmental considerations. Full article
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99 KiB  
Article
Synthesis and Biological Evaluation of New 4β-5-Fu-substituted 4'-Demethylepipodophyllotoxin Derivatives
by Fu-Min Zhang, Xiao-Jun Yao, Xuan Tian and Yong-Qiang Tu
Molecules 2006, 11(11), 849-857; https://doi.org/10.3390/11110849 - 02 Nov 2006
Cited by 20 | Viewed by 8381
Abstract
A series of new 4β-5-Fu-substituted 4'-demethylepipodophyllotoxin derivatives were synthesized and evaluated, together with some previously prepared ones, for their cytotoxic activities against four tumor cell lines (HL60, P388, A549 and BEL7402). Three of these compounds exhibited superior in vitro anticancer activity against P388 [...] Read more.
A series of new 4β-5-Fu-substituted 4'-demethylepipodophyllotoxin derivatives were synthesized and evaluated, together with some previously prepared ones, for their cytotoxic activities against four tumor cell lines (HL60, P388, A549 and BEL7402). Three of these compounds exhibited superior in vitro anticancer activity against P388 and A549 than the reference compound etoposide. In addition, the partition coefficients (P) of all the new and previously synthesized derivatives were determined. Full article
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103 KiB  
Article
Hydantoin Derivatives of L- and D-amino acids: Synthesis and Evaluation of Their Antiviral and Antitumoral Activity
by Zrinka Rajic, Branka Zorc, Silvana Raic-Malic, Katja Ester, Marijeta Kralj, Krešimir Pavelic, Jan Balzarini, Erik De Clercq and Mladen Mintas
Molecules 2006, 11(11), 837-848; https://doi.org/10.3390/11110837 - 01 Nov 2006
Cited by 59 | Viewed by 12765
Abstract
3,5-Disubstituted hydantoin (1,3-imidazolidinedione) derivatives 5a-h wereprepared by base induced cyclization of the corresponding N-(1-benzotriazolecarbonyl)-L-and D-amino acid amides 4a-h. Compounds 5a-h were evaluated for their cytostatic andantiviral activities. Among all the compounds evaluated, 3-benzhydryl-5-isopropylhydantoin (5a) showed a weak but selective inhibitory effect against vaccinia [...] Read more.
3,5-Disubstituted hydantoin (1,3-imidazolidinedione) derivatives 5a-h wereprepared by base induced cyclization of the corresponding N-(1-benzotriazolecarbonyl)-L-and D-amino acid amides 4a-h. Compounds 5a-h were evaluated for their cytostatic andantiviral activities. Among all the compounds evaluated, 3-benzhydryl-5-isopropylhydantoin (5a) showed a weak but selective inhibitory effect against vaccinia virus (EC50 =16 μg/mL; selectivity index: 25). 3-Cyclohexyl-5-phenyl hydantoin (5g) showed inhibitoryactivity against cervical carcinoma (HeLa, IC50 = 5.4 μM) and breast carcinoma (MCF-7,IC50 = 2 μM), but also cytotoxic effects towards human normal fibroblasts (WI 38). On thecontrary, the 3-benzhydryl-5-phenyl substituted hydantoin derivative 5h showed moderateinhibitory activity towards HeLa, MCF-7, pancreatic carcinoma (MiaPaCa-2), lungcarcinoma (H 460) and colon carcinoma (SW 620) (IC50 = 20−23 μM), but no effect on WI38. Full article
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104 KiB  
Article
Regioselective Synthesis of Novel N2- and N4-Substituted 7-Methylpyrazolo[4,5-e][1,2,4]thiadiazines
by Xinyong Liu, Renzhang Yan, Niangen Chen, Wenfang Xu, Maria Teresa Molina and Salvador Vega
Molecules 2006, 11(11), 827-836; https://doi.org/10.3390/11110827 - 01 Nov 2006
Cited by 5 | Viewed by 10098
Abstract
The new compound 7-methylpyrazolo[4,5-e][1,2,4]thiadiazin-3(2H,4H)-one1,1-dioxide (5) was synthesized and its novel mono N2- or N4-substituted derivatives 6and 7 were prepared by regioselective N-alkylation of 5 with different molar ratios ofNaH and alkyl halides. Based on the regioselective alkylation conditions found [...] Read more.
The new compound 7-methylpyrazolo[4,5-e][1,2,4]thiadiazin-3(2H,4H)-one1,1-dioxide (5) was synthesized and its novel mono N2- or N4-substituted derivatives 6and 7 were prepared by regioselective N-alkylation of 5 with different molar ratios ofNaH and alkyl halides. Based on the regioselective alkylation conditions found a facileone-pot synthesis of N2,N4-disubstituted pyrazolo[4,5-e][1,2,4] thiadiazines 8 wasdeveloped. The structures of the newly synthesized compounds were confirmed by IR,1H-NMR, 13C-NMR and MS spectral analysis. Full article
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