Molecules

92 KiB

Open AccessArticle

Synthesis and Biological Activity of 3-(2-Furanyl)-6-Aryl-1,2,4-Triazolo[3,4-b]-1,3,4 –Thiadiazoles

by Li-Xue Zhang, An-Jiang Zhang, Xian-Xing Chen, Xin-Xiang Lei, Xiang-Yun Nan, Dong-Yong Chen and Zi-Yi Zhang

Molecules 2002, 7(8), 681-689; https://doi.org/10.3390/70800681 - 31 Aug 2002

Cited by 51 | Viewed by 23937

Abstract

3-(2-Furanyl)-4-amino-5-mercapto-1,2,4-triazole (1) was prepared from 2-furoic acid through a multi-step reaction sequence. Compound 1 reacted with aromatic acids in the presence of phosphorus oxychloride to give 3-(2-furanyl)-6-aryl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles (2). The structures of all the newly synthesized compounds have been confirmed by elemental analysis, IR, [...] Read more.

3-(2-Furanyl)-4-amino-5-mercapto-1,2,4-triazole (1) was prepared from 2-furoic acid through a multi-step reaction sequence. Compound 1 reacted with aromatic acids in the presence of phosphorus oxychloride to give 3-(2-furanyl)-6-aryl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles (2). The structures of all the newly synthesized compounds have been confirmed by elemental analysis, IR, 1H-NMR, 13C-NMR and mass spectra. The bioassay indicated most of the title compounds possess significant growth promoting effects on mung bean radicles. Full article

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68 KiB

Open AccessArticle

Solid State Deprotection of Acetals and Thioacetals Using Benzyltriphenylphosphonium Peroxymonosulfate

by Abdol Reza Hajipour, Shadpour E. Mallakpour, Iraj Mohammadpoor-Baltork and Hadi Adibi

Molecules 2002, 7(8), 674-680; https://doi.org/10.3390/70800674 - 31 Aug 2002

Cited by 24 | Viewed by 8687

Abstract

A variety of acetals and thioacetals 2 are deprotected to the corresponding parent carbonyl compounds 3 under solvent-free conditions using benzyltriphenylphosphonium peroxymonosulfate (1) in the presence of aluminum chloride. Full article

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135 KiB

Open AccessArticle

NMR Detection of Isomers Arising from Restricted Rotation of the C-N Amide Bond of N-Formyl-o-toluidine and N,N’-bis-Formyl-o-tolidine

by Ramiro Quintanilla-Licea, Juan F. Colunga-Valladares, Adolfo Caballero-Quintero, Cristina Rodríguez-Padilla, Reyes Tamez-Guerra, Ricardo Gómez-Flores and Noemí Waksman

Molecules 2002, 7(8), 662-673; https://doi.org/10.3390/70800662 - 31 Aug 2002

Cited by 53 | Viewed by 14801

Abstract

Full and unambiguous assignment of all ¹H- and ¹³C-NMR resonances of the isomers due to restricted C-N amide bond rotation of N-formyl-o-toluidine and N,N'-bis-formyl-o-tolidine in DMSO-d₆ is reported. The cis-isomer [...] Read more.

Full and unambiguous assignment of all ¹H- and ¹³C-NMR resonances of the isomers due to restricted C-N amide bond rotation of N-formyl-o-toluidine and N,N'-bis-formyl-o-tolidine in DMSO-d₆ is reported. The cis-isomer predominates in the equilibrium mixture of both compounds as 1D-NOE difference experiments show. Full article

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187 KiB

Open AccessArticle

DivCalc: A Utility for Diversity Analysis and Compound Sampling

by Rajeev Gangal

Molecules 2002, 7(8), 657-661; https://doi.org/10.3390/70800657 - 31 Aug 2002

Cited by 2 | Viewed by 7658

Abstract

Diversity, in the form of genetic diversity, chemical diversity etc, is a very important concept in several areas of scientific research, and calculation of diversity is one of the most important considerations in pre-clinical drug discovery research and, in particular, in design of [...] Read more.

Diversity, in the form of genetic diversity, chemical diversity etc, is a very important concept in several areas of scientific research, and calculation of diversity is one of the most important considerations in pre-clinical drug discovery research and, in particular, in design of diverse chemical libraries for combinatorial chemistry and compound selection for High Throughput Screening (HTS). DivCalc is a Windows^TMbased software that implements a previously published method of diversity calculation [1]. This facilitates sampling of a given data matrix to obtain the most diverse compounds that span the entire descriptor space. Full article

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95 KiB

Open AccessArticle

Novel Cytotoxic Oxopyridoindolizines: iso-Propyl-7,8,9-trichloro-6,7,8,9-tetrahydro-5-oxopyrido[2,3-a]-indolizine-10-carboxylates (OPIC)

by Franco Zunino, Ann T. Kotchevar, Michael Waring, Maria Daoudi, Najib Ben Larbi, Mostafa Mimouni, Najat Sam, Assou Zahidi and Taibi Ben-Hadda

Molecules 2002, 7(8), 628-640; https://doi.org/10.3390/70800628 - 31 Aug 2002

Cited by 14 | Viewed by 11023

Abstract

A series of eight new alkyl-7,8,9-trichloro-6,7,8,9-tetrahydro-5-oxopyrido[2,3-a]-indolizine-10-carboxylates (OPIC), analogues of camptothecin (CPT), were prepared in a one-pot reaction of 2,2'-bipyridine-3,3'-dicarboxylic acid (BPA) with a mixture of thionyl chloride/chlorine, followed by addition of the appropriate alcohol. This led to a mixture of OPIC compounds 3a-d, [...] Read more.

A series of eight new alkyl-7,8,9-trichloro-6,7,8,9-tetrahydro-5-oxopyrido[2,3-a]-indolizine-10-carboxylates (OPIC), analogues of camptothecin (CPT), were prepared in a one-pot reaction of 2,2'-bipyridine-3,3'-dicarboxylic acid (BPA) with a mixture of thionyl chloride/chlorine, followed by addition of the appropriate alcohol. This led to a mixture of OPIC compounds 3a-d, 4a-d and 3,3'-dialkoxycarbonyl-2,2'-bipyridines (BPE, 2a-d). The isopropyl OPIC 3c and its corresponding diastereoisomer 4c showed marked activity against three cancer cell lines compared to other analogs. These same diastereoisomers also displayed high cytotoxic activity against five leukemia cell lines, thus the presence of an isopropyl substituent on the carboxylic ester, as opposed to other alkyl substituents, appears to play a key role in the cytotoxic potency of this new class of compounds. Full article

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84 KiB

Open AccessArticle

Synthesis of Substituted 2-Pyridyl-4-phenylquinolines

by Antonino Mamo, Salvatore Nicoletti and N. Cam Tat

Molecules 2002, 7(8), 618-627; https://doi.org/10.3390/70800618 - 31 Aug 2002

Cited by 15 | Viewed by 9421

Abstract

The acid-catalyzed condensation of o-aminobenzophenones with aromatic acetyl derivatives, in a basic methanol/tetrahydrofuran medium, has been used to prepare a series of substituted 2-pyridyl-4-phenylquinolines. Derivatives having two aza binding sites can act as asymmetric bidendate ligands to complex transition metals such as ruthenium, [...] Read more.

The acid-catalyzed condensation of o-aminobenzophenones with aromatic acetyl derivatives, in a basic methanol/tetrahydrofuran medium, has been used to prepare a series of substituted 2-pyridyl-4-phenylquinolines. Derivatives having two aza binding sites can act as asymmetric bidendate ligands to complex transition metals such as ruthenium, osmium or iridium. All the compounds were characterized by elemental analysis, Ei or FAB (+) MS, ¹H- and ¹³C-NMR spectroscopies. Complete assignments of the ¹H spectra were accomplished by using a combination of one- and two-dimensional NMR techniques. Full article

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371 KiB

Open AccessArticle

Towards Highly Activating Leaving Groups: Studies on the Preparation of Some Halogenated Alkyl Sulfonates

by Thomas Netscher and Patrick Bohrer

Molecules 2002, 7(8), 601-617; https://doi.org/10.3390/70800601 - 31 Aug 2002

Cited by 5 | Viewed by 9541

Abstract

The trichloromethylsulfonyl-, dichloromethylsulfonyl-, chlorosulfonyl-, and fluorosulfonyl esters of a neopentyl-type alcohol have been prepared via sulfonylation or sulfinylation followed by oxidation. The preparative usefulness and potential of the transformations are discussed. Full article

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164 KiB

Open AccessArticle

2,3-Bifunctionalized Quinoxalines: Synthesis, DNA Interactions and Evaluation of Anticancer, Anti-tuberculosis and Antifungal Activity

by Michael J. Waring, Taibi Ben-Hadda, Ann T. Kotchevar, Abdelkrim Ramdani, Rachid Touzani, Sghir Elkadiri, Abdelkader Hakkou, Mohamed Bouakka and Tom Ellis

Molecules 2002, 7(8), 641-656; https://doi.org/10.3390/70800641 - 30 Aug 2002

Cited by 106 | Viewed by 13117

Abstract

A variety of 2,3-bifunctionalized quinoxalines (6-14) have been prepared by the condensation of 1,6-disubstituted-hexan-1,3,4,6-tetraones (1-4) with o-phenylenediamine, (R,R)-1,2-diaminocyclohexane and p-nitro-o-phenylenediamine. It is concluded that strong intramolecular N-H----O bonds in the favoured keto-enamine form may be responsible for the minimal biological activities observed in [...] Read more.

A variety of 2,3-bifunctionalized quinoxalines (6-14) have been prepared by the condensation of 1,6-disubstituted-hexan-1,3,4,6-tetraones (1-4) with o-phenylenediamine, (R,R)-1,2-diaminocyclohexane and p-nitro-o-phenylenediamine. It is concluded that strong intramolecular N-H----O bonds in the favoured keto-enamine form may be responsible for the minimal biological activities observed in DNA footprinting, antitubercular, anti-fungal and anticancer tests with these hyper π-conjugated quinoxaline derivatives. However, subtle alteration by addition of a nitro group affecting the charge distribution confers significant improvements in biological effects and binding to DNA. Full article

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275 KiB

Open AccessReview

Chemoinformatics and Drug Discovery

by Jun Xu and Arnold Hagler

Molecules 2002, 7(8), 566-600; https://doi.org/10.3390/70800566 - 30 Aug 2002

Cited by 198 | Viewed by 18417

Abstract

This article reviews current achievements in the field of chemoinformatics and their impact on modern drug discovery processes. The main data mining approaches used in cheminformatics, such as descriptor computations, structural similarity matrices, and classification algorithms, are outlined. The applications of cheminformatics in [...] Read more.

This article reviews current achievements in the field of chemoinformatics and their impact on modern drug discovery processes. The main data mining approaches used in cheminformatics, such as descriptor computations, structural similarity matrices, and classification algorithms, are outlined. The applications of cheminformatics in drug discovery, such as compound selection, virtual library generation, virtual high throughput screening, HTS data mining, and in silico ADMET are discussed. At the conclusion, future directions of chemoinformatics are suggested. Full article

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Molecules, Volume 7, Issue 8 (August 2002) – 9 articles , Pages 566-689

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