Molecules

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Open AccessArticle

Synthesis and Reactions of Some New Heterocyclic Carbohydrazides and Related Compounds as Potential Anticancer Agents

by Abdel Kader Mansour, Mohga M. Eid and Nasser S. A. M. Khalil

Molecules 2003, 8(10), 744-755; https://0-doi-org.brum.beds.ac.uk/10.3390/81000744 - 31 Oct 2003

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Acylation of 3-hydrazino-5,6-diphenyl-1,2,4-triazine (2) and hydrazine hydrate (7) with 4-aryl-1,3,7-triphenyl-8-oxa-1,2,6-triazaspiro[4.4]nona-2,6-dien-9-ones 5a,b gave the corresponding heterocyclic carbohydrazides 6a,b and 8a,b respectively. Conversion of compounds 8a,b into the versatile carbohydrazide derivatives 9a-g, 10, 13 and the related oxadiazoles 11, 12a,b was undertaken. A primary in [...] Read more.

Acylation of 3-hydrazino-5,6-diphenyl-1,2,4-triazine (2) and hydrazine hydrate (7) with 4-aryl-1,3,7-triphenyl-8-oxa-1,2,6-triazaspiro[4.4]nona-2,6-dien-9-ones 5a,b gave the corresponding heterocyclic carbohydrazides 6a,b and 8a,b respectively. Conversion of compounds 8a,b into the versatile carbohydrazide derivatives 9a-g, 10, 13 and the related oxadiazoles 11, 12a,b was undertaken. A primary in vitro test of compound 8a (concentration 10^-4 M) showed activity against leukemia cell lines (CCRFCEM, K-256, MOLT-4, PRMI-8226, SR). Full article

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Open AccessArticle

Novel 4-Aroyl-3-alkoxy-2(5H)-furanones as Precursors for the Preparation of Furo[3,4-b][1,4]-diazepine Ring System

by Hans Zimmer, Christian P. Librera, Sven Hausner, Jeanette Bauer and Adel Amer

Molecules 2003, 8(10), 735-743; https://0-doi-org.brum.beds.ac.uk/10.3390/81000735 - 31 Oct 2003

Cited by 8 | Viewed by 8531

Abstract

A general synthesis of tetronic acid derivatives, namely 4-aroyl-3-alkoxy-2(5H)-furanones, is achieved via the treatment of an anhydrous dimethylformamide (DMF) solution of 4-aroyl-3-hydroxy-2(5H)-furanones with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as base at -10-0°C, followed by the addition of alkyl iodide. Their structural assignments are based on spectroscopic [...] Read more.

A general synthesis of tetronic acid derivatives, namely 4-aroyl-3-alkoxy-2(5H)-furanones, is achieved via the treatment of an anhydrous dimethylformamide (DMF) solution of 4-aroyl-3-hydroxy-2(5H)-furanones with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as base at -10-0°C, followed by the addition of alkyl iodide. Their structural assignments are based on spectroscopic data and confirmed by X-ray crystallography. These furanones were used as starting materials for the preparation of furodiazepines. Full article

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Open AccessArticle

2-(p-Hydroxybenzyl)indoles - Side Products Formed Upon Cleavage of Indole Derivatives from Carboxylated Wang Polymer - an NMR Study

by Felikss Mutulis, Máté Erdélyi, Ilze Mutule, Jana Kreicberga, Sviatlana Yahorava, Aleh Yahorau, Larisa Borisova-Jan and Jarl E.S. Wikberg

Molecules 2003, 8(10), 728-734; https://0-doi-org.brum.beds.ac.uk/10.3390/81000728 - 31 Oct 2003

Cited by 4 | Viewed by 13389

Abstract

Treatment of carboxylated Wang polymer attached to a 2-unsubstituted indole derivative with a trifluoroacetic acid based mixture resulted in a side reaction: p-hydroxybenzylation at the 2-position of the indole ring. The structure of the resulting N-3-aminopropyl)-N-benzyl-4-[2-(4-hydroxybenzyl)-1H-indol-3-yl]-butyramide trifluoroacetate was ascertained by a full assignment [...] Read more.

Treatment of carboxylated Wang polymer attached to a 2-unsubstituted indole derivative with a trifluoroacetic acid based mixture resulted in a side reaction: p-hydroxybenzylation at the 2-position of the indole ring. The structure of the resulting N-3-aminopropyl)-N-benzyl-4-[2-(4-hydroxybenzyl)-1H-indol-3-yl]-butyramide trifluoroacetate was ascertained by a full assignment of its ¹H- and ¹³C-NMR spectra. The side reaction could be suppressed by the use of 1,2-ethanedithiol in high concentrations (16 %). Full article

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