B. Narayana, B. V. Ashalatha, K. K. V. Raj
Dec 1, 2009
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0
Influential Citations
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Quality indicators
Journal
ChemInform
Abstract
Synthesis and studies on antimicrobial, antiinflammatory and antiproliferative activities of heterocycles derived from 4- /5-/6-/7-nitro/5-fluoro/chloro/bromoindole-2-carbohydrazides are discussed. 4-/5-/6-/7-nitroindole-2-carbohydrazides and 5- fluoro/chloro/bromoindole-2-carbohydrazides on treatment with acetyl acetone in methanol have resulted in 2-((3,5- dimethyl-1H-pyrazol-1-yl)carbonyl)-4-/5-/6-/7-nitro-1H-indoles and 2-((3,5-dimethyl-1H-pyrazol-1-yl) carbonyl)-5- fluoro/chloro/bromo-1H-indoles respectively. 4-/6-/7-nitroindole-2-carbohydrazides on treatment with CS2/KOH in methanol have yielded 5-(4-/6-/7-nitro-1H-indol-2-yl)-1,3,4-oxadiazole-2-thiol and with cyanogen bromide yielded 5-(4-/6- /7-nitro-1H-indol-2-yl)-1,3,4-oxadiazol-2-amine. Nitroindole-2-carbohydrazides are also treated with various aromatic carboxylic acids and triethyl orthoformate yielded 2-(5-(aryl)-1,3,4-oxadiazol-2-yl)-4-/5-/6-/7-nitro-1H-indoles and 4-/6-/7- nitro-2-(1,3,4-oxadiazol-2-yl)-1H-indoles, respectively. Structures of the newly synthesized compounds are characterized by analytical and spectral data. for 60-cell line in vitro antitumour assay. Almost all the compounds exhibited moderate to good antiproliferative activity. Results and Discussion Ethyl 4-/5-/6-/7-nitro and methyl 5-fluoro/chloro/ bromoindole-2-carboxylates on reaction with hydra- zine hydrate yielded corresponding 4-/5-/6-/7- nitroindole-2-carbohydrazides and 5-fluoro/chloro/ bromoindole-2-carbohydrazides 1a-g. 4-/5-/6-/7- Nitroindole-2-carbohydrazides and 5-fluoro/chloro/ bromoindole-2-carbohydrazides 1a-g on treatment with acetyl acetone in methanol yielded 2-((3,5- dimethyl-1H-pyrazol-1-yl)carbonyl)-4-/5-/6-/7-nitro and 5-fluoro/chloro/bromo-1H-indoles 2a-g. 4-/6-/7- Nitroindole-2-carbohydrazides 1a-d on treatment with CS2/KOH in methanol resulted in the formation of 5- (4-/6-/7-nitro-1H-indol-2-yl)-1,3,4-oxadiazole-2-thiol 3a-3c and with cyanogen bromide in methanol yielded 5-(4-/6-/7-nitro-1H-indol-2-yl)-1,3,4-oxadia- zol-2-amines 5a-c. The 4-/5-/6-/7-nitroindole-2- carbohydrazides 1a-d were also refluxed with