Synthesis of some new biologically active 1,3,4-oxadiazolyl nitroindoles and a modified Fischer indole synthesis of ethyl nitro indole-2-carboxylates

B Narayana; B V Ashalatha; K K Vijaya Raj; J Fernandes; B K Sarojini

doi:10.1016/j.bmc.2005.04.068

Synthesis of some new biologically active 1,3,4-oxadiazolyl nitroindoles and a modified Fischer indole synthesis of ethyl nitro indole-2-carboxylates

Bioorg Med Chem. 2005 Aug 1;13(15):4638-44. doi: 10.1016/j.bmc.2005.04.068.

Authors

B Narayana¹, B V Ashalatha, K K Vijaya Raj, J Fernandes, B K Sarojini

Affiliation

¹ Department of Post-Graduate Studies and Research in Chemistry, Mangalore University, Mangalagangotri 574 199, India.

PMID: 15927475
DOI: 10.1016/j.bmc.2005.04.068

Abstract

An efficient and modified synthesis of ethyl-4-nitro/5-nitro/6-nitro and 7-nitroindole-2-carboxylates is described. Carbohydrazides of corresponding ethyl nitroindole-2-carboxylates underwent smooth one-step transformation to 1,3,4-oxadiazolyl nitroindoles (4a-l) on reaction with aromatic carboxylic acids in the presence of phosphorus oxychloride. An alternate method to synthesize 1,3,4-oxadiazolyl nitroindoles is also described. Among the newly synthesized 1,3,4-oxadiazolyl nitroindoles, a few compounds are studied for anti-inflammatory activity.

MeSH terms

Animals
Anti-Inflammatory Agents / chemical synthesis
Anti-Inflammatory Agents / chemistry
Anti-Inflammatory Agents / pharmacology
Azo Compounds / chemical synthesis*
Azo Compounds / chemistry
Azo Compounds / pharmacology*
Carboxylic Acids / chemistry*
Edema / pathology
Indoles / chemical synthesis*
Indoles / chemistry
Indoles / pharmacology*
Molecular Structure
Nitrogen / chemistry*
Rats
Structure-Activity Relationship

Substances

Anti-Inflammatory Agents
Azo Compounds
Carboxylic Acids
Indoles
indole
Nitrogen