An efficient combinatorial synthesis of allocolchicine analogues via a triple cascade reaction and their evaluation as inhibitors of insulin aggregation

Subhendu Bhowmik; Shruti Khanna; Kumkum Srivastava; Mohammad Hasanain; Jayanta Sarkar; Sandeep Verma; Sanjay Batra

doi:10.1002/cmdc.201300302

An efficient combinatorial synthesis of allocolchicine analogues via a triple cascade reaction and their evaluation as inhibitors of insulin aggregation

ChemMedChem. 2013 Nov;8(11):1767-72. doi: 10.1002/cmdc.201300302. Epub 2013 Sep 5.

Authors

Subhendu Bhowmik¹, Shruti Khanna, Kumkum Srivastava, Mohammad Hasanain, Jayanta Sarkar, Sandeep Verma, Sanjay Batra

Affiliation

¹ Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, BS 10/1, Sector 10, Jankipuram Extension, Sitapur Rd, Lucknow 226031 (India).

PMID: 24009069
DOI: 10.1002/cmdc.201300302

Abstract

A controlled cascade: A divergent, diastereoselective and efficient one-pot synthesis of allocolchicinoids via a cascade Suzuki-Michael addition-Carbocyclization sequence is described. The utility of the compounds as possible inhibitors of insulin aggregation is also presented.

Keywords: alkaloids; antiaggregation agents; cascade reactions; natural products; one-pot syntheses.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Cattle
Circular Dichroism
Colchicine / analogs & derivatives*
Colchicine / chemical synthesis
Colchicine / chemistry
Colchicine / pharmacology
Combinatorial Chemistry Techniques*
Insulin Antagonists / chemical synthesis
Insulin Antagonists / chemistry*
Insulin Antagonists / pharmacology*
Microscopy, Atomic Force
Molecular Structure
Protein Binding / drug effects
Stereoisomerism

Substances

Insulin Antagonists
allocolchicine
Colchicine