Multi-component assembly of the bicyclic core associated with the tRNA synthetase inhibitors SB-203207 and SB-203208. Application to the synthesis of biologically active analogues

M G Banwell; C F Crasto; C J Easton; T Karoli; D R March; M R Nairn; P J O'Hanlon; M D Oldham; A C Willis; W Yue

Multi-component assembly of the bicyclic core associated with the tRNA synthetase inhibitors SB-203207 and SB-203208. Application to the synthesis of biologically active analogues

Chem Commun (Camb). 2001 Nov 7:(21):2210-1.

Authors

M G Banwell¹, C F Crasto, C J Easton, T Karoli, D R March, M R Nairn, P J O'Hanlon, M D Oldham, A C Willis, W Yue

Affiliation

¹ Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia. mgb@rsc.anu.edu.au

PMID: 12240115

Abstract

The ketone (+/-)-5, which embodies the bicyclic core associated with the title tRNA synthetase inhibitors 1 and 2, has been prepared via a three-component coupling reaction involving 2-(hydroxymethyl)cyclopent-2-enone (15), methylamine (6) and propiolamide (10); straightforward elaboration of the readily derived acetates (-)-21 and (+)-21 has provided the biologically active analogues 23 and 24, respectively, of the title compounds.

Publication types

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

MeSH terms

Amino Acyl-tRNA Synthetases / antagonists & inhibitors*
Enzyme Inhibitors / chemistry*
Enzyme Inhibitors / pharmacology
Indenes / chemistry*
Indenes / pharmacology
Sulfonamides / chemistry*
Sulfonamides / pharmacology

Substances

Enzyme Inhibitors
Indenes
SB 203207
SB 203208
Sulfonamides
Amino Acyl-tRNA Synthetases