Regiospecific synthesis, X-ray crystal structure and biological activities of 5-bromothiophenethyl thioureas

The regiospecific synthesis of 5-bromothiophenethyl thioureas was accomplished in four steps with an overall yield of 40–60%. The requisite regioselectivity for bromination of the thiophene ring was achieved using bromine in acetic acid at low temperatures. The resulting 5-bromothiophenethylamine hy...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2001-09, Vol.42 (38), p.6629-6632
Main Authors: Venkatachalam, Taracad K, Sudbeck, Elise A, Uckun, Fatih M
Format: Article
Language:English
Subjects:
HIV
non-nucleoside inhibitor
reverse transcriptase
thiophene thiourea
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The regiospecific synthesis of 5-bromothiophenethyl thioureas was accomplished in four steps with an overall yield of 40–60%. The requisite regioselectivity for bromination of the thiophene ring was achieved using bromine in acetic acid at low temperatures. The resulting 5-bromothiophenethylamine hydrobromide is an important precursor for the preparation of substituted thioureas. The X-ray crystal structure demonstrates that the bromine atom is indeed located at the 5-position of the thiophene ring. Thiophene carbamate derivatives were brominated regiospecifically and elaborated to furnish 5-bromosubstituted thioureas. Among the derivatives studied for their biological activity, DDE935 inhibited HIV RT with an IC 50 [HTLV IIIB] value of 15 nM.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)01290-4