Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 3: 8-Thiocarboxamido and 8-thioformamido derivatives of cyclazocine

Mark P Wentland; Xufeng Sun; Yigong Bu; Rongliang Lou; Dana J Cohen; Jean M Bidlack

doi:10.1016/j.bmcl.2005.03.056

Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 3: 8-Thiocarboxamido and 8-thioformamido derivatives of cyclazocine

Bioorg Med Chem Lett. 2005 May 16;15(10):2547-51. doi: 10.1016/j.bmcl.2005.03.056.

Authors

Mark P Wentland¹, Xufeng Sun, Yigong Bu, Rongliang Lou, Dana J Cohen, Jean M Bidlack

Affiliation

¹ Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, NY 12180, USA. [email protected]

PMID: 15863314
DOI: 10.1016/j.bmcl.2005.03.056

Abstract

8-Position variants of cyclazocine have been made where the phenolic 8-OH was replaced by thioamide, amidine, guanidine, urea and thiourea groups. High affinity for opioid receptors was observed for the 8-CSNH2 and 8-NHCHS analogues indicating that these groups are isosteric with not only the 8-OH but with the previously synthesized 8-CONH2 and 8-NHCHO cyclazocine derivatives.

Publication types

Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Cyclazocine / chemistry*
Cyclazocine / pharmacology*
Structure-Activity Relationship

Substances

Cyclazocine

Abstract

Publication types

MeSH terms

Substances

Grants and funding