Chemical modification of the insecticidal briantheins X and Y.

Abstract

Manipulation of the allylic chloride functionality in briantheins X and Y provided 10 new analogues of these gorgonian diterpenes as part of a continuing study of structure-activity relationships in this family of insecticidal compounds. Modified Finkelstein reaction conditions led not only to halogen substitution products but also to rearrangement, dehydrohalogenation, and dehydration products. None of the new compounds showed superior insecticidal activity to brianthein X or Y, although most did result in lower weight gains versus controls.

• Authors: John M Cronan, Angela Lee, Jun Liang, Jon Clardy, John H Cardellina
• Journal: Journal of natural products (J Nat Prod) Vol. 73 Issue 3 Pg. 346-51 (Mar 26 2010) ISSN: 1520-6025 [Electronic] United States
• PMID: 19810733 (Publication Type: Journal Article, Research Support, U.S. Gov't, Non-P.H.S.)

Chemical References

• Diterpenes
• brianthein X
• brianthein Y

Topics

• Animals
• Anthozoa (chemistry)
• Crystallography, X-Ray
• Diterpenes (chemistry, isolation & purification, pharmacology)
• Larva (drug effects)
• Manduca (drug effects)
• Molecular Conformation
• Molecular Structure
• Structure-Activity Relationship