Side-chain homologation of nodulisporic acid: synthesis of potent new dienyl derivatives.
A series of new, diene-modified nodulisporic acid analogues (2) bearing diverse functionality at the 3"- and 4"-sites was efficiently prepared from the 3"-aldehyde 3. Biological evaluation of these synthetic nodulisporic acid analogues for systemic flea efficacy identified potent compounds and further clarified the structural requirements for ectoparasite activity.
Ok
Dong
D
Merck Research Laboratories, PO Box 2000, Rahway, NJ 07065-0900, USA.
Li
Chunshi
C
Shih
Thomas L
TL
Salva
Steve
S
Ayer
Michelle B
MB
Colletti
Steven L
SL
Chakravarty
Prasun K
PK
Wyvratt
Matthew J
MJ
Fisher
Michael H
MH
Gregory
Lynn
L
Zakson-Aiken
Michelle
M
Shoop
Wesley L
WL
Schmatz
Dennis M
DM
Meinke
Peter T
PT
D000818:Animals; D002417:Cattle; D004478:Ectoparasitic Infestations / Q000188:drug therapy; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry; D005423:Siphonaptera; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D007211:Indoles; D007306:Insecticides; C110703:nodulisporic acid A