Substitution on the A-ring confers to bryopyran analogues the unique biological activity characteristic of bryostatins and distinct from that of the phorbol esters.
A close structural analogue of bryostatin 1, which differs from bryostatin 1 only by the absence of the C(30) carbomethoxy group (on the C(13) enoate of the B-ring), has been prepared by total synthesis. Biological assays reveal a crucial role for substitution in the bryostatin 1 A-ring in conferring those responses which are characteristic of bryostatin 1 and distinct from those observed with PMA.
Keck
Gary E
GE
Department of Chemistry, University of Utah, 315 South 1400 East, RM 2020, Salt Lake City, Utah 84112, USA.
Poudel
Yam B
YB
Welch
Dennie S
DS
Kraft
Matthew B
MB
Truong
Anh P
AP
Stephens
Jeffrey C
JC
Kedei
Noemi
N
Lewin
Nancy E
NE
Blumberg
Peter M
PM
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D054713:Bryostatins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D015394:Molecular Structure; D010703:Phorbol Esters / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D054713:Bryostatins; D010703:Phorbol Esters; C046785:bryostatin 1