Design and synthesis of 4-acetoxypentanamide derivatives of spliceostatin A and their biological evaluation towards prostate cancer treatment

[Display omitted] We designed and synthesized novel 4-acetoxypentanamide derivatives of spliceostatin A, whose 4-acetoxypentenamide moiety is reduced (7), isomerized (8), or substituted with methyl at the α-position (9). The results of biological evaluation against AR-V7 and the docking analysis of...

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Bibliographic Details
Published inBioorganic & medicinal chemistry letters Vol. 91; p. 129333
Main Authors Hirabayashi, Satoru, Tsuyuguchi, Yuko, Li, Yue, Ohta, Noriko, Yoshikawa, Yusuke, Lin, Bangzhong, Fumimoto, Megumi, Nunomura, Kazuto, Suzuki, Takeyuki, Haruta, Junichi, Nimura, Keisuke, Arisawa, Mitsuhiro
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.07.2023
Elsevier
Subjects
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Humans
Life Sciences & Biomedicine
Male
Michael acceptor
Pharmacology & Pharmacy
Physical Sciences
Prostate cancer
Prostatic Neoplasms - drug therapy
Protein Isoforms
Pyrans
Receptors, Androgen
Science & Technology
Spiro Compounds
Spliceostatin A
Splicing variant
SSA
SF3B2
AR-V7
TBS
Michael acceptor
DIPEA
Et3N
Splicing variant
TFA
LHMDS
AR
TBAF
Spliceostatin A
DMAP
HATU
CRPC
KHMDS
Prostate cancer
ENZALUTAMIDE
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Summary:[Display omitted] We designed and synthesized novel 4-acetoxypentanamide derivatives of spliceostatin A, whose 4-acetoxypentenamide moiety is reduced (7), isomerized (8), or substituted with methyl at the α-position (9). The results of biological evaluation against AR-V7 and the docking analysis of each derivative suggest that the geometry of the 4-acetoxypentenamide moiety of spliceostatin A is important for its biological activity.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2023.129333