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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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
Online AccessGet full text

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Abstract [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.
AbstractList [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.
We designed and synthesized novel 4-acetoxypentanamide derivatives of spliceostatin A, whose 4-acetoxypente-namide moiety is reduced (7), isomerized (8), or substituted with methyl at the & alpha;-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.
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.
ArticleNumber 129333
Author Ohta, Noriko
Arisawa, Mitsuhiro
Hirabayashi, Satoru
Tsuyuguchi, Yuko
Nunomura, Kazuto
Haruta, Junichi
Fumimoto, Megumi
Li, Yue
Yoshikawa, Yusuke
Lin, Bangzhong
Nimura, Keisuke
Suzuki, Takeyuki
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  givenname: Satoru
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  surname: Hirabayashi
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  givenname: Takeyuki
  orcidid: 0000-0002-2137-0276
  surname: Suzuki
  fullname: Suzuki, Takeyuki
  organization: Comprehensive Analysis Center, Sanken, Osaka University, Mihogaoka 8-1, Ibaraki, Osaka 567-0047, Japan
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  givenname: Junichi
  surname: Haruta
  fullname: Haruta, Junichi
  organization: Graduate School of Pharmaceutical Sciences, Osaka University, Yamada-oka 1-6, Suita, Osaka 565-0871, Japan
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  givenname: Keisuke
  orcidid: 0000-0001-9680-2646
  surname: Nimura
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  givenname: Mitsuhiro
  surname: Arisawa
  fullname: Arisawa, Mitsuhiro
  email: arisaw@phs.osaka-u.ac.jp
  organization: Graduate School of Pharmaceutical Sciences, Osaka University, Yamada-oka 1-6, Suita, Osaka 565-0871, Japan
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Keywords 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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Snippet [Display omitted] We designed and synthesized novel 4-acetoxypentanamide derivatives of spliceostatin A, whose 4-acetoxypentenamide moiety is reduced (7),...
We designed and synthesized novel 4-acetoxypentanamide derivatives of spliceostatin A, whose 4-acetoxypente-namide moiety is reduced (7), isomerized (8), or...
We designed and synthesized novel 4-acetoxypentanamide derivatives of spliceostatin A, whose 4-acetoxypentenamide moiety is reduced (7), isomerized (8), or...
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StartPage 129333
SubjectTerms 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
Title Design and synthesis of 4-acetoxypentanamide derivatives of spliceostatin A and their biological evaluation towards prostate cancer treatment
URI https://dx.doi.org/10.1016/j.bmcl.2023.129333
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https://www.ncbi.nlm.nih.gov/pubmed/37207846
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