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3-(4-Hydroxyphenyl)thieno[2,3-b]pyrrolizin-8-one | 373392-92-8

中文名称
——
中文别名
——
英文名称
3-(4-Hydroxyphenyl)thieno[2,3-b]pyrrolizin-8-one
英文别名
——
3-(4-Hydroxyphenyl)thieno[2,3-b]pyrrolizin-8-one化学式
CAS
373392-92-8
化学式
C15H9NO2S
mdl
——
分子量
267.308
InChiKey
JYWVGJQTEUXJKP-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.5
  • 重原子数:
    19
  • 可旋转键数:
    1
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.0
  • 拓扑面积:
    70.5
  • 氢给体数:
    1
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    正溴丁烷3-(4-Hydroxyphenyl)thieno[2,3-b]pyrrolizin-8-onesodium methylate 作用下, 以 甲醇 为溶剂, 反应 3.0h, 以75%的产率得到3-(4-Butoxyphenyl)thieno[2,3-b]pyrrolizin-8-one
    参考文献:
    名称:
    Design, Synthesis, and Evaluation of Novel Thienopyrrolizinones as Antitubulin Agents
    摘要:
    Herein, we describe the structure-activity relationship study of a new 3-aryl-8H-thieno[2,3-b]pyrrolizin-8-one series of antitubulin agents. The pharmacological results from the National Cancer Institute in vitro human disease oriented tumor cell line screening allowed us to identify compound 1d (NSC 676693) as a very efficient antitumoral drug in all cancer cell lines tested. This prompted us to define the structural requirements essential for this antiproliferative activity. Among all analogues synthesized in this study, compound 1o was the most promising, being 10-fold more potent than compound 1d. Its activity over a panel of nine tumoral cell lines was in the nanomolar range for all of the histological types tested, and surprisingly, the resistant KB-A1 cell line was also sensitive to this compound. Moreover, a flow cytometric study showed that L1210 cells treated by the most potent compounds were arrested in the G(2)/M phases of the cell cycle with a significant percentage of cells having reinitiated a cycle of DNA synthesis without cell division. This interesting pharmacological profile, resulting from inhibition of tubulin polymerization, encouraged us to perform preliminary in vivo studies that led to a new prodrug chemical approach.
    DOI:
    10.1021/jm030961z
  • 作为产物:
    参考文献:
    名称:
    Design, synthesis and antiproliferative activity of tripentones: A new series of antitubulin agents
    摘要:
    Structure-activity relationship studies of a new series of tripentones (thieno[2.3-h]pyrrolizin-8-ones), led us to prepare several derivatives with antiproliferative activities. The most promising 3-(3-hydroxy-4-methoxyphenyl)thieno[2.3-b]pyrrolizin-8-one 20 (leukemia L1210. IC50= 15 nM) was shown to be a potent inhibitor of tubulin polymerization. (C) 2001 Elsevier Science Ltd. All rights reserved.
    DOI:
    10.1016/s0960-894x(01)00403-6
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文献信息

  • Design, synthesis and antiproliferative activity of tripentones: A new series of antitubulin agents
    作者:Vincent Lisowski、Cécile Enguehard、Jean-Charles Lancelot、Daniel-Henri Caignard、Stéphanie Lambel、Stéphane Leonce、Alain Pierre、Ghanem Atassi、Pierre Renard、Sylvain Rault
    DOI:10.1016/s0960-894x(01)00403-6
    日期:2001.8
    Structure-activity relationship studies of a new series of tripentones (thieno[2.3-h]pyrrolizin-8-ones), led us to prepare several derivatives with antiproliferative activities. The most promising 3-(3-hydroxy-4-methoxyphenyl)thieno[2.3-b]pyrrolizin-8-one 20 (leukemia L1210. IC50= 15 nM) was shown to be a potent inhibitor of tubulin polymerization. (C) 2001 Elsevier Science Ltd. All rights reserved.
  • Design, Synthesis, and Evaluation of Novel Thienopyrrolizinones as Antitubulin Agents
    作者:Vincent Lisowski、Stéphane Léonce、Laurence Kraus-Berthier、Jana Sopková-de Oliveira Santos、Alain Pierré、Ghanem Atassi、Daniel-Henri Caignard、Pierre Renard、Sylvain Rault
    DOI:10.1021/jm030961z
    日期:2004.3.1
    Herein, we describe the structure-activity relationship study of a new 3-aryl-8H-thieno[2,3-b]pyrrolizin-8-one series of antitubulin agents. The pharmacological results from the National Cancer Institute in vitro human disease oriented tumor cell line screening allowed us to identify compound 1d (NSC 676693) as a very efficient antitumoral drug in all cancer cell lines tested. This prompted us to define the structural requirements essential for this antiproliferative activity. Among all analogues synthesized in this study, compound 1o was the most promising, being 10-fold more potent than compound 1d. Its activity over a panel of nine tumoral cell lines was in the nanomolar range for all of the histological types tested, and surprisingly, the resistant KB-A1 cell line was also sensitive to this compound. Moreover, a flow cytometric study showed that L1210 cells treated by the most potent compounds were arrested in the G(2)/M phases of the cell cycle with a significant percentage of cells having reinitiated a cycle of DNA synthesis without cell division. This interesting pharmacological profile, resulting from inhibition of tubulin polymerization, encouraged us to perform preliminary in vivo studies that led to a new prodrug chemical approach.
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