1-(4-chlorophenyl)-5-(3-iodophenyl)-1H-imidazole | 1391108-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-chlorophenyl)-5-(3-iodophenyl)-1H-imidazole
• 英文别名: 1-(4-Chlorophenyl)-5-(3-iodophenyl)imidazole
• CAS: 1391108-22-7
• 化学式: C₁₅H₁₀ClIN₂
• 分子量: 380.615
• InChiKey: NGBBPBZORGECQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-4-(4-(dimethylamino)-1-(phenylthio)butan-2-ylamino)-3-nitro-N-(4-(piperazin-1-yl)phenyl)benzenesulfonamide 、 1-(4-chlorophenyl)-5-(3-iodophenyl)-1H-imidazole 在 三叔丁基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 以28%的产率得到N-[4-[4-[3-[3-(4-chlorophenyl)imidazol-4-yl]phenyl]piperazin-1-yl]phenyl]-4-[[(2R)-4-(dimethylamino)-1-phenylsulfanylbutan-2-yl]amino]-3-nitrobenzenesulfonamide
  参考文献：
  名称：

  A Potent and Highly Efficacious Bcl-2/Bcl-xL Inhibitor

  摘要：

  Our previously reported Bcl-2/Bcl-xL inhibitor, 4, effectively inhibited tumor growth but failed to achieve complete regression in vivo. We have now performed extensive modifications on its pyrrole core structure, which has culminated in the discovery of 32 (BM-1074). Compound 32 binds to Bcl-2 and Bcl-xL proteins with K-i values of <1 nM and inhibits cancer cell growth with IC50 values of 1-2 nM in four small-cell lung cancer cell lines sensitive to potent and specific Bcl-2/Bcl-xL inhibitors. Compound 32 is capable of achieving rapid, complete, and durable tumor regression in vivo at a well-tolerated dose schedule. Compound 32 is the most potent and efficacious Bcl-2/Bcl-xL inhibitor reported to date.

  DOI：

  10.1021/jm4001105
• 作为产物：
  描述：

  对氯苯胺 在 potassium carbonate 作用下， 以 甲醇 、 乙二醇二甲醚 、 甲苯 为溶剂， 反应 2.0h， 生成 1-(4-chlorophenyl)-5-(3-iodophenyl)-1H-imidazole
  参考文献：
  名称：

  A Potent and Highly Efficacious Bcl-2/Bcl-xL Inhibitor

  摘要：

  Our previously reported Bcl-2/Bcl-xL inhibitor, 4, effectively inhibited tumor growth but failed to achieve complete regression in vivo. We have now performed extensive modifications on its pyrrole core structure, which has culminated in the discovery of 32 (BM-1074). Compound 32 binds to Bcl-2 and Bcl-xL proteins with K-i values of <1 nM and inhibits cancer cell growth with IC50 values of 1-2 nM in four small-cell lung cancer cell lines sensitive to potent and specific Bcl-2/Bcl-xL inhibitors. Compound 32 is capable of achieving rapid, complete, and durable tumor regression in vivo at a well-tolerated dose schedule. Compound 32 is the most potent and efficacious Bcl-2/Bcl-xL inhibitor reported to date.

  DOI：

  10.1021/jm4001105

文献信息

• BCL-2/BCL-XL INHIBITORS FOR USE IN THE TREATMENT OF CANCER
  申请人：The Regents of The University of Michigan

  公开号：EP2668180B1

  公开（公告）日：2018-08-01
• [EN] BCL-2/BCL-XL INHIBITORS AND THERAPEUTIC METHODS USING THE SAME<br/>[FR] INHIBITEURS DE BCL-2/BCL-XL ET MÉTHODES THÉRAPEUTIQUES LES UTILISANT
  申请人：UNIV MICHIGAN

  公开号：WO2012103059A2

  公开（公告）日：2012-08-02

  Inhibitors of Bcl-2/Bcl-xL and compositions containing the same are disclosed. Methods of using the Bcl-2/Bcl-xL inhibitors in the treatment of diseases and conditions wherein inhibition of Bcl-2/Bcl-xL provides a benefit, like cancers, also are disclosed.