5-(4-chlorophenyl)-4-(3-iodophenyl)-1,2-dimethyl-N-(methylsulfonyl)-1H-pyrrole-3-carboxamide | 1428145-89-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-(4-chlorophenyl)-4-(3-iodophenyl)-1,2-dimethyl-N-(methylsulfonyl)-1H-pyrrole-3-carboxamide
• 英文别名: 5-(4-chlorophenyl)-4-(3-iodophenyl)-1,2-dimethyl-N-methylsulfonylpyrrole-3-carboxamide
• CAS: 1428145-89-4
• 化学式: C₂₀H₁₈ClIN₂O₃S
• 分子量: 528.798
• InChiKey: WNBYSTIZEBDBIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  76.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-4-(3-iodophenyl)-1,2-dimethyl-N-(methylsulfonyl)-1H-pyrrole-3-carboxamide 在 copper(l) iodide 、 palladium 10% on activated carbon 、 氢气 、 L-脯氨酸 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 0.25h， 生成 4-[3-[4-(4-aminophenyl)piperazin-1-yl]phenyl]-5-(4-chlorophenyl)-1,2-dimethyl-N-methylsulfonylpyrrole-3-carboxamide
  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：

  ethyl 2-acetyl-4-(4-chlorophenyl)-3-(3-iodophenyl)-4-oxobutanoate 在 4-二甲氨基吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 24.08h， 生成 5-(4-chlorophenyl)-4-(3-iodophenyl)-1,2-dimethyl-N-(methylsulfonyl)-1H-pyrrole-3-carboxamide
  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