(S)-N-(4-(3-(1H-1,2,4-triazol-1-yl)-4-(3,4,5-trimethoxybenzoyl)phenyl)thiazol-2-yl)-2-amino-3-cyclohexylpropaneamide | 1188371-52-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-(4-(3-(1H-1,2,4-triazol-1-yl)-4-(3,4,5-trimethoxybenzoyl)phenyl)thiazol-2-yl)-2-amino-3-cyclohexylpropaneamide
• 英文别名: (S)-N-(4-(3-(1H-1,2,4-triazole-1-yl)-4-(3,4,5-trimethoxybenzoyl)phenyl)thiazol-2-yl)-2-amino-3-cyclohexylpropanamide；(S)-N-(4-(3-(1H-1,2,4-triazol-1-yl)-4-(3,4,5-trimethoxybenzoyl)phenyl)thiazol-2-yl)-2-amino-3-cyclohexylpropanamide；(2S)-2-amino-3-cyclohexyl-N-[4-[3-(1,2,4-triazol-1-yl)-4-(3,4,5-trimethoxybenzoyl)phenyl]-1,3-thiazol-2-yl]propanamide
• CAS: 1188371-52-9
• 化学式: C₃₀H₃₄N₆O₅S
• 分子量: 590.703
• InChiKey: YJNLGGSRZLFSLV-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  172
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-N-(4-(3-(1H-1,2,4-triazol-1-yl)-4-(3,4,5-trimethoxybenzoyl)phenyl)thiazol-2-yl)-2-amino-3-cyclohexylpropaneamide 在 盐酸 作用下， 生成
  参考文献：
  名称：

  Discovery of a potent tubulin polymerization inhibitor: Synthesis and evaluation of water-soluble prodrugs of benzophenone analog

  摘要：

  Prodrugs have proven to be very useful in enhancing aqueous solubility of sparingly water-soluble drugs, thereby increasing in vivo efficacy without a need of special excipients. In vitro and in vivo evaluations of a number of amino acid prodrugs of 1, a previously identified potent tubulin polymerization inhibitor and cytotoxic against various cancer cell lines led to the discovery of 3 center dot HCl (L-valine attached) which is highly efficacious in mouse xenografts bearing human cancer. Pharmacokinetic analysis in rats revealed that compound 1 was released immediately upon administration of 3 center dot HCl intravenously, with rapid clearance of 3 center dot HCl indicating the effective cleavage of prodrug. Compound 3 center dot HCl (CKD-516) has now been progressed to phase 1 clinical trial. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.05.060
• 作为产物：
  描述：

  在 哌啶 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 (S)-N-(4-(3-(1H-1,2,4-triazol-1-yl)-4-(3,4,5-trimethoxybenzoyl)phenyl)thiazol-2-yl)-2-amino-3-cyclohexylpropaneamide
  参考文献：
  名称：

  Discovery of a potent tubulin polymerization inhibitor: Synthesis and evaluation of water-soluble prodrugs of benzophenone analog

  摘要：

  Prodrugs have proven to be very useful in enhancing aqueous solubility of sparingly water-soluble drugs, thereby increasing in vivo efficacy without a need of special excipients. In vitro and in vivo evaluations of a number of amino acid prodrugs of 1, a previously identified potent tubulin polymerization inhibitor and cytotoxic against various cancer cell lines led to the discovery of 3 center dot HCl (L-valine attached) which is highly efficacious in mouse xenografts bearing human cancer. Pharmacokinetic analysis in rats revealed that compound 1 was released immediately upon administration of 3 center dot HCl intravenously, with rapid clearance of 3 center dot HCl indicating the effective cleavage of prodrug. Compound 3 center dot HCl (CKD-516) has now been progressed to phase 1 clinical trial. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.05.060

文献信息

• BENZOPHENONE THIAZOLE DERIVATIVES USEFUL FOR INHIBITING FORMATION OF MICROTUBULE AND METHOD FOR PRODUCING THE SAME
  申请人：Chong Kun Dang Pharmaceutical Corp.

  公开号：EP2272845B1

  公开（公告）日：2015-03-04
• US8362267B2
  申请人：——

  公开号：US8362267B2

  公开（公告）日：2013-01-29