3-[(S)-Cyano-((R)-2-hydroxy-1-phenyl-ethylamino)-methyl]-benzonitrile | 220096-06-0

• 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: 3-[(S)-Cyano-((R)-2-hydroxy-1-phenyl-ethylamino)-methyl]-benzonitrile
• CAS: 220096-06-0
• 化学式: C₁₇H₁₅N₃O
• 分子量: 277.326
• InChiKey: KJVFJAWJOOQKGW-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.84
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-[(S)-Cyano-((R)-2-hydroxy-1-phenyl-ethylamino)-methyl]-benzonitrile 在 lead(IV) acetate 、 盐酸 、 sodium hydroxide 、 三甲基氯硅烷 、 二苯基膦叠氮化物 、 三乙胺 作用下， 生成 3-[(S)-[[4-[(2-amino-6-methyl-4-oxo-3H-quinazolin-5-yl)sulfanyl]benzoyl]amino]-carboxymethyl]benzoic acid
  参考文献：
  名称：

  Synthesis of 5-substituted quinazolinone derivatives and their inhibitory activity in vitro

  摘要：

  Quinazolinone derivatives I and their methyl esters were synthesized and evaluated as nonclassical lipophilic inhibitors of thymidylate synthase. Compounds Ib and Ic containing OH and CO2H as R substituents, respectively, were most effective, indicating that hydrogen bonding may contribute to the increased inhibitory activity. These compounds further showed high cytotoxic activity against tumor cells in culture. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00602-7
• 作为产物：
  描述：

  三甲基氰硅烷 、 3-氰基苯甲醛 、 D-苯甘氨醇 生成 3-[(S)-Cyano-((R)-2-hydroxy-1-phenyl-ethylamino)-methyl]-benzonitrile
  参考文献：
  名称：

  Synthesis of 5-substituted quinazolinone derivatives and their inhibitory activity in vitro

  摘要：

  Quinazolinone derivatives I and their methyl esters were synthesized and evaluated as nonclassical lipophilic inhibitors of thymidylate synthase. Compounds Ib and Ic containing OH and CO2H as R substituents, respectively, were most effective, indicating that hydrogen bonding may contribute to the increased inhibitory activity. These compounds further showed high cytotoxic activity against tumor cells in culture. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00602-7