(S)-2-(3-methoxycarbonylphenylamino)-3-(3-methylphenyl)-propionic acid | 374119-37-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-(3-methoxycarbonylphenylamino)-3-(3-methylphenyl)-propionic acid
• 英文别名: (2S)-2-(3-methoxycarbonylanilino)-3-(3-methylphenyl)propanoic acid
• CAS: 374119-37-6
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: PLRPXIOXIPZQKJ-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-3-(3-allyloxycarbonylphenyl)methoxypropionitrile 、 (S)-2-(3-methoxycarbonylphenylamino)-3-(3-methylphenyl)-propionic acid 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  N-Arylaminonitriles as bioavailable peptidomimetic inhibitors of cathepsin B

  摘要：

  To improve the pharmacokinetics of a previously reported series of dipeptidyl nitrile cathepsin B inhibitors, the P-2-P-3 amide group was replaced with an arylamine. Further optimization of this template resulted in highly potent and selective inhibitors with excellent oral availability. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.006
• 作为产物：
  描述：

  (R)-2-hydroxy-3-m-tolyl-propionic acid 在 吡啶 、 lithium hydroxide 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-2-(3-methoxycarbonylphenylamino)-3-(3-methylphenyl)-propionic acid
  参考文献：
  名称：

  N-Arylaminonitriles as bioavailable peptidomimetic inhibitors of cathepsin B

  摘要：

  To improve the pharmacokinetics of a previously reported series of dipeptidyl nitrile cathepsin B inhibitors, the P-2-P-3 amide group was replaced with an arylamine. Further optimization of this template resulted in highly potent and selective inhibitors with excellent oral availability. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.006

文献信息

• N-substituted peptidyl nitriles as cysteine cathepsin inhibitors
  申请人：——

  公开号：US20030158256A1

  公开（公告）日：2003-08-21

  Compounds of the formula (I), wherein R 1 is aryl or biaryl; R 2 is aryl-lower alkyl, biaryl-lower alkyl, benzo-fused cycloalkyl, cycloalkyl-lower alkyl, bicycloalkyl-lower alkyl, aryloxy-lower alkyl, or aryl-C 2 -C 7 -alkyl in which C 2 -C 7 -alkyl is interrupted by Y; Y is O, S, SO, SO 2 , CO or NR 6 ; R 3 is hydrogen or lower alkyl; or R 2 and R 3 combined are C 2 -C 7 -alkylene or C 2 -C 7 -alkylene interrupted by Y; R 4 is hydrogen or lower alkyl; R 5 is hydrogen, optionally substituted lower alkyl, aryl-lower alkyl, biaryl-lower alkyl, cycloalkyl-lower alkyl, bicycloalkyl-lower alkyl, aryloxy-lower alkyl, or aryl-C 2 -C 7 -alkyl in which C 2 -C 7 -alkyl is interrupted by Y; R 6 is hydrogen, lower alkyl or aryl-lower alkyl; and pharmaceutically acceptable salts thereof, which are useful as cysteine cathepsin inhibitors.

  式（I）的化合物，其中R1是芳基或联苯基；R2是芳基-较低烷基，联苯基-较低烷基，苯并环烷基，环烷基-较低烷基，双环烷基-较低烷基，芳氧基-较低烷基，或芳基-C2-C7-烷基，其中C2-C7-烷基被Y中断；Y是O，S，SO，SO2，CO或NR6；R3是氢或较低烷基；或R2和R3结合形成C2-C7-烷基或C2-C7-烷基被Y中断；R4是氢或较低烷基；R5是氢，可选择取代的较低烷基，芳基-较低烷基，联苯基-较低烷基，环烷基-较低烷基，双环烷基-较低烷基，芳氧基-较低烷基，或芳基-C2-C7-烷基，其中C2-C7-烷基被Y中断；R6是氢，较低烷基或芳基-较低烷基；及其药学上可接受的盐，可用作半胱氨酸蛋白酶抑制剂。
• [EN] N-SUBSTITUTED PEPTIDYL NITRILES AS CYSTEINE CATHEPSIN INHIBITORS<br/>[FR] UTILISATION DE PEPTIDYL NITRILES A SUBSTITUTION- N COMME INHIBITEURS DES CATHEPSINES DE CYSTEINE
  申请人：NOVARTIS AG

  公开号：WO2001087828A1

  公开（公告）日：2001-11-22

  Compounds of the formula (I), wherein R1 is aryl or biaryl; R2 is aryl-lower alkyl, biaryl-lower alkyl, benzo-fused cycloalkyl, cycloalkyl-lower alkyl, bicycloalkyl-lower alkyl, aryloxy-lower alkyl, or aryl-C2-C7-alkyl in which C2-C7-alkyl is interrupted by Y; Y is O, S, SO, SO2, CO or NR6; R3 is hydrogen or lower alkyl; or R2 and R3 combined are C2-C7-alkylene or C2-C7-alkylene interrupted by Y; R4 is hydrogen or lower alkyl; R5 is hydrogen, optionally substituted lower alkyl, aryl-lower alkyl, biaryl-lower alkyl, cycloalkyl-lower alkyl, bicycloalkyl-lower alkyl, aryloxy-lower alkyl, or aryl-C2-C7-alkyl in which C2-C7-alkyl is interrupted by Y; R6 is hydrogen, lower alkyl or aryl-lower alkyl; and pharmaceutically acceptable salts thereof, which are useful as cysteine cathepsin inhibitors.

  该式化合物（I）的化合物，其中R1是芳基或双芳基；R2是芳基-较低烷基，双芳基-较低烷基，苯并环烷基，环烷基-较低烷基，双环烷基-较低烷基，芳氧基-较低烷基，或芳基-C2-C7-烷基，其中C2-C7-烷基被Y中断；Y是O，S，SO，SO2，CO或NR6；R3是氢或较低烷基；或R2和R3结合是C2-C7-亚烷基或C2-C7-亚烷基，其中被Y中断；R4是氢或较低烷基；R5是氢，可选择性取代的较低烷基，芳基-较低烷基，双芳基-较低烷基，环烷基-较低烷基，双环烷基-较低烷基，芳氧基-较低烷基，或芳基-C2-C7-烷基，其中C2-C7-烷基被Y中断；R6是氢，较低烷基或芳基-较低烷基；以及其药学上可接受的盐，它们可用作半胱氨酸蛋白酶抑制剂。
• N-SUBSTITUTED PEPTIDYL NITRILES AS CYSTEINE CATHEPSIN INHIBITORS
  申请人：Novartis AG

  公开号：EP1283825A1

  公开（公告）日：2003-02-19
• US6812237B2
  申请人：——

  公开号：US6812237B2

  公开（公告）日：2004-11-02
• N-Arylaminonitriles as bioavailable peptidomimetic inhibitors of cathepsin B
  作者：Paul D. Greenspan、Kirk L. Clark、Scott D. Cowen、Leslie W. McQuire、Ruben A. Tommasi、David L. Farley、Elizabeth Quadros、David E. Coppa、Zengming Du、Zheng Fang、Huanghai Zhou、John Doughty、Karen T. Toscano、Andrew M. Wigg、Siyuan Zhou

  DOI：10.1016/j.bmcl.2003.08.006

  日期：2003.11

  To improve the pharmacokinetics of a previously reported series of dipeptidyl nitrile cathepsin B inhibitors, the P-2-P-3 amide group was replaced with an arylamine. Further optimization of this template resulted in highly potent and selective inhibitors with excellent oral availability. (C) 2003 Elsevier Ltd. All rights reserved.