(S)-4-Methyl-2-(3-methyl-benzoylamino)-pentanoic acid | 166597-75-7

• 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)-4-Methyl-2-(3-methyl-benzoylamino)-pentanoic acid
• 英文别名: (2S)-4-methyl-2-[(3-methylbenzoyl)amino]pentanoic acid
• CAS: 166597-75-7
• 化学式: C₁₄H₁₉NO₃
• mdl: MFCD16377997
• 分子量: 249.31
• InChiKey: NXVNYFBAKNMHHU-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-Methyl-2-(3-methyl-benzoylamino)-pentanoic acid 在 sodium cyanoborohydride 、 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-{(S)-1-[2-(2,3-Dihydro-indol-1-yl)-ethylcarbamoyl]-3-methyl-butyl}-3-methyl-benzamide
  参考文献：
  名称：

  Arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 2: Optimization of P1 and N-aryl

  摘要：

  A systematic study of anilines led to the discovery of a metabolically robust fluoroindoline replacement for the alkoxy aniline toxicophore in 1. Investigations of the PI pocket resulted in the discovery of a wide tolerance of functionality leading to the discovery of 11 as a potent and selective inhibitor of cathepsin S. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.056
• 作为产物：
  描述：

  L-亮氨酸 、 间甲基苯甲酰氯 在 sodium hydroxide 作用下， 生成 (S)-4-Methyl-2-(3-methyl-benzoylamino)-pentanoic acid
  参考文献：
  名称：

  Arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 2: Optimization of P1 and N-aryl

  摘要：

  A systematic study of anilines led to the discovery of a metabolically robust fluoroindoline replacement for the alkoxy aniline toxicophore in 1. Investigations of the PI pocket resulted in the discovery of a wide tolerance of functionality leading to the discovery of 11 as a potent and selective inhibitor of cathepsin S. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.056

文献信息

• Discovery, characterization and engineering of ligases for amide synthesis
  作者：Michael Winn、Michael Rowlinson、Fanghua Wang、Luis Bering、Daniel Francis、Colin Levy、Jason Micklefield

  DOI：10.1038/s41586-021-03447-w

  日期：2021.5.20

  of the enzyme that catalyses the crucial coupling of coronafacic acid to amino acids remains unknown1,2. Here we characterize a family of enzymes, coronafacic acid ligases (CfaLs), and resolve their structures. We found that CfaL can also produce JA-Ile, despite low similarity with the Jar1 enzyme that is responsible for ligation of JA and l-Ile in plants5. This suggests that Jar1 and CfaL evolved independently

  冠菌素和相关细菌植物毒素是茉莉酰-l-异亮氨酸 (JA-Ile) 激素的模拟物，它介导重要的生理植物信号传导途径1,2,3,4 。冠素类植物毒素会破坏这些重要途径，并具有开发更安全、选择性更强的除草剂的潜力。尽管之前已经研究了冠菌素的生物合成，但催化冠菌酸与氨基酸的关键偶联的酶的性质仍然未知1,2 。在这里，我们表征了一个酶家族——冠状酸连接酶（CfaL），并解析了它们的结构。我们发现 CfaL 也可以产生 JA-Ile，尽管与植物中负责连接 JA 和l -Ile 的 Jar1 酶相似度较低5 。这表明 Jar1 和 CfaL 独立进化以催化类似的反应 - Jar1 产生植物发育必需的化合物4,5 ，而细菌连接酶产生对植物有毒的类似物。我们进一步证明了 CfaL 酶如何用于合成多种酰胺，从而无需保护基团。实现了外消旋供体或受体底物的高选择性动力学拆分，提供纯手性产物。我们还使用结构引导诱变来设计改进的
• Inhibitors of cathepsin S
  申请人：IRM LLC

  公开号：US20040248887A1

  公开（公告）日：2004-12-09

  The present invention provides compounds, compositions and methods for the selective inhibition of cathepsin S. In a preferred aspect, cathepsin S is selectively inhibited in the presence of at least one other cathepsin isozyme. The present invention also provides methods for treating a disease state in a subject by selectively inhibiting cathepsin S.

  本发明提供了化合物、组合物和方法，用于选择性抑制蛋白酶S。在首选方面，当存在至少一种其他蛋白酶同工酶时，选择性抑制蛋白酶S。本发明还提供了通过选择性抑制蛋白酶S治疗受试者的疾病状态的方法。
• INHIBITORS OF CATHEPSIN S
  申请人：Liu Hong

  公开号：US20080242671A1

  公开（公告）日：2008-10-02

  The present invention provides compounds, compositions and methods for the selective inhibition of cathepsin S. In a preferred aspect, cathepsin S is selectively inhibited in the presence of at least one other cathepsin isozyme. The present invention also provides methods for treating a disease state in a subject by selectively inhibiting cathepsin S.

  本发明提供了化合物、组合物和方法，用于选择性抑制蛋白酶S。在首选方面，当存在至少一种其他蛋白酶同工酶时，选择性地抑制蛋白酶S。本发明还提供了通过选择性抑制蛋白酶S治疗受试者疾病状态的方法。
• US7384970B2
  申请人：——

  公开号：US7384970B2

  公开（公告）日：2008-06-10
• [EN] INHIBITORS OF CATHEPSIN S<br/>[FR] INHIBITEURS DE LA CATHEPSINE S
  申请人：IRM LLC

  公开号：WO2004084843A2

  公开（公告）日：2004-10-07

  The present invention provides compounds, compositions and methods for the selective inhibition of cathepsin S. In a preferred aspect, cathepsin S is selectively inhibited in the presence of at least one other cathepsin isozyme. The present invention also provides methods for treating a disease state in a subject by selectively inhibiting cathepsin S.