N-(2-oxo-1-pyrrolidinyl)-L-phenylalanine | 137282-29-2

• 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: N-(2-oxo-1-pyrrolidinyl)-L-phenylalanine
• 英文别名: (S)-2-(2-oxopyrrolidin-1-yl)-3-phenylpropionic acid；(2S)-2-(2-oxo-1-pyrrolidinyl)-3-phenylpropanoic acid；(2S)-2-(2-oxopyrrolidin-1-yl)-3-phenylpropanoic acid
• CAS: 137282-29-2
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: ISBGNMVQIZZFOS-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-oxo-1-pyrrolidinyl)-L-phenylalanine 在 氰基磷酸二乙酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 2-Methoxycarbonylmethoxy-5-{(S)-2-[(S)-2-(2-oxo-pyrrolidin-1-yl)-3-phenyl-propionylamino]-2-pentylcarbamoyl-ethyl}-benzoic acid methyl ester
  参考文献：
  名称：

  Inhibitors of protein tyrosine phosphatase

  摘要：

  本发明涉及小分子量、非肽类的蛋白酪氨酸磷酸酶1（PTP1）的化学式I和II的抑制剂，用于治疗和/或预防非胰岛素依赖型糖尿病（NIDDM）。

  公开号：

  US06353023B1
• 作为产物：
  描述：

  4-((S)-1-Methoxycarbonyl-2-phenyl-ethylamino)-butyric acid ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 46.0h， 生成 N-(2-oxo-1-pyrrolidinyl)-L-phenylalanine
  参考文献：
  名称：

  New modified heterocyclic phenylalanine derivatives. Incorporation into potent inhibitors of human renin

  摘要：

  Modified heterocyclic phenylalanine analogues designed as replacements for the P3-P4 region were synthesized and incorporated into renin inhibitors. These inhibitors were found to have significant activity versus human recombinant renin, as well as in vivo activity. The compounds proved to be very resistant to chymotrypsin degradation, as exemplified by compound 8, which remained greater than 60% intact after a 24-h exposure to chymotrypsin. In contrast, the Boc-Phe analogue was nearly completely degraded after 1 h. Compound 6 proved to be the most potent renin inhibitor with an IC50 = 8.9 nM. These stable cyclized phenylalanines should prove to be generally useful as a substitute for Boc-Phe in protease inhibitors.

  DOI：

  10.1021/jm00083a005

文献信息

• Modification of the N-terminus of peptidomimetic protein tyrosine phosphatase 1B (PTP1B) inhibitors: identification of analogues with cellular activity
  作者：Scott D. Larsen、F.Craig Stevens、Thomas J. Lindberg、Paul M. Bodnar、Theresa J. O'Sullivan、Heinrich J. Schostarez、Barbara J. Palazuk、John E. Bleasdale

  DOI：10.1016/s0960-894x(02)01065-x

  日期：2003.3

  Low molecular weight peptidomimetic compounds based on 0-malonyl tyrosine and 0-carboxymethyl salicylic acid are potent inhibitors of PTP1B. Modifications of the N-terminal Boc-Phe moiety were undertaken in an effort to improve physical chemical properties and to achieve cellular activity. Although Phe ultimately proved to be the optimal N-terminal amino acid, several viable replacements for the Boc group were identified, two of which afforded analogues that were effective at enhancing the insulin-stimulated uptake of 2-deoxyglucose by L6 myocytes. (C) 2003 Elsevier Science Ltd. All rights reserved.
• INHIBITORS OF PROTEIN TYROSINE PHOSPHATASE
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP1019364A2

  公开（公告）日：2000-07-19
• US6353023B1
  申请人：——

  公开号：US6353023B1

  公开（公告）日：2002-03-05
• US6410585B1
  申请人：——

  公开号：US6410585B1

  公开（公告）日：2002-06-25
• [EN] INHIBITORS OF PROTEIN TYROSINE PHOSPHATASE<br/>[FR] INHIBITEURS DE LA PROTEINE TYROSINE PHOSPHATASE
  申请人：——

  公开号：WO1999011606A2

  公开（公告）日：1999-03-11

  [EN] The present invention comprises small molecular weight, non-peptidic inhibitors of formula (I) and (II) of Protein Tyrosine Phosphatase 1 (PTP1) which are useful for the treatment and/or prevention of Non-Insulin Dependent Diabetes Mellitus (NIDDM).
  [FR] Cette invention a trait à des inhibiteurs non peptidiques, de faible poids moléculaire, correspondant aux formules I et II, de la protéine tyrosine phosphatase utilisés pour le traitement et la prévention du diabète sucré non-insulino-dépendant.