methyl 2-hydroxy-6-[4-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-nitrophenyl)propanoyl]amino]butoxy]benzoate | 474917-81-2

• 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: methyl 2-hydroxy-6-[4-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-nitrophenyl)propanoyl]amino]butoxy]benzoate
• CAS: 474917-81-2
• 化学式: C₂₆H₃₃N₃O₉
• 分子量: 531.563
• InChiKey: YRACDASTFNKZQG-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  169
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxy-6-[4-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-nitrophenyl)propanoyl]amino]butoxy]benzoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到methyl 2-(4-{[4-amino-N-(tert-butoxycarbonyl)-L-phenylalanyl]amino}butoxy)-6-hydroxybenzoate
  参考文献：
  名称：

  Identification of a monoacid-Based, cell permeable, selective inhibitor of protein tyrosine phosphatase 1B

  摘要：

  Monoacid-based PTP1B inhibitors with improved physiochemical properties have been investigated. A (2-hydroxy-phenoxy) acetic acid-based phosphotyrosyl mimetic has been linked with an optimized second arylphosphate binding site ligand to produce compound 20 with low micromolar potency against PTP1B, good selectivity over TCPTP (20-fold) and high cell permeability in the Caco-2 system.

  DOI：

  10.1016/j.bmcl.2003.08.064
• 作为产物：
  描述：

  2,6-二羟基苯甲酸甲酯 在 盐酸 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2-hydroxy-6-[4-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-nitrophenyl)propanoyl]amino]butoxy]benzoate
  参考文献：
  名称：

  Identification of a monoacid-Based, cell permeable, selective inhibitor of protein tyrosine phosphatase 1B

  摘要：

  Monoacid-based PTP1B inhibitors with improved physiochemical properties have been investigated. A (2-hydroxy-phenoxy) acetic acid-based phosphotyrosyl mimetic has been linked with an optimized second arylphosphate binding site ligand to produce compound 20 with low micromolar potency against PTP1B, good selectivity over TCPTP (20-fold) and high cell permeability in the Caco-2 system.

  DOI：

  10.1016/j.bmcl.2003.08.064

文献信息

• Selective protein tyrosine phosphatatase inhibitors
  申请人：——

  公开号：US20020169157A1

  公开（公告）日：2002-11-14

  Compounds of formula (I) 1 or therapeutically acceptable salts thereof, are selective protein tyrosine kinase-B (PTP1B) inhibitors. Preparation of the compounds, compositions containing the compounds, and treatment of disorders using the compounds are disclosed.

  式（I）1的化合物或其治疗上可接受的盐是选择性蛋白酪氨酸激酶B（PTP1B）抑制剂。揭示了该化合物的制备、含有该化合物的组合物以及使用该化合物治疗疾病的方法。
• [EN] SELECTIVE PROTEIN TYROSINE PHOSPHATATASE INHIBITORS<br/>[FR] INHITIBTEURS SELECTIFS DE LA PROTEINE TYROSINE PHOSPHATATASE
  申请人：ABBOTT LAB

  公开号：WO2003072537A2

  公开（公告）日：2003-09-04

  Compounds of formula (I), or therapeutically acceptable salts thereof, are selective protein tyrosine kinase-B (PTP1B) inhibitors. Preparation of the compounds, compositions containing the compounds, and treatment of disorders using the compounds are disclosed.
• Identification of a monoacid-Based, cell permeable, selective inhibitor of protein tyrosine phosphatase 1B
  作者：Zhili Xin、Gang Liu、Cele Abad-Zapatero、Zhonghua Pei、Bruce G. Szczepankiewicz、Xiaofeng Li、Tianyuan Zhang、Charles W. Hutchins、Philip J. Hajduk、Stephen J. Ballaron、Michael A. Stashko、Thomas H. Lubben、James M. Trevillyan、Michael R. Jirousek

  DOI：10.1016/j.bmcl.2003.08.064

  日期：2003.11

  Monoacid-based PTP1B inhibitors with improved physiochemical properties have been investigated. A (2-hydroxy-phenoxy) acetic acid-based phosphotyrosyl mimetic has been linked with an optimized second arylphosphate binding site ligand to produce compound 20 with low micromolar potency against PTP1B, good selectivity over TCPTP (20-fold) and high cell permeability in the Caco-2 system.