2-{[4-(2-acetylamino-2-allyloxycarbonyl-ethyl)-2-ethyl-phenyl]-tert-butoxyoxalyl-amino}-benzoic acid | 402924-99-6

• 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: 2-{[4-(2-acetylamino-2-allyloxycarbonyl-ethyl)-2-ethyl-phenyl]-tert-butoxyoxalyl-amino}-benzoic acid
• 英文别名: 2-{4-[2-(Acetylamino)-3-(allyloxy)-3-oxopropyl][tert-butoxy(oxo)acetyl]-2-ethylanilino}benzoic acid；2-[4-(2-acetamido-3-oxo-3-prop-2-enoxypropyl)-2-ethyl-N-[2-[(2-methylpropan-2-yl)oxy]-2-oxoacetyl]anilino]benzoic acid
• CAS: 402924-99-6
• 化学式: C₂₉H₃₄N₂O₈
• 分子量: 538.598
• InChiKey: RTNZMYJTQFZWMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-{[4-(2-acetylamino-2-allyloxycarbonyl-ethyl)-2-ethyl-phenyl]-tert-butoxyoxalyl-amino}-benzoic acid 在 吗啉 、 四(三苯基膦)钯 、 四丁基氟化铵 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 2-[(4-{2-Acetylamino-2-[4-(1-carbamoyl-2-phenyl-ethylcarbamoyl)-butylcarbamoyl]-ethyl}-2-ethyl-phenyl)-tert-butoxyoxalyl-amino]-benzoic acid benzhydryl ester
  参考文献：
  名称：

  Potent, selective inhibitors of protein tyrosine phosphatase 1B

  摘要：

  We have previously reported a novel series of oxalyl-aryl-amino benzoic acid-based, catalytic site-directed, competitive, reversible protein tyrosine phosphatase 1B (PTP1B) inhibitors. With readily access to key intermediates, we utilized a solution phase parallel synthesis approach and rapidly identified a highly potent PTP1B inhibitor (19, K(i)=76 nM) with moderate selectivity (5-fold) over T-cell PTPase (TCPTP) through interacting with a second phosphotyrosine binding site (site 2) in the close proximity to the catalytic site.

  DOI：

  10.1016/s0960-894x(03)00302-0
• 作为产物：
  描述：

  allyl 2-(acetylamino)-3-(4-amino-3-ethylphenyl)propanoate 在 copper diacetate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 生成 2-{[4-(2-acetylamino-2-allyloxycarbonyl-ethyl)-2-ethyl-phenyl]-tert-butoxyoxalyl-amino}-benzoic acid
  参考文献：
  名称：

  Potent, selective inhibitors of protein tyrosine phosphatase 1B

  摘要：

  We have previously reported a novel series of oxalyl-aryl-amino benzoic acid-based, catalytic site-directed, competitive, reversible protein tyrosine phosphatase 1B (PTP1B) inhibitors. With readily access to key intermediates, we utilized a solution phase parallel synthesis approach and rapidly identified a highly potent PTP1B inhibitor (19, K(i)=76 nM) with moderate selectivity (5-fold) over T-cell PTPase (TCPTP) through interacting with a second phosphotyrosine binding site (site 2) in the close proximity to the catalytic site.

  DOI：

  10.1016/s0960-894x(03)00302-0

文献信息

• Amino (oxo) acetic acid protein tyrosine phosphatase inhibitors
  申请人：——

  公开号：US20020035137A1

  公开（公告）日：2002-03-21

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

  式（I）的化合物或其治疗上可接受的盐是蛋白酪氨酸激酶PTP1B的抑制剂。公开了该化合物的制备、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。
• 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。
• 1-phenyl imidazol-2-one biphenylmethyl compounds for treatment of circulatory disorders
  申请人：G.D. Searle & Co.

  公开号：US20020038035A1

  公开（公告）日：2002-03-28

  A class of 1-phenyl imidazol-2-one biphenylmethyl compounds is described for use in treatment of circulatory disorders. Compounds of particular interest are angiotensin II antagonists of the formula 1 wherein each of R 1 , R 2 and R 3 is independently selected from hydrido, alkyl, alkoxy, cyano, halo, hydroxy, carboxyl, alkoxycarbonyl, formyl and acetyl; alkylcarbonyl and haloalkylcarbonyl; with the proviso that at least one of R 1 , R 2 and R 3 must be a substituent other than hydrido, and with the further proviso that when each of R 1 and R 3 is hydrido, then R 2 cannot be chloro; wherein R 4 is hydrido; wherein R 5 is alkyl; and wherein R 6 is tetrazolyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof. These compounds are particularly useful in treatment or control of hypertension and congestive heart failure.

  描述了一类1-苯基咪唑-2-酮联苯甲基化合物，用于治疗循环系统疾病。特别感兴趣的化合物是式1的血管紧张素II拮抗剂，其中R1、R2和R3中的每个都是独立选择的，包括氢基、烷基、烷氧基、氰基、卤基、羟基、羧基、烷氧羰基、甲酰基和乙酰基；烷基羰基和卤代烷基羰基；但必须满足R1、R2和R3中至少有一个是除氢基以外的取代基，并且进一步必须满足当R1和R3都是氢基时，R2不能是氯；其中R4是氢基；其中R5是烷基；其中R6是四唑基；或其立体异构体或互变异构体或其药学上可接受的盐。这些化合物在治疗或控制高血压和充血性心力衰竭方面特别有用。
• [EN] SELECTIVE PROTEIN TYROSINE PHOSPHATASE INHIBITORS<br/>[FR] INHIBITEURS SELECTIFS DE PROTEINE TYROSINE PHOSPHATASE
  申请人：ABBOTT LAB

  公开号：WO2003020688A1

  公开（公告）日：2003-03-13

  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.

  式(I)的化合物或其治疗上可接受的盐是选择性的蛋白酪氨酸激酶-B (PTP1B) 抑制剂。本文披露了该化合物的制备、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。
• 1-(substituted phenyl)-4-biphenylmethyl-imidazol-2-one derivatives, their preparation and their use as angiotensin II antagonists
  申请人：G.D. SEARLE & CO.

  公开号：EP0978515A2

  公开（公告）日：2000-02-09

  A class of 1-phenyl imidazol-2-one biphenylmethyl compounds is described for use in treatment of circulatory disorders. Compounds of particular interest are angiotensin II antagonists of the formula wherein each of R1, R2 and R3 is independently selected from hydrogen, alkyl, alkoxy, cyano, halo, hydroxy, nitro, amino, alkylamino,carboxyl, alkoxycarbonyl, formyl, alkylcarbonyl and haloalkylcarbonyl; with the proviso that at least one of R1, R2 and R3 must be a substituent other than hydrogen, and with the further proviso that when each of R1 and R3 is hydrogen, then R2 cannot be chloro; wherein R4 is selected from hydrogen, alkyl, halo, haloalkyl, formyl, carboxyl and alkoxyalkyl; wherein R5 is selected from alkyl, phenyl, phenylalkyl, cycloalkyl and cycloalkylalkyl; and wherein R6 is an acidic group selected from COOH and or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof. These compounds are particularly useful in treatment or control of hypertension and congestive heart failure.

  描述了一类用于治疗循环系统疾病的 1-苯基咪唑-2-酮联苯甲基化合物。特别感兴趣的化合物是式中的血管紧张素 II 拮抗剂 其中 R1、R2 和 R3 各自独立地选自氢、烷基、烷氧基、氰基、卤代、羟基、硝基、氨基、烷基氨基、羧基、烷氧羰基、甲酰基、烷基羰基和卤代烷基羰基；但 R1、R2 和 R3 中至少有一个必须是除氢以外的取代基，而且当 R1 和 R3 都是氢时，R2 不能是氯；其中 R4 选自氢、烷基、卤代、卤代烷基、甲酰基、羧基和烷氧基烷基； 其中 R5 选自烷基、苯基、苯基烷基、环烷基和环烷基烷基；以及其中 R6 是选自 COOH 和 或其立体异构体或同系物或其药学上可接受的盐。 这些化合物尤其适用于治疗或控制高血压和充血性心力衰竭。