(1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide | 871357-93-6

• 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: (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide
• 英文别名: (1S,2S,3R,4R)-3-[(2-chloro-5-fluoropyrimidin-4-yl)amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide
• CAS: 871357-93-6
• 化学式: C₁₂H₁₂ClFN₄O
• 分子量: 282.705
• InChiKey: NEHLKISJRXQNDS-CRYJXSNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  80.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide 在 Cobalt ligand complex 苯硅烷 、 caesium carbonate 、 三乙胺 、 lithium dihydrido borata-bicyclo[3.3.0]nonane 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.92h， 生成 (1R,2S,3R,4R,5R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)-5-((N-(3-nitrobenzyl)-acetamido)methyl)bicyclo[2.2.1]heptane-2-carboxamide
  参考文献：
  名称：

  MACROCYCLICS PYRIMIDINES AS AURORA KINASE INHIBITORS

  摘要：

  公开了抑制蛋白激酶酶的大环衍生物化合物，以及包括这些化合物的药物组合物和合成方法。这些化合物在治疗由于未受调控和/或受干扰的激酶活性导致的增殖性疾病方面具有用途，如癌症、银屑病、病毒和细菌感染、炎症和自身免疫疾病。

  公开号：

  US20110294801A1
• 作为产物：
  描述：

  tert-butyl exo-4-oxo-3-azatricyclo[4.2.1.02,5]non-7-ene-3-carboxylate 在 ammonium hydroxide 、 碳酸氢钠 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 (1S,2S,3R,4R)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide
  参考文献：
  名称：

  Pyrazole diaminopyrimidines as dual inhibitors of KDR and Aurora B kinases

  摘要：

  In an effort to identify kinase inhibitors with dual KDR/Aurora B activity and improved aqueous solubility compared to the Abbott dual inhibitor ABT-348, a series of novel pyrazole pyrimidines structurally related to kinase inhibitor AS703569 were prepared. SAR work provided analogs with significant cellular activity, measureable aqueous solubility and moderate antitumor activity in a mouse tumor model after weekly ip dosing. Unfortunately these compounds were pan-kinase inhibitors that suffered from narrow therapeutic indices which prohibited their use as antitumor agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.067

文献信息

• PYRIMIDINE INHIBITORS OF KINASES
  申请人：Curtin Michael

  公开号：US20100317680A1

  公开（公告）日：2010-12-16

  The present invention relates to compounds of formula (I) or pharmaceutical acceptable salts, wherein A 1 , A 2 , A 3 , A 4 , X and Y are defined in the description. The present invention relates also to methods of making said compounds, and compositions containing said compounds which are useful for inhibiting kinases such as aurora and KDR.

  本发明涉及式(I)的化合物或药用可接受的盐，其中A1、A2、A3、A4、X和Y在描述中有定义。本发明还涉及制备所述化合物的方法，以及含有所述化合物的组合物，用于抑制aurora和KDR等激酶。
• Stereoisomerically Enriched 3-Aminocarbonyl Bicycloheptene Pyrimidinediamine Compounds and their Uses
  申请人：Argade Ankush

  公开号：US20080051412A1

  公开（公告）日：2008-02-28

  The present invention provides stereoisomers and stereoisomeric mixtures of 3-aminocarbonyl-bicycloheptene-2,4-pyrimidinediamine compounds having antiproliferative activity, compositions comprising the compounds and methods of using the compounds to inhibit cellular proliferation and to treat proliferate diseases such as tumorigenic cancers.

  本发明提供了具有抗增殖活性的3-氨基羰基-双环庚烯-2,4-嘧啶二胺化合物的立体异构体和立体异构体混合物，包括含有该化合物的组合物和使用该化合物抑制细胞增殖和治疗增殖性疾病，如肿瘤性癌症的方法。
• Stereoisomerically Enriched 3-Aminocarbonyl Bicycloheptene Pyrimidinediamine Compounds And Their Uses
  申请人：Argade Ankush

  公开号：US20070179140A1

  公开（公告）日：2007-08-02

  The present invention provides stereoisomers and stereoisomeric mixtures of 3-aminocarbonyl-bicycloheptene-2,4-pyrimidinediamine compounds having antiproliferative activity, compositions comprising the compounds and methods of using the compounds to inhibit cellular proliferation and to treat proliferate diseases such as tumorigenic cancers.

  本发明提供了3-氨基甲酰基双环庚烯-2,4-嘧啶二胺化合物的立体异构体和立体异构体混合物，具有抗增殖活性，包括该化合物的组合物和使用该化合物抑制细胞增殖和治疗增殖性疾病，如肿瘤癌症的方法。
• Cycloalkyl Substituted Pyrimidinediamine Compounds And Their Uses
  申请人：Li Hui

  公开号：US20070299060A1

  公开（公告）日：2007-12-27

  The present disclosure provides 2,4-pyrimidinediamine compounds having antiproliferative activity, compositions comprising the compounds and methods of using the compounds to inhibit cellular proliferation and to treat proliferate diseases such as tumorigenic cancers.

  本公开提供具有抗增殖活性的2,4-嘧啶二胺化合物，包含该化合物的组合物以及使用该化合物抑制细胞增殖和治疗增殖性疾病，如肿瘤性癌症的方法。
• PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE N-CARBAMATE PROTECTED BETA-LACTAMS BY OPTICAL RESOLUTION EMPLOYING A CANDIDA ANTARCTICA LIPASE
  申请人：Rigel Pharmaceuticals, Inc.

  公开号：EP1812581B1

  公开（公告）日：2009-01-28