4-amino-3-cyclohex-1-enyl-benzonitrile | 915006-68-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-amino-3-cyclohex-1-enyl-benzonitrile
• 英文别名: 4-amino-3-(cyclohexen-1-yl)benzonitrile
• CAS: 915006-68-7
• 化学式: C₁₃H₁₄N₂
• 分子量: 198.268
• InChiKey: SULZZNMMXCPKTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-amino-3-cyclohex-1-enyl-benzonitrile 在 三甲基甲硅烷基锡 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 5-Cyano-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(1H-tetrazol-5-yl)-phenyl]-amide
  参考文献：
  名称：

  Enhancement of kinase selectivity in a potent class of arylamide FMS inhibitors

  摘要：

  Structure-activity relationship (SAR) studies on a highly potent series of arylamide FMS inhibitors were carried out with the aim of improving FMS kinase selectivity, particularly over KIT. Potent compound 17r (FMS IC50 0.7 nM, FMS cell IC50 6.1 nM) was discovered that had good PK properties and a greater than fivefold improvement in selectivity for FMS over KIT kinase in a cellular assay relative to the previously reported clinical candidate 4. This improved selectivity was manifested in vivo by no observed decrease in circulating reticulocytes, a measure of bone safety, at the highest studied dose. Compound 17r was highly active in a mouse pharmacodynamic model and demonstrated disease-modifying effects in a dose-dependent manner in a strep cell wall-induced arthritis model of rheumatoid arthritis in rats. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.061
• 作为产物：
  描述：

  对硝基苯甲腈 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成 4-amino-3-cyclohex-1-enyl-benzonitrile
  参考文献：
  名称：

  Enhancement of kinase selectivity in a potent class of arylamide FMS inhibitors

  摘要：

  Structure-activity relationship (SAR) studies on a highly potent series of arylamide FMS inhibitors were carried out with the aim of improving FMS kinase selectivity, particularly over KIT. Potent compound 17r (FMS IC50 0.7 nM, FMS cell IC50 6.1 nM) was discovered that had good PK properties and a greater than fivefold improvement in selectivity for FMS over KIT kinase in a cellular assay relative to the previously reported clinical candidate 4. This improved selectivity was manifested in vivo by no observed decrease in circulating reticulocytes, a measure of bone safety, at the highest studied dose. Compound 17r was highly active in a mouse pharmacodynamic model and demonstrated disease-modifying effects in a dose-dependent manner in a strep cell wall-induced arthritis model of rheumatoid arthritis in rats. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.061

文献信息

• c-fms kinase inhibitors
  申请人：Player R. Mark

  公开号：US20060258666A1

  公开（公告）日：2006-11-16

  The invention is directed to compounds of Formula II: wherein A, R 1 , R 2 , R 3 , R 4 , X, Y and W are set forth in the specification, as well as solvates, hydrates, tautomers or pharmaceutically acceptable salts thereof, that inhibit protein tyrosine kinases, especially c-fms kinase.

  本发明涉及公式II的化合物： 其中A、R1、R2、R3、R4、X、Y和W在说明书中有所阐述，以及其溶剂化物、水合物、互变异构体或药学上可接受的盐，其可抑制蛋白酪氨酸激酶，特别是c-fms激酶。
• Iron-catalyzed intramolecular C–H amination for the synthesis of N–H carbazoles and indoles
  作者：Zheng-Lin Wang、Yun-Hao Zhang、Jun-Yu Huang、Jian Zhou、Ya-Qin Yu、Dexin Feng、Da-Zhen Xu

  DOI：10.1039/d3gc00518f

  日期：——

  The development of aerobic oxidative C–H/N–H cross-coupling catalyzed by the first-row transition metals is attractive yet challenging. Here, the first iron-catalyzed intramolecular cross-dehydrogenative coupling for the synthesis of carbazoles and indoles using air as the oxidant is reported. The general and efficient protocol allows for C–N bond formation under green conditions with excellent functional

  由第一排过渡金属催化的有氧氧化 C-H/N-H 交叉偶联的发展具有吸引力但具有挑战性。在这里，报道了第一个铁催化的分子内交叉脱氢偶联，用于使用空气作为氧化剂合成咔唑和吲哚。通用且高效的协议允许在绿色条件下形成 C-N 键，具有出色的官能团相容性，以良好的收率提供范围广泛的 N-H 咔唑和吲哚。令人印象深刻的是，所有咔唑都是由 2-环己烯基氨基芳烃通过C-H 胺化和芳构化过程失去 6H 制备的。此外，它还适用于 C–O 键的形成。
• C-FMS KINASE INHIBITORS
  申请人：Janssen Pharmaceutica NV

  公开号：EP2016057A1

  公开（公告）日：2009-01-21
• US7790724B2
  申请人：——

  公开号：US7790724B2

  公开（公告）日：2010-09-07
• [EN] C-FMS KINASE INHIBITORS<br/>[FR] Inhibiteurs de la c-fms kinase
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2007123516A1

  公开（公告）日：2007-11-01

  [EN] The invention is directed to compounds of Formula II: wherein A, R₁, R₂, R₃, R₄, X, Y and W are set forth in the specification, as well as solvates, hydrates, tautomers or pharmaceutically acceptable salts thereof, that inhibit protein tyrosine kinases, especially c-fms kinase.
  [FR] L'invention concerne des composés de Formule II dans laquelle A, R₁, R₂, R₃, R₄, X, Y et W sont définis dans la description ainsi que des solvates, des hydrates, des tautomères ou des sels pharmaceutiquement acceptables de ceux-ci qui inhibent les protéine tyrosine kinases, notamment la c-fms kinase.