ethyl 1-(2-cyanoethyl)indazole-5-carboxylate | 192944-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: ethyl 1-(2-cyanoethyl)indazole-5-carboxylate
• 英文别名: 1-(2-cyanoethyl)-5-ethoxycarbonylindazole
• CAS: 192944-86-8
• 化学式: C₁₃H₁₃N₃O₂
• 分子量: 243.265
• InChiKey: STLCCOUHPUXGDU-UHFFFAOYSA-N

物化性质

• 熔点：
  106-109 °C
• 沸点：
  431.2±25.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-(2-cyanoethyl)indazole-5-carboxylate 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 19.0h， 生成 ethyl 1-(3-aminopropyl)indazole-5-carboxylate
  参考文献：
  名称：

  Disubstituted Indazoles as Potent Antagonists of the Integrin α_vβ₃

  摘要：

  A new series of indazole-containing alpha(v)beta(3) integrin antagonists is described. Starting with lead compound 18a, variations in a number of structural features were explored with respect to inhibition of the binding of beta(3)-transfected 293 cells to fibrinogen and to selectivity for alpha(v)beta(3) over GPIIbIIIa, another RGD-binding integrin. Indazoles attached to a 2-aminopyridine or 2-aminoimidazole by a propylene linker at the indazole 1-position and to a diaminopropionate derivative via a 5-carboxylate amide provided the best potency with moderate selectivity. Several differences in the SAR of the diaminopropionate moiety were observed between this series and a series of isoxazoline-based selective GPIIbIIIa antagonists. Compound 34a (SM256) was a potent antagonist of alpha(v)beta(3) (IC50 2.3 nM) with 9-fold selectivity over GPIIbIIIa.

  DOI：

  10.1021/jm990049j
• 作为产物：
  描述：

  丙烯腈 、 1H-吲唑-5-甲酸乙酯 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 以90%的产率得到ethyl 1-(2-cyanoethyl)indazole-5-carboxylate
  参考文献：
  名称：

  Disubstituted Indazoles as Potent Antagonists of the Integrin α_vβ₃

  摘要：

  A new series of indazole-containing alpha(v)beta(3) integrin antagonists is described. Starting with lead compound 18a, variations in a number of structural features were explored with respect to inhibition of the binding of beta(3)-transfected 293 cells to fibrinogen and to selectivity for alpha(v)beta(3) over GPIIbIIIa, another RGD-binding integrin. Indazoles attached to a 2-aminopyridine or 2-aminoimidazole by a propylene linker at the indazole 1-position and to a diaminopropionate derivative via a 5-carboxylate amide provided the best potency with moderate selectivity. Several differences in the SAR of the diaminopropionate moiety were observed between this series and a series of isoxazoline-based selective GPIIbIIIa antagonists. Compound 34a (SM256) was a potent antagonist of alpha(v)beta(3) (IC50 2.3 nM) with 9-fold selectivity over GPIIbIIIa.

  DOI：

  10.1021/jm990049j

文献信息

• US5760028A
  申请人：——

  公开号：US5760028A

  公开（公告）日：1998-06-02
• Disubstituted Indazoles as Potent Antagonists of the Integrin α_vβ₃
  作者：Douglas G. Batt、Joseph J. Petraitis、Gregory C. Houghton、Dilip P. Modi、Gary A. Cain、Martha H. Corjay、Shaker A. Mousa、Peter J. Bouchard、Mark S. Forsythe、Patricia P. Harlow、Frank A. Barbera、Susan M. Spitz、Ruth R. Wexler、Prabhakar K. Jadhav

  DOI：10.1021/jm990049j

  日期：2000.1.1

  A new series of indazole-containing alpha(v)beta(3) integrin antagonists is described. Starting with lead compound 18a, variations in a number of structural features were explored with respect to inhibition of the binding of beta(3)-transfected 293 cells to fibrinogen and to selectivity for alpha(v)beta(3) over GPIIbIIIa, another RGD-binding integrin. Indazoles attached to a 2-aminopyridine or 2-aminoimidazole by a propylene linker at the indazole 1-position and to a diaminopropionate derivative via a 5-carboxylate amide provided the best potency with moderate selectivity. Several differences in the SAR of the diaminopropionate moiety were observed between this series and a series of isoxazoline-based selective GPIIbIIIa antagonists. Compound 34a (SM256) was a potent antagonist of alpha(v)beta(3) (IC50 2.3 nM) with 9-fold selectivity over GPIIbIIIa.