tert-butyl 3-[1-[3-(N-triphenylmethylimidazol-2-ylamino)propyl]indazol-5-ylcarbonylamino]-2(S)-aminopropionate | 257293-59-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: tert-butyl 3-[1-[3-(N-triphenylmethylimidazol-2-ylamino)propyl]indazol-5-ylcarbonylamino]-2(S)-aminopropionate
• CAS: 257293-59-7
• 化学式: C₄₀H₄₃N₇O₃
• 分子量: 669.827
• InChiKey: VHRYFRGEZNKZGS-UMSFTDKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  50.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  129.09
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-[1-[3-(N-triphenylmethylimidazol-2-ylamino)propyl]indazol-5-ylcarbonylamino]-2(S)-aminopropionate 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 3-[1-[3-(N-imidazol-2-ylamino)propyl]indazol-5-ylcarbonylamino]-2(S)-(4-methoxybenzenesulfonylamino)propionic acid trifluoroacetate
  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：

  (S)- 3 -氨基- 2 -羰基氨基丙酸叔丁酯 在 10percent Pd/C 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 tert-butyl 3-[1-[3-(N-triphenylmethylimidazol-2-ylamino)propyl]indazol-5-ylcarbonylamino]-2(S)-aminopropionate
  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