(S)-2-(3-Benzyl-ureido)-3-({1-[3-(pyridin-2-ylamino)-propyl]-1H-indazole-5-carbonyl}-amino)-propionic acid tert-butyl ester | 1025894-12-5

• 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: (S)-2-(3-Benzyl-ureido)-3-({1-[3-(pyridin-2-ylamino)-propyl]-1H-indazole-5-carbonyl}-amino)-propionic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-(benzylcarbamoylamino)-3-[[1-[3-(pyridin-2-ylamino)propyl]indazole-5-carbonyl]amino]propanoate
• CAS: 1025894-12-5
• 化学式: C₃₁H₃₇N₇O₄
• 分子量: 571.679
• InChiKey: ZCNHSTVPLJPACV-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 (S)-2-(3-Benzyl-ureido)-3-({1-[3-(pyridin-2-ylamino)-propyl]-1H-indazole-5-carbonyl}-amino)-propionic acid tert-butyl ester 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-[1-[3-(N-pyridin-2-ylamino)propyl]indazol-5-ylcarbonylamino]-2(S)-(phenylmethylaminocarbonylamino)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：

  tert-butyl 3-[1-[3-(N-pyridin-2-ylamino)propyl]indazol-5-ylcarbonylamino]-2(S)-(benzyloxycarbonylamino)propionate 在 10percent Pd/C 氢气 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (S)-2-(3-Benzyl-ureido)-3-({1-[3-(pyridin-2-ylamino)-propyl]-1H-indazole-5-carbonyl}-amino)-propionic acid tert-butyl ester
  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