(S)-3-[4-Amino-3-(3-phenyl-thioureido)-benzoylamino]-2-benzenesulfonylamino-propionic acid tert-butyl ester | 215050-26-3

• 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)-3-[4-Amino-3-(3-phenyl-thioureido)-benzoylamino]-2-benzenesulfonylamino-propionic acid tert-butyl ester
• CAS: 215050-26-3
• 化学式: C₂₇H₃₁N₅O₅S₂
• 分子量: 569.706
• InChiKey: HCHUQEMQAMMTBR-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  151.65
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-3-[4-Amino-3-(3-phenyl-thioureido)-benzoylamino]-2-benzenesulfonylamino-propionic acid tert-butyl ester 在 三乙胺 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以81%的产率得到(S)-2-Benzenesulfonylamino-3-[(2-phenylamino-3H-benzoimidazole-5-carbonyl)-amino]-propionic acid tert-butyl ester
  参考文献：
  名称：

  Design, synthesis and biological evaluation of nonpeptide integrin antagonists

  摘要：

  Recent studies demonstrated that peptide and antibody antagonists of integrin alpha(v)beta(3) block angiogenesis and tumor growth. In this article, the design, synthesis and biological evaluation of a series of nitroaryl ether-based, nonpeptide mimetics are described. The design of these compounds was based on Merck's arylether/alpha-aminoacid/guanidine framework and incorporates a novel nitroaryl system. The synthesized mimetics were tested against a variety of integrins (alpha(v)beta(3), alpha(IIb)beta(3), and alpha(v)beta(5)) in order to determine their binding selectivity and ability to inhibit cell adhesion. Selected compounds were also tested for their ability to inhibit angiogenesis in vivo in the CAM (chick chorioallantoic membrane) assay. From the generated compound library, compounds 16 and 19 proved to be potent and selective inhibitors of alpha(IIb)beta(3) (IC50 = 14 nM) whereas compound 11 showed excellent in vivo inhibition of angiogenesis (at 30 mu g/embryo). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00090-x
• 作为产物：
  描述：

  3-硝基-4-氟苯甲酰氯 在 palladium on activated charcoal 氨 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 (S)-3-[4-Amino-3-(3-phenyl-thioureido)-benzoylamino]-2-benzenesulfonylamino-propionic acid tert-butyl ester
  参考文献：
  名称：

  Design, synthesis and biological evaluation of nonpeptide integrin antagonists

  摘要：

  Recent studies demonstrated that peptide and antibody antagonists of integrin alpha(v)beta(3) block angiogenesis and tumor growth. In this article, the design, synthesis and biological evaluation of a series of nitroaryl ether-based, nonpeptide mimetics are described. The design of these compounds was based on Merck's arylether/alpha-aminoacid/guanidine framework and incorporates a novel nitroaryl system. The synthesized mimetics were tested against a variety of integrins (alpha(v)beta(3), alpha(IIb)beta(3), and alpha(v)beta(5)) in order to determine their binding selectivity and ability to inhibit cell adhesion. Selected compounds were also tested for their ability to inhibit angiogenesis in vivo in the CAM (chick chorioallantoic membrane) assay. From the generated compound library, compounds 16 and 19 proved to be potent and selective inhibitors of alpha(IIb)beta(3) (IC50 = 14 nM) whereas compound 11 showed excellent in vivo inhibition of angiogenesis (at 30 mu g/embryo). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00090-x