(S)-3-Amino-2-(naphthalene-2-sulfonylamino)-propionic acid | 215050-29-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-3-Amino-2-(naphthalene-2-sulfonylamino)-propionic acid
• 英文别名: (2S)-3-amino-2-(naphthalen-2-ylsulfonylamino)propanoic acid
• CAS: 215050-29-6
• 化学式: C₁₃H₁₄N₂O₄S
• 分子量: 294.331
• InChiKey: SBTKTTGTVUCKTI-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-3-Amino-2-(naphthalene-2-sulfonylamino)-propionic acid 在 硫酸 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-3-(4-Fluoro-3-nitro-benzoylamino)-2-(naphthalene-2-sulfonylamino)-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：

  (S)-2-(Naphthalene-2-sulfonylamino)-succinamic acid 在 sodium hydroxide 、 溴 作用下， 以 水 为溶剂， 以81%的产率得到(S)-3-Amino-2-(naphthalene-2-sulfonylamino)-propionic acid
  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

文献信息

• [EN] BISPIPERIDINES AS ANTITHROMBOTIC AGENTS<br/>[FR] BISPIPERIDINES COMME AGENTS ANTITHROMBOTIQUES
  申请人：LAFON LABOR

  公开号：WO2000003986A1

  公开（公告）日：2000-01-27

  La présente invention concerne des composés de formule (I) dans laquelle R1, R2, R3, Z1, Z2 et A sont tels que définis à la revendication 1. Ces composés sont des inhibiteurs de la fixation du fibrinogène sur les récepteurs plaquettaires Gp IIb/IIIa et sont utilisables en thérapeutique comme antithrombotiques.

  本发明涉及式（I）的化合物，其中R1、R2、R3、Z1、Z2和A如权利要求1所定义。这些化合物是Gp IIb/IIIa血小板受体上纤维蛋白原结合的抑制剂，并可用于治疗作为抗血栓药物。
• BISPIPERIDINES COMME AGENTS ANTITHROMBOTIQUES
  申请人：CEPHALON FRANCE

  公开号：EP1098878B1

  公开（公告）日：2003-12-17
• PIPERAZINONES SUBSTITUEES ET LEURS APPLICATIONS EN THERAPEUTIQUE
  申请人：LABORATOIRE L. LAFON

  公开号：EP1098889A1

  公开（公告）日：2001-05-16
• [EN] SUBSTITUTED PIPERAZONES AND THEIR THERAPEUTIC USES<br/>[FR] PIPERAZINONES SUBSTITUEES ET LEURS APPLICATIONS EN THERAPEUTIQUE
  申请人：LAFON LABOR

  公开号：WO2000004001A1

  公开（公告）日：2000-01-27

  La présente invention concerne des composés de formule générale (I), dans laquelle R1, R2, R3, R4 et R5 sont tels que définis à la revendication 1. Ces composés sont utilisables en thérapeutique comme antithrombotiques.