(S)-2-(tert-butoxycarbonyl)amino-3-(quinolin-2-ylsulfonyl)propanoic acid | 1029146-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (S)-2-(tert-butoxycarbonyl)amino-3-(quinolin-2-ylsulfonyl)propanoic acid
• CAS: 1029146-74-4
• 化学式: C₁₇H₂₀N₂O₆S
• 分子量: 380.422
• InChiKey: RCYFLWCIPBGGEF-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  122.66
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(tert-butoxycarbonyl)amino-3-(quinolin-2-ylsulfonyl)propanoic acid 、 H-Apns-Dmt-NH(o-methylbenzyl) hydrochloride 在 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Combination of Non-natural d-Amino Acid Derivatives and Allophenylnorstatine−Dimethylthioproline Scaffold in HIV Protease Inhibitors Have High Efficacy in Mutant HIV

  摘要：

  Several non-natural D-amino acid derivatives were introduced as P(2)/P(3) residues in allophenylnorstatine-containing (Apns; (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid) HIV protease inhibitors. The synthetic analogues exhibited potent inhibitory activity against HIV-1 protease enzyme and HIV-1 replication in MT-4 cells. Structure-activity relationships revealed that D-cysteine or serine derivatives contributed to highly potent anti-HIV activities. Interestingly, anti-HIV activity of all the D-amino acid-introduced inhibitors was remarkably enhanced in their anti-HIV activities against a Nelfinavir-resistant clone, which has a D30N mutation in the protease, over that of the wild-type strain. HIV inhibitory activity of several analogues was moderately affected by an inclusion of alpha(1)-acid glycoprotein in the test medium.

  DOI：

  10.1021/jm701555p
• 作为产物：
  描述：

  (S)-2-<(tert-butoxycarbonyl)amino>-3-(2-quinolinylthio)propionic acid 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 生成 (S)-2-(tert-butoxycarbonyl)amino-3-(quinolin-2-ylsulfonyl)propanoic acid
  参考文献：
  名称：

  Combination of Non-natural d-Amino Acid Derivatives and Allophenylnorstatine−Dimethylthioproline Scaffold in HIV Protease Inhibitors Have High Efficacy in Mutant HIV

  摘要：

  Several non-natural D-amino acid derivatives were introduced as P(2)/P(3) residues in allophenylnorstatine-containing (Apns; (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid) HIV protease inhibitors. The synthetic analogues exhibited potent inhibitory activity against HIV-1 protease enzyme and HIV-1 replication in MT-4 cells. Structure-activity relationships revealed that D-cysteine or serine derivatives contributed to highly potent anti-HIV activities. Interestingly, anti-HIV activity of all the D-amino acid-introduced inhibitors was remarkably enhanced in their anti-HIV activities against a Nelfinavir-resistant clone, which has a D30N mutation in the protease, over that of the wild-type strain. HIV inhibitory activity of several analogues was moderately affected by an inclusion of alpha(1)-acid glycoprotein in the test medium.

  DOI：

  10.1021/jm701555p