(S)-2-(tert-butoxycarbonyl)amino-3-(4-fluorophenylsulfonyl)propanoic acid | 169168-70-1

• 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-(tert-butoxycarbonyl)amino-3-(4-fluorophenylsulfonyl)propanoic acid
• 英文别名: (2S)-3-(4-fluorophenyl)sulfonyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 169168-70-1
• 化学式: C₁₄H₁₈FNO₆S
• 分子量: 347.364
• InChiKey: KPGYYKBXCTWKFL-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-2-(tert-butoxycarbonyl)amino-3-(4-fluorophenylsulfonyl)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-<(p-fluorophenyl)thio>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-(4-fluorophenylsulfonyl)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

文献信息

• Inhibitors of HIV protease useful for the treatment of aids
  申请人：ELI LILLY AND COMPANY

  公开号：EP0604185A1

  公开（公告）日：1994-06-29

  The present invention provides novel HIV protease inhibitors of formula I, pharmaceutical formulations containing those compounds and methods of treating and/or preventing HIV infection and/or AIDS. wherein: R is a group having the formula: R² is an amino acid side chain or -(CH₂)y-X-R2a; y is 0, 1 or 2; and X, R⁰, R³ and Y¹ are as defined in the application.

  本发明提供了式 I 的新型 HIV 蛋白酶抑制剂、含有这些化合物的药物制剂以及治疗和/或预防 HIV 感染和/或艾滋病的方法。 其中 R 是具有式的基团： R² 是氨基酸侧链或-(CH₂)y-X-R2a； y 是 0、1 或 2； X、R⁰、R³ 和 Y¹ 如本申请中所定义。
• Inhibitors of HIV protease useful for the treatment of AIDS
  申请人：ELI LILLY AND COMPANY

  公开号：EP0604185B1

  公开（公告）日：1999-03-24
• EP0744948A4
  申请人：——

  公开号：EP0744948A4

  公开（公告）日：1997-06-11
• PROTEASE INHIBITORS
  申请人：ELI LILLY AND COMPANY

  公开号：EP0744948A1

  公开（公告）日：1996-12-04
• US5480887A
  申请人：——

  公开号：US5480887A

  公开（公告）日：1996-01-02