N-benzyloxycarbonyl-β-methanesulfonyl-L-valine | 174562-82-4

• 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: N-benzyloxycarbonyl-β-methanesulfonyl-L-valine
• 英文别名: (2R)-3-methyl-3-methylsulfonyl-2-(phenylmethoxycarbonylamino)butanoic acid
• CAS: 174562-82-4
• 化学式: C₁₄H₁₉NO₆S
• 分子量: 329.374
• InChiKey: FSLRFOINIXADPF-LLVKDONJSA-N

物化性质

• 沸点：
  584.5±50.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 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：
  6

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-β-methanesulfonyl-L-valine 、 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 为溶剂， 生成 [(R)-1-((S)-1-{(2R,3S)-3-[2-(Ethyl-isopropyl-sulfamoyl)-ethyl]-oxiranyl}-2-phenyl-ethylcarbamoyl)-2-methanesulfonyl-2-methyl-propyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of irreversible HIV-1 protease inhibitors containing sulfonamide and sulfone as amide bond isosteres

  摘要：

  Novel irreversible HIV-1 protease inhibitors containing sulfonamide and sulfone as amide bond isosteres were designed, synthesized, and kinetically characterized, A representative compound 2 displayed rapid, time-dependent inactivation of HIV-1 protease and high potency in cell culture with IC50 of 6.6 nM. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10054-3
• 作为产物：
  描述：

  L-青霉胺 在 sodium methylate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 N-benzyloxycarbonyl-β-methanesulfonyl-L-valine
  参考文献：
  名称：

  β-Methanesulfonyl-L-valine as a novel, unnatural amino acid surrogate for P2 in the design of HIV protease inhibitors.

  摘要：

  beta-Methanesulfonyl-L-valine as a surrogate for asparagine and valine was designed, synthesized, and characterized. A representative compound 1 showed IC50 of 4.9 nM.

  DOI：

  10.1016/0960-894x(96)00086-8

文献信息

• Irreversible HIV protease inhibitors, intermediates, compositions and processes for the preparation thereof
  申请人：LG Chemical Limited

  公开号：EP0687675A2

  公开（公告）日：1995-12-20

  Novel cis-epoxide compounds of formula (I) are useful for treating or preventing diseases caused by HIV infection: wherein A, B, R1 to R4 and n have the same meanings as defined in the specification. The novel HIV protease inhibitor of the formula (I) has a specific structure to form a stable bonding with the enzyme active site, which entails a highly enhanced irreversible inhibition against HIV protease.

  式 (I) 的新型顺式环氧化合物可用于治疗或预防由 HIV 感染引起的疾病： 其中 A、B、R1 至 R4 和 n 的含义与说明书中的定义相同。 式（I）的新型 HIV 蛋白酶抑制剂具有特定的结构，可与酶活性位点形成稳定的结合，从而高度增强对 HIV 蛋白酶的不可逆抑制作用。
• US5696134A
  申请人：——

  公开号：US5696134A

  公开（公告）日：1997-12-09
• β-Methanesulfonyl-L-valine as a novel, unnatural amino acid surrogate for P2 in the design of HIV protease inhibitors.
  作者：Chihyo Park、Hoil Choi、Young-Chan Son、Chang Sun Lee、Nakyen Choy、Jong Sung Koh、Tae Gyu Lee、Young Do Kwon、Sung Chun Kim、Heungsik Yoon

  DOI：10.1016/0960-894x(96)00086-8

  日期：1996.3

  beta-Methanesulfonyl-L-valine as a surrogate for asparagine and valine was designed, synthesized, and characterized. A representative compound 1 showed IC50 of 4.9 nM.
• Synthesis of irreversible HIV-1 protease inhibitors containing sulfonamide and sulfone as amide bond isosteres
  作者：Nakyen Choy、Ho-il Choi、Won Hee Jung、Chung Ryeol Kim、Heungsik Yoon、Sung Chun Kim、Tae Gyu Lee、Jong Sung Koh

  DOI：10.1016/s0960-894x(97)10054-3

  日期：1997.10

  Novel irreversible HIV-1 protease inhibitors containing sulfonamide and sulfone as amide bond isosteres were designed, synthesized, and kinetically characterized, A representative compound 2 displayed rapid, time-dependent inactivation of HIV-1 protease and high potency in cell culture with IC50 of 6.6 nM. (C) 1997 Published by Elsevier Science Ltd.