(2S)-1-[[[(2S)-2-benzyl-3-[[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino]-3-oxopropyl]sulfonimidoyl]methyl]-N-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide | 1085743-71-0

• 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: (2S)-1-[[[(2S)-2-benzyl-3-[[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino]-3-oxopropyl]sulfonimidoyl]methyl]-N-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide
• CAS: 1085743-71-0
• 化学式: C₃₅H₄₆N₆O₄S
• 分子量: 646.854
• InChiKey: YNTRIKRNVQWHMV-LQNVDPHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  147
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2S)-1-[[(2S)-2-Benzyl-3-[[(1S,2R)-2-hydroxyindan-1-yl]amino]-3-oxo-propyl]sulfinylmethyl]-N-tert-butyl-4-(3-pyridylmethyl)piperazine-2-carboxamide 在 2,4,6-三甲基苯磺酰羟胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到(2S)-1-[[[(2S)-2-benzyl-3-[[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino]-3-oxopropyl]sulfonimidoyl]methyl]-N-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide
  参考文献：
  名称：

  Design and synthesis of sulfoximine based inhibitors for HIV-1 protease

  摘要：

  A new class of potent sulfoximine inhibitors for HIV-1 protease has been designed and synthesized. Substitution of the sulfoximine moiety into different parent compounds yields different inhibition effects. While our previously studied sulfoximine-based inhibitors display potency of 2.5 nM (IC(50)) against HIV-1 protease, introduction of the sulfoximine moiety into the asymmetric Indinavir yielded only micromolar inhibition. Docking studies showed structural variations in their modes of binding which explains this unexpected observation. The implication of these observations in the development of other sulfoximine inhibitors is discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.044

文献信息

• Design and synthesis of sulfoximine based inhibitors for HIV-1 protease
  作者：Abbas Raza、Yuk Yin Sham、Robert Vince

  DOI：10.1016/j.bmcl.2008.09.044

  日期：2008.10

  A new class of potent sulfoximine inhibitors for HIV-1 protease has been designed and synthesized. Substitution of the sulfoximine moiety into different parent compounds yields different inhibition effects. While our previously studied sulfoximine-based inhibitors display potency of 2.5 nM (IC(50)) against HIV-1 protease, introduction of the sulfoximine moiety into the asymmetric Indinavir yielded only micromolar inhibition. Docking studies showed structural variations in their modes of binding which explains this unexpected observation. The implication of these observations in the development of other sulfoximine inhibitors is discussed. (C) 2008 Elsevier Ltd. All rights reserved.