3-(dimethylamino)benzenemethanesulfonic acid | 396733-72-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(dimethylamino)benzenemethanesulfonic acid
• 英文别名: [3-(dimethylamino)phenyl]methanesulfonic acid
• CAS: 396733-72-5
• 化学式: C₉H₁₃NO₃S
• 分子量: 215.273
• InChiKey: HDVMWEXVEJBTDB-UHFFFAOYSA-N

物化性质

• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(dimethylamino)benzenemethanesulfonic acid 、 (3S,3aR,6aS)-1-(cyclopropylcarbonyl)-3-methyl-4-[(2S)-pyrrolidin-2-ylcarbonyl]hexahydropyrrolo[3,2-b]pyrrol-2(1H)-one hydrochloride 在 三光气 、 三乙胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以22%的产率得到3-{[((2S)-2-{[(3aS,6S,6aR)-4-(cyclopropylcarbonyl)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrol-2(2H)-yl]carbonyl}pyrrolidin-1-yl)sulfonyl]methyl}-N,N-dimethylbenzamide
  参考文献：
  名称：

  Design and Synthesis of Pyrrolidine-5,5-trans-lactams (5-Oxohexahydropyrrolo[3,2-b]pyrroles) as Novel Mechanism-Based Inhibitors of Human Cytomegalovirus Protease. 2. Potency and Chirality

  摘要：

  The stereospecific synthesis of a series of alpha-methylpyrrolidine-5,5-trans-lactam inhibitors of human cytomegalovirus (HCMV) protease is described. Examination of the SAR in this series has defined the size and chirality of the alpha-substituent, optimized the acyl substituent on the lactam nitrogen, and defined the steric constraint of this functionality. The SAR of the functionality on the pyrrolidine nitrogen of the trans-lactam has been investigated, and this has led to the discovery of potent serine protease inhibitors that are highly selective for the viral enzyme over the mammalian enzymes elastase, thrombin, and acetylcholine esterase. The mechanism of action of our lead compounds has been established by mass spectrometry, and enzymatic degradation of HCMV deltaAla protease acylated with these inhibitors showed that Ser 132 is the active site nucleophile. The crystal structure of HCMV protease was obtained and used to model the conformationally restricted, chiral (S)-proline-alpha-methyl-5,5-trans-lactams into the active site groove of the enzyme, enabling us to direct and rationalize the SAR in this series. The activity against HCMV deltaAla protease is the greatest with inhibitors based on the dansyl-(S)-proline alpha-methyl-5,5-trans-lactam template, which have low nanomolar activity against the viral enzyme.

  DOI：

  10.1021/jm0102203