[(3S)-四氢呋喃-3-基]N-[(2S,3S)-4-[(2S)-4-[(2S)-4-[(2R)-1-氨基-1-氧代-3-苯基丙烷-2-基]-2-(2-甲基丙基)-3-氧代-1H-吡咯-2-基]-3-氧代-2-(苯基甲基)-1H-吡咯-2-基]-3-羟基-1-苯基丁烷-2-基]氨基甲酸酯 | 173240-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [(3S)-四氢呋喃-3-基]N-[(2S,3S)-4-[(2S)-4-[(2S)-4-[(2R)-1-氨基-1-氧代-3-苯基丙烷-2-基]-2-(2-甲基丙基)-3-氧代-1H-吡咯-2-基]-3-氧代-2-(苯基甲基)-1H-吡咯-2-基]-3-羟基-1-苯基丁烷-2-基]氨基甲酸酯
• 中文别名: 3,4,5-三甲氧基-N-[(1E)-吡啶-4-基甲亚基]苯胺盐酸
• 英文名称: Carbamic acid, ((1S,2S)-3-((2S,5'S)-4-((1R)-2-amino-2-oxo-1-(phenylmethyl)ethyl)-2,3,4',5'-tetrahydro-2-(2-methylpropyl)-3,4'-dioxo-5'-(phenylmethyl)(2,3'-bi-1H-pyrrol)-5'-yl)-2-hydroxy-1-(phenylmethyl)propyl)-, (3S)-tetrahydro-3-furanyl ester
• 英文别名: [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(2S)-4-[(2S)-4-[(2R)-1-amino-1-oxo-3-phenylpropan-2-yl]-2-(2-methylpropyl)-3-oxo-1H-pyrrol-2-yl]-2-benzyl-3-oxo-1H-pyrrol-2-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate
• CAS: 173240-66-9
• 化学式: C₄₃H₅₀N₄O₇
• 分子量: 734.893
• InChiKey: MWGYNCKUZMAZOR-KHQFFOCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  54
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  169
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (S)-4-苄基-3-(3-苯基丙酰基)噁唑烷丁-2-酮 在 咪唑 、 lead(IV) acetate 、 盐酸 、 sodium hydroxide 、 四氧化锇 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 正丁基锂 、 N-甲基吲哚酮 、 jones reagent 、 氨 、 sodium hexamethyldisilazane 、 双(三甲基硅烷基)氨基钾 、 5,5-二甲基-1,3-环己二酮 、 臭氧 、 三乙胺 、 乙酰氯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 43.67h， 生成 [(3S)-四氢呋喃-3-基]N-[(2S,3S)-4-[(2S)-4-[(2S)-4-[(2R)-1-氨基-1-氧代-3-苯基丙烷-2-基]-2-(2-甲基丙基)-3-氧代-1H-吡咯-2-基]-3-氧代-2-(苯基甲基)-1H-吡咯-2-基]-3-羟基-1-苯基丁烷-2-基]氨基甲酸酯
  参考文献：
  名称：

  Pyrrolinone-Based HIV Protease Inhibitors. Design, Synthesis, and Antiviral Activity: Evidence for Improved Transport

  摘要：

  Pyrrolinone-based peptidomimetics, the first mimics of beta-strands, are potent inhibitors of HIV-1 protease. Importantly, the bis(pyrrolinones) described herein proved to be more active in cellular antiviral assays compared with an analogous peptide-derived inhibitor even though they are less effective in inhibiting the isolated protease. These results suggest that pyrrolinone inhibitors offer better transport properties than the corresponding peptide-based peptidomimetics; we attribute this effect to decreased solvation of the mimetics. Structure-activity relationships for the pyrrolinones correlate well with those reported for related peptides, consistent with similar modes of binding.

  DOI：

  10.1021/ja00150a011

文献信息

• Pyrrolinone-Based HIV Protease Inhibitors. Design, Synthesis, and Antiviral Activity: Evidence for Improved Transport
  作者：Amos B Smith、Ralph Hirschmann、Alexander Pasternak、Mark C. Guzman、Akihisa Yokoyama、Paul A. Sprengeler、Paul L. Darke、Emilio A. Emini、William A. Schleif

  DOI：10.1021/ja00150a011

  日期：1995.11

  Pyrrolinone-based peptidomimetics, the first mimics of beta-strands, are potent inhibitors of HIV-1 protease. Importantly, the bis(pyrrolinones) described herein proved to be more active in cellular antiviral assays compared with an analogous peptide-derived inhibitor even though they are less effective in inhibiting the isolated protease. These results suggest that pyrrolinone inhibitors offer better transport properties than the corresponding peptide-based peptidomimetics; we attribute this effect to decreased solvation of the mimetics. Structure-activity relationships for the pyrrolinones correlate well with those reported for related peptides, consistent with similar modes of binding.