benzyl (2R)-2-[(2R,3S)-3-[[(2R,3R)-1-[[(2R)-1-[(2R)-2-[(2R)-2-carbamoylpyrrolidine-1-carbonyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]carbamoyl]-2-hydroxy-5-methylhexyl]pyrrolidine-1-carboxylate | 1602491-09-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: benzyl (2R)-2-[(2R,3S)-3-[[(2R,3R)-1-[[(2R)-1-[(2R)-2-[(2R)-2-carbamoylpyrrolidine-1-carbonyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]carbamoyl]-2-hydroxy-5-methylhexyl]pyrrolidine-1-carboxylate
• CAS: 1602491-09-7
• 化学式: C₄₁H₆₄N₆O₈
• 分子量: 768.995
• InChiKey: HDSQRSXAGFUINW-HCCIIKIBSA-N

物化性质

• 沸点：
  1000.385±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.195±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  55
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  192
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (S)-2-((R)-2-((R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)pyrrolidin-2-yl)-1-hydroxyethyl)-4-methylpentanoic acid 、 氯甲酸苄酯 、 Fmoc-D-脯氨酸 、 Fmoc-D-缬氨酸 、 Fmoc-D-异亮氨酸 在 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以3.8 mg的产率得到benzyl (2R)-2-[(2R,3S)-3-[[(2R,3R)-1-[[(2R)-1-[(2R)-2-[(2R)-2-carbamoylpyrrolidine-1-carbonyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]carbamoyl]-2-hydroxy-5-methylhexyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Effect of prime-site sequence of retro-inverso-modified HTLV-1 protease inhibitor

  摘要：

  The effects of additional substituents covering the prime-site of retro-inverso (RI)-modified HTLV-1 protease inhibitors containing a hydroxyethylamine isoster were clarified. Stereo-selective construction of the most potent isoster backbone was achieved by the Evans-aldol reaction. Addition of N-acetylated D-amino acid corresponding to the P-2(1) site gave an RI-modified inhibitor showing superior inhibitory activity to the previous inhibitor. Inhibitory activities of the newly synthesized inhibitors suggest that partially modified RI inhibitors would interact with HTLV-1 protease in the same manner as the parent hydroxyethylamine inhibitor. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.050

文献信息

• Effect of prime-site sequence of retro-inverso-modified HTLV-1 protease inhibitor
  作者：Chiyuki Awahara、Tadashi Tatsumi、Saki Furuta、Gen Shinjoh、Hiroyuki Konno、Kazuto Nosaka、Kazuya Kobayashi、Yasunao Hattori、Kenichi Akaji

  DOI：10.1016/j.bmc.2014.02.050

  日期：2014.4

  The effects of additional substituents covering the prime-site of retro-inverso (RI)-modified HTLV-1 protease inhibitors containing a hydroxyethylamine isoster were clarified. Stereo-selective construction of the most potent isoster backbone was achieved by the Evans-aldol reaction. Addition of N-acetylated D-amino acid corresponding to the P-2(1) site gave an RI-modified inhibitor showing superior inhibitory activity to the previous inhibitor. Inhibitory activities of the newly synthesized inhibitors suggest that partially modified RI inhibitors would interact with HTLV-1 protease in the same manner as the parent hydroxyethylamine inhibitor. (C) 2014 Elsevier Ltd. All rights reserved.