<(S,R)-3-<<(R,S)-3-<<(1,1-dimethylethoxy)carbonyl>amino>-2-hydroxy-4-phenylbutyl>amino>-2-hydroxy-1-(phenylmethyl)propyl>methylcarbamic acid 1,1-dimethylethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: <(S,R)-3-<<(R,S)-3-<<(1,1-dimethylethoxy)carbonyl>amino>-2-hydroxy-4-phenylbutyl>amino>-2-hydroxy-1-(phenylmethyl)propyl>methylcarbamic acid 1,1-dimethylethyl ester
• 英文别名: Aminodiol deriv. 16；tert-butyl N-[(2S,3R)-3-hydroxy-4-[[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutyl]amino]-1-phenylbutan-2-yl]-N-methylcarbamate
• 化学式: C₃₁H₄₇N₃O₆
• 分子量: 557.731
• InChiKey: SSBSSFRLIFONBL-GWMMUDDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  {(1S,2R)-1-Benzyl-3-[((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-2-hydroxy-propyl}-methyl-carbamic acid tert-butyl ester 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以72%的产率得到<(S,R)-3-<<(R,S)-3-<<(1,1-dimethylethoxy)carbonyl>amino>-2-hydroxy-4-phenylbutyl>amino>-2-hydroxy-1-(phenylmethyl)propyl>methylcarbamic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Amino Diol HIV Protease Inhibitors. 1. Design, Synthesis, and Preliminary SAR

  摘要：

  A series of HIV protease inhibitors containing a novel C-2 symmetrical ''aminodiol'' core structure were prepared from amino acid starting materials. The ability of the aminodiols to inhibit HIV replication in cell culture is comparable to their ability to inhibit the isolated enzyme, a result compatible with good cell membrane penetration by this class of compounds. Optimization of the structure-activity in this series led to aminodiol 9a (K-i = 100 nM; ED(50) (HIV-1) = 80 nM) containing P-1/P-1', benzyl and P-2/P-2' Boc substituents. Compound 9a is a selective inhibitor of HIV protease versus other aspartyl proteases such as human renin, human cathepsin D, and porcine pepsin. In addition, 9a is equipotent against HIV-1 and HIV-2 in cell culture and demonstrates similar activity in infected T-lymphocytes and PBMCs. After iv and oral administration in rats, 9a displayed significant oral bioavailability (ca. 40%) and a promising plasma elimination half-life (4 h).

  DOI：

  10.1021/jm00038a005