benzyl N-[(E,2S,5R)-5-benzyl-7-chloro-6-hydroxy-1-naphthalen-2-ylsulfanylhept-3-en-2-yl]carbamate | 1027968-49-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: benzyl N-[(E,2S,5R)-5-benzyl-7-chloro-6-hydroxy-1-naphthalen-2-ylsulfanylhept-3-en-2-yl]carbamate
• CAS: 1027968-49-5
• 化学式: C₃₂H₃₂ClNO₃S
• 分子量: 546.13
• InChiKey: RYMJLMPOVDKBMI-DYWCMWQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  83.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl N-[(E,2S,5R)-5-benzyl-7-chloro-6-hydroxy-1-naphthalen-2-ylsulfanylhept-3-en-2-yl]carbamate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以1.43 g的产率得到N-[1(S)-(2-naphthylthiomethyl)-4(R)-[2(R,S)-oxiranyl]-5-phenylpent-2(E)-enyl](phenylmethoxy)formamide
  参考文献：
  名称：

  Reduction of Peptide Character of HIV Protease Inhibitors That Exhibit Nanomolar Potency against Multidrug Resistant HIV-1 Strains

  摘要：

  Novel HIV protease inhibitors containing a hydroxyethylamine dipeptide isostere as a transition state-mimic king structure were synthesized by combining substructures of known HIV protease inhibitors. Among them, TYA5 and TYB5 were proven to be not only potent enzyme inhibitors (K-i = 0.12 nM and 0.10 nM, respectively) but also strong anti-HIV agents (IC50 = 9.5 nM and 66 nM, respectively), even against viral strains with multidrug resistance. Furthermore, insertion of an (E)-alkene dipeptide isostere at the P-1-P-2 position of TYB5 led to development of a purely nonpeptidic protease inhibitor, TYB1 (K-i = 0.38 nM, IC50 = 160 nM).

  DOI：

  10.1021/jm020537i
• 作为产物：
  描述：

  1(R)-[2-(tert-butyldimethylsiloxy)-1(R)-[[N-(phenylmethoxy)carbonyl]amino]ethyl]prop-2-enyl acetate 在 吡啶 、 盐酸 、 甲醇 、 sodium tetrahydroborate 、 六氟合硅酸 、 sodium hydride 、 sodium carbonate 、 臭氧 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 氯仿 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 9.25h， 生成 benzyl N-[(E,2S,5R)-5-benzyl-7-chloro-6-hydroxy-1-naphthalen-2-ylsulfanylhept-3-en-2-yl]carbamate
  参考文献：
  名称：

  Reduction of Peptide Character of HIV Protease Inhibitors That Exhibit Nanomolar Potency against Multidrug Resistant HIV-1 Strains

  摘要：

  Novel HIV protease inhibitors containing a hydroxyethylamine dipeptide isostere as a transition state-mimic king structure were synthesized by combining substructures of known HIV protease inhibitors. Among them, TYA5 and TYB5 were proven to be not only potent enzyme inhibitors (K-i = 0.12 nM and 0.10 nM, respectively) but also strong anti-HIV agents (IC50 = 9.5 nM and 66 nM, respectively), even against viral strains with multidrug resistance. Furthermore, insertion of an (E)-alkene dipeptide isostere at the P-1-P-2 position of TYB5 led to development of a purely nonpeptidic protease inhibitor, TYB1 (K-i = 0.38 nM, IC50 = 160 nM).

  DOI：

  10.1021/jm020537i

文献信息

• Reduction of Peptide Character of HIV Protease Inhibitors That Exhibit Nanomolar Potency against Multidrug Resistant HIV-1 Strains
  作者：Hirokazu Tamamura、Yasuhiro Koh、Satoshi Ueda、Yoshikazu Sasaki、Tomonori Yamasaki、Manabu Aoki、Kenji Maeda、Yoriko Watai、Hisashi Arikuni、Akira Otaka、Hiroaki Mitsuya、Nobutaka Fujii

  DOI：10.1021/jm020537i

  日期：2003.4.1

  Novel HIV protease inhibitors containing a hydroxyethylamine dipeptide isostere as a transition state-mimic king structure were synthesized by combining substructures of known HIV protease inhibitors. Among them, TYA5 and TYB5 were proven to be not only potent enzyme inhibitors (K-i = 0.12 nM and 0.10 nM, respectively) but also strong anti-HIV agents (IC50 = 9.5 nM and 66 nM, respectively), even against viral strains with multidrug resistance. Furthermore, insertion of an (E)-alkene dipeptide isostere at the P-1-P-2 position of TYB5 led to development of a purely nonpeptidic protease inhibitor, TYB1 (K-i = 0.38 nM, IC50 = 160 nM).