(S)-2-tert-Butoxycarbonylamino-3-[4-(1,2-dihydroxy-ethyl)-phenyl]-propionic acid benzyl ester | 1027897-56-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-tert-Butoxycarbonylamino-3-[4-(1,2-dihydroxy-ethyl)-phenyl]-propionic acid benzyl ester
• 英文别名: benzyl (2S)-3-[4-(1,2-dihydroxyethyl)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1027897-56-8
• 化学式: C₂₃H₂₉NO₆
• 分子量: 415.486
• InChiKey: DKNDSRRKXWENGQ-XJDOXCRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-tert-Butoxycarbonylamino-3-[4-(1,2-dihydroxy-ethyl)-phenyl]-propionic acid benzyl ester 在 palladium on activated charcoal sodium tetrahydroborate 、 sodium periodate 、 氢气 作用下， 以 乙醚 、 乙醇 、 乙酸乙酯 为溶剂， 反应 8.33h， 生成 N-boc-4-hydroxymethylphenylalanine
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Biological Evaluation of Irreversible Human Rhinovirus 3C Protease Inhibitors. 2. Peptide Structure−Activity Studies

  摘要：

  The structure-based design, chemical synthesis, and biological evaluation of various peptide-derived human rhinovirus (HRV) 3C protease (3CP) inhibitors are described. These compounds are comprised of an ethyl propenoate Michael acceptor moiety and a tripeptidyl binding determinant. The systematic modification of each amino acid residue present in the binding determinant as well as the N-terminal functionality is described. Such modifications are shown to provide irreversible HRV-14 3CP inhibitors with anti-3CP activities (k(obs)/[I]) ranging from 60 to 280 000 M-1 s(-1) and antiviral EC50's which approach 0.15 mu M. An optimized inhibitor which incorporates several improvements identified by the structure-activity studies is also described. This molecule displays very rapid irreversible inhibition of HRV-14 3CP (k(obs)/[I] = 800 000 M-1 s(-1)) and potent antiviral activity against HRV-14 in cell culture (EC50 = 0.056 mu M). A 1.9 Angstrom crystal structure of an S-alkylthiocarbamate-containing inhibitor complexed with HRV-8 3CP is also detailed.

  DOI：

  10.1021/jm9800696
• 作为产物：
  描述：

  Boc-4-碘-L-苯丙氨酸 在 4-二甲氨基吡啶 、 四氧化锇 、 四(三苯基膦)钯 、 2,6-二叔丁基-4-甲基苯酚 、 N-甲基吗啉氧化物 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 丙酮 为溶剂， 反应 15.0h， 生成 (S)-2-tert-Butoxycarbonylamino-3-[4-(1,2-dihydroxy-ethyl)-phenyl]-propionic acid benzyl ester
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Biological Evaluation of Irreversible Human Rhinovirus 3C Protease Inhibitors. 2. Peptide Structure−Activity Studies

  摘要：

  The structure-based design, chemical synthesis, and biological evaluation of various peptide-derived human rhinovirus (HRV) 3C protease (3CP) inhibitors are described. These compounds are comprised of an ethyl propenoate Michael acceptor moiety and a tripeptidyl binding determinant. The systematic modification of each amino acid residue present in the binding determinant as well as the N-terminal functionality is described. Such modifications are shown to provide irreversible HRV-14 3CP inhibitors with anti-3CP activities (k(obs)/[I]) ranging from 60 to 280 000 M-1 s(-1) and antiviral EC50's which approach 0.15 mu M. An optimized inhibitor which incorporates several improvements identified by the structure-activity studies is also described. This molecule displays very rapid irreversible inhibition of HRV-14 3CP (k(obs)/[I] = 800 000 M-1 s(-1)) and potent antiviral activity against HRV-14 in cell culture (EC50 = 0.056 mu M). A 1.9 Angstrom crystal structure of an S-alkylthiocarbamate-containing inhibitor complexed with HRV-8 3CP is also detailed.

  DOI：

  10.1021/jm9800696