methyl (2S)-3-[4-(2-cyclohexylethoxy)-3-(4-hydroxybutyl)phenyl]-2-(phenylmethoxycarbonylamino)propanoate | 204513-80-4

• 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: methyl (2S)-3-[4-(2-cyclohexylethoxy)-3-(4-hydroxybutyl)phenyl]-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 204513-80-4
• 化学式: C₃₀H₄₁NO₆
• 分子量: 511.659
• InChiKey: JGFCGSZMBZLOIJ-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S)-3-[4-(2-cyclohexylethoxy)-3-(4-hydroxybutyl)phenyl]-2-(phenylmethoxycarbonylamino)propanoate 在 palladium on activated charcoal N-甲基吗啉 、 咪唑 、 lithium hydroxide 、 sodium azide 、 硼烷 、 甲基三苯氧基碘磷 、 水 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -5.0~70.0 ℃ 、206.84 kPa 条件下， 反应 18.0h， 生成 tert-butyl N-[4-[5-[(2S)-2-amino-3-[tert-butyl(dimethyl)silyl]oxypropyl]-2-(2-cyclohexylethoxy)phenyl]butyl]carbamate
  参考文献：
  名称：

  Novel Biologically Active Nonpeptidic Inhibitors of MyristoylCoA:Protein N-Myristoyltransferase

  摘要：

  A new class of biologically active nonpeptidic inhibitors of Candida albicans NMT has been synthesized starting from the octapeptide ALYASKLS-NH2 (2). The synthetic strategy entailed the preparation of novel protected Ser-Lys mimics 9 and 12 from (S)- or (R)-3-iodotyrosine and then grafting key enzyme recognition elements in a stepwise manner. Like 2, compounds 16, 17, and 18 are competitive Candida NMT inhibitors that bind to the peptide recognition site of the enzyme. Moreover, 16-18 have an affinity comparable to that of 2 even though they are devoid of peptide bonds. In contrast to 2, these nonpeptidic inhibitors exhibit antifungal activity.

  DOI：

  10.1021/jm980001q
• 作为产物：
  描述：

  3-iodo-L-tyrosine methyl ester hydrochloride 在 palladium on activated charcoal N-甲基吗啉 、 copper(l) iodide 、 (Ph₃)2PPdCl₂ 、 四丁基氟化铵 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 10.0~25.0 ℃ 、344.73 kPa 条件下， 反应 40.25h， 生成 methyl (2S)-3-[4-(2-cyclohexylethoxy)-3-(4-hydroxybutyl)phenyl]-2-(phenylmethoxycarbonylamino)propanoate
  参考文献：
  名称：

  Novel Biologically Active Nonpeptidic Inhibitors of MyristoylCoA:Protein N-Myristoyltransferase

  摘要：

  A new class of biologically active nonpeptidic inhibitors of Candida albicans NMT has been synthesized starting from the octapeptide ALYASKLS-NH2 (2). The synthetic strategy entailed the preparation of novel protected Ser-Lys mimics 9 and 12 from (S)- or (R)-3-iodotyrosine and then grafting key enzyme recognition elements in a stepwise manner. Like 2, compounds 16, 17, and 18 are competitive Candida NMT inhibitors that bind to the peptide recognition site of the enzyme. Moreover, 16-18 have an affinity comparable to that of 2 even though they are devoid of peptide bonds. In contrast to 2, these nonpeptidic inhibitors exhibit antifungal activity.

  DOI：

  10.1021/jm980001q

文献信息

• Novel Biologically Active Nonpeptidic Inhibitors of MyristoylCoA:Protein <i>N</i>-Myristoyltransferase
  作者：Balekudru Devadas、Sandra K. Freeman、Charles A. McWherter、Nandini S. Kishore、Jennifer K. Lodge、Emily Jackson-Machelski、Jeffrey I. Gordon、James A. Sikorski

  DOI：10.1021/jm980001q

  日期：1998.3.1

  A new class of biologically active nonpeptidic inhibitors of Candida albicans NMT has been synthesized starting from the octapeptide ALYASKLS-NH2 (2). The synthetic strategy entailed the preparation of novel protected Ser-Lys mimics 9 and 12 from (S)- or (R)-3-iodotyrosine and then grafting key enzyme recognition elements in a stepwise manner. Like 2, compounds 16, 17, and 18 are competitive Candida NMT inhibitors that bind to the peptide recognition site of the enzyme. Moreover, 16-18 have an affinity comparable to that of 2 even though they are devoid of peptide bonds. In contrast to 2, these nonpeptidic inhibitors exhibit antifungal activity.