tert-butyl N-[4-[5-[(2S)-2-amino-3-[tert-butyl(dimethyl)silyl]oxypropyl]-2-(2-cyclohexylethoxy)phenyl]butyl]carbamate | 209472-50-4

• 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: tert-butyl N-[4-[5-[(2S)-2-amino-3-[tert-butyl(dimethyl)silyl]oxypropyl]-2-(2-cyclohexylethoxy)phenyl]butyl]carbamate
• CAS: 209472-50-4
• 化学式: C₃₂H₅₈N₂O₄Si
• 分子量: 562.909
• InChiKey: YUSSJMZGYPLSQT-NDEPHWFRSA-N

物化性质

• 沸点：
  630.924±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.992±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.77
• 重原子数：
  39
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  82.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[4-[5-[(2S)-2-amino-3-[tert-butyl(dimethyl)silyl]oxypropyl]-2-(2-cyclohexylethoxy)phenyl]butyl]carbamate 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 19.5h， 生成 N-{(S)-2-[3-(4-Amino-butyl)-4-(2-cyclohexyl-ethoxy)-phenyl]-1-hydroxymethyl-ethyl}-2-{4-[4-(2-methyl-imidazol-1-yl)-butyl]-phenyl}-acetamide
  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 、 咪唑 、 lithium hydroxide 、 copper(l) iodide 、 sodium azide 、 (Ph₃)2PPdCl₂ 、 硼烷 、 四丁基氟化铵 、 甲基三苯氧基碘磷 、 水 、 氢气 、 溶剂黄146 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -5.0~70.0 ℃ 、344.73 kPa 条件下， 反应 58.25h， 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

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.