(S)-ethyl 2-(2-(2-(tert-butoxycarbonylamino)-4-methylpentanamido)thiazol-4-yl)acetate | 1316304-12-7

• 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)-ethyl 2-(2-(2-(tert-butoxycarbonylamino)-4-methylpentanamido)thiazol-4-yl)acetate
• 英文别名: (S)-Ethyl 2-(2-(2-(tert-butoxycarbonylamino)-4-methylpentanamido)thiazol-4-yl) acetate (7a)；ethyl 2-[2-[[(2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]-1,3-thiazol-4-yl]acetate
• CAS: 1316304-12-7
• 化学式: C₁₈H₂₉N₃O₅S
• 分子量: 399.511
• InChiKey: REXAHXMUTUFHGK-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-ethyl 2-(2-(2-(tert-butoxycarbonylamino)-4-methylpentanamido)thiazol-4-yl)acetate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 7.0h， 以88%的产率得到ethyl 2-[2-[[(2S)-2-amino-4-methylpentanoyl]amino]-1,3-thiazol-4-yl]acetate
  参考文献：
  名称：

  Design, synthesis, and biological activity of thiazole derivatives as novel influenza neuraminidase inhibitors

  摘要：

  A series of novel influenza neuraminidase (NA) inhibitors based on thiazole core were synthesized and evaluated for their ability to inhibit NA of influenza A virus (H3N2). All compounds were synthesized in good yields starting from commercially available 2-amino-4-thiazole-acetic ester using a suitable synthetic strategy. These compounds showed moderate inhibitory activity against influenza A NA. The most potent compound of this series is compound 4d (IC50 = 3.43 mu M), which is about 20-fold less potent than oseltamivir, and could be used to design novel influenza NA inhibitors that exhibit increased activity based on thiazole ring.

  DOI：

  10.3109/14756366.2010.534732
• 作为产物：
  描述：

  L-亮氨酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.17h， 生成 (S)-ethyl 2-(2-(2-(tert-butoxycarbonylamino)-4-methylpentanamido)thiazol-4-yl)acetate
  参考文献：
  名称：

  Design, synthesis, and biological activity of thiazole derivatives as novel influenza neuraminidase inhibitors

  摘要：

  A series of novel influenza neuraminidase (NA) inhibitors based on thiazole core were synthesized and evaluated for their ability to inhibit NA of influenza A virus (H3N2). All compounds were synthesized in good yields starting from commercially available 2-amino-4-thiazole-acetic ester using a suitable synthetic strategy. These compounds showed moderate inhibitory activity against influenza A NA. The most potent compound of this series is compound 4d (IC50 = 3.43 mu M), which is about 20-fold less potent than oseltamivir, and could be used to design novel influenza NA inhibitors that exhibit increased activity based on thiazole ring.

  DOI：

  10.3109/14756366.2010.534732