(S)-ethyl 2-(2-(2-(tert-butoxycarbonylamino)-3-phenylpropanamido)thiazol-4-yl)acetate | 163486-55-3

• 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)-3-phenylpropanamido)thiazol-4-yl)acetate
• 英文别名: (S)-Ethyl 2-(2-(2-(tert-butoxycarbonylamino)-3-phenylpropanamido)thiazol-4-yl) acetate (9a)；ethyl 2-[2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-1,3-thiazol-4-yl]acetate
• CAS: 163486-55-3
• 化学式: C₂₁H₂₇N₃O₅S
• 分子量: 433.528
• InChiKey: BOVTVNPNAGCEPF-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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)-3-phenylpropanamido)thiazol-4-yl)acetate 在 盐酸 、 lithium hydroxide monohydrate 作用下， 以 1,4-二氧六环 、 水 、 乙酸乙酯 为溶剂， 反应 7.0h， 生成 (S)-2-(2-(2-amino-3-phenylpropanamido)thiazol-4-yl)acetic acid
  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-苯丙氨酸 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)-3-phenylpropanamido)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

文献信息

• Gold catalysis on immobilized substrates: a heteroannulation approach to the solid-supported synthesis of indoles
  作者：Agustina La-Venia、Sebastián A. Testero、Mirta P. Mischne、Ernesto G. Mata

  DOI：10.1039/c2ob06881h

  日期：——

  A gold-catalyzed cyclization of immobilized 2-alkynylanilines was developed as the key step in the synthetic sequence for the preparation of 2-substituted indoles. These results demonstrate the potential of the unexplored combination of gold catalysis and solid-phase organic synthesis.

  作为制备 2-取代吲哚的合成序列中的关键步骤，开发了固定化 2-炔基苯胺的金催化环化。这些结果证明了金催化与固相有机合成这一尚未开发的组合所具有的潜力。
• Design, synthesis, and biological activity of thiazole derivatives as novel influenza neuraminidase inhibitors
  作者：Yu Liu、Lei Zhang、Jianzhi Gong、Hao Fang、Ailin Liu、Guanhua Du、Wenfang Xu

  DOI：10.3109/14756366.2010.534732

  日期：2011.8.1

  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.