1,3-thiazol-5-ylmethyl N-aminocarbamate | 1551455-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-thiazol-5-ylmethyl N-aminocarbamate
• CAS: 1551455-49-2
• 化学式: C₅H₇N₃O₂S
• 分子量: 173.195
• InChiKey: OKRDBJVNORLSRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(3-((2-isopropylthiazol-4-yl)methyl)-3-methylureido)-3-methyl-N-((S)-4-oxo-1-phenylbutan-2-yl)butanamide 、 1,3-thiazol-5-ylmethyl N-aminocarbamate 在 sodium cyanoborohydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 thiazol-5-ylmethyl N-[benzyl-[(3S)-3-[[(2S)-2-[[(2-isopropylthiazol-4-yl)methyl-methyl-carbamoyl]amino]-3-methyl-butanoyl]amino]-4-phenyl-butyl]amino]carbamate
  参考文献：
  名称：

  Structure–activity relationships of diamine inhibitors of cytochrome P450 (CYP) 3A as novel pharmacoenhancers, part I: Core region

  摘要：

  Ritonavir (RTV), an HIV-1 protease inhibitor (PI), is also a potent mechanism-based inhibitor of human cytochrome P450 3A (CYP3A) and has been widely prescribed as a pharmacoenhancer. As a boosting agent for marketed PIs, it reduces pill burden, and improves compliance. Removal of the hydroxyl group from RTV reduces, but does not eliminate HIV PI activity and does not affect CYP3A inhibition. Herein we report the discovery of a novel series of CYP3A inhibitors that are devoid of antiviral activity. The synthesis and evaluation of analogs with extensive modifications of the 1,4-diamine core along with the structure activity relationships with respect to anti-HIV activity, CYP3A inhibitory activity, selectivity against other CYP enzymes and the human pregnane X receptor (PXR) will be discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.058
• 作为产物：
  描述：

  ((5-噻唑基)甲基)-(4-硝基苯基)碳酸酯 在 肼 作用下， 生成 1,3-thiazol-5-ylmethyl N-aminocarbamate
  参考文献：
  名称：

  Structure–activity relationships of diamine inhibitors of cytochrome P450 (CYP) 3A as novel pharmacoenhancers, part I: Core region

  摘要：

  Ritonavir (RTV), an HIV-1 protease inhibitor (PI), is also a potent mechanism-based inhibitor of human cytochrome P450 3A (CYP3A) and has been widely prescribed as a pharmacoenhancer. As a boosting agent for marketed PIs, it reduces pill burden, and improves compliance. Removal of the hydroxyl group from RTV reduces, but does not eliminate HIV PI activity and does not affect CYP3A inhibition. Herein we report the discovery of a novel series of CYP3A inhibitors that are devoid of antiviral activity. The synthesis and evaluation of analogs with extensive modifications of the 1,4-diamine core along with the structure activity relationships with respect to anti-HIV activity, CYP3A inhibitory activity, selectivity against other CYP enzymes and the human pregnane X receptor (PXR) will be discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.058