methyl 2-[(tert-butoxycarbonyl)amino]-4-chloro-1,3-thiazole-5-carboxylate | 804482-36-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-[(tert-butoxycarbonyl)amino]-4-chloro-1,3-thiazole-5-carboxylate
• 英文别名: Methyl 2-((tert-butoxycarbonyl)amino)-4-chlorothiazole-5-carboxylate；methyl 4-chloro-2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazole-5-carboxylate
• CAS: 804482-36-8
• 化学式: C₁₀H₁₃ClN₂O₄S
• 分子量: 292.743
• InChiKey: LLFPBHPPKRRNMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲基锂 、 methyl 2-[(tert-butoxycarbonyl)amino]-4-chloro-1,3-thiazole-5-carboxylate 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 以98%的产率得到tert-butyl [4-chloro-5-(1-hydroxy-1-methylethyl)-1,3-thiazol-2-yl]carbamate
  参考文献：
  名称：

  Studies of nonnucleoside HIV-1 reverse transcriptase inhibitors. Part 1: Design and synthesis of thiazolidenebenzenesulfonamides

  摘要：

  A random high-throughput screening (HTS) program to discover novel normucleoside reverse transcriptase inhibitors (NNRTIs) has been carried out with MT-4 cells against a nevirapine-resistant virus, HIV-1(IIIB-R). The primary hit, a thiazolidene-benzenesulfonamide derivative, possessed good activity. A systematic modification program examining various substituents at the 3-, 4-, and 5-positions on the thiazole ring afforded compounds with enhanced anti-HIV-1 and reverse transcriptase (RT) inhibitory activities. These results confirm the important role of the substituents at these positions and the thiazolidenebenzenesulfonamide motif as a valuable lead series for the next generation NNRTIs. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.08.050
• 作为产物：
  描述：

  2-甲基-2-丙基(4-氯-5-甲酰基-1,3-噻唑-2-基)氨基甲酸酯 在 4-二甲氨基吡啶 、 sodium chlorite 、 potassium dihydrogenphosphate 、 2-甲基-2-丁烯 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 16.0h， 生成 methyl 2-[(tert-butoxycarbonyl)amino]-4-chloro-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  Studies of nonnucleoside HIV-1 reverse transcriptase inhibitors. Part 1: Design and synthesis of thiazolidenebenzenesulfonamides

  摘要：

  A random high-throughput screening (HTS) program to discover novel normucleoside reverse transcriptase inhibitors (NNRTIs) has been carried out with MT-4 cells against a nevirapine-resistant virus, HIV-1(IIIB-R). The primary hit, a thiazolidene-benzenesulfonamide derivative, possessed good activity. A systematic modification program examining various substituents at the 3-, 4-, and 5-positions on the thiazole ring afforded compounds with enhanced anti-HIV-1 and reverse transcriptase (RT) inhibitory activities. These results confirm the important role of the substituents at these positions and the thiazolidenebenzenesulfonamide motif as a valuable lead series for the next generation NNRTIs. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.08.050