methyl 5-isopropyl-3-methyl-2-{[(3-nitrophenyl)sulfonyl]imino}-2,3-dihydro-1,3-thiazole-4-carboxylate

• 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: methyl 5-isopropyl-3-methyl-2-{[(3-nitrophenyl)sulfonyl]imino}-2,3-dihydro-1,3-thiazole-4-carboxylate
• 英文别名: methyl (2Z)-5-isopropyl-3-methyl-2-(3-nitrophenyl)sulfonylimino-thiazole-4-carboxylate；methyl (2Z)-3-methyl-2-(3-nitrophenyl)sulfonylimino-5-propan-2-yl-1,3-thiazole-4-carboxylate
• 化学式: C₁₅H₁₇N₃O₆S₂
• 分子量: 399.448
• InChiKey: LFGXXVVLMPMFNY-NXVVXOECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  156
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 5-isopropyl-3-methyl-2-{[(3-nitrophenyl)sulfonyl]imino}-2,3-dihydro-1,3-thiazole-4-carboxylate 在 ammonium hydroxide 、 氯化亚砜 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 氯仿 为溶剂， 反应 4.25h， 以65%的产率得到(2Z)-5-isopropyl-3-methyl-2-(3-nitrophenyl)sulfonylimino-thiazole-4-carboxamide
  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：

  3-硝基苯磺酰氯 在 吡啶 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 methyl 5-isopropyl-3-methyl-2-{[(3-nitrophenyl)sulfonyl]imino}-2,3-dihydro-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  Regioselective Alkylation of Thiazolylsulfonamides: Direct and Efficient Synthesis of 3‐Alkylthiazolidene Derivatives

  摘要：

  Various N-3-alkylated thiazolidenesulfonamide derivatives were efficiently prepared by the direct endo-selective alkylation of thiazolylsulfonamides. The effects of different bases and solvents were investigated, and the NaH-THF combination was found to be the most effective at conferring high yields and endo-selectivity.

  DOI：

  10.1080/00397910500186730