N-(5-tert-butyl-3-ethyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-3-nitrobenzenesulfonamide

• 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: N-(5-tert-butyl-3-ethyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-3-nitrobenzenesulfonamide
• 英文别名: (NZ)-N-(5-tert-butyl-3-ethyl-4-methyl-thiazol-2-ylidene)-3-nitro-benzenesulfonamide；(NZ)-N-(5-tert-butyl-3-ethyl-4-methyl-1,3-thiazol-2-ylidene)-3-nitrobenzenesulfonamide
• 化学式: C₁₆H₂₁N₃O₄S₂
• 分子量: 383.492
• InChiKey: ZMBHEFAFPIBBJU-ICFOKQHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 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 24.0h， 生成 N-(5-tert-butyl-3-ethyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-3-nitrobenzenesulfonamide
  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

文献信息

• Regioselective Alkylation of Thiazolylsulfonamides: Direct and Efficient Synthesis of 3‐Alkylthiazolidene Derivatives
  作者：Naoyuki Masuda、Osamu Yamamoto、Masahiro Fujii、Tetsuro Ohgami、Ayako Moritomo、Toru Kontani、Shunji Kageyama、Mitsuaki Ohta

  DOI：10.1080/00397910500186730

  日期：2005.9.1

  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.