methyl 5-isopropyl-2-{[(3-nitrophenyl)sulfonyl]amino}-1,3-thiazole-4-carboxylate | 804482-42-6

• 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-2-{[(3-nitrophenyl)sulfonyl]amino}-1,3-thiazole-4-carboxylate
• 英文别名: Methyl 2-[(3-nitrophenyl)sulfonylamino]-5-propan-2-yl-1,3-thiazole-4-carboxylate
• CAS: 804482-42-6
• 化学式: C₁₄H₁₅N₃O₆S₂
• 分子量: 385.422
• InChiKey: KSEALHPLTHWZHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  562.6±60.0 °C(Predicted)
• 密度：
  1.476±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  168
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 5-isopropyl-2-{[(3-nitrophenyl)sulfonyl]amino}-1,3-thiazole-4-carboxylate 在 ammonium hydroxide 、 sodium hydride 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 17.25h， 生成 (NZ)-N-(4-cyano-5-isopropyl-3-methyl-thiazol-2-ylidene)-3-nitro-benzenesulfonamide
  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-氨基-5-异丙基-1,3-噻唑-4-羧酸甲酯 、 3-硝基苯磺酰氯 在 吡啶 作用下， 反应 12.0h， 以75%的产率得到methyl 5-isopropyl-2-{[(3-nitrophenyl)sulfonyl]amino}-1,3-thiazole-4-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

文献信息

• Studies of nonnucleoside HIV-1 reverse transcriptase inhibitors. Part 1: Design and synthesis of thiazolidenebenzenesulfonamides
  作者：Naoyuki Masuda、Osamu Yamamoto、Masahiro Fujii、Tetsuro Ohgami、Jiro Fujiyasu、Toru Kontani、Ayako Moritomo、Masaya Orita、Hiroyuki Kurihara、Hironobu Koga、Hideaki Nakahara、Shunji Kageyama、Mitsuaki Ohta、Hiroshi Inoue、Toshifumi Hatta、Hiroshi Suzuki、Kenji Sudo、Yasuaki Shimizu、Eiichi Kodama、Masao Matsuoka、Masatoshi Fujiwara、Tomoyuki Yokota、Shiro Shigeta、Masanori Baba

  DOI：10.1016/j.bmc.2004.08.050

  日期：2004.12

  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.
• 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.