ethyl N-(4-p-nitrophenyl-2-thiazolyl)carbamate | 83758-18-3

• 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: ethyl N-(4-p-nitrophenyl-2-thiazolyl)carbamate
• 英文别名: ethyl N-[4-(4-nitrophenyl)-1,3-thiazol-2-yl]carbamate
• CAS: 83758-18-3
• 化学式: C₁₂H₁₁N₃O₄S
• 分子量: 293.303
• InChiKey: SVHUEZMHCWXWTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl N-(4-p-nitrophenyl-2-thiazolyl)carbamate 在 palladium/carbon catalyst 作用下， 以 乙酸乙酯 为溶剂， 生成 ethyl N-(4-p-aminophenyl-2-thiazolyl)carbamate
  参考文献：
  名称：

  N-(4-Phenyl-2-thiazolyl)carbamate derivatives

  摘要：

  本发明提供了新的化学化合物，即N-(4-苯基-2-噻唑基)氨基甲酸酯衍生物，以及制备该化合物的方法和含有氨基甲酸酯衍生物的药物组合物。具体来说，本发明提供了具有免疫调节活性的N-(4-苯基-2-噻唑基)氨基甲酸酯衍生物，因此对于类风湿性关节炎等免疫性疾病有效，并且对于病毒性疾病或低毒性的癌症免疫疗法也具有用处。

  公开号：

  US04511574A1
• 作为产物：
  描述：

  2-溴-4'-硝基苯乙酮 在 三乙胺 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 5.0h， 生成 ethyl N-(4-p-nitrophenyl-2-thiazolyl)carbamate
  参考文献：
  名称：

  Synthesis, anticonvulsant and toxicity screening of thiazolyl–thiadiazole derivatives

  摘要：

  Various thiazole-substituted thiadiazole derivatives (7a-t) were designed and synthesized using substituted acetophenones and substituted anilines as starting materials. Thiazole and thiadiazole moieties being anticonvulsants were clubbed together to get the titled compounds and their in vivo anticonvulsant screening were performed by two most adopted seizure models, maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (scPTZ). Three compounds 7i, 7l and 7n were found to be potent in both the screens with comparable ED50 and better TD50 values than some standard drugs. These compounds were also found to exert lesser toxic effects on liver.

  DOI：

  10.1007/s00044-010-9313-6

文献信息

• N-(4-PHENYL-2-THIAZOLYL)CARBAMATE DERIVATIVES, PROCESS FOR THEIR PREPARATION, AND MEDICINAL COMPOSITION CONTAINING SAME
  申请人：MITSUI TOATSU KAGAKU KABUSHIKI KAISHA

  公开号：EP0068033A1

  公开（公告）日：1983-01-05

  N-(4-Phenyl-2-thiazolyl)carbamate derivatives represented by the general formula (1): (wherein R, represents a lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, a nitro group or an amino group, and R2 represents a lower alkyl group or a halogenated lower alkyl group), a process for their preparation, and an immunity-controlling medicinal composition containing same, effective for chronic articular rheumatism, viral diseases, cancer, etc.

  通式（1）代表的 N-(4-苯基-2-噻唑基)氨基甲酸酯衍生物（其中 R 代表低级烷硫基、低级烷基亚磺酰基、低级烷基亚磺酰基、硝基或氨基，R2 代表低级烷基或卤代低级烷基）、其制备方法以及含有这些衍生物的免疫调节药物组合物，对慢性关节风湿病、病毒性疾病、癌症等有效。
• Triazole incorporated thiazoles as a new class of anticonvulsants: Design, synthesis and in vivo screening
  作者：Nadeem Siddiqui、Waquar Ahsan

  DOI：10.1016/j.ejmech.2009.12.062

  日期：2010.4

  Various 3-[4-(substituted phenyl)-1,3-thiazol-2-ylamino1-4-(substituted phenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thiones (7a-t) were designed keeping in view the structural requirements suggested in the pharmacophore model for anticonvulsant activity. Thiazole and triazole moieties being anticonvulsants were clubbed together to get the titled compounds and their in vivo anticonvulsant screening were performed by two most adopted seizure models, maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (scPTZ). Two compounds 7d and 7f showed significant anticonvulsant activity in both the screens with ED50 values 23.9 mg/kg and 13.4 mg/kg respectively in MES screen and 178.6 mg/kg and 81.6 mg/kg respectively in scPTZ test. They displayed a wide margin of safety with Protective index (PI), median hypnotic dose (HD50) and median lethal dose (LD50) much higher than the standard drugs. (C) 2010 Elsevier Masson SAS. All rights reserved.
• CAKAHO, ISAO;JOKOYAMA, TATSURO;KADZITANI, SEHJTARO;OKADZAKI, YUTAKA;TOKUD+
  作者：CAKAHO, ISAO、JOKOYAMA, TATSURO、KADZITANI, SEHJTARO、OKADZAKI, YUTAKA、TOKUD+

  DOI：——

  日期：——
• JPS57188578A
  申请人：——

  公开号：JPS57188578A

  公开（公告）日：1982-11-19
• US4511574A
  申请人：——

  公开号：US4511574A

  公开（公告）日：1985-04-16