3-(4-chlorophenyl)-6-(4-nitrophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine | 68469-13-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-chlorophenyl)-6-(4-nitrophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine
• 英文别名: 3-(4-chloro-phenyl)-6-(4-nitro-phenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine；7H-3-(p-Chlorphenyl)-6-(p-nitrophenyl)-s-triazolo<3,4-b><1,3,4>thiadiazin
• CAS: 68469-13-6
• 化学式: C₁₆H₁₀ClN₅O₂S
• mdl: MFCD05705766
• 分子量: 371.807
• InChiKey: CUNRKJOPMNPMQS-UHFFFAOYSA-N

物化性质

• 熔点：
  215 °C(Solv: ethanol (64-17-5))
• 沸点：
  605.1±65.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(4-chloro-benzoyl)-1H-imidazole 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 15.5h， 生成 3-(4-chlorophenyl)-6-(4-nitrophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine
  参考文献：
  名称：

  Preliminary SAR and biological evaluation of antitubercular triazolothiadiazine derivatives against drug-susceptible and drug-resistant Mtb strains

  摘要：

  Following up the SAR study of triazolothiadiazoles for their antitubercular activities targeting Mt SD in our previous study, on the principle of scaffold hopping, the C3 and C6 positions of triazolothiadiazine were examined systematically to define a preliminary structure-activity relationship (SAR) with respect to biological activity. This study herein highlights the potential of two highly potent advanced leads 6c-3, 6g-3 and several other compounds with comparable potencies as promising new candidates for the treatment of TB (6c-3, MIC-H37Rv = 0.25 mu g/mL; MIC-MDRTB = 2.0 mu g/mL; MIC-RDRTB = 0.25 mu g/mL; Mt SD-IC50 = 86.39 mu g/mL; and 6g-3, MIC-H37Rv = 1.0 mu g/mL; MIC-MDRTB = 4.0 mu g/mL; MICRDRTB = 2.0 mu g/mL; Mt SD-IC50 = 73.57 mu g/mL). Compounds 6c-3 and 6g-3 possessed a para-nitro phenyl at the 6 position showed low Vero and HepG2 cells toxicity, turning out to be two excellent lead candidates for preclinical trials. In addition, in vitro Mt SD inhibitory assay indicates that Mt SD is at least one of the targets for their antitubercular activity. Thus, they may turn out to be promising multidrug-resistance- reversing agents. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.10.027

文献信息

• Potential Broad Spectrum Anthelmintics IV: Design, Synthesis, and Antiparasitic Screening of Certain 3,6-Disubstituted- (7H) -s -triazolo- [3,4-b][1,3,4]thiadiazine Derivatives
  作者：M.A. El-Dawy、A.-Mohsen M.E. Omar、Abla M. Ismail、A.A.B. Hazzaa

  DOI：10.1002/jps.2600720111

  日期：1983.1

  Abstract A series of 3,6-disubstituted-(7H)-s-triazolo[3,4-b][l,3,4]- thiadiazine derivatives were prepared. The compounds were designed to obtain structural similarities and/or bear isosteric relation with certain fused systems encountered in some well-known antiparasitic drugs. The substituents in all products were selected according to the Topliss scheme. Preliminary screening for antiparasitic

  摘要制备了一系列3,6-二取代-（7H）-s-三唑并[3,4-b] [1,3,4]-噻二嗪衍生物。设计这些化合物以获得与某些众所周知的抗寄生虫药物中遇到的某些融合系统的结构相似性和/或具有等位关系。根据Topliss方案选择所有产物中的取代基。使用A虫（Ascaris vitulorum）初步筛选抗寄生虫活性表明，6取代的衍生物通常比3取代的衍生物更具活性，并且π效应比σ效应更为明显。
• 1H and13C NMR spectral characterization of some novel 7H-1,2,4-triazolo[3, 4-b] [1,3,4] thiadiazine derivatives
  作者：Xinxiang Lei、Lixue Zhang、Anjiang Zhang、Xiaoxia Ye、Jing Xiong

  DOI：10.1002/mrc.1940

  日期：2007.3

  Some novel 1, 2, 4‐triazolo[3,4‐b][1,3,4]thiadiazines derivatives were synthesized. The complete 1H and 13C NMR chemical shift assignments were analyzed on one‐ and two‐dimensional NMR techniques, including DEPT, NOE‐DIF, COSY, HMBC, and HSQC. Copyright © 2006 John Wiley & Sons, Ltd.

  合成了一些新型的 1, 2, 4-三唑并[3,4-b][1,3,4]噻二嗪衍生物。完整的 1H 和 13C NMR 化学位移分配在一维和二维 NMR 技术上进行分析，包括 DEPT、NOE-DIF、COSY、HMBC 和 HSQC。版权所有 © 2006 John Wiley & Sons, Ltd.
• Bala,S. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1978, vol. 16B, p. 481 - 483
  作者：Bala,S. et al.

  DOI：——

  日期：——
• EL-DAWY, M. A.;A. -MOHSEN, M. E. OMAR;ISMAIL, A. M.;HAZZAA, A. A. B., J. PHARM. SCI., 1983, 72, N 1, 45-50
  作者：EL-DAWY, M. A.、A. -MOHSEN, M. E. OMAR、ISMAIL, A. M.、HAZZAA, A. A. B.

  DOI：——

  日期：——
• BALA S.; GUPTA R. P.; SACHDEVA M. L.; SINGH A.; PUJARI H. K., INDIAN J. CHEM., 1978, B 16 NO 6, 481-483
  作者：BALA S.、 GUPTA R. P.、 SACHDEVA M. L.、 SINGH A.、 PUJARI H. K.

  DOI：——

  日期：——