7H-3-(4-Chlorophenyl)-6-phenyl-s-triazolo<3,4-b><1,3,4>thiadiazine | 68469-09-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 7H-3-(4-Chlorophenyl)-6-phenyl-s-triazolo<3,4-b><1,3,4>thiadiazine
• 英文别名: 3-(4-chlorophenyl)-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine；3-(p-chlorophenyl)-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thidiazine；3-(p-chlorophenyl)-6-phenyl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine；3-(4-chloro-phenyl)-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine；7H-3-(p-Chlorphenyl)-6-phenyl-s-triazolo<3,4-b><1,3,4>thiadiazin
• CAS: 68469-09-0
• 化学式: C₁₆H₁₁ClN₄S
• mdl: MFCD03783435
• 分子量: 326.809
• InChiKey: NVQHPQIKJXYCFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  235 °C(Solv: ethanol (64-17-5))
• 沸点：
  534.3±52.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 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：
  68.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7H-3-(4-Chlorophenyl)-6-phenyl-s-triazolo<3,4-b><1,3,4>thiadiazine 生成 3-(p-chlorophenyl)-6-phenyl-1H-pyrazolo[5,1-c][1,2,4]triazole
  参考文献：
  名称：

  Pyrolytic desulfurization ring contraction of condensed thiadiazines as a general route towards pyrazoloazines and pyrazoloazoles with a bridgehead (ring junction) nitrogen atom

  摘要：

  Pyrolytic conversion of [1,2,4]triazino[3,4-b][1,3,4]thiadiazin-4-ones, [1,3,4]thiadiazino[2,3-b]quinazolin-10-ones and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines into their corresponding pyrazolo[5,1-c][1,2,4]triazin-4-ones, Pyrazolo[4,3-b]quinazolin-9-ones and pyrazolo[5,1-b][1,2,4]triazoles via desulfurization ring contraction is described. The starting condensed 1,3,4-thiadiazines were prepared from the corresponding readily available 4-amino-3-thioxo-1,2,4-triazin-5(4H)-ones, 3-amino-2,3-dihydro-2-thioxo-quinazolin-4(1H)-one and 4-amino-3(2H)-thioxo-1,2,4-triazoles upon reaction with the appropriate alpha-haloketones in two steps, or directly in one step in ethylpyridinium tetrafluoroborate (ionic liquid, IL). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.067
• 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 7H-3-(4-Chlorophenyl)-6-phenyl-s-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。
• Studies on nitrophenylfuran derivatives
  作者：B.Shivarama Holla、P.M. Akberali、M.K. Shivananda

  DOI：10.1016/s0014-827x(01)01124-7

  日期：2001.12

  studies. The formation of 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines rather than 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazepines in the above condensation was unambiguously confirmed by X-ray crystallographic analysis of one of them. A possible mechanism is proposed to account for the formation of nitrophenylfurfurylidene-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines. Some of the newly synthesized triazolothiadiazines

  描述了从取代的苯乙酮和对硝基苯基糠醛开始合成四个1-芳基-3- [5-（对硝基苯基）-2-呋喃基] -2-丙烯-1-酮。然后将这些丙烯酮转化为相应的二溴衍生物，该二溴衍生物在脱氢溴化后得到α-溴丙烯酮而不是炔酮。这些二溴丙烷与4-氨基-5-巯基-1,2,4-三唑的缩合产生一类新的硝基苯基糠基亚基1,2,4-三唑并噻二嗪。在分析，红外光谱，核磁共振和质谱研究的基础上，建立了硝基苯基糠基亚基1,2,4-三唑并噻二嗪的结构。1,2,4-三唑并[3,4-b] -1,3,4-噻二嗪而不是1,2,4-三唑并[3,4-b] -1,3,4-噻二氮杂的形成通过其中之一的X射线晶体分析清楚地证实了上述缩合。提出了一种可能的机制来解释硝基苯基糠基亚基1,2,4-三唑[3,4-b] -1,3,4-噻二嗪的形成。筛选了一些新合成的三唑并噻二嗪的抗菌和抗病毒特性。
• Eweiss, N. F.; Bahajaj, A. A., Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 1173 - 1182
  作者：Eweiss, N. F.、Bahajaj, A. A.

  DOI：——

  日期：——
• Ring transformation of 1,3,4-oxadiazole to s-triazole-fused heterocycles. New synthetic route for thiazolo[2,3-c]-s-triazole and 7H-s-triazolo[3,4-b][1,3,4]thiadiazine
  作者：Tadashi Sasaki、Eikoh Ito、Ikuo Shimizu

  DOI：10.1021/jo00135a014

  日期：1982.7
• 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：——