5-(4-bromophenyl)-N-(4-methylphenyl)-2-amino-1,3,4-thiadiazole | 92433-18-6

• 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: 5-(4-bromophenyl)-N-(4-methylphenyl)-2-amino-1,3,4-thiadiazole
• 英文别名: 5-(4-bromophenyl)-N-(p-tolyl)-1,3,4-thiadiazol-2-amine；5-(4-bromophenyl)-N-p-tolyl-1,3,4-thiadiazol-2-amine；5-(4-bromophenyl)-N-(4-methylphenyl)-1,3,4-thiadiazol-2-amine
• CAS: 92433-18-6
• 化学式: C₁₅H₁₂BrN₃S
• 分子量: 346.25
• InChiKey: GBYLUTDNWQNRBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对溴苯甲酰肼 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 5-(4-bromophenyl)-N-(4-methylphenyl)-2-amino-1,3,4-thiadiazole
  参考文献：
  名称：

  1,3,4-Thiadiazole Derivatives. Synthesis, Structure Elucidation, and Structure−Antituberculosis Activity Relationship Investigation

  摘要：

  A series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized, the compounds structures were elucidated and screened for the antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the tested compounds, 2-phenylamino-5-(4-fluorophenyl)-1,3,4-thiadiazole 22 showed the highest inhibitory activity. The relationships between the structures of compounds and their antituberculosis activity were investigated by the Electronic-Topological Method (ETM) and feed forward neural networks (FFNNs) trained with the back-propagation algorithm. As a result of the approach, a system of pharmacophores and anti-pharmacophores has been found that effectively separates compounds of the examination set into groups of active and inactive compounds. The system can be applied to the screening and design of new active compounds possessing skeletons similar to those used in the present study.

  DOI：

  10.1021/jm0495632

文献信息

• Synthesis of 2-amino-substituted-1,3,4-thiadiazoles via 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) mediated intramolecular C–S bond formation in thiosemicarbazones
  作者：Sarangthem Joychandra Singh、Suresh Rajamanickam、Anupal Gogoi、Bhisma K. Patel

  DOI：10.1016/j.tetlet.2016.01.083

  日期：2016.3

  An effective oxidative intramolecular cyclization (C–S bond formation) of thiosemicarbazones using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) has been developed to afford a diverse array of 2-amino-substituted-1,3,4-thiadiazoles. The attractive features of this protocol are operational simplicity, obviates the need of expensive transition-metal catalysts and broad substrate scope.

  已开发出使用2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）的硫半脲的有效氧化分子内环化（CS键形成），以提供各种2-氨基取代的- 1,3,4-噻二唑。该协议的吸引人的特点是操作简单，无需昂贵的过渡金属催化剂和广泛的底物范围。
• Thiadiazole derivatives as New Class of β-glucuronidase inhibitors
  作者：Uzma Salar、Muhammad Taha、Nor Hadiani Ismail、Khalid Mohammed Khan、Syahrul Imran、Shahnaz Perveen、Abdul Wadood、Muhammad Riaz

  DOI：10.1016/j.bmc.2016.03.020

  日期：2016.4

  Thiadiazole derivatives 1–24 were synthesized via a single step reaction and screened for in vitro β-glucuronidase inhibitory activity. All the synthetic compounds displayed good inhibitory activity in the range of IC50 = 2.16 ± 0.01–58.06 ± 1.60 μM as compare to standard d-saccharic acid 1,4-lactone (IC50 = 48.4 ± 1.25 μM). Molecular docking study was conducted in order to establish the structure–activity

  噻二唑衍生物1 – 24通过一步反应合成，并筛选了体外β-葡萄糖醛酸苷酶抑制活性。 与标准d-蔗糖酸1,4-内酯相比，所有合成化合物在IC 50 = 2.16±0.01–58.06±1.60μM范围内均表现出良好的抑制活性（IC 50  = 48.4± 1.25μM ）。为了建立结构-活性关系（SAR），进行了分子对接研究，该关系表明噻二唑以及两个芳基部分（芳基和N-芳基）都具有抑制作用。所有合成化合物均通过1 H光谱技术进行表征，13 C NMR和EIMS。
• Complexes of silicon and phosphorus chlorides with nitrogen-containing bases as the condensing agents in the synthesis of amides
  作者：L. V. Besgubenko、S. E. Pipko、A. D. Sinitsa

  DOI：10.1134/s1070363212080099

  日期：2012.8

  High effectiveness of new condensing agents on the basis of complexes of silicon and phosphorus chlorides with nitrogen-containing bases in the synthesis of amides from carboxylic acids and amines and also in heterocyclization is shown. Factors affecting the readiness of formation of the amide bond and the yields of the final products are established.
• Srinivasan,V.R.; Ramachander,G., Indian Journal of Chemistry, 1963, vol. 1, p. 234 - 236
  作者：Srinivasan,V.R.、Ramachander,G.

  DOI：——

  日期：——
• 1,3,4-Thiadiazole Derivatives. Synthesis, Structure Elucidation, and Structure−Antituberculosis Activity Relationship Investigation
  作者：Elçin E. Oruç、Sevim Rollas、Fatma Kandemirli、Nathaly Shvets、Anatholy S. Dimoglo

  DOI：10.1021/jm0495632

  日期：2004.12.1

  A series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized, the compounds structures were elucidated and screened for the antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the tested compounds, 2-phenylamino-5-(4-fluorophenyl)-1,3,4-thiadiazole 22 showed the highest inhibitory activity. The relationships between the structures of compounds and their antituberculosis activity were investigated by the Electronic-Topological Method (ETM) and feed forward neural networks (FFNNs) trained with the back-propagation algorithm. As a result of the approach, a system of pharmacophores and anti-pharmacophores has been found that effectively separates compounds of the examination set into groups of active and inactive compounds. The system can be applied to the screening and design of new active compounds possessing skeletons similar to those used in the present study.