2-hydrazono-3,5-diphenyl-2,3-dihydro-1,3,4-thiadiazole | 204316-58-5

• 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: 2-hydrazono-3,5-diphenyl-2,3-dihydro-1,3,4-thiadiazole
• 英文别名: (3,5-diphenyl-1,3,4-thiadiazol-2-ylidene)hydrazine
• CAS: 204316-58-5
• 化学式: C₁₄H₁₂N₄S
• 分子量: 268.342
• InChiKey: HRMKQMWYNYTUFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.2
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-hydrazono-3,5-diphenyl-2,3-dihydro-1,3,4-thiadiazole 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 N,N'-bis-(3,5-diphenyl-3H-[1,3,4]thiadiazol-2-ylidene)-hydrazine
  参考文献：
  名称：

  Synthesis of 1,3,4-thiadiazines, bis-1,3,4-thiadiazoles, [1,2,4]triazino[3,4-b][1,3,4]thiadiazine, thiazolines from carbonothioic dihydrazide

  摘要：

  A novel and efficient synthesis of 1,3,4-thiadiazines, bis-1,3,4-thiadiazoles, [1,2,4]triazino[3,4-b][1,3,4] thiadiazine, and thiazolines is reported from the reaction of alpha-haloketo hydrazonoyl halides with carbonothioic dihydrazide or its analogues. The structures were elucidated on the basis of their elemental analysis, spectral data and an alternative synthetic route. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.011
• 作为产物：
  描述：

  (3,5-diphenyl-3H-[1,3,4]thiadiazol-2-ylidene)-nitroso-amine 在 溶剂黄146 、 锌 作用下， 生成 2-hydrazono-3,5-diphenyl-2,3-dihydro-1,3,4-thiadiazole
  参考文献：
  名称：

  Emam, Hussein A.; Zohdl, Hussein F.; Abdelhamid, Abdou O., Journal of Chemical Research, Miniprint, 1998, # 1, p. 169 - 179

  摘要：

  DOI：

文献信息

• Synthesis and antimicrobial activity of new thiazole and thiadiazole derivatives <i>via</i> ethyl pyruvate
  作者：Fatma M. Saleh、Abdou O. Abdelhamid、Hamdi M. Hassaneen

  DOI：10.1080/17415993.2019.1694678

  日期：2020.3.3

  Reaction of ethyl 2-(2-((methylthio)carbonothioyl)hydrazono)propanoate (2) and ethyl 2-(2-carbamothioyl-hydrazono)propanoate (3) with hydrazonoyl halides 4 a-e afforded the corresponding thiadiazoles 5 a-e. Also, treatment of compound 2 with α-ketohydrazonoyl halides 12a-f in absolute ethanol and in the presence of triethylamine gave the corresponding thiadiazoles 13a-f; while reaction of ethyl 2-(2-ca

  摘要 2-(2-((甲硫基)碳硫酰) 腙)丙酸乙酯(2)和2-(2-氨基甲硫酰-腙)丙酸乙酯(3)与腙酰卤4ae的反应得到相应的噻二唑5ae。同样，在无水乙醇中和在三乙胺存在下用α-酮腙酰卤12a-f处理化合物2得到相应的噻二唑13a-f；而 2-(2-氨基甲硫酰基-腙)丙酸乙酯 (3) 与 α-酮腙酰卤化物 12 反应得到噻唑衍生物 15。此外，化合物 3 与腙酰氯 12f 反应得到噻唑酮衍生物 18。抗菌研究使用两种-革兰氏阳性细菌和两革兰氏阴性细菌。数据显示，噻唑衍生物 17a 对敏感菌株 S. 的 MIC 值（高效衍生物）达到最低。MIC 值为 160 µg/ml 的金黄色葡萄球菌。图形概要
• Synthesis and SAR Study of the Novel Thiadiazole–Imidazole Derivatives as a New Anticancer Agents
  作者：Sobhi Mohamed Gomha、Hassan Mohamed Abdel-aziz、Khaled Dessouky Khalil

  DOI：10.1248/cpb.c16-00344

  日期：——

  In the present study, a novel series of 2-(2-(3-aryl-5-substituted-1,3,4-thiadiazol-2(3H)-ylidene)hydrazinyl)-4,4-diphenyl-1H-imidazol-5(4H)-one derivatives were designed and prepared via the reaction of the most versatile, hitherto unreported 2-(5-oxo-4,4-diphenyl-4,5-dihydro-1H-imidazol-2-yl)-N-phenylhydrazinecarbothioamide with the appropriate hydrazonoyl halides. In addition, some thiazole derivatives were prepared. The structures of the newly synthesized compounds were established based on spectroscopic evidences and their alternative syntheses. Some of the newly synthesized compounds have been evaluated for their anticancer activity against a liver carcinoma cell line HEPG2-1. Moreover, their structure–activity relationship (SAR) was explored for further development in this area. The results indicated that many of the tested compounds showed moderate to high anticancer activity with respective to doxorubicin as a reference drug. Consequently, the new synthesized series of thiadiazole–imidazole derivatives are considered as powerful anticancer agents.

  本研究中，设计并合成了一系列新型2-(2-(3-芳基-5-取代-1,3,4-噻二唑-2(3H)-亚基)酰肼基)-4,4-二苯基-1H-咪唑-5(4H)-酮衍生物，其合成方法是通过将迄今未报道的最通用的2-(5-氧-4,4-二苯基-4,5-二氢-1H-咪唑-2-基)-N-苯基酰肼硫脲与适当的酰肼基卤化物反应。此外，还合成了一些噻唑衍生物。新合成化合物的结构基于光谱证据及其替代合成方法进行确定。其中一些新合成化合物已针对肝癌HEPG2-1细胞系评估了其抗癌活性。此外，探讨了它们的构效关系(SAR)，为进一步开发该领域提供依据。结果表明，许多测试化合物显示出中等到高水平的抗癌活性，相对于参考药物阿霉素。因此，新合成的一系列噻二唑-咪唑衍生物被认为是强效的抗癌剂。
• Synthesis and molecular docking of some new bis-thiadiazoles as anti-hypertensive α-blocking agents
  作者：Waleed A. M. A. El-Enany、Sobhi M. Gomha、Ahmed K El-Ziaty、Wesam Hussein、Mohamed M. Abdulla、Shaimaa A. Hassan、Hanan A. Sallam、Rania S. Ali

  DOI：10.1080/00397911.2019.1683207

  日期：2020.1.2

  Moreover, all the novel synthesized derivatives were screened for their antihypertensive α-blocking efficacy against to assess their pharmaceutical significance. The encouraging promising results obtained from antihypertensive α-blocking activity studies on the newly synthesized derivatives make the synthesis of a new series of these compounds and studying of their pharmaceutical importance an active

  摘要 通过 2,2'-对苯二甲酰双（N-苯基肼碳硫酰胺）与多种腙酰氯在含有催化量 TEA 的乙醇中反应，以高收率合成了 12 种双噻二唑衍生物。所有新合成的化合物均通过物理和化学工具（FT-IR、1H NMR、13C NMR 和质谱）进行表征。此外，筛选了所有新型合成衍生物的抗高血压 α 阻断功效，以评估其药学意义。从对新合成衍生物的抗高血压 α 阻断活性研究中获得的令人鼓舞的有希望的结果使这些化合物的新系列的合成及其药物重要性的研究成为越来越多研究的活跃领域。最活跃的衍生物 15b 针对人多巴胺 D3 受体的分子对接由分子操作环境 (MOE 2014. 0901) 程序执行。图形概要
• Reactions with Hydrazonoyl Halides 61¹: Synthesis of 2,3-Dihydro-1,3,4-Thiadiazoles
  作者：Abdou O. Abdelhamid、Mamdouh A. M. Afifi

  DOI：10.1080/10426500801968185

  日期：2008.10.7

  stituted 1,3,4-thiadiazolines and 2-[4-(2,3-dimethyl-5-oxo-1-phenyl(3-pyrazolin-4-yl))(1,3-thiazol-2-yl)]cyanomethylene}-3-phenyl-5-substitu- ted 1,3,4-thiadiazolines were synthesized from hydrazonoyl halides and 4--2-aza-2-[(methylthiothioxomethyl)amino]vinyl}-2,3-dimethyl-1-phenyl-3-pyrazoin-5-one and 2-[4-(2,3-dimethyl-5-oxo-1-phenyl-3-pyrazolin-4-yl)-1,3-thiazol-2-yl]ethane-nitrile, respectively

  2-[1,2-二氮杂-3-(2,3-二甲基-5-氧代-1-苯基(3-吡唑啉-4-基))丙-2-亚苯基]-3-苯基-5-取代的1 ,3,4-噻二唑啉和 2-[4-(2,3-二甲基-5-氧代-1-苯基(3-吡唑啉-4-基))(1,3-噻唑-2-基)]氰基亚甲基}-3-苯基-5-取代的1,3,4-噻二唑啉由腙酰卤化物和4--2-氮杂-2-[(甲硫基硫代甲基)氨基]乙烯基}-2,3-二甲基-1合成-苯基-3-吡唑啉-5-酮和2-[4-(2,3-二甲基-5-氧代-1-苯基-3-吡唑啉-4-基)-1,3-噻唑-2-基]乙腈，分别。所有合成化合物都尽可能通过元素分析、光谱和替代合成路线进行阐明。
• Synthesis of Certain New Thiazole and 1,3,4-Thiadiazole Derivatives via the Utility of 3-Acetylindole
  作者：Abdou O. Abdelhamid、Sobhi M. Gomha、Saher M. Kandeel

  DOI：10.1002/jhet.2740

  日期：2017.3

  2‐(2‐(1‐(1H‐Indol‐3‐yl)ethylidene)‐hydrazinyl)‐4‐substituted 5‐(aryldiazenyl)thiazoles and 5‐((1‐(1H‐indol‐3‐yl)ethylidene)hydrazono)‐2‐substituted‐4‐phenyl‐4,5‐dihydro‐1,3,4‐thiadiazoles were synthesized via reaction of hydrazonoyl halides and 2‐(1‐(1H‐indol‐3‐yl)ethylidene)hydrazine‐1‐carbothioamide and alkyl 2‐(1‐(1H‐indol‐3‐yl)ethylidene)hydrazine‐1‐carbodithioate in ethanolic triethylamine. Structures

  2-（2-（1-（1- ħ -吲哚-3-基）亚乙基）-hydrazinyl）-4-取代的-5-（aryldiazenyl）噻唑和5 - （（1-（1- ħ -吲哚-3-基）通过酰卤与2-（1-（1-（1 H-吲哚-3-基）乙炔基）的反应合成了亚乙基）hydr唑啉）-2-取代-4-苯基-4,5-二氢-1,3,4-噻二唑乙醇三乙胺中的）肼-1-碳硫酰胺和烷基2-（1-（1 H-吲哚-3-基）亚乙基）肼-1-碳二硫酸酯。根据元素分析，光谱数据和可能的替代合成路线，阐明了新合成的结构。