2-(4-chloro-phenyl)-5-hydrazino-[1,3,4]thiadiazole | 59758-31-5

• 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-(4-chloro-phenyl)-5-hydrazino-[1,3,4]thiadiazole
• 英文别名: (2E)-5-(4-chlorophenyl)-2-hydrazinylidene-2,3-dihydro-1,3,4-thiadiazole；[5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl]hydrazine
• CAS: 59758-31-5
• 化学式: C₈H₇ClN₄S
• 分子量: 226.689
• InChiKey: ZMWACMXYZYHWDA-UHFFFAOYSA-N

物化性质

• 熔点：
  308-310 °C(Solv: ethanol (64-17-5))
• 沸点：
  365.2±44.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-chloro-phenyl)-5-hydrazino-[1,3,4]thiadiazole 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-{[5-(4-chloro-phenyl)-[1,3,4]thiadiazol-2-yl]-hydrazono}-propionic acid
  参考文献：
  名称：

  Shafiee,A. et al., Journal of Heterocyclic Chemistry, 1976, vol. 13, p. 117 - 121

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(4-氯苯基)-1,3,4-噻二唑-2-硫醇 在 hydrazine hydrate monohydrate 作用下， 生成 2-(4-chloro-phenyl)-5-hydrazino-[1,3,4]thiadiazole
  参考文献：
  名称：

  Synthesis and spectral characterization of Zn(II) microsphere series for antimicrobial application

  摘要：

  Microsphere series have been synthesized by reacting zinc(II) acetate dihydrate with Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole/oxadiazole/triazole with salicylaldehyde. Elemental analysis suggests that the complexes have 1:2 and 1:1 stoichiometry of the type [Zn(L)(2)(H2O)(2)] and [Zn(L')(2)(H2O)(2)]; LH = Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thia/oxadiazole with salicylaldehyde; L'H-2 = Schiff bases derived from 3-(substituted phenyl)-4-amino-5-hydrazino-1,2,4-triazole and salicylaldehyde and were characterized by elemental analyses, IR, H-1 NMR and C-13 NMR spectral data. Scanning electron microscopy (SEM) showed that synthesized materials have microsphere like structure and there EDX analysis comparably matches with elemental analysis. For the antimicrobial application Schiff bases and their zinc(II) complexes were screened for four bacteria e.g. Bacillus subtilis, Pseudomonas aeruginosa, Salmonella typhi, Streptococcus pyogenes and four fungi e.g. Cyrtomium falcatum, Aspergillus niger, Fusarium oxysporium and Curvularia pallescence by the reported method. Schiff base and Zn(II) compounds showed significant antimicrobial activities. However, activities increase upon chelation. Thermal analysis (TGA) data of compound (10) showed its stability up to 300 degrees C. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.06.009

文献信息

• SUBSTITUTED DIHYDROPYRAZOLONES AND USE THEREOF AS HIF-PROLYL-4 -HYDROXYLASE INHIBITORS
  申请人：Thede Kai

  公开号：US20120264704A1

  公开（公告）日：2012-10-18

  The present application relates to novel substituted dihydropyrazolone derivatives, processes for their preparation, their use for treatment and/or prophylaxis of diseases and their use for the preparation of medicaments for treatment and/or prophylaxis of diseases, in particular cardiovascular and hematological diseases and kidney diseases, and for promoting wound healing.

  本申请涉及新颖的取代二氢吡唑酮衍生物，其制备方法，其用于治疗和/或预防疾病的用途，以及用于制备治疗和/或预防疾病的药物，特别是心血管和血液病以及肾脏疾病，并促进伤口愈合。
• Synthesis, spectral characterization and antimicrobial studies of nano-sized oxovanadium(IV) complexes with Schiff bases derived from 5-(phenyl/substituted phenyl)-2-hydrazino-1,3,4-thiadiazole and indoline-2,3-dione
  作者：M.K. Sahani、U. Yadava、O.P. Pandey、S.K. Sengupta

  DOI：10.1016/j.saa.2014.01.041

  日期：2014.5

  oxovanadium(IV) complexes with Schiff bases derived by the condensation of 5-(phenyl/substituted phenyl)-2-hydrazino-1,3,4-thiadiazoles and indoline-2,3-dione have been prepared in ethanol in the presence of sodium acetate. Micro-analytical data, magnetic susceptibility, UV–Vis, IR, EPR and XRD spectral techniques were used to confirm the structures. Electronic absorption spectra of the complexes suggest

  在乙醇中制备了一类新的与席夫碱形成的氧杂钒（IV）配合物，该席夫碱是由5-（苯基/取代的苯基）-2-肼基-1,3,4-噻二唑与二氢吲哚-2,3-二酮缩合得到的。在乙酸钠存在下。微观分析数据，磁化率，UV-Vis，IR，EPR和XRD光谱技术用于确认结构。配合物的电子吸收光谱表明为方形-金字塔形几何形状。氧钒（IV）配合物具有单斜晶系，并且发现粒径为18.0 nm至24.0 nm（纳米尺寸）。测定了合成化合物对黑曲霉真菌，炭疽菌和炭疽菌腐烂的体外抗真菌活性。和体外抗菌活性通过筛选针对革兰氏阴性化合物（确定大肠杆菌和伤寒沙门氏菌）和革兰氏阳性（金黄色葡萄球菌和枯草芽孢杆菌）的细菌菌株。氧钒（IV）配合物比游离配体具有更高的抗菌作用。
• Synthesis, X-ray crystal structure and optical properties of novel 1,3,5-triarylpyrazoline derivatives and the fluorescent sensor for Cu2+
  作者：Sheng-Qing Wang、Ying Gao、Hao-Yan Wang、Xiao-Xin Zheng、Shi-Li Shen、Yan-Ru Zhang、Bao-Xiang Zhao

  DOI：10.1016/j.saa.2012.12.062

  日期：2013.4

  showed that the absorption maxima of the compounds vary from 366 to 370 nm depending on the group bound to benzene rings. The maximum emission spectra of the compounds in dichloromethane were dependent on nature of groups in benzene ring. Furthermore, the compound 3b can be used to determine Cu2+ ion with high selectivity and a low detection limit in the DMF:H2O = 1:1 (v/v) solution.

  通过查尔酮和5-芳基-2-肼基-1,3,4-噻二唑的反应合成了一系列新颖的1,3,5-三芳基吡唑啉衍生物，产率为43.3–84.7％。使用IR，1 H NMR和HRMS光谱以及X射线衍射分析对化合物的结构进行表征。在二氯甲烷，甲苯，乙腈，N，N-二甲基甲酰胺和四氢呋喃中研究了该化合物的吸收和荧光特性。结果表明，取决于与苯环结合的基团，化合物的最大吸收在366至370 nm之间变化。化合物在二氯甲烷中的最大发射光谱取决于苯环中基团的性质。此外，化合物3b可用于在DMF：H 2 O = 1：1（v / v）溶液中以高选择性和低检测限测定Cu 2+离子。
• D-A-D based reversible fluorescent probe for selective detection and cell imaging of copper ion
  作者：Hejia Xu、Anqi Wang、Luyang Qin、Mengzhu Mo、Yi Zhou、Chengwei Lü、Liwei Zou

  DOI：10.1016/j.chemphys.2022.111571

  日期：2022.8

  Two D-A-D fluorescent probes (X1 and X2) were constructed based on coumarin and 1,3,4-thiadiazole moieties and were used for visual inspection and fluorescent response of Cu2+. Both of them demonstrated high selectivity and sensitivity towards Cu2+ in DMSO-Tris-HCl solution (v/v 3:1, pH = 7.4) through distinct fluorescence and colorimetric variation. The detection limits of X1 and X2 were achieved

  基于香豆素和1,3,4-噻二唑部分构建了两个DAD荧光探针（X1和X2 ），用于Cu 2+的目测和荧光响应。通过明显的荧光和比色变化，它们都表现出对 DMSO-Tris-HCl 溶液（v/v 3:1，pH = 7.4）中 Cu 2+的高选择性和灵敏度。X1和X2的检测限分别为 13.6 nM 和 12.3 nM。此外，通过将 EDTA 添加到X1/X2 + Cu 2+中，它们被证明是可逆传感器解决方案，并实际应用于试纸检测和细胞成像。密度泛函理论计算用于指导探针开发和探测机制探索的实验。
• Shams El-Dine Sh.; Jawad; Mahmoud, Pharmazie, 1984, vol. 39, # 2, p. 101 - 103
  作者：Shams El-Dine Sh.、Jawad、Mahmoud

  DOI：——

  日期：——