5-(4-nitrophenyl)-1,3,4-thiadiazole-2-thiol | 81188-34-3

• 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-nitrophenyl)-1,3,4-thiadiazole-2-thiol
• 英文别名: 5-(4-Nitrophenyl)-1,3,4-thiadiazole-2(3h)-thione；5-(4-nitrophenyl)-3H-1,3,4-thiadiazole-2-thione
• CAS: 81188-34-3
• 化学式: C₈H₅N₃O₂S₂
• 分子量: 239.279
• InChiKey: YJYUNJMROJTQFR-UHFFFAOYSA-N

物化性质

• 熔点：
  221-224 °C(Solv: ethanol (64-17-5))
• 沸点：
  389.0±44.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-nitrophenyl)-1,3,4-thiadiazole-2-thiol 在 hydrazine hydrate monohydrate 作用下， 生成 [5-(4-nitrophenyl)-1,3,4-thiadiazol-2-yl]hydrazine
  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
• 作为产物：
  描述：

  4-硝基苯酰肼 在 硫酸 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 5-(4-nitrophenyl)-1,3,4-thiadiazole-2-thiol
  参考文献：
  名称：

  使用杂环硫酮和芳烃有效形成CS键

  摘要：

  苯硫基杂环化合物因其多样的生物学活性和医学前景而被广泛使用。在此，报道了一种简便的方法。在CsF存在下，与芳烃反应形成芳基-S键的1,3,4-氧杂噻唑并噻吩-2-硫酮的芳基化反应具有良好的收率和优异的选择性。反应在短时间内完成，无需使用昂贵的试剂和催化剂。目前的反应体系是一种处理苯硫基杂环化合物的有效方法，它揭示了一种可持续的方法，并在未来的有机合成中具有更好的应用前景。

  DOI：

  10.1016/j.tet.2020.131829

文献信息

• Synthesis and biological evaluation of novel disulfides incorporating 1,3,4-thiadiazole scaffold as promising antitumor agents
  作者：Sha Li、Hai-Xin Wang、Hai-Ying Liu、Fen Jing、Xiao-Yun Fu、Cai-Wen Li、Yan-Ping Shi、Bao-Quan Chen

  DOI：10.1007/s00044-019-02389-3

  日期：2019.9

  and A549 lines. Bioassay indicated that some compounds showed stronger antitumor effects than reference drugs PX-12 and 5-fluorouracil. Among these screened compounds, compound 7h showed excellent biological activities in inhibiting SMMC-7721 cell proliferation with IC50 at 1.93 ± 0.08 μM. Compounds 7k and 7i manifested highly effective growth inhibitory activity versus MCF-7 cells, with IC50 at 3.04 ± 0

  在本研究中，制备了十四个含二硫基的2,5-二取代的1,3,4-噻二唑衍生物。通过IR，NMR，MS和元素分析鉴定了所得化合物7a – 7n。使用针对SMMC-7721，MCF-7和A549品系的标准CCK-8分析法研究了它们的体外抗增殖特性。生物测定表明，某些化合物显示出比参考药物PX-12和5-氟尿嘧啶更强的抗肿瘤作用。在这些筛选出的化合物中，化合物7h以1.93±0.08μM的IC 50抑制SMMC-7721细胞增殖具有优异的生物学活性。化合物7k和7i与MCF-7细胞相比，具有明显的高效生长抑制活性，IC 50分别为3.04±0.09和3.54±0.17μM。对于A549细胞，发现化合物7m具有最高的抗肿瘤效力，IC 50为3.67±0.13μM。
• Synthesis and biological activities of benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety
  作者：Xu Tang、Zhongbo Wang、Xinmin Zhong、Xiaobin Wang、Lijuan Chen、Ming He、Wei Xue

  DOI：10.1080/10426507.2018.1539992

  日期：2019.3.4

  Abstract A series of benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety were designed, synthesized and evaluated for their antibacterial, antifungal and antiviral activities. The bioassay results indicated that most of target compounds showed good antiviral activities against tobacco mosaic virus (TMV) and antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia

  摘要 设计、合成了一系列带有 1,3,4-噻二唑部分的苯并噻唑衍生物，并评估了它们的抗菌、抗真菌和抗病毒活性。生物测定结果表明，大多数目标化合物对烟草花叶病毒（TMV）表现出良好的抗病毒活性和对米黄单胞菌的抗菌活性。oryzae (Xoo) 和青枯病菌 (Rs)。特别是，标题化合物 5k (N-(5-甲氧基苯并[d]噻唑-2-基)-2-((5-(2-甲苯基)-1,3,4-噻二唑-2-基)硫代)乙酰胺)和标题化合物5a(N-(5-硝基苯并[d]噻唑-2-基)-2-((5-(4-(三氟甲基)苯基)-1)的抗-Rs作用) ,3,4-噻二唑-2-基）硫代）乙酰胺）在 100 µg/mL 时分别达到 52.4% 和 71.6%，优于双甲噻唑（32.0% 和 52.3%）。此外，标题化合物5i (N-(5-甲氧基苯并[d]噻唑-2-基)-2-((5-(4-硝基苯基)-1,3,4-噻二唑-2-基)的保护和灭活活性)硫）乙酰胺）对
• Synthesis and antibacterial activity of novel lincomycin derivatives. II. Exploring (7S)-7-(5-aryl-1,3,4-thiadiazol-2-yl-thio)-7-deoxylincomycin derivatives
  作者：Ko Kumura、Yoshinari Wakiyama、Kazutaka Ueda、Eijiro Umemura、Takashi Watanabe、Megumi Kumura、Takuji Yoshida、Keiichi Ajito

  DOI：10.1038/ja.2016.139

  日期：2017.5

  The synthesis and antibacterial activity of (7S)-7-(5-aryl-1,3,4-thiadiazol-2-yl-thio)-7-deoxylincomycin derivatives are described. These derivatives were mainly prepared by the Mitsunobu reaction of 2,3,4-tris-O-(trimethylsilyl)lincomycin and the corresponding thiols. Exploring structure-activity relationships of the substituent at the 5 position of a thiadiazole ring revealed that compounds with

  描述了（7S）-7-（5-芳基-1,3,4-噻二唑-2-基-硫基）-7-脱氧林可霉素衍生物的合成和抗菌活性。这些衍生物主要是通过2,3,4-三-O-（三甲基甲硅烷基）林可霉素与相应的硫醇的Mitsunobu反应制备的。探索噻二唑环的5位上的取代基的构效关系，发现具有邻位取代苯基的化合物与具有未取代的报道的化合物（1）相比，具有erm基因的肺炎链球菌和化脓性链球菌显示出改善的抗菌活性。苯环。
• Synthesis and anti-Helicobacter pylori activity of 5-(nitroaryl)-1,3,4-thiadiazoles with certain sulfur containing alkyl side chain
  作者：Alireza Foroumadi、Ardeshir Rineh、Saeed Emami、Farideh Siavoshi、Sadegh Massarrat、Fatemeh Safari、Saeed Rajabalian、Mehraban Falahati、Ensieh Lotfali、Abbas Shafiee

  DOI：10.1016/j.bmcl.2008.04.033

  日期：2008.6

  A series of 5-(nitroaryl)-1,3,4-thiadiazoles bearing certain sulfur containing alkyl side chain similar to pendent residue in tinidazole molecule were synthesized and evaluated against Helicobacter pylori using disk diffusion method. The synthesized compounds were also evaluated for their antibacterial, antifungal and cytotoxic effects. Study of the structure-activity relationships of this series of

  合成了一系列5-（硝基芳基）-1,3,4-噻二唑，它们带有类似于替硝唑分子中侧基的某些含硫烷基侧链，并使用圆盘扩散法对幽门螺杆菌进行了评估。还评估了合成的化合物的抗菌，抗真菌和细胞毒性作用。对这一系列化合物的构效关系的研究表明，硝基芳基单元的结构和1,3,4-噻二唑环2位上的侧基均显着影响抗H。幽门螺杆菌活动。尽管含有硝基噻吩系列中2- [2-（乙基磺酰基）乙硫基]侧链的化合物7a是针对幽门螺杆菌临床分离株测试的最有效的化合物，硝基咪唑6c和7c由于具有抗H的特性而被认为是更有前途的化合物。幽门螺杆菌活性除细胞毒性作用较小外。
• Facile synthesis of novel fluorinated thieno[2,3-d]pyrimidine derivatives containing 1,3,4-thiadiazole
  作者：Xin Jian Song、Zheng Chao Duan、Yu Shao、Xing Gao Dong

  DOI：10.1016/j.cclet.2012.02.007

  日期：2012.5

  Abstract A series of novel fluorinated thieno[2,3-d]pyrimidine derivatives incorporating 1,3,4-thiadiazole were synthesized by a facile microwave-assisted procedure, including the cyclization of 2-aminothiophene-3-carbonitrile with trifluoroacetic acid, chlorination and nucleophilic substitution reaction. This protocol offered such advantages as mild reaction conditions, short reaction time, simple

  摘要通过简便的微波辅助方法，包括2-氨基噻吩-3-甲腈与三氟乙酸的环化反应，氯化反应，合成了一系列新的含1,3,4-噻二唑的氟化噻吩并[2,3-d]嘧啶衍生物。和亲核取代反应。该方案具有反应条件温和，反应时间短，纯化简单，收率高等优点。产物的结构通过1 H NMR，MS，元素分析和X射线衍射进行表征。