4-amino-5-(4-nitrophenyl)-1,2,4-triazole-3-thiol | 36209-50-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-amino-5-(4-nitrophenyl)-1,2,4-triazole-3-thiol
• 英文别名: 4-amino-5-(4-nitrophenyl)-4H-1,2,4-triazole-3-thiol；4-amino-3-(4-nitrophenyl)-1H-1,2,4-triazole-5-thione
• CAS: 36209-50-4
• 化学式: C₈H₇N₅O₂S
• 分子量: 237.242
• InChiKey: ZYJYOCGKQGVVKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 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：
  132
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-5-(4-nitrophenyl)-1,2,4-triazole-3-thiol 在 盐酸 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 生成 2-(1-(2-(4-((1-(2-hydroxyphenyl)ethylidene)amino)-5-(4-nitrophenyl)-4H-1,2,4-triazol-3-yl)hydrazineylidene)ethyl)phenol
  参考文献：
  名称：

  Synthesis, spectral characterization and biological activity of zinc(II) complexes with 3-substituted phenyl-4-amino-5-hydrazino-1, 2, 4-triazole Schiff bases

  摘要：

  New Zn(II) complexes have been synthesized by the reactions of zinc(II) acetate with Schiff bases derived from 3-substituted phenyl-4-amino-5-hydrazino-1, 2, 4-triazole and benzaldehyde, 2-hydroxyacetophenone or indoline-2,3-dione. All these complexes are soluble in DMF and DMSO; low molar conductance values indicate that they are non-electrolytes. Elemental analyses suggest that the complexes have 1:1 stoichiometry of the type [ZnL(H(2)O)(2)], [ZnL'(OAc)(2)(H(2)O)(2)] (L=dianionic Schiff bases derived from 3-(substituted phenyl)-4-amino-5-hydrazino-1, 2, 4-triazole and 2-hydroxyacetophenone or indoline-2,3-dione; L'=neutral Schiff bases derived from 3-(substituted phenyl)-4-amino-5-hydrazino-1, 2, 4-triazole and benzaldehyde) and they were characterized by FT-IR, (1)H NMR, (13)C NMR and FAB mass. All these Schiff bases and their complexes have also been screened for their antibacterial activities against Bacillus subtilis, Escherichia coli and antifungal activities against Colletotrichum falcatum, Aspergillus niger, Fusarium oxysporium and Carvularia pallescence by petriplates methods.

  DOI：

  10.1016/j.saa.2011.08.019
• 作为产物：
  描述：

  5-(4-硝基苯基)-1,3,4-恶二唑-2(3H)-硫酮 在 一水合肼 、 盐酸 作用下， 以 水 为溶剂， 反应 18.0h， 以46%的产率得到4-amino-5-(4-nitrophenyl)-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  含有两个稠合五原子杂环的推拉偶氮发色团及其非线性光学特性

  摘要：

  我们开发了合成推拉偶氮发色团的方法，该发色团含有 s-三唑并 [3,4-b] 噻二唑杂环，与电子受体基团（硝基苯基）的存在相容，作为三唑和噻二唑环上的取代基. 合成生色团的线性和非线性光学特性已通过 EFISH 技术、电光吸收光谱和 DFT 计算进行表征。综合结果表明发色团性质的显着调节取决于杂环上的取代模式。观察到并表征了发色团周围 N=N 键的快速紫外驱动反式异构化和较慢的热驱动顺式反异构化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900218

文献信息

• Synthesis of Triazole Based Novel Ionic Liquids and Salts
  作者：Geetika Bhasin、Richa Srivastava、Ram Singh

  DOI：10.1080/00304948.2017.1343037

  日期：2017.7.4

  on the development of nitrogen-rich heterocyclic energetic salts that should have low vapor pressure, higher density and better thermal stability. To extend the scope of triazolium based ILs, we have synthesized different aryl substituted, 4-amino1-ethyl-3-mercapto-5-phenyl-4H-[1,2,4]triazol-1-ium salts. The synthesis of ionic liquids and salts based on 4-amino-1,2,4-triazole has been done as shown

  离子液体 (IL) 或有机离子盐由有机阳离子和无机或有机阴离子组成。在 100°C 或低于 100°C 熔化的离子盐被称为离子液体。这些分子显示出特殊的特性，例如低蒸气压、宽温度范围内的流动性、高热稳定性、离子导电性、结构可设计性和溶解各种化学物质的能力。It is possible to form any specific IL's composition depending on one's needs, and the desired chemical and physical properties can be realized in a single salt, by proper selection of the component ions. 因此，离子液体的多功能性通过选择合适的离子组合而产生。IL 在化学和材料科学的几乎每个分支中都很普遍，包括催化、有机合成、分离和分析、
• New Heparanase-Inhibiting Triazolo-Thiadiazoles Attenuate Primary Tumor Growth and Metastasis
  作者：Uri Barash、Shobith Rangappa、Chakrabhavi Dhananjaya Mohan、Divakar Vishwanath、Ilanit Boyango、Basappa Basappa、Israel Vlodavsky、Kanchugarakoppal S. Rangappa

  DOI：10.3390/cancers13122959

  日期：——

  Compelling evidence ties heparanase, an endoglycosidase that cleaves heparan sulfate side (HS) chains of proteoglycans, with all steps of tumor development, including tumor initiation, angiogenesis, growth, metastasis, and chemoresistance. Moreover, heparanase levels correlate with shorter postoperative survival of cancer patients, encouraging the development of heparanase inhibitors as anti-cancer drugs. Heparanase-inhibiting heparin/heparan sulfate-mimicking compounds and neutralizing antibodies are highly effective in animal models of cancer progression, yet none of the compounds reached the stage of approval for clinical use. The present study focused on newly synthesized triazolo–thiadiazoles, of which compound 4-iodo-2-(3-(p-tolyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl)phenol (4-MMI) was identified as a potent inhibitor of heparanase enzymatic activity, cell invasion, experimental metastasis, and tumor growth in mouse models. To the best of our knowledge, this is the first report showing a marked decrease in primary tumor growth in mice treated with small molecules that inhibit heparanase enzymatic activity. This result encourages the optimization of 4-MMI for preclinical and clinical studies primarily in cancer but also other indications (i.e., colitis, pancreatitis, diabetic nephropathy, tissue fibrosis) involving heparanase, including viral infection and COVID-19.

  引人注目的证据将肝素酶与肿瘤发展的所有阶段联系起来，包括肿瘤的发生、血管生成、生长、转移和化疗抵抗。此外，肝素酶水平与癌症患者术后生存时间较短相关，鼓励开发肝素酶抑制剂作为抗癌药物。抑制肝素酶的肝素/肝素硫酸模拟化合物和中和抗体在癌症进展的动物模型中非常有效，但是这些化合物中没有一个达到了临床使用批准的阶段。本研究侧重于新合成的三唑-噻二唑类化合物，其中4-碘-2-(3-(对甲苯基)-[1,2,4]三唑[3,4-b][1,3,4]噻二唑-6-基)酚（4-MMI）被确定为对肝素酶酶活性、细胞侵袭、实验性转移和小鼠模型中肿瘤生长的有效抑制剂。据我们所知，这是第一份报告显示用抑制肝素酶酶活性的小分子治疗的小鼠原发肿瘤生长显著减少。这一结果鼓励优化4-MMI，主要用于癌症但也包括其他适应症（如结肠炎、胰腺炎、糖尿病肾病、组织纤维化）的临床前和临床研究，这些适应症涉及肝素酶，包括病毒感染和COVID-19。
• Synthesis, docking and evaluation of antioxidant and antimicrobial activities of novel 1,2,4-triazolo[3,4-b][1,3,4]thiadiazol-6-yl)selenopheno[2,3-d]pyrimidines
  作者：Y. Kotaiah、K. Nagaraju、N. Harikrishna、C. Venkata Rao、L. Yamini、M. Vijjulatha

  DOI：10.1016/j.ejmech.2014.01.006

  日期：2014.3

  synthesized compounds were evaluated for their antimicrobial activity against Gram +ve and Gram −ve bacteria and antifungal activity by well diffusion method. Compounds 10d, 10h and 10i showed promising antioxidant, antibacterial as well as antifungal activity and these were found to be the most potent activity molecules when compared with that of standard drugs. Molecules docking studies have been performed

  合成了一系列1,2,4-（三唑并[3,4- b ] [1,3,4]噻二唑-6-基）硒代苯并[2,3- d ]嘧啶（10a – j），并带有各种取代基苯胺和苯甲酸。通过IR，1 H和13 C NMR和LC-MS光谱数据确定了新合成化合物的结构。通过DPPH，NO和H 2 O 2自由基清除方法评价了合成化合物的抗氧化活性。通过良好扩散方法评估了新合成的化合物对革兰氏+ ve和革兰氏ve细菌的抗菌活性和抗真菌活性。化合物10d，10h和10i显示出有希望的抗氧化剂，抗菌以及抗真菌活性，与标准药物相比，它们是最有效的活性分子。已经对革兰氏+ ve细菌的金黄色葡萄球菌（SA）进行了分子对接研究。
• Synthesis and Antimicrobial Activity of Piperine Analogues Containing 1,2,4-Triazole Ring
  作者：Kottakki Naveen Kumar、Karteek Rao Amperayani、V. Ravi Sankar Ummdi、Uma Devi Parimi

  DOI：10.14233/ajchem.2019.21876

  日期：2019.4.15

  A series 1,2,4-triazole piperine analogues (TP1-TP6) were designed and synthesized. The structures were confirmed using 1H NMR and 13C NMR. Antibacterial study was done using Gram-positive (Staphylococcus aureus and Bacillus cereus) and Gram-negative micro-organisms (E. coli and Pseudomonas aeruginosa) by disc diffusion method. Compound containing chloro substitution (TP6) showed the highest effect

  设计并合成了一系列1,2,4-三唑胡椒碱类似物(TP1-TP6)。使用1H NMR和13C NMR确认结构。通过纸片扩散法使用革兰氏阳性微生物（金黄色葡萄球菌和蜡样芽孢杆菌）和革兰氏阴性微生物（大肠杆菌和铜绿假单胞菌）进行抗菌研究。含有氯取代的化合物(TP6)表现出最高的活性，而化合物TP1、TP3、TP4、TP5表现出中等活性。
• Synthesis, Antimicrobial, and Antioxidant Activities of Some Fused Heterocyclic [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazole Derivatives
  作者：Gangadhara Seelolla、Venkateswarlu Ponneri

  DOI：10.1002/jhet.2348

  日期：2016.5

  synthesized a series of [1,2,4]triazolo[3,4‐b][1,3,4]thiadiazole derivatives (6a, 6b, 6c, 6d, 6e, 6f and 7a, 7b, 7c, 7d, 7e, 7f) by using simple starting materials, namely, β‐amino acids and different aromatic acid hydrazides. The newly synthesized compounds were characterized by mass, IR, 1H, and13C‐NMR spectral data analysis. The newly synthesized compounds were tested for their antimicrobial activities and

  在目前的工作中，我们合成了一系列[1,2,4] triazolo [3,4-b] [1,3,4]噻二唑衍生物（6a，6b，6c，6d，6e，6f和7a，7b，7c，7d，7e，7f），方法是使用简单的原料，即β-氨基酸和不同的芳族酸酰肼。通过质量，IR，1 H和13 C-NMR光谱数据分析对新合成的化合物进行了表征。测试了新合成的化合物的抗菌活性和抗氧化性能。复合当分别与参考药物环丙沙星和氟康唑相比时，6c是有效的微生物剂，特别是针对金黄色葡萄球菌（MIC 3.12 µg / mL）和白色念珠菌（MIC 6.25 µg / mL）。合成的化合物的抗氧化活性也通过1,1-二苯基-2-吡咯酰肼，一氧化氮和过氧化氢自由基清除方法进行了评估。由于苯环上存在供电子基团，化合物6c，6f，7c和7f表现出良好的自由基清除活性。