4-氨基-3-疏基-5-(2-氯苯基)-[1,2,4-]噻唑 | 13229-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-氨基-3-疏基-5-(2-氯苯基)-[1,2,4-]噻唑
• 英文名称: 4-amino-5-(2-chlorophenyl)-4H-1,2,4-triazole-3-thiol
• 英文别名: 4-amino-3-(2-chlorophenyl)-1H-1,2,4-triazole-5-thione
• CAS: 13229-02-2
• 化学式: C₈H₇ClN₄S
• 分子量: 226.689
• InChiKey: LCHRECYVKFDKAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 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：
  85.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-氨基-3-疏基-5-(2-氯苯基)-[1,2,4-]噻唑 在 hydrazine hydrate monohydrate 、 硫酸 作用下， 以 乙醇 为溶剂， 生成 2-((2-(5-(2-chlorophenyl)-4-((2-hydroxybenzylidene)amino)-4H-1,2,4-triazol-3-yl)hydrazineylidene)methyl)phenol
  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：

  2-氯苯甲酸甲酯 在 一水合肼 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 4-氨基-3-疏基-5-(2-氯苯基)-[1,2,4-]噻唑
  参考文献：
  名称：

  一些新型3,6-二取代1,2,4-三唑并[3,4-b]1,3,4-噻二唑衍生物的合成及生物活性

  摘要：

  一系列芳族酰肼 3a-j 是通过将酯 2a-j 与水合肼在甲醇中回流制备的，它们是通过酯化 1a-j 制备的。乙酰肼 3a-j 在用二硫化碳和甲醇氢氧化钾处理后产生二硫代氨基甲酸钾盐 4a-j，在与水合肼一起回流时产生取代的 4-氨基-5-芳基-3H-1,2,4-三唑-3-硫酮5a-j。目标化合物 6a-j 通过在多磷酸存在下在回流下缩合呋喃-3-羧酸来合成。通过IR、1 H NMR、13 C NMR、元素分析和质谱研究对新合成化合物的结构进行了表征。筛选所有合成的化合物的脲酶、乙酰胆碱酯酶抑制、抗氧化和碱性磷酸酶抑制活性。几乎所有的化合物 6a-j 对脲酶和乙酰胆碱酯酶的活性均优于参考药物。化合物 6f 和 6g 是比参考没食子酸正丙酯更有效的自由基清除剂。与参考 KH2PO4 相比，化合物 6b 和 6h 显示出优异的碱性磷酸酶活性。

  DOI：

  10.5012/bkcs.2012.33.12.3943

文献信息

• Synthesis and Biological Evaluation of Novel Glycosyl-Containing 1,2,4-Triazolo[3,4-<i>b</i>][1,3,4]Thiadiazole Derivatives as Acetylcholinesterase Inhibitors
  作者：Xiu-Jian Liu、Lei Wang、Long Yin、Feng-Chang Cheng、Hui-Min Sun、Wei-Wei Liu、Da-Hua Shi、Zhi-Ling Cao

  DOI：10.3184/174751917x15064232103047

  日期：2017.10

  An efficient protocol for the synthesis of novel glycosyl-containing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole derivatives starting from the commercially available D-glucosamine hydrochloride is described by reaction of glycosyl isothiocyanate with various aminotriazoles in DMF. Glycosyl isothiocyanate is an important intermediate and synthetic methods are discussed. The acetylcholinesterase inhibitory

  通过异硫氰酸糖基反应描述了一种从市售 D-氨基葡萄糖盐酸盐开始合成新型含糖基的 1,2,4-三唑 [3,4-b][1,3,4] 噻二唑衍生物的有效方案与 DMF 中的各种氨基三唑。糖基异硫氰酸酯是一种重要的中间体，并对其合成方法进行了讨论。这些化合物的乙酰胆碱酯酶抑制活性通过 Ellman 方法测试。发现大多数化合物表现出超过 90% 的抑制作用，随后评估了它们的 IC50 值。
• Synthesis of heterocycles. Part<b>VI</b>. Synthesis and antimicrobial activity of some 4-amino-5-aryl-1,2,4-triazole-3-thiones and their derivatives
  作者：N. F. Eweiss、A. A. Bahajaj、E. A. Elsherbini

  DOI：10.1002/jhet.5570230540

  日期：1986.9

  react with hydrazine hydrate to give the corresponding acid hydrazides VI which in turn condenses with acid chlorides and aldehydes to afford respectively 1-[(4-amino-5-aryl-1,2,4-triazol-3-ylthio)acetyl]-2-aroylhydrazines VII and aryl methylene (4-amino-5-aryl-1,2,4-triazol-3-ylthio)acethydrazones VIII. The antimicrobial activities of the above compounds were screened against different strains of bacteria

  4-氨基-5-芳基-1,2,4-三唑-3-硫酮Ⅰ与酰氯反应生成4-酰基氨基-5-芳基1,2,4-三唑-3-硫酮Ⅱ。化合物I还与碘甲烷，氯乙腈和溴乙酸甲酯反应，生成双-（4-氨基-5-芳基-1,2,4-三唑-3-基硫基）甲烷III，4-氨基-5-芳基-3-氰基甲硫基1,2,4-三唑IV和4-氨基- 5-芳基-3-羰基甲氧基甲基硫基1,2,4-三唑V。化合物V与水合肼反应，得到相应的酰肼VI，其依次与酰氯和醛缩合，分别得到1-[（4-氨基-5-芳基-1,2,4-三唑-3-基硫基）乙酰基] -2-芳酰基肼和芳基亚甲基（4-氨基-5-芳基-1，2，4-三唑-3-基硫基）乙hydrVIII。筛选了上述化合物对不同菌株的细菌和真菌的抗微生物活性。
• Synthesis of 1,3-Bis[(3-aryl)-S-triazolo[3,4-<i>b</i>]-[1,3,4]thiadiazole-6-yl]benzenes
  作者：Dejiang Li、Deqing Long、Heqing Fu

  DOI：10.1080/10426500500265008

  日期：2006.3.1

  1,3-bis[(3-aryl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-6-yl]benzenes 2 were synthesized in high yields by the reaction of 3-aryl 4-amino-5-mercapto-1,2,4-triazole 1 with m-phthalic acid.

  1,3-双[(3-芳基)-s-三唑并[3,4-b]-[1,3,4]噻二唑-6-基]苯2通过3-芳基反应以高产率合成4-氨基-5-巯基-1,2,4-三唑 1 与间苯二甲酸。
• Synthesis and Biological Evaluation of Kojic Acid Derivatives Containing 1,2,4-triazole as Potent Tyrosinase Inhibitors
  作者：Wenlin Xie、Jingai Zhang、Xiaojing Ma、Wenqian Yang、Ying Zhou、Xufu Tang、Yan Zou、Hui Li、Jingjing He、Shimin Xie、Yunhui Zhao、Fengping Liu

  DOI：10.1111/cbdd.12577

  日期：2015.11

  A series of 5-substituted-3-[5-hydroxy-4-pyrone-2-yl-methymercapto]-4-amino-1,2,4-triazole derivatives were synthesized by nucleophilic substitution reaction of 5-hydroxy-2-chloromethyl -4H-pyran-4-one with 5-substituted-3-mercapto-4-amino-1,2,4-triazole, and their inhibitory effects on mushroom tyrosinase were evaluated. The results indicated that most of the synthesized compounds exhibited significant

  通过5-羟基-2-的亲核取代反应，合成了一系列5-取代的-3- [5-羟基5-吡喃-2-基-甲基巯基] -4-氨基-1,2,4-三唑衍生物。评价了具有5-取代的-3-巯基-4-氨基-1,2,4-三唑的氯甲基-4H-吡喃-4-酮及其对蘑菇酪氨酸酶的抑制作用。结果表明，大多数合成的化合物显示出显着的抑制活性。具体而言，5-（4-氯苯基）-3- [5-羟基-4-吡喃-2-基-甲基巯基] -4-氨基-1,2,4-三唑（6j）表现出最强的酪氨酸酶抑制活性IC50值为4.50 +/- 0.34微米。化合物（6j）的动力学研究表明，该化合物对酪氨酸酶的抑制作用属于竞争性抑制剂。同时，还讨论了结构-活性关系。
• Facile synthesis of new 10-substituted-5H-naphtho[1,2-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-5-ones
  作者：Jabbar Khalafy、Mahsa Mohammadlou、Miri Mahmoody、Fatemeh Salami、Ahmad Poursattar Marjani

  DOI：10.1016/j.tetlet.2015.02.002

  日期：2015.3

  50 °C gave the corresponding 2-[(4-amino-5-aryl-4H-1,2,4-triazol-3-yl)thio]naphthalene-1,4-diones. Their treatment with EtOH/HCl under reflux conditions produced 10-substituted-5H-naphtho[1,2-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-5-ones through intramolecular cyclization.

  2-溴-1,4-萘醌与4-氨基-5-芳基-4 H -1,2,4-三唑-3-硫醇在乙醇中于50°C反应，得到相应的2-[（（4-氨基-5-芳基-4 H -1,2,4-三唑-3-基）硫]萘-1,4-二酮。在回流条件下用EtOH / HCl处理可产生10-取代的5 H-萘[1,2- e ] [1,2,4]三唑[3,4- b ] [1,3,4]噻二嗪-5 -通过分子内环化的一个。