5-(4-aminophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione | 23455-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-aminophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
• 英文别名: 3-(4-aminophenyl)-1H-1,2,4-triazole-5(4H)-thione；5-(4-amino-phenyl)-2,4-dihydro-[1,2,4]triazole-3-thione；5-(4-aminophenyl)-1,2-dihydro-1,2,4-triazole-3-thione
• CAS: 23455-78-9
• 化学式: C₈H₈N₄S
• 分子量: 192.244
• InChiKey: ZFPXYLWYSNUYNG-UHFFFAOYSA-N

物化性质

• 熔点：
  282 °C
• 沸点：
  340.5±44.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 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：
  94.5
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-(4-aminophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 在 碘 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (E)-4-(3-((2,3-diiodoallyl)thio)-1H-1,2,4-triazol-5-yl)aniline
  参考文献：
  名称：

  First regioselective iodocyclization reaction of 3-aryl-5-(prop-2-ynylthio)-1H-1,2,4-triazoles

  摘要：

  The regioselective iodocyclization reaction of 3-aryl-5-(prop-2-ynylthio)-1H-1,2,4-triazoles is described for the first time. The iodocyclization reaction of 3-aryl-5-(prop-2-ynylthio)-1H-1,2,4-triazoles using molecular iodine afforded diiodo-compound which on Cul-catalyzed intramolecular C-N coupling reaction gave six-membered 2-aryl-51141,2,4]triazolo[5,1-b][1,3]thiazines, whereas, the five membered 3-aryl-5,6-dihydrothiazolo[2,3-c][1,2,4]triazoles were obtained exclusively when the iodocyclization reaction of 3-aryl-5-(prop-2-ynylthio)-1H-1,2,4-triazoles was carried out using NIS. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.07.006
• 作为产物：
  描述：

  potassium;N-[(4-aminobenzoyl)amino]carbamodithioate 在 ammonium hydroxide 作用下， 反应 10.0h， 生成 5-(4-aminophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  Synthesis and biological evaluation of 1,2,4-triazole-3-thione and 1,3,4-oxadiazole-2-thione as antimycobacterial agents

  摘要：

  Resistance among dormant mycobacteria leading to multidrug‐resistant and extremely drug‐resistant tuberculosis is one of the major threats. Hence, a series of 1,2,4‐triazole‐3‐thione and 1,3,4‐oxadiazole‐2‐thione derivatives (4a–5c) have been synthesized and screened for their antitubercular activity against Mycobacterium tuberculosis H37Ra (H37Ra). The triazolethiones 4b and 4v showed high antitubercular activity (both MIC and IC50) against the dormant H37Ra by in vitro and ex vivo. They were shown to have more specificity toward mycobacteria than other Gram‐negative and Gram‐positive pathogenic bacteria. The cytotoxicity was almost insignificant up to 100 μg/ml against THP‐1, A549, and PANC‐1 human cancer cell lines, and solubility was high in aqueous solution, indicating the potential of developing these compounds further as novel therapeutics against tuberculosis infection.

  DOI：

  10.1111/cbdd.12939

文献信息

• Synthesis and in vitro Evaluation of West Nile Virus Protease Inhibitors Based on the 2-{6-[2-(5-Phenyl-4<i>H</i>-{1,2,4]triazol-3-ylsulfanyl)acetylamino]benzothiazol-2-ylsulfanyl}acetamide Scaffold
  作者：Sanjay Samanta、Ting Liang Lim、Yulin Lam

  DOI：10.1002/cmdc.201300114

  日期：2013.6

  NS2B‐NS3 protease inhibitor with a 2‐6‐[2‐(5‐phenyl‐4H‐[1,2,4]triazol‐3‐ylsulfanyl)acetylamino]benzothiazol‐2‐ylsulfanyl}acetamide scaffold was identified during screening. Optimization of this initial hit by synthesis and screening of a focused compound library with this scaffold led to the identification of a novel uncompetitive inhibitor (1 a24, IC50=3.4±0.2 μM) of the WNV NS2B‐NS3 protease. Molecular

  近年来，由西尼罗河病毒（WNV）感染引起的临床症状严重程度恶化，老年人神经侵袭性疾病的发生频率增加。由于目前尚无成功的抗WNV疗法用于人类，因此迫切需要为开发新的针对该病毒的化学疗法而不断努力。由于其在病毒复制中的重要性及其独特的底物偏爱性，病毒NS2B-NS3蛋白酶是有希望的病毒抑制靶标。在这项研究中，WNV NS2B-NS3蛋白酶抑制剂具有2- 6- [2-（5-苯基-4H]在筛选过程中发现了[[1,2,4]三唑-3-基硫烷基]乙酰氨基]苯并噻唑-2-基硫基}乙酰胺支架。通过合成和的筛选该初始命中的优化聚焦化合物库与此支架导致的新颖非竞争性抑制剂的鉴定（1 A24，IC 50 = 3.4±0.2μ中号的WNV的NS2B-NS3蛋白酶）。1 a24分子对接至WNV蛋白酶表明该化合物干扰NS2B辅因子与NS3蛋白酶的生产性相互作用，并且是WNV NS3蛋白酶的变构抑制剂。
• Process for production of vinyl chloride polymer
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP0172427A2

  公开（公告）日：1986-02-26

  This process is a process for production of a vinyl chloride polymer by suspension polymerization or emulsion polymerization of vinyl chloride monomer or a mixture of vinyl chloride monomer with a vinyl monomer copolymerizable with said vinyl chloride monomer in an aqueous medium, characterized in that the polymerization is carried out in a polymerizer, the inner wall surface and portions of the auxiliary equipment thereof which may come into contact with the monomer during polymerization being previously coated with a scaling preventive comprising at least one selected from dyes, pigments and aromatic or heterocyclic compounds having at least 5 conjugated π bonds, while controlling the chloride ion concentration in the reaction mixture to not higher than 100 ppm. According to said process, scaling onto the inner wall surface of a polymerizer, etc. during polymerization can be prevented effectively and surely.

  该工艺是通过氯乙烯单体或氯乙烯单体与可与所述氯乙烯单体共聚的乙烯基单体混合物在水介质中进行悬浮聚合或乳液聚合来生产氯乙烯聚合物的工艺，其特征在于聚合是在聚合器中进行的、内壁表面及其辅助设备中可能在聚合过程中与单体接触的部分事先涂上一层防垢剂，该防垢剂至少包括一种选自染料、颜料和至少有 5 个共轭 π 键的芳香族或杂环化合物的防垢剂，同时控制反应混合物中的氯离子浓度不高于 100 ppm。根据上述工艺，可有效、可靠地防止聚合过程中聚合器等内壁表面结垢。
• Oxidation and Reduction of 4-Acetamidobenzaldehyde Thiosemicarbazone
  作者：Robert Duschinsky、Harold Gainer

  DOI：10.1021/ja01153a512

  日期：1951.9
• NEGATIVE-WORKING RADIATION-SENSITIVE COMPOSITIONS AND IMAGEABLE MATERIALS
  申请人：Eastman Kodak Company

  公开号：EP2047333B1

  公开（公告）日：2010-03-31
• NEGATIVE-WORKING IMAGEABLE MATERIALS
  申请人：Tao Ting

  公开号：US20080044767A1

  公开（公告）日：2008-02-21

  A negative-working imageable element includes a combination of a specific polymeric binder comprising pendant allyl ester groups with an highly efficient iodonium borate free radical initiator to provide solvent resistance, excellent digital imaging speed (sensitivity) and can be imaged and developed without a preheat step to provide lithographic printing plates. The polymeric binder can be prepared with a precursor polymer having pendant carboxy groups that are converted to allyl ester groups using an allyl-containing halide in the presence of a base in order to avoid gelation. The desired iodonium borates are diaryliodonium borates having substituents on the aryl rings.