4-benzyl-5-(4-methoxyphenyl)-4H-1,2,4-triazole-3-thiol | 23282-98-6

• 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-benzyl-5-(4-methoxyphenyl)-4H-1,2,4-triazole-3-thiol
• 英文别名: 4-benzyl-3-(4-methoxyphenyl)-1H-1,2,4-triazole-5-thione
• CAS: 23282-98-6
• 化学式: C₁₆H₁₅N₃OS
• mdl: MFCD02671622
• 分子量: 297.381
• InChiKey: UWLJJENTOJDKBN-UHFFFAOYSA-N

物化性质

• 熔点：
  206 °C(Solv: methanol (67-56-1))
• 沸点：
  429.5±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  69
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯乙酸 、 4-benzyl-5-(4-methoxyphenyl)-4H-1,2,4-triazole-3-thiol 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以85%的产率得到[4-benzyl-5-(4-methoxyphenyl)-4H-1,2,4-triazol-3-ylsulfanyl]acetic acid
  参考文献：
  名称：

  Synthesis of new 4,5-substituted 4H-1,2,4-triazole-3-thiols and their sulfanyl derivatives

  摘要：

  Reaction of hydrazides of 4-alkoxybenzoic acids with benzyl isothiocyanate followed by cyclization with thiosemicarbazide afforded a series of new 4,5-substituted 4H-1,2,4-triazole-3-thiols. S-Alkylation of the latter led to the formation of the corresponding 4,5-substituted sulfanyl derivatives of 4H-1,2,4-triazoles.

  DOI：

  10.1134/s1070363215030160
• 作为产物：
  描述：

  异硫氰酸苯甲酯 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 7.4h， 生成 4-benzyl-5-(4-methoxyphenyl)-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  Synthesis of new 4,5-substituted 4H-1,2,4-triazole-3-thiols and their sulfanyl derivatives

  摘要：

  Reaction of hydrazides of 4-alkoxybenzoic acids with benzyl isothiocyanate followed by cyclization with thiosemicarbazide afforded a series of new 4,5-substituted 4H-1,2,4-triazole-3-thiols. S-Alkylation of the latter led to the formation of the corresponding 4,5-substituted sulfanyl derivatives of 4H-1,2,4-triazoles.

  DOI：

  10.1134/s1070363215030160

文献信息

• 4-Aralkyl-5-substituted-1,2,4-triazole-5-thiols
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0323737A1

  公开（公告）日：1989-07-12

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are described in which, n is 0 to 5; X¹ to X⁵ are any accessible combination of hydrogen, halogen, C₁₋₆alkyl, C₁₋₆alkoxy, cyano, nitro, SONH₂, SO₂NH₂, SO₂CH₃, SO₂CH₂F, SO₂CHF₂, SO₂CF₃, CF₃, CHO, OH, CH₂OH, CO₂H, or CO₂CpH2p+1 wherein p is 1 to 4; R¹ is phenyl substituted by X¹ to X⁵, C₁₋₄alkyl, C₃₋₆cycloalkyl, or an arylC₁₋₄alkyl group substituted by X¹ to X⁵; R² is hydrogen, C₁₋₄alkyl or (CH₂)m-CO₂R³; m is 0 to 5; and R³ is H or C₁₋₄alkyl. These compounds are dopamine-β-hydroxylase inhibitors. Pharmaceutical compositions are described as are methods of use. Processes for the preparation of these compounds are described.

  描述了式（I）的化合物及其药学上可接受的盐，其中，n为0至5；X¹至X⁵为氢、卤素、C₁₋₆烷基、C₁₋₆烷氧基、氰基、硝基、SONH₂、SO₂NH₂、SO₂CH₃、SO₂CH₂F、SO₂CHF₂、SO₂CF₃、CF₃、CHO、OH、CH₂OH、CO₂H或CO₂CpH2p+1的任意可访问组合，其中p为1至4；R¹为被X¹至X⁵取代的苯基、C₁₋₄烷基、C₃₋₆环烷基或被X¹至X⁵取代的芳基C₁₋₄烷基基团；R²为氢、C₁₋₄烷基或（CH₂）m-CO₂R³；m为0至5；R³为H或C₁₋₄烷基。这些化合物是多巴胺-β-羟基化酶抑制剂。描述了药物组合物以及使用方法。描述了这些化合物的制备过程。
• Synthesis, Molecular Docking and Evaluation of Library of 3-Mercapto-1,2,4-Triazole Derivatives as Antimicrobial Agents
  作者：Swarnagowri Nayak、Santosh L. Gaonkar、Sushruta S. Hakkimane、Swapna B、Nitinkumar S. Shetty

  DOI：10.14233/ajchem.2021.23472

  日期：——

  Due to the increasing microbial resistance to antibacterial and antifungal drugs, the development of new antimicrobial agents is an urgent priority. In search of newer antimicrobial agents, a series of 4,5-disubstituted-3-mercapto-1,2,4-triazole derivatives were synthesized from aromatic acids and substituted isothiocyanates. The in silico study was performed to study the binding interactions of the synthesized compounds with the active pocket of CYP51. Among the synthesized 3-mercapto-triazole derivatives, compounds 6r, 6s and 6u exhibited promising antimicrobial activity comparable to standard drugs. The results suggested that the structural modification to 3-mercapto-1,2,4-triazole derivatives could lead to promising antimicrobial scaffolds.

  由于细菌对抗菌药物和抗真菌药物的耐药性不断增加，开发新的抗微生物药物成为当务之急。在寻找新型抗微生物药物的过程中，从芳香酸和取代异硫氰酸酯合成了一系列4,5-二取代-3-巯基-1,2,4-三唑衍生物。进行了体外研究以研究合成化合物与CYP51活性口袋的结合相互作用。在合成的3-巯基-三唑衍生物中，化合物6r、6s和6u表现出与标准药物可比的有前景的抗微生物活性。结果表明，对3-巯基-1,2,4-三唑衍生物进行结构修饰可以产生有前景的抗微生物骨架。
• Alkylation, amino(hydroxy)methylation, and cyanoethylation of 5-substituted 4-phenyl-4H-1,2,4-triazole-3-thiols
  作者：M. A. Kaldrikyan、N. S. Minasyan、R. G. Melik-Ogandzanyan

  DOI：10.1134/s1070363216020171

  日期：2016.2

  Reactions of 1,2,4-triazole-3-thiols with 2-bromopropionic acid, 2-bromocaproic acid, ethylene chlorohydrine, chloroacetamide, 3-bromo-4-methoxybenzyl chloride, 2-methoxy-5-acetylbenzyl chloride, and 2-(2-chlorophenoxy)ethyl chloride in the presence of KOH have afforded new 3-sulfanyl-1,2,4-triazoles in high yields. Aminomethylation of 1,2,4-triazole-3-thiols in the presence of formaldehyde has given

  1,2,4-三唑-3-硫醇与2-溴丙酸，2-溴己酸，乙烯氯醇，氯乙酰胺，3-溴-4-甲氧基苄基氯，2-甲氧基-5-乙酰基苄基氯和2-的反应在KOH存在下的（2-氯苯氧基）乙基氯以高收率提供了新的3-硫烷基-1,2,4-三唑。在甲醛存在下1,2,4-三唑-3-硫醇的氨甲基化反应产生了相应的2-氨基甲基-2 H -1,2,4-三唑-3（4 H）-硫酮。三唑-3-硫醇与福尔马林和丙烯腈的相互作用导致形成N 2-羟甲基-和3-（2-氰基乙基）硫烷基衍生物。
• Development of 3,5-Dinitrophenyl-Containing 1,2,4-Triazoles and Their Trifluoromethyl Analogues as Highly Efficient Antitubercular Agents Inhibiting Decaprenylphosphoryl-β-<scp>d</scp>-ribofuranose 2′-Oxidase
  作者：Galina Karabanovich、Jan Dušek、Karin Savková、Oto Pavliš、Ivona Pávková、Jan Korábečný、Tomáš Kučera、Hana Kočová Vlčková、Stanislav Huszár、Zuzana Konyariková、Klára Konečná、Ondřej Jand’ourek、Jiřina Stolaříková、Jana Korduláková、Kateřina Vávrová、Petr Pávek、Věra Klimešová、Alexandr Hrabálek、Katarína Mikušová、Jaroslav Roh

  DOI：10.1021/acs.jmedchem.9b00912

  日期：2019.9.12

  We report herein the discovery of 3,5-dinitrophenyl 1,2,4-triazoles with excellent and selective antimycobacterial activities against Mycobacterium tuberculosis strains, including clinically isolated multidrug-resistant strains. Thorough structure activity relationship studies of 3,5-dinitrophenyl-containing 1,2,4-triazoles and their trifluoromethyl analogues revealed the key role of the position of the 3,5-dinitrophenyl fragment in the antitubercular efficiency. Among the prepared compounds, the highest in vitro antimycobacterial activities against M. tuberculosis H(37)Rv and against seven clinically isolated multidrug-resistant strains of M. tuberculosis were found with S-substituted 4-alkyl-5-(3,5-dinitrophenyl)-4H-1,2,4-triazole-3-thiols and their 3-nitro-5-(trifluoromethyl)phenyl analogues. The minimum inhibitory concentrations of these compounds reached 0.03 mu M, which is superior to all the current first-line anti-tuberculosis drugs. Furthermore, almost all compounds with excellent antimycobacterial activities exhibited very low in vitro cytotoxicities against two proliferating mammalian cell lines. The docking study indicated that these compounds acted as the inhibitors of decaprenylphosphoryl-beta-D-ribofuranose 2'-oxidase enzyme, which was experimentally confirmed by two independent radiolabeling experiments.
• Malbec, Frederique; Milcent, Rene; Barbier, Geo, Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 1689 - 1698
  作者：Malbec, Frederique、Milcent, Rene、Barbier, Geo

  DOI：——

  日期：——