4-苄基-5-(4-氯苯基)-4H-[1,2,4]噻唑-3-硫醇 | 23282-92-0

• 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-苄基-5-(4-氯苯基)-4H-[1,2,4]噻唑-3-硫醇
• 中文别名: 4-苄基-5-(4-氯-苯基)-4H-[1,2,4]三唑-3-硫醇；4-(苄基)-5-(4-氯苯基)-2H-1,2,4-三唑-3-硫酮；5-(4-氯苯基)-4-(苯基甲基)-2H-1,2,4-三唑-3-硫酮
• 英文名称: 4-benzyl-5-(4-chlorophenyl)-4H-1,2,4-triazole-3-thiol
• 英文别名: 5-(4-Chlor-phenyl)-4-benzyl-3-mercapto-4H-1.2.4-triazol；4-benzyl-5-(4-chloro-phenyl)-2,4-dihydro-[1,2,4]triazole-3-thione；3-mercapto-4-benzyl-5-(4-chlorophenyl)-1,2,4-triazole；4-benzyl-3-(4-chlorophenyl)-1H-1,2,4-triazole-5-thione
• CAS: 23282-92-0
• 化学式: C₁₅H₁₂ClN₃S
• mdl: MFCD01164033
• 分子量: 301.799
• InChiKey: ZGCSGEGQJRCSDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 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：

  乙烯基正丁醚 、 4-苄基-5-(4-氯苯基)-4H-[1,2,4]噻唑-3-硫醇 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以88%的产率得到4-benzyl-1-(1-butoxyethyl)-3-(4-chlorophenyl)-1H-1,2,4-triazole-5(4H)-thione
  参考文献：
  名称：

  杂环硫醇和5-取代的-1 H-四唑向乙烯基醚的非催化加成

  摘要：

  与取代基烷基无关的1-取代的1 H-四唑-5-硫醇和4-取代的4 H-1,2,4-三唑-3-硫醇的烷基化导致形成S-烷基化产物在杂环上。在这项工作中，我们发现在没有催化剂的情况下，取代的1 H-四唑-5-硫醇和4 H-1,2,4-三唑-3-硫醇易于与乙烯基醚反应，专门形成N-取代的1 H -四唑-5（4 H）-硫酮和1 H -1,2,4-三唑-5（4 H）-硫酮。此外，5-取代-1 H的反应在相同条件下用乙烯基醚合成-四唑，有选择地产生2，5-二取代的四唑。

  DOI：

  10.1016/j.tetlet.2017.08.058
• 作为产物：
  描述：

  4-氯苯甲酰肼 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 4-苄基-5-(4-氯苯基)-4H-[1,2,4]噻唑-3-硫醇
  参考文献：
  名称：

  Development of 3,5-Dinitrophenyl-Containing 1,2,4-Triazoles and Their Trifluoromethyl Analogues as Highly Efficient Antitubercular Agents Inhibiting Decaprenylphosphoryl-β-d-ribofuranose 2′-Oxidase

  摘要：

  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.

  DOI：

  10.1021/acs.jmedchem.9b00912

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。
• 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：——
• MALBEC, F.;MILCENT, R.;BARBIER, G., J. HETEROCYCL. CHEM., 1984, 21, N 6, 1689-1698
  作者：MALBEC, F.、MILCENT, R.、BARBIER, G.

  DOI：——

  日期：——
• METHOD OF PREPARING LITHOGRAPHIC PRINTING PLATE
  申请人：Taguchi Yoshinori

  公开号：US20100081771A1

  公开（公告）日：2010-04-01

  A method for preparing a lithographic printing plate includes treating a lithographic printing plate precursor including a hydrophilic support and an image-forming layer containing the following (i) to (iii) with an aqueous solution having a buffering ability: (i) a binder polymer comprising a repeating unit having a structure represented by the following formula (1); (ii) an ethylenically unsaturated compound; and (iii) a polymerization initiator, P-L-(CO 2 H) n (1) wherein P represents a part constituting a main chain skeleton of the polymer, L represents an (n+1) valent connecting group, and n represents an integer of 1 or more.