4-苯基-5-(2'-羟基苯基)-3-巯基-1,2,4-三唑 | 81518-26-5

• 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-苯基-5-(2'-羟基苯基)-3-巯基-1,2,4-三唑
• 英文名称: 4-phenyl-5-(2'-hydroxyphenyl)-3-mercapto-1,2,4-triazole
• 英文别名: 5-(o-hydroxyphenyl)-4-phenyl-4H-1,2,4-triazole-3-thiol；5-(2-hydroxyphenyl)-4-phenyl-1,2,4-triazole-3-thiol；3H-1,2,4-Triazole-3-thione, 2,4-dihydro-5-(2-hydroxyphenyl)-4-phenyl-；3-(2-hydroxyphenyl)-4-phenyl-1H-1,2,4-triazole-5-thione
• CAS: 81518-26-5
• 化学式: C₁₄H₁₁N₃OS
• mdl: MFCD00099431
• 分子量: 269.327
• InChiKey: OPECQRMMGCXRAG-UHFFFAOYSA-N

物化性质

• 熔点：
  300-301 °C(Solv: 1,4-dioxane (123-91-1); ethanol (64-17-5))
• 沸点：
  407.5±47.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-苯基-5-(2'-羟基苯基)-3-巯基-1,2,4-三唑 在 sodium methylate 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 1,9-dibenzena-2,8-(3,5)-1,2,4-triazola-10,14-dioxa-3,7-dithia-2(4),8(4)-diphenyl-12-oxocyclotetradecaphane
  参考文献：
  名称：

  1,2,4-三唑烷和1,3,4-恶二唑烷的新型合成：狄克曼凝聚法

  摘要：

  Dieckmann缩合首次被用于合成新型1,2,4-三唑烷和1,3,4-恶二唑烷。使bis-1,3,4-恶二唑-2-硫醇1a和1b与溴乙酸乙酯反应生成二酯2a和2b。将二酯2a和2b在干燥条件下用甲醇钠的甲醇溶液处理，得到所需的对称1,3,4-恶二唑烷3a和3b。类似地，含1,2,4-三唑部分大环化合物前体的二酯，即，图6a，图6b，10，13A，13B和13C是从合成图5a，图5b，9，图12A，12B，和12C分别。这些二酯，得到对称的酮的狄克曼缩合反应图7a，图7b，11，14A，14B，和14C。在常规的Dieckmann产物被稀无机酸中和期间原位水解后，观察到CO 2的挤出，从而以高收率提供高度对称的酮。此外，酮14a，14b和通过与Lawesson试剂的反应将14c转化成它们各自的硫酮。所有产物均以良好的产率合成，并且通过各种光谱学工具和元素分析证实了结构。J.杂环化​​学。，（2012）。

  DOI：

  10.1002/jhet.729
• 作为产物：
  描述：

  N-salicylyl 4-phenylthiosemicarbazide 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 12.0h， 生成 4-苯基-5-(2'-羟基苯基)-3-巯基-1,2,4-三唑
  参考文献：
  名称：

  1-[(1R, 2S)-2-氟环丙基]环丙沙星-1,2,4-三唑-5(4H)-硫酮杂化物的设计、合成和抗菌评价

  摘要：

  设计、合成和评估了一类新的 1-[(1R,2S)-2-氟环丙基]环丙沙星 (CPFX)-1,2,4-三唑-5(4H)-硫酮杂化物 6a-6o对一组临床上重要的药物敏感和耐药革兰氏阳性和革兰氏阴性病原体的抗菌活性。我们的结果表明，所有杂种 6a - 6o 对受试菌株，尤其是革兰氏阴性病原体具有很强的效力。合成的杂合体比亲本 1-[(1R,2S)-2-氟环丙基]CPFX (1) 更有效，并且与 CPFX 和左氧氟沙星对大多数测试病原体的作用相当，值得进一步研究。

  DOI：

  10.1002/cbdv.201800261

文献信息

• Pharmacomodulations of the benzoyl-thiosemicarbazide scaffold reveal antimicrobial agents targeting d-alanyl-d-alanine ligase in bacterio
  作者：Alice Ameryckx、Lionel Pochet、Gang Wang、Esra Yildiz、Bouazza Es Saadi、Johan Wouters、Françoise Van Bambeke、Raphaël Frédérick

  DOI：10.1016/j.ejmech.2020.112444

  日期：2020.8

  scaffold to identify new Ddl inhibitors with antibacterial potency. Five novel series of thiosemicarbazide analogues, 1,2,4-thiotriazole-3-thiones, 1,3,4-thiadiazoles, phenylthiosemicarbazones, diacylthiosemicarbazides and thioureas were synthesized via straightforward procedures, then tested against Ddl and on susceptible or resistant bacterial strains. Among these, the thiosemicarbazone and thiotriazole

  d -Alanyl- d丙氨酸连接酶（DDL）是参与肽聚糖生物合成的细菌酶中的验证和有吸引力的目标。在目前的工作中，我们调查了苯甲酰基硫代氨基脲骨架的药物调节，以鉴定具有抗菌效力的新型Ddl抑制剂。通过简单的方法合成了五个新系列的硫代氨基脲类似物1,2,4-硫代三唑-3-硫酮，1,3,4-噻二唑，苯基硫代氨基脲，二酰基硫代氨基脲和硫脲，然后针对Ddl以及易感或耐药细菌菌株进行了测试。在这些当中，硫半脲和硫代三唑被认为是最有前途的支架，其在微摩尔范围内具有Ddl抑制能力。水杨醛-4（N）-（3,4-二氯苯基）硫半脲33是我们研究中最好的化合物之一，对VRE菌株的抗菌活性为3.12–6.25μM（1.06–2.12μg/ mL），而对VRE菌株的抗菌活性为12.5–25.0μM（4.25） –8.50μg/ mL），针对MRSA和VRSA菌株。对Ddl抑制剂4-（3,4-二氯苯基）-5-（2-羟苯基）-2
• Synthesis and Biological Evaluation of 1,2,4-Triazoles and 1,3,4-Oxadiazoles Derivatives Linked to 1,4-Dihydropyridines Scaffold
  作者：Maghsoud Ziaie、Karim Akbari Dilmaghani、Amir Tukmechi

  DOI：10.17344/acsi.2017.3506

  日期：2017.12.15

  A series of diethyl-2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate derivative coupled to 1,3,4-oxadiazole-5-thiones and 1,2,4-triazole-5-thiones moieties at C2,C6 positions of 1,4-dihydropyridine ring system was prepared. This linkage was carried out by the reaction of 1,3,4-oxadiazole-5-thiones and 1,2,4-triazole-5-thiones with 2,6-dibromomethyl-3,5-diethoxycarbonyl-4-phenyl-1,4-dihydropyridine

  一系列与1,3,4-恶二唑-5-硫酮和1,2,4-三唑-5偶联的2,6-二甲基-4-苯基-1,4-二氢吡啶-3,5-二羧酸二乙基酯衍生物制备了在1，4-二氢吡啶环系统的C2，C6位的-硫酮部分。该连接通过1,3,4-恶二唑-5-硫酮和1,2,4-三唑-5-硫酮与2,6-二溴甲基-3,5-二乙氧基羰基-4-苯基-1的反应进行1,4-二氢吡啶以碳酸钾为弱碱，无水丙酮为溶剂。通过FT-IR，1H NMR，13C NMR光谱数据，元素分析和FAB-MS对新合成的化合物进行了表征。与恩诺沙星和两性霉素作为通常用于治疗这种感染的参考药物相比，在体外测试了所合成的化合物对大肠杆菌和烟曲霉的抗微生物和抗真菌活性。合成的化合物对测试的细菌和真菌显示出不同的抑制区。化合物8d显示出对大肠杆菌和烟曲霉的更多拮抗活性。
• Synthesis of 5‐Aryl‐3‐Glycosylthio‐4‐Phenyl‐4H‐1,2,4‐Triazoles and Their Acyclic Analogs Under Conventional and Microwave Conditions
  作者：El Sayed H. El‐Ashry、Nagwa Rashed、Laila F. Awad、El Sayed Ramadan、Somia M. Abdel‐Maggeed、Nagat Rezki

  DOI：10.1080/07328300802030795

  日期：2008.5

  Under microwave irradiation (MWI), 4-phenyl-5-substituted-4H-1,2,4-triazole-3-thiol derivatives 7 and 8 were synthesized in a good yield by intramolecular cyclization of the aroyl phenyl thiosemicarbazides 5 and 6. The respective triazolylglycosides (Str-glycosides) 12-17 were obtained by reaction of triazoles 7 and 8 with glycosyl halides 9-11 in dry acetone in the presence of potassium carbonate as base under both conventional and MWI conditions. Alkylation of 7 and 8 with haloalchols 18-20 in boiling ethanolic solution containing sodium ethoxide as a base gave the corresponding alkylated analogs 21-26. MWI conditions led to higher yield in shorter reaction time than the conventional method. Treatment of 26 with tosyl chloride gave the unexpected product 29 and not 27 or 28. Oxidation of 26 with sodium metaperiodate afforded triazole 8 and not the aldehyde 30. Attempted glycosylation and alkylation of the phenolic OH group in triazole 8 were unsuccessful; this was proved by theoretical calculations using the AM1 semi-empirical method.
• Synthesis of a Series of Novel Tetra-tert-butylcalix[4]arene Linked to 1,2,4-Triazole and 1,3,4-Oxadiazole Derivatives
  作者：Karim Akbari Dilmaghani、Zahra Dono Ghezelbash

  DOI：10.17344/acsi.2016.2637

  日期：2016.12.15

  A series of tetra-tert-butylcalix[4] arene linked to 1,2,4-triazole-5-thiones and 1,3,4-oxadiazole-5-thiones derivatives at lower rim were synthesized by the reaction of 1,2,4-triazole-5-thione and 1,3,4-oxadiazole-5-thione with 5,11,17,23-tetra-tert-butyl-25,27-bis(3-bromopropoxy)-26,28-dihydroxycalix[4] arene (2). The synthesized compounds were characterized by FT-IR, H-1 NMR, C-13 NMR spectral data, elemental analysis and ESI-MS.
• Search for factors affecting antibacterial activity and toxicity of 1,2,4-triazole-ciprofloxacin hybrids
  作者：Tomasz Plech、Barbara Kaproń、Agata Paneth、Urszula Kosikowska、Anna Malm、Aleksandra Strzelczyk、Paweł Stączek、Łukasz Świątek、Barbara Rajtar、Małgorzata Polz-Dacewicz

  DOI：10.1016/j.ejmech.2015.04.058

  日期：2015.6

  A series of 1,2,4-triazole-based compounds was designed as potential antibacterial agents using molecular hybridization approach. The target compounds (23-44) were synthesized by Mannich reaction of 1,2,4-triazole-3-thione derivatives with ciprofloxacin (CPX) and formaldehyde. Their potent antibacterial effect on Gram-positive bacteria was accompanied by similarly strong activity against Gram-negative strains. The toxicity of the CPX-triazole hybrids for bacterial cells was even up to 18930 times higher than the toxicity for human cells. The results of enzymatic studies showed that the antibacterial activity of the CPX-triazole hybrids is not dependent solely on the degree of their affinity to DNA gyrase and topoisomerase IV. (C) 2015 Elsevier Masson SAS. All rights reserved.