5-(4-ethoxyphenyl)-4-amino-3-mercapto-4H-1,2,4-triazole

• 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-ethoxyphenyl)-4-amino-3-mercapto-4H-1,2,4-triazole
• 英文别名: 4-amino-5-(4-ethoxyphenyl)-4H-[1,2,4]triazole-3-thiol；4-amino-5-(4-ethoxyphenyl)-4H-1,2,4-triazole-3-thiol；4-amino-3-(4-ethoxyphenyl)-1H-1,2,4-triazole-5-thione
• 化学式: C₁₀H₁₂N₄OS
• mdl: MFCD06655372
• 分子量: 236.297
• InChiKey: XYCKNRBDYPLFBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  95
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-ethoxyphenyl)-4-amino-3-mercapto-4H-1,2,4-triazole 在 甲醇 、 乙醇 、 potassium hydroxide 、 zinc(II) chloride 作用下， 以 苯 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Panwar, Hemant; Chaudhary, Nidhi; Singh, Shishupal, Asian Journal of Chemistry, 2012, vol. 24, # 6, p. 2651 - 2656

  摘要：

  DOI：
• 作为产物：
  描述：

  对乙氧基苯甲酸 在 硫酸 、 一水合肼 、 三乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 35.0h， 生成 5-(4-ethoxyphenyl)-4-amino-3-mercapto-4H-1,2,4-triazole
  参考文献：
  名称：

  Design, Synthesis and Evaluation of Antitubercular Activity of Novel 1,2,4-Triazoles Against MDR Strain of Mycobacterium tuberculosis

  摘要：

  耐药性结核分枝杆菌多种形式的出现促使了新机制药物的探索。最近，氟康唑作为一种基于唑类的抗结核药物，因其靶向分枝杆菌细胞色素P450而受到广泛关注。在本研究中，我们设计了基于氟康唑结构的新型1,2,4-三唑衍生物，并评估了其对结核分枝杆菌H37Rv及多药耐药（MDR）分枝杆菌的体外抗结核活性。

  DOI：

  10.1007/s11094-018-1714-8

文献信息

• A General and Efficient Method for the Selective Synthesis of β-Hydroxy Sulfides and β-Hydroxy Sulfoxides Catalyzed by Gallium(III) Triflate
  作者：Weike Su、Jiuxi Chen、Huayue Wu、Can Jin

  DOI：10.1021/jo0700124

  日期：2007.6.1

  triflate-catalyzed ring opening of epoxides affords β-hydroxy sulfides with high regioselectivity and chemoselectivity in high yields (84−97%) under solvent-free conditions. Additionally, a simple, efficient, and environmentally benign one-pot procedure for the synthesis of β-hydroxy sulfoxides in sole water has been developed for the first time. The process, promoted by a H2O2−Ga(OTf)3 system, affords β-hydroxy

  在无溶剂条件下，三氟甲磺酸镓（III）催化环氧化物的开环可提供具有高区域选择性和化学选择性的β-羟基硫化物，产率高（84-97％）。另外，首次开发了在单一水中合成β-羟基亚砜的简单，有效且对环境无害的一锅法。通过H 2 O 2 -Ga（OTf）3系统的促进，该过程以高收率（81-94％）和高化学选择性提供了β-羟基亚砜，而没有检测到对β-羟基砜的过度氧化。反应后催化剂可以容易地回收并重新使用而没有明显的活性损失。
• Synthesis and Structure of Novel 1,2,4-triazole Derivatives Containing the 2,4-dinitrophenylthio Group
  作者：Qichun Ding、Xinxiang Lei、Jianyu Jin、Lixue Zhang、Huiai Du、Haile Zhang

  DOI：10.3184/030823409x401961

  日期：2009.2

  Some novel 1,2,4-triazole derivatives containing the 2,4-dinitrophenylthio group have been synthesised in high yields by means of the reactions of 3-substituted-4-amino −1 H-1,2,4-triazole-5(4 H)-thiones or ( E)-3-aryl-4-(benzylideneamino)-1 H-1,2,4-triazole-5(4 H)-thiones with 1-chloro-2,4-dinitrobenzene. The ( E)-3-aryl-4-(benzylideneamino)-1 H-1,2,4-triazole-5(4 H)-thiones were prepared by the reaction of 4-amino-3-aryl-2 H-1,2,4-triazole-3(4 H)-thiones and diverse aromatic aldehydes. The 2, 4-dinitrophenyl group linked to the S atom, not to the N atom, was confirmed by the crystal structures. The structures of all the compounds were determined by elemental analysis, IR, MS, ¹H NMR and ¹³C NMR.

  通过 3-取代-4-氨基-1 H-1,2,4-三唑-5(4 H)-硫酮或 ( E)-3- 芳基-4-(亚苄基氨基)-1 H-1,2,4-三唑-5(4 H)-硫酮与 1-氯-2,4-二硝基苯的反应，高产合成了一些含有 2,4-二硝基苯硫基的新型 1,2,4-三唑衍生物。4- 氨基-3-芳基-2 H-1,2,4-三唑-3(4 H)-硫酮与多种芳香醛反应制备了(E)-3-芳基-4-(苄亚氨基)-1 H-1,2,4-三唑-5(4 H)-硫酮。晶体结构证实，2, 4-二硝基苯基与 S 原子而非 N 原子相连。所有化合物的结构都是通过元素分析、红外光谱、质谱、1H NMR 和 13C NMR 确定的。
• Synthesis of chiral fused heterocyclic compounds containing 1,2,4-triazole ring
  作者：Haoxin Shi、Zhongyi Wang、Haijian Shi

  DOI：10.1002/jhet.5570380206

  日期：2001.3

  A series of new chiral (S)-3-ary1-6-pyrrolidin-2-yl-[1,2,4]triazolo[3,4-b]thiadiazole (II1-5), (S)-1-(3-aryl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl)-ethylamine (II6-8) and (S)-1,2-bis(3-aryl-[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazol-6-yl)-ethylamine (II9-11) were prepared by the condensation of 3-aryl-4-amino-5-mercapto-1,2,4-triazoles with different L-amino acids in the presence of phosphorus

  一系列新的手性（S）-3-ary1-6-吡咯烷-2-基-[1,2,4]三唑[3,4- b ]噻二唑（II 1-5），（S）-1- （3-芳基-[1,2,4]三唑并[3,4- b ] [1,3,4]噻二唑-6-基）-乙胺（II 6-8）和（S）-1,2-通过3的缩合反应制得双（3-芳基-[1,2,4]三唑-[3,4- b ] [1,3,4]噻二唑-6-基）-乙胺（II 9-11）在氯氧化磷存在下，使用具有不同L-氨基酸的-芳基-4-氨基-5-巯基-1,2,4-三唑，并对其抗菌活性进行了评估。
• 1H and13C NMR spectral characterization of some novel 7H-1,2,4-triazolo[3, 4-b] [1,3,4] thiadiazine derivatives
  作者：Xinxiang Lei、Lixue Zhang、Anjiang Zhang、Xiaoxia Ye、Jing Xiong

  DOI：10.1002/mrc.1940

  日期：2007.3

  Some novel 1, 2, 4‐triazolo[3,4‐b][1,3,4]thiadiazines derivatives were synthesized. The complete 1H and 13C NMR chemical shift assignments were analyzed on one‐ and two‐dimensional NMR techniques, including DEPT, NOE‐DIF, COSY, HMBC, and HSQC. Copyright © 2006 John Wiley & Sons, Ltd.

  合成了一些新型的 1, 2, 4-三唑并[3,4-b][1,3,4]噻二嗪衍生物。完整的 1H 和 13C NMR 化学位移分配在一维和二维 NMR 技术上进行分析，包括 DEPT、NOE-DIF、COSY、HMBC 和 HSQC。版权所有 © 2006 John Wiley & Sons, Ltd.
• Synthesis and Biological Activities of Some Novel Triazolothiadiazines and Schiff Bases Derived from 1,2,4-Triazole
  作者：Sannu Zhou、Lixue Zhang、Jianyu Jin、Anjiang Zhang、Xinxiang Lei、Jianshuang Lin、Jiangwei He、Haile Zhang

  DOI：10.1080/10426500600976884

  日期：2007.1.1

  3-substituted-4-amino-5-mercapto-1,2,4-triazoles are versatile compounds for constructing various biologically active heterocycles. To find more 1,2,4-triazole derivatives that may possess significant biological activities, we synthesized a number of novel 3-(4-ethoxyphenyl)-6-aryl-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines and 4(arylmethylidene)amino-5-(4-ethoxyphenyl)-3-mercapto-4H-1,2,4-triazoles. All the title compounds were characterized by elemental analysis and NMR data, and the compound 5f was investigated with X-ray crystallography (CCDC No. 611639). The plant-growth regulating effects of those Schiff bases were examined, and they showed an inhibiting effect on the growth of wheat radicles and radish radicles.