3-(4-氯-3-甲基苯氧基甲基)-4-氨基-5-巯基-1,2,4-三唑 | 118794-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(4-氯-3-甲基苯氧基甲基)-4-氨基-5-巯基-1,2,4-三唑
• 英文名称: 3-(4-chloro-3-methylphenoxymethyl)-4-amino-5-mercapto-1,2,4-triazole
• 英文别名: 4-amino-5-[(4-chloro-3-methylphenoxy)methyl]-4H-1,2,4-triazole-3-thiol；4-amino-3-[(4-chloro-3-methylphenoxy)methyl]-1H-1,2,4-triazole-5-thione
• CAS: 118794-57-3
• 化学式: C₁₀H₁₁ClN₄OS
• mdl: MFCD13813598
• 分子量: 270.743
• InChiKey: CHINMOARWFJATM-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C(Solv: 1,4-dioxane (123-91-1); ethanol (64-17-5))
• 沸点：
  410.7±55.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 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：

  3-(4-氯-3-甲基苯氧基甲基)-4-氨基-5-巯基-1,2,4-三唑 在 硫酸 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 4.0h， 生成 5-[(4-chloro-3-methylphenoxy)methyl]-4-[[5-(4-methoxy-2-nitrophenyl)furan-2-yl]methylideneamino]-2-[(4-methylpiperazin-1-yl)methyl]-1,2,4-triazole-3-thione
  参考文献：
  名称：

  某些表征1,2,4-三唑的曼尼希碱的合成表征和抗癌活性研究。

  摘要：

  合成了一系列3-取代的4- [5-（4-（4-甲氧基-2-硝基苯基）-2-糠基]氨基-5-巯基-1,2,4-三唑（3）。用甲醛和各种仲胺将化合物3进行氨基甲基化，可得到曼尼希碱4和5。这些化合物基于IR，1 H-NMR，质谱数据和元素分析进行​​了表征。筛选了新合成的化合物对一组来自60种细胞系的抗癌活性，这些细胞系来自7种癌症，即肺癌，结肠癌，黑素瘤，肾癌，卵巢癌，CNS和白血病。一些化合物的效力稍强。

  DOI：

  10.1016/s0223-5234(03)00128-4
• 作为产物：
  描述：

  在 一水合肼 作用下， 以 水 为溶剂， 以59%的产率得到3-(4-氯-3-甲基苯氧基甲基)-4-氨基-5-巯基-1,2,4-三唑
  参考文献：
  名称：

  Holla, B. Shivarama; Kalluraya, Balakrishna, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 683 - 685

  摘要：

  DOI：

文献信息

• Synthesis and studies on some new fluorine containing triazolothiadiazines as possible antibacterial, antifungal and anticancer agents
  作者：B. Shivarama Holla、B. Sooryanarayana Rao、B.K. Sarojini、P.M. Akberali、N. Suchetha Kumari

  DOI：10.1016/j.ejmech.2006.02.001

  日期：2006.5

  Synthesis of a series of 7-arylidene-6-(2,4-dichlorophenyl)-3-aryloxymethyl/anilinomethyl-1,2,4-triazolo[3 ,4-b]-1,3,4-thiadiazines (3) by the condensation of 3-aryl-1-(2,4-dichloro-5-fluorophenyl)-2-bromo-propen-1-one (1) and 4-amino-5-mercapto-3-aryloxymethyl/anilinomethyl-1,2,4-triazoles (2) is described. The newly synthesized compounds were characterized by elemental analysis IR, 1H NMR and mass

  一系列7-亚芳基-6-（2,4-二氯苯基）-3-芳氧基甲基/苯胺基甲基-1,2,4-三唑[3,4-b] -1,3,4-噻二嗪的合成（3） 3-芳基-1-（2，4-二氯-5-氟苯基）-2-溴丙烯-1-酮（1）与4-氨基-5-巯基-3-芳氧基甲基/苯胺基甲基-1的缩合反应描述了，2，4-三唑（2）。通过元素分析IR，1 H NMR和质谱数据对新合成的化合物进行了表征。测试了这些化合物对大肠杆菌，金黄色葡萄球菌（Smith），铜绿假单胞菌（Gessard），枯草芽孢杆菌和白色念珠菌的抗菌活性。还筛选了一些新合成的化合物的抗癌活性。其中化合物3m，3o，3q显示出体外抗癌活性。
• SYNTHESIS OF SOME NEW 1,2,4-TRIAZOLO[3,4-<i>b</i>]-THIADIAZOLE DERIVATIVES AS POSSIBLE ANTICANCER AGENTS
  作者：K. Subrahmanya Bhat、D. Jagadeesh Prasad、Boja Poojary、B. Shivarama Holla

  DOI：10.1080/10426500490464186

  日期：2004.8

  derivatives, whereas with α-bromoketones gives a six-membered heterocycle. In this article we report the synthesis of a series of 1,2,4-triazolo[3,4-b]thiadiazoles 5 starting from 4-amino-3-substituted-5-mercapto-1,2,4-triazoles 3 and fluorobenzoic acids 4 using phosphorous oxychloride as cyclizing agent. Fourteen of the newly synthesized compounds were screened for anticancer properties. Four among them

  3-Substituted-4-amino-5-mercapto-1,2,4-triazoles 是用于构建各种生物活性杂环的通用合成子。它们与羧酸的环化得到稠合的五元衍生物，而与 α-溴酮环化得到六元杂环。在本文中，我们报道了一系列 1,2,4-三唑并 [3,4-b] 噻二唑 5 的合成，这些化合物以 4-氨基-3-取代-5-巯基-1,2,4-三唑 3 和以三氯氧化磷为环化剂制备氟苯甲酸4。筛选了 14 种新合成的化合物的抗癌特性。其中四个显示出体外抗癌活性。
• Kalluraya, Balakrishna; D'Souza, Alphonsus, Journal of the Indian Chemical Society, 1995, vol. 72, # 2, p. 137 - 140
  作者：Kalluraya, Balakrishna、D'Souza, Alphonsus

  DOI：——

  日期：——
• Design and synthesis of benzothiazole-6-sulfonamides acting as highly potent inhibitors of carbonic anhydrase isoforms I, II, IX and XII
  作者：Diaa A. Ibrahim、Deena S. Lasheen、Maysoun Y. Zaky、Amany W. Ibrahim、Daniela Vullo、Mariangela Ceruso、Claudiu T. Supuran、Dalal A. Abou El Ella

  DOI：10.1016/j.bmc.2015.05.019

  日期：2015.8

  A series of novel 2-aminobenzothiazole derivatives bearing sulfonamide at position 6 was designed, synthesized and investigated as inhibitors of four isoforms of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1), the cytosolic CA I and II, and the tumor-associated isozymes CA IX and XII. Docking and binding energy studies were carried out to reveal details regarding the favorable interactions between the scaffolds of these new inhibitors and the active sites of the investigated CA isoforms. Most of the novel compounds were acting as highly potent inhibitors of the tumor-associated hCA IX and hCA XII with K(I)s in the nanomolar range. The ubiquitous and dominant rapid cytosolic isozyme hCA II was also inhibited with K(I)s ranging from 3.5 to 45.4 nM. The favorable interactions between some of the new compounds and the active site of different CA isoforms were delineated by using molecular docking which may be useful for designing compounds with high affinity and selectivity for some CAs with biomedical applications. (C) 2015 Elsevier Ltd. All rights reserved.
• Studies on arylfuran derivatives
  作者：B Shivarama Holla、B Sooryanarayana Rao、K Shridhara、P.M Akberali

  DOI：10.1016/s0014-827x(00)00033-1

  日期：2000.5

  A series of 3-substituted-4-[5-(2,4-dichlorophenyl)-2-furfurylidine]amino-5-me rcapto-1, 2,4-triazoles (3) are synthesised. Aminomethylation of 3 with formaldehyde and a primary/secondary amine furnished Mannich bases 4 and 5. Both Schiff bases 3 and Mannich bases 4 and 5 are characterised on the basis of IR, 1H NMR, mass spectral data and elemental analysis. All the newly synthesised compounds are tested for their antibacterial activities. Some of the selected compounds are also tested for their fungicidal and herbicidal properties.