2-(3,4,5-trimethoxyphenyl)-5-(phenylamino)-1,3,4-thiadiazole | 35314-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3,4,5-trimethoxyphenyl)-5-(phenylamino)-1,3,4-thiadiazole
• 英文别名: phenyl-[5-(3,4,5-trimethoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-amine；2-(3',4',5'-Trimethoxyphenyl)-5-anilino-1,3,4-thiadiazol；N-Phenyl-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-amine
• CAS: 35314-01-3
• 化学式: C₁₇H₁₇N₃O₃S
• 分子量: 343.406
• InChiKey: IHQQQGSNZIZOSG-UHFFFAOYSA-N

物化性质

• 熔点：
  233-235 °C(Solv: chloroform (67-66-3); ethanol (64-17-5))
• 沸点：
  504.1±60.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酰肼 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-(3,4,5-trimethoxyphenyl)-5-(phenylamino)-1,3,4-thiadiazole
  参考文献：
  名称：

  1,3,4-THIADIAZOLES. REGIOSELECTIVE O-DEMETHYLATION ON DEHYDRATIVE CYCLIZATION OF 1-(3,4,5-TRIMETHOXYBENZOYL)4-SUBSTITUTED THIOSEMICARBAZIDES WITH SULPHURIC ACID

  摘要：

  Cyclization of 1-(3,4,5-trimethoxybenzoyl)-4-substituted thiosemicarbazides 2a-g with sulphuric acid at ambient temperature afforded the selectively demethylated products 2-(4-hydroxy-3,5-dimethoxyphenyl)5-substituted amino-1,3,4-thiodiazoles 4a-g. Meanwhile, dehydrative cyclization of 1-(3,4,5-trimethoxybenzoyl)-4-(benzyl or t-butyl)thiosemicarbazides 2h,i with sulphuric acid yielded 2-(4-hydroxy-3,5-dimethoxyphenyl)-5-amino-1,3,4-thiadiazole 5. On the other hand, dehydration of 2h,i by heating with phosphorus oxychloride yielded 2-(3,4,5-trimethoxyphenyl)-5-amino-1,3,4-thiadiazole 6.

  DOI：

  10.1080/10426500490485525

文献信息

• FeCl3-promoted synthesis of 1,3,4-thiadiazoles under combined microwave and ultrasound irradiation in water
  作者：Huangdi Feng、Xili Ying、Yanqing Peng、Erik V. Van der Eycken、Chuanduo Liu、Shanshan Zhao、Gonghua Song

  DOI：10.1007/s00706-012-0846-x

  日期：2013.5

  AbstractAn eco-friendly and efficient synthesis of substituted 1,3,4-thiadiazole derivatives has been developed. This aqueous heterogeneous approach proceeds smoothly and quickly under combined microwave and ultrasound irradiation in the presence of FeCl3. Graphical Abstract

  摘要已经开发了一种环保，高效的取代1,3,4-噻二唑衍生物的合成方法。在FeCl 3的存在下，在微波和超声联合照射下，这种水相非均质方法可以平稳，快速地进行。 图形概要
• Mazzone; Bonina; Puglisi, Farmaco, Edizione Scientifica, 1982, vol. 37, # 10, p. 685 - 700
  作者：Mazzone、Bonina、Puglisi、Arrigo、Cosentino、Blandino

  DOI：——

  日期：——
• Synthesis and hypoglycemic activity of 3-aryl(or pyridyl)-5-alkyl(or aryl)amino-1,3,4-thiadiazoles and some sulfonylurea derivatives of 4H-1,2,4-triazoles
  作者：C. V. Deliwala、M. Y. Mhasalkar、M. H. Shah、P. D. Pilankar、S. T. Nikam、K. G. Anantanarayanan

  DOI：10.1021/jm00292a035

  日期：1971.10
• One-pot synthesis and anticancer studies of 2-arylamino-5-aryl-1,3,4-thiadiazoles
  作者：Dalip Kumar、Buchi Reddy Vaddula、Kuei-Hua Chang、Kavita Shah

  DOI：10.1016/j.bmcl.2011.02.083

  日期：2011.4

  A series of 2-arylamino-5-aryl-1,3,4-thiadiazoles 1a-j were synthesized and screened for their anticancer activity against various human cancer cell lines. The novel one-pot synthesis of 1,3,4-thiadiazoles was achieved by refluxing aryl aldehydes, hydrazine hydrate, and aryl isothiocyanates in methanol followed by oxidative cyclization with ferric ammonium sulfate. The compounds 1g-j with trimethoxyphenyl at the C-5 position displayed extremely potent anticancer activity with at least twofold selectivity (IC(50): 4.3-9.2 mu M). The nature of substituent on the C-2 arylamino ring may be critical in opting for the selectivity towards a particular cancer cell. (C) 2011 Elsevier Ltd. All rights reserved.
• MAZZONE, G.;BONINA, F.;PUGLISI, G.;ARRIGO, REINA, R.;COSENTINO, C.;BLANDI+, FARMACO ED. SCI., 1982, 37, N 10, 685-700
  作者：MAZZONE, G.、BONINA, F.、PUGLISI, G.、ARRIGO, REINA, R.、COSENTINO, C.、BLANDI+

  DOI：——

  日期：——