5-(3-Nitro-phenoxymethyl)-[1,3,4]thiadiazol-2-ylamine | 299935-53-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(3-Nitro-phenoxymethyl)-[1,3,4]thiadiazol-2-ylamine
• 英文别名: 5-[(3-Nitrophenoxy)methyl]-1,3,4-thiadiazol-2-amine
• CAS: 299935-53-8
• 化学式: C₉H₈N₄O₃S
• 分子量: 252.254
• InChiKey: KXWHRXVHEVASTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  香豆素-3-甲酰氯 、 5-(3-Nitro-phenoxymethyl)-[1,3,4]thiadiazol-2-ylamine 反应 0.13h， 以87%的产率得到
  参考文献：
  名称：

  Solvent-Free Synthesis of 2-Amino-5-Aryloxymenthyl1-1,3,4-Thiadiazoles and Their Coumarin or Benzofuran Bis-Heterocyclic Dericatives

  摘要：

  2-amino-5-aryloxymethyl-1,3,4-thiadiazoles were synthesized rapidly by a microwave-accelerated solvent- free procedure in high yield via the condensation of thiosemicarbazide with aryloxyacetic acids using poly(ethylene glycol)-supported dichlorophosphate as a dehydration reagent. The solvent- free N-acylation of 2-amino-5-aryloxymethyl-1,3,4-thiadiazoles with coumarin-3-carboxylic acid chloride or benzofuran-2-carboxylic acid chloride efficiently afforded corresponding bis-heterocyclic derivatives, 2-(coumarin-3-carboxamido)-5-aryloxymethyl-1,3,4-thiadiazoles, and 2-( benzofuran-2-carboxamido)-5-aryloxymethyl-1,3,4-thiadiazoles. The strategy has advantages of no organic solvent pollution, an elevated reaction rate, an improved yield, and a simple work-up procedure.

  DOI：

  10.1080/104265090969577
• 作为产物：
  描述：

  2-(2-(3-nitrophenoxy)acetyl)hydrazine-1-carbothioamide 在 磷酸 作用下， 反应 2.0h， 以56%的产率得到5-(3-Nitro-phenoxymethyl)-[1,3,4]thiadiazol-2-ylamine
  参考文献：
  名称：

  7-甲基-2-（苯氧甲基）-5 H- [1,3,4]噻二唑[3,2 - a ]嘧啶-5-酮衍生物的合成及黄嘌呤氧化酶抑制活性

  摘要：

  血尿酸水平升高（高尿酸血症）是痛风的根本原因。黄嘌呤氧化酶是催化次黄嘌呤氧化为黄嘌呤然后变为尿酸的关键酶。别嘌醇是一种广泛使用的黄嘌呤氧化酶抑制剂，是治疗痛风的最常用药物。但是，一小部分人却遭受别嘌醇的不良影响，包括胃肠道不适，皮疹和超敏反应。此外，尿酸水平升高被认为是心血管疾病的独立危险因素。因此，使用副作用最小的类别嘌呤醇类药物是对抗痛风的理想药物选择。在这项研究中，我们报告了一系列有效的嘧啶5一类似物和一类新的黄嘌呤氧化酶抑制剂的合成。所有合成的嘧啶-5-酮类似物均通过光谱技术和元素分析进行​​表征。四（在该类别的20个合成分子中，图6a，6b，6d和6f）显示出对三种不同的黄嘌呤氧化酶的良好抑制作用，基于它们各自的IC 50值，它们比别嘌呤醇更有效。分子建模和对接研究表明，分子6a与黄嘌呤氧化酶的关键成分钼－氧－硫（MOS）复合物具有很好的相互作用。这些结果突出了鉴定出一种新型的黄

  DOI：

  10.1016/j.bmc.2010.11.034

文献信息

• A NEW ROUTE TO 2-(5-ARYL-2-FUROYLAMIDO)-5-ARYLOXYMETHYL-1,3,4-THIADIAZOLES
  作者：Xicun Wang、Zheng Li、Yuxia Da

  DOI：10.1081/scc-120003160

  日期：2002.1

  ABSTRACT The 2-(5-aryl-2-furoylamido)-5-aryloxymethyl-1,3,4-thiadiazoles 4 1–18 are synthesized by the reaction of 5-aryl-2-furoic acids 1 with phenylsulfonyl chloride and 2-amino-5-aryloxymethyl-1,3,4-thiadiazoles 3 under phase transfer catalysis.

  摘要 2-(5-芳基-2-呋喃酰胺基)-5-芳氧基甲基-1,3,4-噻二唑 4 1–18 是通过 5-芳基-2-呋喃酸 1 与苯磺酰氯和 2-氨基-5-芳氧基甲基-1,3,4-噻二唑 3 在相转移催化下。
• Synthesis of 2‐(5‐Substituted‐1,3,4‐thiadiazolo‐2‐ylimino)‐4‐thiazolidinones under Microwave Irradiation
  作者：Xi-Cun Wang、Guo-Li Huang、Zheng-Jun Quan、Cheng-Wei Lv、Wen-Long Yang

  DOI：10.1080/00397910701845852

  日期：2008.2.1

  Fifteen 2-(5-substituted-1,3,4-thiadiazolo-2-ylimino)-4-thiazolidinones were efficiently synthesized from the reaction of ammonium thiocyanate with 2-chloro-N-(5-substutited-1,3,4-thiadiazolo-2-yl)acetamides under microwave irradiation. The target compounds were obtained in better yields (75-98%) and shorter time (5min) than with conventional heating.
• Synthesis and X-ray characterization of 2,5,6-trisubstituted imidazo[2,1-b][1,3,4]thiadiazole derivatives
  作者：Yu-Xia Da、Ji-Hua Zhu、Zhang Zhang、Xiao-Dong Jia、Cai-Xia Yang、Zheng-Jun Quan

  DOI：10.1002/jhet.678

  日期：2012.1

  AbstractA series of 2,5,6‐trisubstituted imidazo[2,1‐b][1,3,4]thiadiazoles via Mannich reaction of imidazo[2,1‐b][1,3,4]thiadiazoles with morpholine and formaldehyde were synthesized. Structures of all the newly synthesized compounds are well supported by spectral data such as IR, NMR, Mass, and Elemental analysis. Compound 3a has been confirmed by X‐ray diffraction studies. J. Heterocyclic Chem., (2012).
• Synthesis and xanthine oxidase inhibitory activity of 7-methyl-2-(phenoxymethyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one derivatives
  作者：K.R. Sathisha、Shaukath A. Khanum、J.N. Narendra Sharath Chandra、F. Ayisha、S. Balaji、Gopal K. Marathe、Shubha Gopal、K.S. Rangappa

  DOI：10.1016/j.bmc.2010.11.034

  日期：2011.1

  gastrointestinal upset, skin rashes and hypersensitivity reactions. Moreover, an elevated level of uric acid is considered as an independent risk factor for cardiovascular diseases. Therefore use of allopurinol-like drugs with minimum side effects is the ideal drug of choice against gout. In this study, we report the synthesis of a series of pyrimidin-5-one analogues as effective and a new class of xanthine oxidase

  血尿酸水平升高（高尿酸血症）是痛风的根本原因。黄嘌呤氧化酶是催化次黄嘌呤氧化为黄嘌呤然后变为尿酸的关键酶。别嘌醇是一种广泛使用的黄嘌呤氧化酶抑制剂，是治疗痛风的最常用药物。但是，一小部分人却遭受别嘌醇的不良影响，包括胃肠道不适，皮疹和超敏反应。此外，尿酸水平升高被认为是心血管疾病的独立危险因素。因此，使用副作用最小的类别嘌呤醇类药物是对抗痛风的理想药物选择。在这项研究中，我们报告了一系列有效的嘧啶5一类似物和一类新的黄嘌呤氧化酶抑制剂的合成。所有合成的嘧啶-5-酮类似物均通过光谱技术和元素分析进行​​表征。四（在该类别的20个合成分子中，图6a，6b，6d和6f）显示出对三种不同的黄嘌呤氧化酶的良好抑制作用，基于它们各自的IC 50值，它们比别嘌呤醇更有效。分子建模和对接研究表明，分子6a与黄嘌呤氧化酶的关键成分钼－氧－硫（MOS）复合物具有很好的相互作用。这些结果突出了鉴定出一种新型的黄
• Solvent-Free Synthesis of 2-Amino-5-Aryloxymenthyl1-1,3,4-Thiadiazoles and Their Coumarin or Benzofuran Bis-Heterocyclic Dericatives
  作者：Zheng Li、Jin-Lan Yu、Jing-Ya Yang、Wei Zhu、Yan-Long Zhao、Yu-Lin Xing、Xi-Cun Wang

  DOI：10.1080/104265090969577

  日期：2006.1.1

  2-amino-5-aryloxymethyl-1,3,4-thiadiazoles were synthesized rapidly by a microwave-accelerated solvent- free procedure in high yield via the condensation of thiosemicarbazide with aryloxyacetic acids using poly(ethylene glycol)-supported dichlorophosphate as a dehydration reagent. The solvent- free N-acylation of 2-amino-5-aryloxymethyl-1,3,4-thiadiazoles with coumarin-3-carboxylic acid chloride or benzofuran-2-carboxylic acid chloride efficiently afforded corresponding bis-heterocyclic derivatives, 2-(coumarin-3-carboxamido)-5-aryloxymethyl-1,3,4-thiadiazoles, and 2-( benzofuran-2-carboxamido)-5-aryloxymethyl-1,3,4-thiadiazoles. The strategy has advantages of no organic solvent pollution, an elevated reaction rate, an improved yield, and a simple work-up procedure.