5-[(3-Bromophenoxy)methyl]-1,3,4-thiadiazol-2-amine | 299443-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[(3-Bromophenoxy)methyl]-1,3,4-thiadiazol-2-amine
• CAS: 299443-53-1
• 化学式: C₉H₈BrN₃OS
• 分子量: 286.152
• InChiKey: PLOGFBZADVMTDP-UHFFFAOYSA-N

物化性质

• 熔点：
  151-153 °C(Solvent: Ethanol)
• 沸点：
  450.8±51.0 °C(predicted)
• 密度：
  1.697±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 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：
  89.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[(3-Bromophenoxy)methyl]-1,3,4-thiadiazol-2-amine 、 2,5-己二酮 在 溶剂黄146 作用下， 反应 1.0h， 以60%的产率得到2-((3-bromophenoxy)methyl)-5-(2,5-dimethyl-1H-pyrrol-1-yl)-1,3,4-thiadiazole
  参考文献：
  名称：

  Synthesis, evaluation and in silico molecular modeling of pyrroyl-1,3,4-thiadiazole inhibitors of InhA

  摘要：

  Enoyl acyl carrier protein reductase (ENR) is an essential type II fatty acid synthase (FAS-II) pathway enzyme that is an attractive target for designing novel antitubercular agents. Herein, we report sixty-eight novel pyrrolyl substituted aryloxy-1,3,4-thiadiazoles synthesized by three-step optimization processes. Three-dimensional quantitative structure-activity relationships (3D-QSAR) were established for pyrrolyl substituted aryloxy-1,3,4-thiadiazole series of InhA inhibitors using the comparative molecular field analysis (CoMFA). Docking analysis of the crystal structure of ENR performed by using Surflex-Dock in Sybyl-X 2.0 software indicates the occupation of pyrrolyl substituted aryloxy 1,3,4-thiadiazole into hydrophobic pocket of InhA enzyme. Based on docking and database alignment rules, two computational models were established to compare their statistical results. The analysis of 3D contour plots allowed us to investigate the effect of different substituent groups at different positions of the common scaffold. In vitro testing of ligands using biological assays substantiated the efficacy of ligands that were screened through in silico methods. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.03.001
• 作为产物：
  描述：

  [[2-(3-bromophenoxy)acetyl]amino]thiourea 在 磷酸 作用下， 反应 2.0h， 以57%的产率得到5-[(3-Bromophenoxy)methyl]-1,3,4-thiadiazol-2-amine
  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

• 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
• Synthesis, evaluation and in silico molecular modeling of pyrroyl-1,3,4-thiadiazole inhibitors of InhA
  作者：Shrinivas D. Joshi、Uttam A. More、Deepshikha Koli、Manoj S. Kulkarni、Mallikarjuna N. Nadagouda、Tejraj M. Aminabhavi

  DOI：10.1016/j.bioorg.2015.03.001

  日期：2015.4

  Enoyl acyl carrier protein reductase (ENR) is an essential type II fatty acid synthase (FAS-II) pathway enzyme that is an attractive target for designing novel antitubercular agents. Herein, we report sixty-eight novel pyrrolyl substituted aryloxy-1,3,4-thiadiazoles synthesized by three-step optimization processes. Three-dimensional quantitative structure-activity relationships (3D-QSAR) were established for pyrrolyl substituted aryloxy-1,3,4-thiadiazole series of InhA inhibitors using the comparative molecular field analysis (CoMFA). Docking analysis of the crystal structure of ENR performed by using Surflex-Dock in Sybyl-X 2.0 software indicates the occupation of pyrrolyl substituted aryloxy 1,3,4-thiadiazole into hydrophobic pocket of InhA enzyme. Based on docking and database alignment rules, two computational models were established to compare their statistical results. The analysis of 3D contour plots allowed us to investigate the effect of different substituent groups at different positions of the common scaffold. In vitro testing of ligands using biological assays substantiated the efficacy of ligands that were screened through in silico methods. (C) 2015 Elsevier Inc. All rights reserved.