2-amino-5-(α-naphthyloxymethyl)-1,3,4-thiadiazole | 364360-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-amino-5-(α-naphthyloxymethyl)-1,3,4-thiadiazole
• 英文别名: 2-amino-5-α-naphthoxymethyl-1,3,4-thiadiazole；5-[(naphthalen-1-yloxy)methyl]-1,3,4-thiadiazol-2-amine；5-[(1-naphthalenyloxy)methyl]-1,3,4-thiadiazol-2-amine；5-(naphthalen-1-yloxymethyl)-1,3,4-thiadiazol-2-amine
• CAS: 364360-14-5
• 化学式: C₁₃H₁₁N₃OS
• mdl: MFCD01028942
• 分子量: 257.316
• InChiKey: UCXMSADTGQFJKL-UHFFFAOYSA-N

物化性质

• 熔点：
  216 °C(Solv: ethanol (64-17-5))
• 沸点：
  503.1±52.0 °C(Predicted)
• 密度：
  1.379±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.076
• 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：

  2,5-己二酮 、 2-amino-5-(α-naphthyloxymethyl)-1,3,4-thiadiazole 在 溶剂黄146 作用下， 反应 1.0h， 以60%的产率得到2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-((naphthalen-1-yloxy)methyl)-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：

  萘酚 在 sodium hydroxide 、 三氯氧磷 作用下， 以 水 为溶剂， 反应 4.5h， 生成 2-amino-5-(α-naphthyloxymethyl)-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

文献信息

• One-Pot Synthesis of Phenylallyl Substituted Unsymmetrical Ureas Under Microwave Irradiation
  作者：Lan-Qin Chai、Wei-Peng Chen、Xiao-Qiang Wang、Jian-Lin Ge

  DOI：10.1080/10426500701407441

  日期：2007.9.13

  unsymmetrical ureas were synthesized in a one-pot procedure by reactions of cinnamoyl isocyanate, which was prepared from cinnamoyl azide by Curtius rearrangement, with various aromatic amines, 2-amino-5-aryl-1,3,4-thiadiazoles and 2-amino-5-aryloxymethylene-1,3,4-thiadiazoles under microwave irradiation. Compared to conventional methods, this synthesis has the advantages of mild reaction conditions

  通过Curtius重排由肉桂酰叠氮化物制备的肉桂酰异氰酸酯与各种芳香胺，2-氨基-5-芳基-1,3,4反应在一锅法中合成了一系列苯基烯丙基取代的不对称脲-噻二唑和 2-氨基-5-芳氧基亚甲基-1,3,4-噻二唑在微波辐射下。与常规方法相比，该合成方法具有反应条件温和、易于操作、收率高等优点。产品已通过分析和光谱（IR 和 1H NMR）数据表征。
• 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 Benzofuryl Substituted Unsymmetrical Ureas Under Microwave Irradiation
  作者：Lan-Qin Chai、Yony-Xi Chen、Wei-Peng Chen、Qi Ding

  DOI：10.1080/10426500802176689

  日期：2009.2.3

  2-benzofuryl substituted unsymmetrical ureas were synthesized by reactions of benzofuroyl isocyanate, which was prepared from benzofuroyl azide by Curtius rearrangement, with various aromatic amines, 2-amino-5-(benzo-2-furyl)-1,3,4-thiadiazole, and 2-amino-5-aryloxymethylene-1,3, 4-thiadiazoles under microwave irradiation. Compared to conventional methods, this synthesis has the advantages of mild reaction

  由苯并呋喃酰叠氮化物经库尔提斯重排制备的苯并呋喃酰异氰酸酯与各种芳香胺、2-氨基-5-(苯并-2-呋喃基)-1,3反应合成了一系列2-苯并呋喃基取代的不对称脲， 4-噻二唑和 2-氨基-5-芳氧基亚甲基-1,3, 4-噻二唑在微波辐射下。与常规方法相比，该合成方法具有反应条件温和、易于操作、收率高等优点。产品已通过分析和光谱（IR 和 1 H NMR）数据表征。
• 含吩噻嗪基及1,3,4-噻二唑基Mannich碱类化合 物及其制备方法和应用
  申请人：陕西科技大学

  公开号：CN103288816B

  公开（公告）日：2016-04-06

  含吩噻嗪基及1,3,4-噻二唑基Mannich碱类化合物及其制备方法和应用，以吩噻嗪、甲醛溶液、1,3,4-噻二唑衍生物为原料，以乙醇为溶剂在室温下搅拌反应，然后将得到的反应液中的溶剂蒸出，反应器中的剩余物即为粗品，将粗品重结晶，即得含吩噻嗪基及1,3,4-噻二唑基Mannich碱。本发明操作步骤简单、后处理方便，产率高，且该化合物能够在制备抗革兰氏菌药物中的应用。
• THIADIAZOLE DERIVATIVES, INHIBITORS OF STEAROYL-COA DESATURASE
  申请人：Bouillot Anne Marie Jeanne

  公开号：US20100120669A1

  公开（公告）日：2010-05-13

  The present invention relates to substituted thiadiazole compounds of the formula (I): and pharmaceutically acceptable salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds for modulating SCD activity.

  本发明涉及公式（I）的取代噻二唑化合物及其药学上可接受的盐，含有它们的制药组合物以及它们在医学上的应用。特别地，本发明涉及用于调节SCD活性的化合物。