amino-5-(β-naphthyl)-1,3,4-thiadiazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: amino-5-(β-naphthyl)-1,3,4-thiadiazole
• 英文别名: 5-(naphthalen-2-yl)-1,3,4-thiadiazol-2-amine；2-Amino-5-(2-naphthyl)-1,3,4-thiadiazole；5-naphthalen-2-yl-1,3,4-thiadiazol-2-amine
• 化学式: C₁₂H₉N₃S
• mdl: MFCD02664100
• 分子量: 227.29
• InChiKey: XFDSCEVGRGOSAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基8-氯-8-氧代辛酸 、 amino-5-(β-naphthyl)-1,3,4-thiadiazole 在 盐酸羟胺 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N¹-hydroxy-N⁸-(5-(naphthalen-2-yl)-1,3,4-thiadiazol-2-yl)octanediamide
  参考文献：
  名称：

  Improved antiproliferative activity of 1,3,4-thiadiazole-containing histone deacetylase (HDAC) inhibitors by introduction of the heteroaromatic surface recognition motif

  摘要：

  A series of 1,3,4-thiadiazole-containing hydroxamic acids, in accord with the common pharmacophore of histone deacetylase (HDAC) inhibitors (a Zn2+ binding moiety-a linker-a surface recognition motif), was identified as submicromolar HDAC inhibitors by our group. In this study, we continued our efforts to develop 1,3,4-thiadiazole bearing hydroxamate analogues by modifying the surface recognition motif. We found that 1,3,4-thiadiazoles having a heteroaromatic substituent showed better HDAC inhibitory activity in enzymatic assay and higher antiproliferative potency in cellular assay compared to SAHA. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.039
• 作为产物：
  描述：

  氨基硫脲 、 2-萘甲酸 在 三氯氧磷 、 水 作用下， 反应 4.5h， 以95%的产率得到amino-5-(β-naphthyl)-1,3,4-thiadiazole
  参考文献：
  名称：

  Improved antiproliferative activity of 1,3,4-thiadiazole-containing histone deacetylase (HDAC) inhibitors by introduction of the heteroaromatic surface recognition motif

  摘要：

  A series of 1,3,4-thiadiazole-containing hydroxamic acids, in accord with the common pharmacophore of histone deacetylase (HDAC) inhibitors (a Zn2+ binding moiety-a linker-a surface recognition motif), was identified as submicromolar HDAC inhibitors by our group. In this study, we continued our efforts to develop 1,3,4-thiadiazole bearing hydroxamate analogues by modifying the surface recognition motif. We found that 1,3,4-thiadiazoles having a heteroaromatic substituent showed better HDAC inhibitory activity in enzymatic assay and higher antiproliferative potency in cellular assay compared to SAHA. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.039

文献信息

• Carboxylic acid derivatives, medicaments comprising these compounds, their use and processes for their production
  申请人：Boehringer Ingelheim Pharma KG

  公开号：US20030055263A1

  公开（公告）日：2003-03-20

  The present application relates to the use of the carboxylic acid derivatives of general formula R 1 —A—B—R 2 (I) wherein R 1 , R 2 , A and B are defined as in claim 1 , the isomers and the salts thereof, particularly the physiologically acceptable salts thereof, which have an inhibitory effect on telomerase, processes for the preparation thereof, pharmaceutical compositions containing these compounds and the use thereof as well as the preparation thereof.

  本申请涉及一般公式R1—A—B—R2(I)的羧酸衍生物的使用，其中R1、R2、A和B的定义如权利要求1中所述，其异构体和盐，特别是其生理上可接受的盐，对端粒酶具有抑制作用，其制备方法，含有这些化合物的药物组合物以及其用途，以及其制备方法。
• 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。
• [DE] CARBONSÄUREDERIVATE, DIESE VERBINDUNGEN ENTHALTENDE ARZNEIMITTEL, DEREN VERWENDUNG UND HERSTELLUNG<br/>[EN] CARBOXYLIC ACID DERIVATIVES, MEDICAMENTS CONTAINING THESE COMPOUNDS, THEIR USE AND THE PRODUCTION THEREOF<br/>[FR] DERIVES D'ACIDE CARBOXYLIQUE, MEDICAMENTS CONTENANT CES COMPOSES, LEUR UTILISATION ET LEUR PRODUCTION
  申请人：BOEHRINGER INGELHEIM PHARMA

  公开号：WO2003006443A2

  公开（公告）日：2003-01-23

  Die vorliegende Anmeldung betrifft die Verwendung der Carbonsäurederivate der allgemeinen Formel R1 - A - B - R2 (I), in der R1, R2, A und B wie im Anspruch 1 definiert sind, deren Isomere und deren Salze, insbesondere deren physiologisch verträglichen Salze, welche eine Hemmwirkung auf die Telomerase aufweisen, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung sowie deren Herstellung.
• Improved antiproliferative activity of 1,3,4-thiadiazole-containing histone deacetylase (HDAC) inhibitors by introduction of the heteroaromatic surface recognition motif
  作者：Peng Guan、Lei Wang、Xuben Hou、Yichao Wan、Wenfang Xu、Weiping Tang、Hao Fang

  DOI：10.1016/j.bmc.2014.09.039

  日期：2014.11

  A series of 1,3,4-thiadiazole-containing hydroxamic acids, in accord with the common pharmacophore of histone deacetylase (HDAC) inhibitors (a Zn2+ binding moiety-a linker-a surface recognition motif), was identified as submicromolar HDAC inhibitors by our group. In this study, we continued our efforts to develop 1,3,4-thiadiazole bearing hydroxamate analogues by modifying the surface recognition motif. We found that 1,3,4-thiadiazoles having a heteroaromatic substituent showed better HDAC inhibitory activity in enzymatic assay and higher antiproliferative potency in cellular assay compared to SAHA. (C) 2014 Elsevier Ltd. All rights reserved.