5-[(3-氯苯基)甲基]-1,3,4-噻二唑-2-胺 | 39181-49-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-[(3-氯苯基)甲基]-1,3,4-噻二唑-2-胺
• 英文名称: 5-(3-chlorobenzyl)[1.3.4]thiadiazol-2-ylamine
• 英文别名: 5-(3-chloro-benzyl)-[1,3,4]thiadiazol-2-ylamine；5-[(2-chlorophenyl)methyl]-1,3,4-thiadiazol-2-amine；2-Amino-5-(3-chlorbenzyl)thiadiazol；5-[(3-Chlorophenyl)methyl]-1,3,4-thiadiazol-2-amine
• CAS: 39181-49-2
• 化学式: C₉H₈ClN₃S
• mdl: MFCD02664062
• 分子量: 225.702
• InChiKey: JYCFJJIHQAFOMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 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：

  对硝基苯磺酰氯 、 5-[(3-氯苯基)甲基]-1,3,4-噻二唑-2-胺 在 吡啶 作用下， 以47%的产率得到
  参考文献：
  名称：

  Divergent effects of compounds on the hydrolysis and transpeptidation reactions of γ-glutamyl transpeptidase

  摘要：

  A novel class of inhibitors of the enzyme gamma-glutamyl transpeptidase (GGT) were evaluated. The analog OU749 was shown previously to be an uncompetitive inhibitor of the GGT transpeptidation reaction. The data in this study show that it is an equally potent uncompetitive inhibitor of the hydrolysis reaction, the primary reaction catalyzed by GGT in vivo. A series of structural analogs of OU749 were evaluated. For many of the analogs, the potency of the inhibition differed between the hydrolysis and transpeptidation reactions, providing insight into the malleability of the active site of the enzyme. Analogs with electron withdrawing groups on the benzosulfonamide ring, accelerated the hydrolysis reaction, but inhibited the transpeptidation reaction by competing with a dipeptide acceptor. Several of the OU749 analogs inhibited the transpeptidation reaction by slow onset kinetics, similar to acivicin. Further development of inhibitors of the GGT hydrolysis reaction is necessary to provide new therapeutic compounds.

  DOI：

  10.3109/14756366.2011.597748
• 作为产物：
  描述：

  3-氯苯乙酸 、 氨基硫脲 在 三氯氧磷 、 potassium hydroxide 作用下， 反应 4.75h， 生成 5-[(3-氯苯基)甲基]-1,3,4-噻二唑-2-胺
  参考文献：
  名称：

  Divergent effects of compounds on the hydrolysis and transpeptidation reactions of γ-glutamyl transpeptidase

  摘要：

  A novel class of inhibitors of the enzyme gamma-glutamyl transpeptidase (GGT) were evaluated. The analog OU749 was shown previously to be an uncompetitive inhibitor of the GGT transpeptidation reaction. The data in this study show that it is an equally potent uncompetitive inhibitor of the hydrolysis reaction, the primary reaction catalyzed by GGT in vivo. A series of structural analogs of OU749 were evaluated. For many of the analogs, the potency of the inhibition differed between the hydrolysis and transpeptidation reactions, providing insight into the malleability of the active site of the enzyme. Analogs with electron withdrawing groups on the benzosulfonamide ring, accelerated the hydrolysis reaction, but inhibited the transpeptidation reaction by competing with a dipeptide acceptor. Several of the OU749 analogs inhibited the transpeptidation reaction by slow onset kinetics, similar to acivicin. Further development of inhibitors of the GGT hydrolysis reaction is necessary to provide new therapeutic compounds.

  DOI：

  10.3109/14756366.2011.597748

文献信息

• THIADIAZOLE AND OXADIAZOLE DERIVATIVES, PREPARATION THEREOF AND THERAPEUTIC USE THEREOF
  申请人：Fett Eykmar

  公开号：US20120040984A1

  公开（公告）日：2012-02-16

  The invention relates to compounds of the formula (I) either (i) in the state of a base or an acid addition salt, or (ii) in the state of an acid or a base addition salt, as well as to a method for preparing same and to the therapeutic applications thereof.

  这项发明涉及到化合物的公式（I），无论是（i）处于碱态或酸盐形式，还是（ii）处于酸态或碱盐形式，以及制备该化合物的方法和其治疗应用。
• Synthesis of Highly Functionalized Phosphorus Ylids Containing Heterocyclic Rings and the Related Iminophosphoranes
  作者：Hojatollah Khabazzadeh、Kazem Saidi、Hassan Sheibani、Mohammad Reza Islami

  DOI：10.1080/10426500701407482

  日期：2007.7.19

  Crystalline phosphorus ylides are obtained in excellent yields from the 1:1:1 addition reaction between triphenylphosphine, dimethyl acetylenedicarboxylate (DMAD) and NH and SH acids, such as 2-amino-4-phenyl thiazole, 2-amino-5-(3-chloro-benzyl) thiadiazole, 3-amino-2-methyl quinazolin-4-one and 3-amino-2-mercapto quinazolin-4-one. These stabilized phosphoranes undergo a smooth intramolecular reaction

  通过三苯基膦、乙炔二甲酸二甲酯 (DMAD) 与 NH 和 SH 酸（如 2-氨基-4-苯基噻唑、2-氨基-5-（3 -氯-苄基）噻二唑、3-氨基-2-甲基喹唑啉-4-one和3-氨基-2-巯基喹唑啉-4-one。这些稳定的正膦在沸腾的甲苯中进行平稳的分子内反应，以优异的产率生产芳基亚氨基正膦。
• Thiadiazole and oxadiazole derivatives, preparation thereof and therapeutic use thereof
  申请人：Fett Eykmar

  公开号：US08546391B2

  公开（公告）日：2013-10-01

  The invention relates to compounds of the formula (I) either (i) in the state of a base or an acid addition salt, or (ii) in the state of an acid or a base addition salt, as well as to a method for preparing same and to the therapeutic applications thereof.

  本发明涉及公式（I）化合物，它们可以是（i）作为碱或酸加成盐的状态，或者（ii）作为酸或碱加成盐的状态，以及制备它们的方法和其治疗应用。
• Synthesis and multiparametric evaluation of thiadiazoles and oxadiazoles as diacylglycerol acyltransferase type 1 inhibitors
  作者：Patrick Mougenot、Claudie Namane、Eykmar Fett、Florence Goumy、Rommel Dadji-Faïhun、Gwladys Langot、Catherine Monseau、Bénédicte Onofri、François Pacquet、Cécile Pascal、Olivier Crespin、Majdi Ben-Hassine、Jean-Luc Ragot、Thao Van-Pham、Christophe Philippo、Florence Chatelain-Egger、Philippe Péron、Jean-Christophe Le Bail、Etienne Guillot、Philippe Chamiot-Clerc、Marie-Aude Chabanaud、Marie-Pierre Pruniaux、Jérôme Ménegotto、Friedemann Schmidt、Olivier Venier、Fabrice Viviani、Eric Nicolai

  DOI：10.1016/j.bmcl.2015.11.046

  日期：2016.1

  Chemical modulation of a formerly disclosed DGAT-1 inhibitor resulted in the identification of a compound with a suitable profile for preclinical development. Optimisation of solubility is discussed and a PK/PD study is presented. (C) 2015 Elsevier Ltd. All rights reserved.
• DÉRIVÉS DE THIADIAZOLES ET D'OXADIAZOLES, LEUR PRÉPARATION ET LEUR APPLICATION EN THÉRAPEUTIQUE
  申请人：SANOFI

  公开号：EP2391611A1

  公开（公告）日：2011-12-07