5-(3,4-dichloro-benzyl)-[1,3,4]thiadiazol-2-ylamine | 39181-51-6

• 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-(3,4-dichloro-benzyl)-[1,3,4]thiadiazol-2-ylamine
• 英文别名: 5-[(3,4-dichlorophenyl)methyl]-1,3,4-thiadiazol-2-amine；2-Amino-5-(3,4-dichlorbenzyl)-thiadiazol；5-(3,4-Dichlorobenzyl)-1,3,4-thiadiazol-2-amine
• CAS: 39181-51-6
• 化学式: C₉H₇Cl₂N₃S
• mdl: MFCD01191260
• 分子量: 260.147
• InChiKey: DAYHQPPTGMEUTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 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-(3,4-dichloro-benzyl)-[1,3,4]thiadiazol-2-ylamine 在 吡啶 作用下， 以49%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：

  3,4-二氯苯乙酸 、 氨基硫脲 在 三氯氧磷 、 potassium hydroxide 作用下， 反应 4.75h， 以61%的产率得到5-(3,4-dichloro-benzyl)-[1,3,4]thiadiazol-2-ylamine
  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 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。
• Synthesis of bilaterally thiadiazole substituted vic-dioxime ligands and investigation of their polymeric metal complexes
  作者：Omar Khalid、Mojahid Salah、Ahmed Hamdi Mirghani、Hakan Tahtaci、Ahmet Coskun、Saban Uysal

  DOI：10.1016/j.molstruc.2024.139234

  日期：2024.12

  acetimidoyl) chloride (OKS3)” was obtained from the reaction of OKS2 with hydroxylamine hydrochloride in ethanol media at 40 °C. Then, our three original target vic-dioxime compounds (OKL1-OKL3) were synthesized from the reaction of substituted 2-amino-1,3,4-thiadiazole compounds with OKS3. Structural characterizations of all synthesized organic compounds were made using elemental analysis, FTIR, H and C NMR

  在本研究中，合成了三种新型取代的1,3,4-噻二唑衍生的vic-二肟配体及其相应的聚合物过渡金属（Co和Ni）配合物，并对其结构进行了表征。为此，二苯醚与氯乙酰氯以1:2的摩尔比通过弗里德尔-克来福特反应得到4,4'-双(氯乙酰基二苯基)醚(OKS1)。我们的第一个起始肟化合物“2,2′-(氧双(4,1-亚苯基))双(N-羟基-2-氧代乙酰亚氨基)氯化物(OKS2)”是由OKS1与亚硝酸丁酯在1:的反应中获得的。在HCl气体的催化下，摩尔比为2。然后，我们最终的起始vic-二肟化合物“2,2′-(氧双(4,1-亚苯基))双(N-羟基-2-(羟基亚氨基)乙酰亚胺酰基)氯化物(OKS3)”由OKS2的反应获得与盐酸羟胺在乙醇介质中在40°C下。然后，通过取代的2-氨基-1,3,4-噻二唑化合物与OKS3的反应合成了我们的三种原始目标vic-二肟化合物(OKL1-OKL3)。所有合成的有机化合物的结构表征均采用元素分析、FTIR、H
• Neue Imidazo(2.1-b)-(1.3.4)-thiadiazole, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
  申请人：BAYER AG

  公开号：EP0005783B1

  公开（公告）日：1981-12-30
• US4265898A
  申请人：——

  公开号：US4265898A

  公开（公告）日：1981-05-05