3-(2-(3-chlorobenzyl)-2H-tetrazol-5-yl)aniline | 1333393-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2-(3-chlorobenzyl)-2H-tetrazol-5-yl)aniline
• 英文别名: 3-[2-(3-Chloro-benzyl)-2H-tetrazol-5-yl]-phenylamine；3-[2-[(3-chlorophenyl)methyl]tetrazol-5-yl]aniline
• CAS: 1333393-90-0
• 化学式: C₁₄H₁₂ClN₅
• 分子量: 285.736
• InChiKey: ANSLDXQMHSUCMK-UHFFFAOYSA-N

物化性质

• 沸点：
  531.2±60.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-(3-chlorobenzyl)-2H-tetrazol-5-yl)aniline 、 (E)-2-(3-chlorophenyl)ethenesulfonyl chloride 在 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以61%的产率得到(E)-2-(3-chlorophenyl)-N-[3-[2-[(3-chlorophenyl)methyl]tetrazol-5-yl]phenyl]ethenesulfonamide
  参考文献：
  名称：

  Synthesis and biochemical evaluation of triazole/tetrazole-containing sulfonamides against thrombin and related serine proteases

  摘要：

  A small library of 25 triazole/tetrazole-based sulfonamides have been synthesized and further evaluated for their inhibitory activity against thrombin, trypsin, tryptase and chymase. In general, the triazole-based sulfonamides inhibited thrombin more efficiently than the tetrazole counterparts. Particularly, compound 26 showed strong thrombin inhibition (K-i = 880 nM) and significant selectivity against other human related serine proteases like trypsin (K-i = 729 mu M). Thrombin binding affinity of the same compound was determined by ITC and demonstrated that the binding of this new triazole-based scaffold is enthalpically driven, making it a good candidate for further development. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.023
• 作为产物：
  描述：

  间硝基苯腈 在 sodium azide 、 三乙胺 、 zinc dibromide 、 锌 作用下， 以 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 76.5h， 生成 3-(2-(3-chlorobenzyl)-2H-tetrazol-5-yl)aniline
  参考文献：
  名称：

  [EN] HIGH AFFINITY BETA LACTAMASE INHIBITORS
  [FR] INHIBITEURS DE BÊTA-LACTAMASES À FORTE AFFINITÉ

  摘要：

  β内酰胺酶抑制剂及其在治疗细菌感染中的应用被披露。

  公开号：

  WO2013056079A1

文献信息

• [EN] HIGH AFFINITY BETA LACTAMASE INHIBITORS<br/>[FR] INHIBITEURS DE BÊTA-LACTAMASES À FORTE AFFINITÉ
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2013056079A1

  公开（公告）日：2013-04-18

  Inhibitors of beta lactamases and their use in treating bacterial infections are dicslosed.

  β内酰胺酶抑制剂及其在治疗细菌感染中的应用被披露。
• US20140256778A1
  申请人：——

  公开号：——

  公开（公告）日：——
• Aryl azoles based scaffolds for disrupting tumor microenvironment
  作者：Alberto Pla-López、Paula Martínez-Colomina、Laura Cañada-García、Laura Fuertes-Monge、Jose C. Orellana-Palacios、Alejandro Valderrama-Martínez、Marikena Pérez-Sosa、Miguel Carda、Eva Falomir

  DOI：10.1016/j.bmc.2023.117490

  日期：2023.11
• US9730913B2
  申请人：——

  公开号：US9730913B2

  公开（公告）日：2017-08-15
• Synthesis and biochemical evaluation of triazole/tetrazole-containing sulfonamides against thrombin and related serine proteases
  作者：Rogelio Siles、Yuko Kawasaki、Patrick Ross、Ernesto Freire

  DOI：10.1016/j.bmcl.2011.07.023

  日期：2011.9

  A small library of 25 triazole/tetrazole-based sulfonamides have been synthesized and further evaluated for their inhibitory activity against thrombin, trypsin, tryptase and chymase. In general, the triazole-based sulfonamides inhibited thrombin more efficiently than the tetrazole counterparts. Particularly, compound 26 showed strong thrombin inhibition (K-i = 880 nM) and significant selectivity against other human related serine proteases like trypsin (K-i = 729 mu M). Thrombin binding affinity of the same compound was determined by ITC and demonstrated that the binding of this new triazole-based scaffold is enthalpically driven, making it a good candidate for further development. (C) 2011 Elsevier Ltd. All rights reserved.