4-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)aniline | 21776-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)aniline
• 英文别名: 2-(p-Amino-phenyl)-5-chlor-benzotriazol；4-(5-chloro-benzotriazol-2-yl)-aniline；4-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)benzenamine；4-(5-chlorobenzotriazol-2-yl)aniline
• CAS: 21776-70-5
• 化学式: C₁₂H₉ClN₄
• 分子量: 244.683
• InChiKey: IJFPCAVUTGZDIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 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：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  硫酸二乙酯 、 4-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)aniline 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以66%的产率得到4-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-N,N-diethylaniline
  参考文献：
  名称：

  Antiviral activities of 5-chlorobenzotriazole derivatives

  摘要：

  In this study, we designed and synthesized a series of new 5-chlorobenzotriazole derivatives. Compounds were tested for cytotoxicity and antiviral activity in cell-based assays against several positive single-stranded RNA viruses: BVDV, YFV, CVB-5, and Sb-1; two negative single-stranded RNA viruses: RSV and VSV; a double-stranded RNA virus (Reo-1); and two DNA viruses: VV and HSV-1. N-[4-(5-Chloro-2H-benzo[d][1,2,3]triazol-2-yl)phenyl]-3,4,5-trimethoxybenzamide turned out to be the most potent compound against bovine viral diarrhea virus (BVDV). Its activity was shown to be comparable to the activity of the reference drug NM 107 (EC50 3.0 vs. 1.7 mu M). It is going to be used as a lead compound for future antiviral drug developments.[GRAPHICS].

  DOI：

  10.1007/s00706-018-2234-7
• 作为产物：
  描述：

  5-chloro-2-(4-nitrophenyl)-2H-benzo[d][1,2,3]triazole 在 tin(ll) chloride 、 sodium carbonate 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 5.0h， 以63%的产率得到4-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)aniline
  参考文献：
  名称：

  Compounds and amyloid probes thereof for therapeutic and imaging uses

  摘要：

  本发明提供了化合物及其淀粉样探针，使得可以通过体内成像诊断AD并定量评估脑部区域中淀粉沉积（斑块）的程度或进展的方法。优选地，本发明的淀粉样探针可以穿过血脑屏障，并区分AD脑与正常脑。可以将淀粉样探针以适量用于体内成像淀粉沉积的方式给患者。本发明的淀粉样探针还可用于检测和定量包括但不限于唐氏综合症、家族性AD和载脂蛋白E4等位基因纯合子在内的疾病中的淀粉沉积。在一个方面，这些化合物可用于治疗或预防包括但不限于AD和2型糖尿病的疾病。该发明的化合物和淀粉样探针包括其类似物、盐、药物组合物、衍生物、前药、外消旋混合物或互变异构体。

  公开号：

  US20070258887A1

文献信息

• COMPOUNDS AND AMYLOID PROBES THEREOF FOR THERAPEUTIC AND IMAGING USES
  申请人：Tamagnan Gilles D.

  公开号：US20100143251A1

  公开（公告）日：2010-06-10

  The present invention provides compounds and amyloid probes thereof that allow for an antemortem method of diagnosing AD and quantitating the extent or progression of amyloid deposits (plaques) by in vivo imaging of amyloid and/or amyloid deposits in the regions of the brain. Preferably, an amyloid probe of the invention can cross the blood-brain barrier and distinguish AD brain from normal brain. An amyloid probe can be administered to a patient in amounts suitable for in vivo imaging of amyloid deposits. Amyloid probes of the invention can also be used to detect and quantitate amyloid deposits in diseases including, without limitation, Down's syndrome, familial AD and homozygotes for the apolipoprotein E4 allele. In one aspect, the compounds may be used in the treatment or prophylaxis of diseases that include, without limitation, AD and type 2 diabetes mellitus. The compounds and amyloid probes of the invention include analogs, salts, pharmaceutical compositions, derivatives, prodrugs, racemic mixtures or tautomeric forms thereof.

  本发明提供了化合物及其淀粉样探针，可通过体内成像淀粉样和/或脑部区域的淀粉样沉积物，从而实现诊断AD和量化淀粉样沉积物（斑块）的程度或进展的生前方法。优选地，本发明的淀粉样探针可以穿过血脑屏障，区分AD脑和正常脑。可以向患者施用本发明的淀粉样探针，以适量成像淀粉样沉积物。本发明的淀粉样探针还可用于检测和量化包括但不限于唐氏综合症、家族性AD和载脂蛋白E4等位基因纯合子在内的疾病中的淀粉样沉积物。在一方面，这些化合物可以用于治疗或预防包括但不限于AD和2型糖尿病的疾病。本发明的化合物和淀粉样探针包括其类似物、盐、制药组合物、衍生物、前药、外消旋混合物或其互变异构体。
• US7700616B2
  申请人：——

  公开号：US7700616B2

  公开（公告）日：2010-04-20
• [EN] COMPOUNDS AND AMYLOID PROBES THEREOF FOR THERAPEUTIC AND IMAGING USES<br/>[FR] COMPOSÉS ET SONDES AMYLOÏDES DE CEUX-CI POUR DES UTILISATIONS THÉRAPEUTIQUES ET EN IMAGERIE
  申请人：MOLECULAR NEUROIMAGING LLC

  公开号：WO2008118122A2

  公开（公告）日：2008-10-02

  (EN) The present invention provides compounds and amyloid probes thereof that allow for an anlsmortem method of diagnosing AD and quantitating the extent or progression of amyloid deposits (plaques) by in vivo imaging of amyloid and/or amyloid deposits in the 5 regions of the brain Preferably an amyloid probe of the invention can cross the blood-brain barrier and distinguish AD brain from normal brain An amyloid probe can be administered to a patient in amounts suitable for in vivo imaging of amyloid deposits Amyloid probes of the invention can also be used to detect and quantitate amyloid deposits in diseases including, without limitation Down's syndrome familial AD and homozygotes for the apolipoprotein 10 E4 allele The compounds and amyloid probes of the invention include analogs, salts, pharmaceutical compositions derivatives prodrugs, racemic mixtures or tautomeric forms thereof.(FR) La présente invention concerne des composés et des sondes amyloïdes de ceux-ci qui permettent la mise en œuvre d'un procédé antemortem de diagnostic de AD et de quantification de l'étendue ou de la progression de dépôts amyloïdes (plaques) par imagerie in vivo d'amyloïde et/ou de dépôts amyloïdes dans les régions du cerveau. De préférence, une sonde d'amyloïde de l'invention peut traverser la barrière hématoencéphalique et distinguer un cerveau atteint d'AD d'un cerveau normal. Une sonde amyloïde peut être administrée à un patient dans des quantités appropriées pour une imagerie in vivo des dépôts amyloïdes. Des sondes amyloïdes de l'invention peuvent également être utilisées pour détecter et quantifier des dépôts amyloïdes dans des maladies comprenant, sans s'y limiter, le syndrome de Down, l'AD familial et des homozygotes pour l'allèle E4 d'apolipoprotéine. Dans un aspect, les composés peuvent être utilisés dans le traitement ou la prophylaxie des maladies qui comprennent, sans s'y limiter, AD et le diabète sucré de type 2. Les composés et sondes amyloïdes de l'invention comprennent les analogues, sels, compositions pharmaceutiques, dérivés, promédicaments, mélanges racémiques ou formes tautomères de ceux-ci.
• Compounds and amyloid probes thereof for therapeutic and imaging uses
  申请人：Tamagnan D. Gilles

  公开号：US20070258887A1

  公开（公告）日：2007-11-08

  The present invention provides compounds and amyloid probes thereof that allow for an antemortem method of diagnosing AD and quantitating the extent or progression of amyloid deposits (plaques) by in vivo imaging of amyloid and/or amyloid deposits in the regions of the brain. Preferably, an amyloid probe of the invention can cross the blood-brain barrier and distinguish AD brain from normal brain. An amyloid probe can be administered to a patient in amounts suitable for in vivo imaging of amyloid deposits. Amyloid probes of the invention can also be used to detect and quantitate amyloid deposits in diseases including, without limitation, Down's syndrome, familial AD and homozygotes for the apolipoprotein E4 allele. In one aspect, the compounds may be used in the treatment or prophylaxis of diseases that include, without limitation, AD and type 2 diabetes mellitus. The compounds and amyloid probes of the invention include analogs, salts, pharmaceutical compositions, derivatives, prodrugs, racemic mixtures or tautomeric forms thereof.

  本发明提供了化合物及其淀粉样探针，使得可以通过体内成像诊断AD并定量评估脑部区域中淀粉沉积（斑块）的程度或进展的方法。优选地，本发明的淀粉样探针可以穿过血脑屏障，并区分AD脑与正常脑。可以将淀粉样探针以适量用于体内成像淀粉沉积的方式给患者。本发明的淀粉样探针还可用于检测和定量包括但不限于唐氏综合症、家族性AD和载脂蛋白E4等位基因纯合子在内的疾病中的淀粉沉积。在一个方面，这些化合物可用于治疗或预防包括但不限于AD和2型糖尿病的疾病。该发明的化合物和淀粉样探针包括其类似物、盐、药物组合物、衍生物、前药、外消旋混合物或互变异构体。
• Antiviral activities of 5-chlorobenzotriazole derivatives
  作者：Roberta Ibba、Paola Corona、Antonio Carta、Paolo Giunchedi、Roberta Loddo、Giuseppina Sanna、Ilenia Delogu、Sandra Piras

  DOI：10.1007/s00706-018-2234-7

  日期：2018.7

  In this study, we designed and synthesized a series of new 5-chlorobenzotriazole derivatives. Compounds were tested for cytotoxicity and antiviral activity in cell-based assays against several positive single-stranded RNA viruses: BVDV, YFV, CVB-5, and Sb-1; two negative single-stranded RNA viruses: RSV and VSV; a double-stranded RNA virus (Reo-1); and two DNA viruses: VV and HSV-1. N-[4-(5-Chloro-2H-benzo[d][1,2,3]triazol-2-yl)phenyl]-3,4,5-trimethoxybenzamide turned out to be the most potent compound against bovine viral diarrhea virus (BVDV). Its activity was shown to be comparable to the activity of the reference drug NM 107 (EC50 3.0 vs. 1.7 mu M). It is going to be used as a lead compound for future antiviral drug developments.[GRAPHICS].