(RS)-1-(4'-cyanophenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline | 1349744-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (RS)-1-(4'-cyanophenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 4-(6-Methoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)benzonitrile；4-(6-methoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)benzonitrile
• CAS: 1349744-09-7
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: XMHMCAIGUSIYPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (RS)-1-(4'-cyanophenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline 在 磺酰胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.33h， 以60%的产率得到(RS)-1-(4'-cyanophenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-2-sulfonamide
  参考文献：
  名称：

  Synthesis and biological profile of new 1,2,3,4-tetrahydroisoquinolines as selective carbonic anhydrase inhibitors

  摘要：

  In a previous paper we identified several 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-sulfonamides that displayed inhibitory effects toward selected carbonic anhydrase isozymes at micromolar concentration. In order to deepen the structure-activity relationships (SARs) and identify novel compounds with improved activity, we synthesized a series of monomethoxy analogues of the previously investigated dimethoxy derivatives. The evaluation of biological profile has been focused on in vitro effects against several CA isoforms. The new monomethoxy derivatives showed higher hCA inhibitory effects against several isoforms compared to the dimethoxy analogues. Particularly, some of these compounds (e. g., 1b and 1h) showed low nanomolar K(I) values and excellent selectivity for hCA IX and hCA XIV versus hCA I and II inhibition. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.015
• 作为产物：
  描述：

  4-氰基苯甲醛 在 三氟乙酸 作用下， 反应 0.34h， 生成 (RS)-1-(4'-cyanophenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Synthesis and biological profile of new 1,2,3,4-tetrahydroisoquinolines as selective carbonic anhydrase inhibitors

  摘要：

  In a previous paper we identified several 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-sulfonamides that displayed inhibitory effects toward selected carbonic anhydrase isozymes at micromolar concentration. In order to deepen the structure-activity relationships (SARs) and identify novel compounds with improved activity, we synthesized a series of monomethoxy analogues of the previously investigated dimethoxy derivatives. The evaluation of biological profile has been focused on in vitro effects against several CA isoforms. The new monomethoxy derivatives showed higher hCA inhibitory effects against several isoforms compared to the dimethoxy analogues. Particularly, some of these compounds (e. g., 1b and 1h) showed low nanomolar K(I) values and excellent selectivity for hCA IX and hCA XIV versus hCA I and II inhibition. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.015

文献信息

• Synthesis and biological profile of new 1,2,3,4-tetrahydroisoquinolines as selective carbonic anhydrase inhibitors
  作者：Rosaria Gitto、Francesca Maria Damiano、Laura De Luca、Stefania Ferro、Daniela Vullo、Claudiu T. Supuran、Alba Chimirri

  DOI：10.1016/j.bmc.2011.10.015

  日期：2011.12

  In a previous paper we identified several 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-sulfonamides that displayed inhibitory effects toward selected carbonic anhydrase isozymes at micromolar concentration. In order to deepen the structure-activity relationships (SARs) and identify novel compounds with improved activity, we synthesized a series of monomethoxy analogues of the previously investigated dimethoxy derivatives. The evaluation of biological profile has been focused on in vitro effects against several CA isoforms. The new monomethoxy derivatives showed higher hCA inhibitory effects against several isoforms compared to the dimethoxy analogues. Particularly, some of these compounds (e. g., 1b and 1h) showed low nanomolar K(I) values and excellent selectivity for hCA IX and hCA XIV versus hCA I and II inhibition. (C) 2011 Elsevier Ltd. All rights reserved.