((3S,4R)-4-(benzyloxy)-3-(hydroxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl) (2-hydroxy-4-methoxyphenyl)methanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: ((3S,4R)-4-(benzyloxy)-3-(hydroxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl) (2-hydroxy-4-methoxyphenyl)methanone
• 英文别名: (2-hydroxy-4-methoxyphenyl)-[(3S,4R)-3-(hydroxymethyl)-4-phenylmethoxy-3,4-dihydro-1H-isoquinolin-2-yl]methanone
• 化学式: C₂₅H₂₅NO₅
• 分子量: 419.477
• InChiKey: WSLNCBNAAXUECZ-LADGPHEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ((3S,4R)-4-(benzyloxy)-3,4-dihydroisoquinolin-3-yl)methanol 在 sodium tetrahydroborate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 ((3S,4R)-4-(benzyloxy)-3-(hydroxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl) (2-hydroxy-4-methoxyphenyl)methanone
  参考文献：
  名称：

  Design, synthesis and biological evaluations of chirally pure 1,2,3,4-tertrahydroisoquinoline analogs as anti-cancer agents

  摘要：

  A series of fifteen chiral 1,2,3,4-tetrahydroisoquinoline (THIQ) derivatives have been synthesized and their antiproliferative properties have been studied. The in vitro screening was performed against five cancer cell lines; MCF-7 (breast cancer), A549 (lung cancer), DU-145 (prostate cancer), Hela (cervical cancer) and HepG2 (liver cancer). Most of the compounds showed promising activity with IC50 Values ranging from 0.72 to 92.6 mu M. Among them, compounds 9a and 9b have shown significant activity against human prostate cancer cell line, i.e., DU-145 with IC50 value 0.72 and 1.23 mu M respectively. To investigate the mechanism of action, detailed biological studies of compounds 9a and 9b were carried out on the human prostate cancer cell line, DU-145. Flow cytometric analysis revealed that these compounds induced cell cycle arrest at G2/M phase. Tubulin polymerization assay and immunofluorescence analysis results suggested that these compounds effectively inhibit microtubule assembly formation in DU-145. The apoptosis inducing properties were evaluated by DNA fragmentation analysis, Caspase-3 activity assay, Annexin V-FITC assay and Western blot analysis of proapoptotic protein, Bax and antiapoptotic protein Bcl-2. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.030

文献信息

• Design, synthesis and biological evaluations of chirally pure 1,2,3,4-tertrahydroisoquinoline analogs as anti-cancer agents
  作者：Triparagiri Ramanivas、Bottu Sushma、V. Lakshma Nayak、Kunta Chandra Shekar、Ajay Kumar Srivastava

  DOI：10.1016/j.ejmech.2015.01.030

  日期：2015.3

  A series of fifteen chiral 1,2,3,4-tetrahydroisoquinoline (THIQ) derivatives have been synthesized and their antiproliferative properties have been studied. The in vitro screening was performed against five cancer cell lines; MCF-7 (breast cancer), A549 (lung cancer), DU-145 (prostate cancer), Hela (cervical cancer) and HepG2 (liver cancer). Most of the compounds showed promising activity with IC50 Values ranging from 0.72 to 92.6 mu M. Among them, compounds 9a and 9b have shown significant activity against human prostate cancer cell line, i.e., DU-145 with IC50 value 0.72 and 1.23 mu M respectively. To investigate the mechanism of action, detailed biological studies of compounds 9a and 9b were carried out on the human prostate cancer cell line, DU-145. Flow cytometric analysis revealed that these compounds induced cell cycle arrest at G2/M phase. Tubulin polymerization assay and immunofluorescence analysis results suggested that these compounds effectively inhibit microtubule assembly formation in DU-145. The apoptosis inducing properties were evaluated by DNA fragmentation analysis, Caspase-3 activity assay, Annexin V-FITC assay and Western blot analysis of proapoptotic protein, Bax and antiapoptotic protein Bcl-2. (C) 2015 Elsevier Masson SAS. All rights reserved.