2-((4-azidophenyl)sulfonyl)-1,2,3,4-tetrahydroisoquinoline | 1615201-43-8

• 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: 2-((4-azidophenyl)sulfonyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-(4-azidophenyl)sulfonyl-3,4-dihydro-1H-isoquinoline
• CAS: 1615201-43-8
• 化学式: C₁₅H₁₄N₄O₂S
• 分子量: 314.368
• InChiKey: SPBLUPREVHDBFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  86.14
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  苯基炔丙基醚 、 2-((4-azidophenyl)sulfonyl)-1,2,3,4-tetrahydroisoquinoline 在 copper(ll) sulfate pentahydrate 、 Vitamin C 作用下， 以 水 、 叔丁醇 为溶剂， 以84%的产率得到2-((4-(4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl)phenyl)sulfonyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Design, synthesis and molecular docking studies of novel N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-based triazoles with potential anticancer activity

  摘要：

  A novel series of N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinolines (14-33) containing triazole moiety were designed and synthesized through rational cycloadditions using the modified Pictet-Spengler reaction and the Click chemistry. Antiproliferative activity against four cancer cell lines (e.g., HuCCA-1, HepG2, A549 and MOLT-3) revealed that many substituted triazole analogs of benzoates (20, 29) and benzaldehydes (30,32) exhibited anticancer activity against all of the tested cancer cell lines in which the ester analog 20 was shown to be the most potent compound against HuCCA-1 (IC50=0.63 mu M) and A549 (IC50 = 0.57 mu M) cell lines. Triazoles bearing phenyl (15, 24), tolyl (26, 27), acetophenone (19), benzoate (20, 29), benzaldehyde (21, 30) and naphthalenyl (25) substituents showed stronger anticancer activity against HepG2 cells than that of the etoposide. Interestingly, the p-tolyl analog (27) displayed the most potent inhibitory activity (1050 = 0.56 mu M) against HepG2 cells without affecting normal cells. Of the investigated tetrahydroisoquinoline-triazoles, the promising compounds 20 and 27 were selected for molecular docking against AKR1C3, which was identified to be a plausible target site. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.019
• 作为产物：
  描述：

  2-((4-硝基苯基)磺酰基)-1,2,3,4-四氢异喹啉 在 盐酸 、 tin(II) chloride dihdyrate 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 4.75h， 生成 2-((4-azidophenyl)sulfonyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Design, synthesis and molecular docking studies of novel N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-based triazoles with potential anticancer activity

  摘要：

  A novel series of N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinolines (14-33) containing triazole moiety were designed and synthesized through rational cycloadditions using the modified Pictet-Spengler reaction and the Click chemistry. Antiproliferative activity against four cancer cell lines (e.g., HuCCA-1, HepG2, A549 and MOLT-3) revealed that many substituted triazole analogs of benzoates (20, 29) and benzaldehydes (30,32) exhibited anticancer activity against all of the tested cancer cell lines in which the ester analog 20 was shown to be the most potent compound against HuCCA-1 (IC50=0.63 mu M) and A549 (IC50 = 0.57 mu M) cell lines. Triazoles bearing phenyl (15, 24), tolyl (26, 27), acetophenone (19), benzoate (20, 29), benzaldehyde (21, 30) and naphthalenyl (25) substituents showed stronger anticancer activity against HepG2 cells than that of the etoposide. Interestingly, the p-tolyl analog (27) displayed the most potent inhibitory activity (1050 = 0.56 mu M) against HepG2 cells without affecting normal cells. Of the investigated tetrahydroisoquinoline-triazoles, the promising compounds 20 and 27 were selected for molecular docking against AKR1C3, which was identified to be a plausible target site. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.019

文献信息

• Synthesis and molecular docking of 1,2,3-triazole-based sulfonamides as aromatase inhibitors
  作者：Ratchanok Pingaew、Veda Prachayasittikul、Prasit Mandi、Chanin Nantasenamat、Supaluk Prachayasittikul、Somsak Ruchirawat、Virapong Prachayasittikul

  DOI：10.1016/j.bmc.2015.04.036

  日期：2015.7

  A series of 1,4-disubstituted-1,2,3-triazoles (13-35) containing sulfonamide moiety were synthesized and evaluated for their aromatase inhibitory effects. Most triazoles with open-chain sulfonamide showed significant aromatase inhibitory activity (IC50 = 1.3-9.4 mu M). Interestingly, the meta analog of triazole-benzene-sulfonamide (34) bearing 6,7-dimethoxy substituents on the isoquinoline ring displayed the most potent aromatase inhibitory activity (IC50 = 0.2 mu M) without affecting normal cell. Molecular docking of these triazoles against aromatase revealed that the compounds could snugly occupy the active site of the enzyme through hydrophobic, pi-pi stacking, and hydrogen bonding interactions. The potent compound 34 was able to form hydrogen bonds with Met374 and Ser478 which were suggested to be the essential residues for the promising inhibition. The study provides compound 34 as a potential lead molecule of anti-aromatase agent for further development. (C) 2015 Elsevier Ltd. All rights reserved.