A Garratt-Braverman cyclization route towards the synthesis of phenanthridine derivatives and their DNA-binding studies

被引：6
作者：
Mandal, Arundhoti [1 ]
Bhattacharya, Prabuddha [3 ]
Das, Amit K. [2 ]
Basak, Amit [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India
[2] Indian Inst Technol, Dept Biotechnol, Kharagpur 721302, W Bengal, India
[3] Adamas Univ, Dept Chem, Kolkata 700126, India
来源：
TETRAHEDRON | 2019年 / 75卷 / 13期
关键词：
Phenanthridine; Garratt-Braverman cyclization; UV-Vis absorption; Fluorescence; Ethidium bromide; Docking; BISPROPARGYL SULFONES; CRYSTAL-STRUCTURE; METAL-FREE; ANTITUMOR; CONSTITUENTS; ANTICANCER; OXIDATION; ALKALOIDS; ARYLATION; ETHERS;
D O I：
10.1016/j.tet.2019.02.020
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Garratt-Braverman cyclization has been employed to synthesize a series of dihydroisofuran fused phenanthridine derivatives. The established protocol proposes a simpler synthetic alternative to have access to these therapeutically relevant cytotoxic scaffolds. Single crystal X-ray data unambiguously confirmed the structures of the synthesized phenanthridine derivatives. UV-Vis absorption titration with calf thymus DNA followed by fluorescence-based competitive ethidium bromide displacement assay established the synthesized target compounds as potent DNA-intercalating agents with intrinsic binding constant of the range 10(3)-10(5). Results obtained from the molecular docking further justified the spectroscopically obtained results. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1975 / 1987
页数：13
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