Synthesis of crescent shaped heterocycle-fused aromatics via Garratt-Braverman cyclization and their DNA-binding studies

Ghosh, Debaki ; Basu, Souradeep ; Singha, Monisha ; Das, Joyee ; Bhattacharya, Prabuddha ; Basak, Amit (2017) Synthesis of crescent shaped heterocycle-fused aromatics via Garratt-Braverman cyclization and their DNA-binding studies Tetrahedron Letters, 58 (21). pp. 2014-2018. ISSN 0040-4039

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Official URL: http://doi.org/10.1016/J.Tetlet.2017.04.003

Related URL: http://dx.doi.org/10.1016/J.Tetlet.2017.04.003

Abstract

Three crescent shaped heterocycle-fused phenanthrene based systems 1–3 have been synthesized starting from benzene (or substituted benzene) 1,2-bis-propargyl alcohols. Bis-alkylation with propargylic bromides provided the key intermediate, the bis-propargyl bis-ethers. In spite of the possibility of many competing reactions, the latter underwent facile double Garratt-Braverman cyclization to provide compounds 1–3 in near quantitative yield, in a striking reaction involving the formation of four C–C bonds in a single step. Compounds 1–3 showed binding interaction with DNA, predominantly, via groove binding along with partial intercalation (combilexins). Molecular docking study supported the proposed binding modes.

Item Type:Article
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ID Code:130048
Deposited On:05 Dec 2022 05:46
Last Modified:05 Dec 2022 05:46

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