Article: Synthesis of Crescent Shaped Heterocycle-fused Aromatics via Garratt-Braverman Cyclization and Their DNA-binding Studies
2017
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- ... ...
| 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 propsed binding modes. |
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| Keywords | DNA ; alcohols ; benzene ; bromides ; chemical bonding ; chemical reactions ; chemical structure ; molecular models ; phenanthrene | |||||
| Language | English | |||||
| Size | p. . | |||||
| Publishing place | Elsevier Ltd | |||||
| Document type | Article | |||||
| Note | Pre-press version | |||||
| ZDB-ID | 204287-3 | |||||
| ISSN | 1873-3581 ; 0040-4039 | |||||
| ISSN (online) | 1873-3581 | |||||
| ISSN | 0040-4039 | |||||
| DOI | 10.1016/j.tetlet.2017.04.003 | |||||
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| Database | NAL-Catalogue (AGRICOLA) |
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