Addy, Partha Sarathi ; Dutta, Sansa ; Biradha, Kumar ; Basak, Amit (2012) A facile Garratt–Braverman cyclization route to intercalative DNA-binding bis-quinones Tetrahedron Letters, 53 (1). pp. 19-22. ISSN 0040-4039
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Official URL: http://doi.org/10.1016/j.tetlet.2011.10.030
Related URL: http://dx.doi.org/10.1016/j.tetlet.2011.10.030
Abstract
Bispropargyl ethers (both symmetrical and non-symmetrical) equipped with 1,4-dimethoxyaryl groups were synthesized. Under strongly basic conditions (KOBut/toluene/reflux), these ethers underwent Garratt–Braverman type cyclization to the tetramethoxy bi-aryl systems in high yields presumably via the bisallenes. The products could be successfully converted to the bis-quinones via CAN-mediated demethylation cum oxidation. This two-step protocol offers a simple route to bis-quinones, connected by C1–C2′ bonds, in good yields. Fluorescence based EB-displacement assay, CD spectroscopy and viscosity measurements confirmed the DNA-binding ability of the synthesized quinones via intercalation.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 129896 |
| Deposited On: | 21 Nov 2022 10:48 |
| Last Modified: | 05 Dec 2022 05:28 |
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