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Issue 11, 2017
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Intramolecular macrolactonization, photophysical and biological studies of new class of polycyclic pyrrole derivatives

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Abstract

Herein, we report an efficient synthesis of N-substituted pyrrole derivatives and their application to construct macrocyclic oxazocinone via a two-component coupling reaction followed by base mediated intramolecular cyclization. This methodology provides an easy two-step approach to constitute a library of fused pyrrolo-oxazocinone derivatives in good yields under mild reaction conditions. The present methodology offers an easy access to the synthesis of a library of fluorescent pyrole derivatives. Among them, tert-butyl 2-(2-(3-hydroxypropyl)-7-methoxy-4,5-dihydro-2H-benzo[e]isoindol-1-yl)acetate has been employed in bio-analytical imaging which shows efficient cellular internalization along with no obvious cellular toxicity.

Graphical abstract: Intramolecular macrolactonization, photophysical and biological studies of new class of polycyclic pyrrole derivatives

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Supplementary files

Article information


Submitted
20 Jan 2017
Accepted
21 Feb 2017
First published
02 Mar 2017

Org. Biomol. Chem., 2017,15, 2411-2421
Article type
Paper

Intramolecular macrolactonization, photophysical and biological studies of new class of polycyclic pyrrole derivatives

S. K. Mondal, A. Mandal, S. K. Manna, S. A. Ali, M. Hossain, V. Venugopal, A. Jana and S. Samanta, Org. Biomol. Chem., 2017, 15, 2411
DOI: 10.1039/C7OB00160F

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