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Synthesis of novel 1,2-diphenylpyrrole derivatives using organophosphorus reagents and their antitumour activities

Posted on 24. June, 2014.

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Compounds containing the pyrrolidine ring are widely distributed in nature. Moreover, the pyrrolidine ring is present as the main part in the pyrrolidine alkaloids such as hygrine and cuscohygrine, and also in various types of alkaloidal skeletons such as nicotine and the physostigma venenosum alkaloids.

Previously, it has been reported that 1,5-diphenylpyrrole-2,3-dione derivatives possess analgesic, notropic, anti-inflammatory, antibacterial and antiviral activities. This together with our interest in organophosphorus chemistry has encouraged the synthesis of new organophosphorus compounds incorporating such structural units that may possibly lead to further biological activity.

The present study deals with the reaction of 4-(furan-3-ylcarbonyl)-1,5-diphenylpyrrolidine-2,3-dione 1 with six classes of organophosphorus reagent: carboalkoxymethylene triphenylphosphoranes 2a,b, triphenyl (phenylimino)-λ5-phosphane 3, trialkylphosphonoacetates 4a,b, trialkylphosphites 5a-c, tris (dialkylamino)phosphines 6a,b, and Lawesson’s reagent 7 (see image above).
Several of the products showed antitumour activity.

Read the full article in Journal of Chemical Research, Volume 38, No.6, June 2014, pp. 325-330.

Authors: Ewies F. Ewiesa, Naglaa F. Elsayeda, Leila S. Boulosa and Abdel-Mohsen M. Solimanb

aDepartment of Organometallic and Organometalloid Chemistry, and bTherapeutic Chemistry Department, National Research Centre, El‑Buhouth St, PO 12622, Dokki, Giza, Egypt

DOI:10.3184/174751914X13976652851990