An efficient one-pot synthesis and docking studies of bioactive new antiproliferative dispiro[oxindole/acenaphthylenone‒benzofuranone] pyrrolidine scaffolds.

Autor: Sutariya TR; Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar Dist. Anand, Gujarat, 388120, India., Brahmbhatt GC; Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar Dist. Anand, Gujarat, 388120, India., Atara HD; Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar Dist. Anand, Gujarat, 388120, India., Parmar NJ; Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar Dist. Anand, Gujarat, 388120, India. njpchemdeptspu@yahoo.co.in., RajniKant; Post-Graduate Department of Physics, University of Jammu, Jammu, Tawi, 180006, India., Gupta VK; Post-Graduate Department of Physics, University of Jammu, Jammu, Tawi, 180006, India., Lagunes I; BioLab, Instituto Universitario de Bio-Orgánica 'Antonio González' (IUBO-AG), Universidad de La Laguna, C/Astrofísico Francisco Sánchez 2, 38206, La Laguna, Spain., Padrón JM; BioLab, Instituto Universitario de Bio-Orgánica 'Antonio González' (IUBO-AG), Universidad de La Laguna, C/Astrofísico Francisco Sánchez 2, 38206, La Laguna, Spain., Murumkar PR; Faculty of Pharmacy, Kalabhavan Campus, The Maharaja Sayajirao University of Baroda, Vadodara, 390 001, India., Sharma MK; Faculty of Pharmacy, Kalabhavan Campus, The Maharaja Sayajirao University of Baroda, Vadodara, 390 001, India., Yadav MR; Faculty of Pharmacy, Kalabhavan Campus, The Maharaja Sayajirao University of Baroda, Vadodara, 390 001, India.
Jazyk: angličtina
Zdroj: Molecular diversity [Mol Divers] 2023 Nov 08. Date of Electronic Publication: 2023 Nov 08.
DOI: 10.1007/s11030-023-10741-4
Abstrakt: A new and efficient method has been developed to synthesize dispiro[oxindole/acenaphthylenone-benzofuranone]pyrrolidine compounds. This is done by triggering the 1,3-dipolar cycloaddition reaction of azomethine ylides by reacting isatin/acenaphthoquinone with L-picolinic acid/L-proline/sarcosine/L-thioproline/tetrahydroisoquinolines, in a highly regioselective manner in an ionic liquid [DBU][Ac] with 4'-chloro-auron[2-(4-chlorobenzylidene)benzofuran-3(2H)-one]. Single-crystal X-ray diffraction data support the proposed structures of the new compounds. The heterocycles derived from amino acids such as L-picolinic acid, L-proline, and L-thioproline showed significant inhibitory effects against six human solid tumors, including lung, breast, cervix, colon, and others. These new structures were also tested in the active sites of the MDM2 receptor to further study their antiproliferative effects.
(© 2023. The Author(s), under exclusive licence to Springer Nature Switzerland AG.)
Databáze: MEDLINE
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