Journal Article
Design, Synthesis, and Evaluation of the Anticancer Properties of Novel Quinone Bearing Carbamyl β-Lactam Hybrids
Payili, N; Yennam, S; Rekula, SR; Naidu, CG; Bobde, Y; Ghosh, B
Journal of Heterocyclic Chemistry
ISSN: 0022-152X
HeteroCorporation
This paper describes a simple and practical protocol for the direct synthesis of a series of new hybrid molecules of carbamyl β-lactam derivatives bearing quinone moiety via [2 + 2] cycloaddition of Staudinger reaction. The β-lactam ring is tolerating carbamylation and further leads to a variety of quinone hybrid derivatives. The structures of the compounds were characterized by IR, MS, nuclear magnetic resonance, and high-resolution mass spectra analysis. All the new synthesized compounds were screened for their in vitro antiproliferative activity using an MTT assay analysis. Out of 14 derivatives synthesized in the current study, compounds 9h, 9k, 9i, and 9b exhibited the very good anticancer activities in B16F10 cell line. © 2018 Wiley Periodicals, Inc.
1 [2 (3,6 dioxocyclohexa 1,4 dien 1 yl) 4 oxo 1 phenylazetidin 3 yl] 2 methyl pyrrolidine 1,2 dicarboxylate; 2 (3,6 dioxocyclohexa 1,4 dien 1 yl) 4 oxo 1 phenylazetidin 3 yl 2 methyl pyrrolidine 1 carboxylate; 2 (3,6 dioxocyclohexa 1,4 dien 1 yl) 4 oxo 1 phenylazetidin 3 yl 4 methyl piperidine 1 carboxylate; 2 (3,6 dioxocyclohexa 1,4 dien 1 yl) 4 oxo 1 phenylazetidin 3 yl diethylcarbamate; 2 (3,6 dioxocyclohexa 1,4 dien 1 yl) 4 oxo 1 phenylazetidin 3 yl dimethyl carbamate; 2 (3,6 dioxocyclohexa 1,4 dien 1 yl) 4 oxo 1 phenylazetidin 3 yl dipropylcarbamate; 2 (3,6 dioxocyclohexa 1,4 dien 1 yl) 4 oxo 1 phenylazetidin 3 yl methoxy(methyl) carbamate; 2 (3,6 dioxocyclohexa 1,4 dien 1 yl) 4 oxo 1 phenylazetidin 3 yl morpholine 4 carboxylate; 2 (3,6 dioxocyclohexa 1,4 dien 1 yl) 4 oxo 1 phenylazetidin 3 yl piperidine 1 carboxylate; 2 (3,6 dioxocyclohexa 1,4 dien 1 yl) 4 oxo 1 phenylazetidin 3 yl pyrrolidine 1 carboxylate; antineoplastic agent; beta lactam derivative; carbamyl beta lactam quinone hybrid; unclassified drug; animal cell; antineoplastic activity; antiproliferative activity; Article; B16F10 cell line; carbamoylation; carbon nuclear magnetic resonance; cycloaddition; drug design; drug screening; drug structure; drug synthesis; high performance liquid chromatography; IC50; in vitro study; infrared spectroscopy; mass spectrometry; melanoma cell line; mouse; MTT assay; nonhuman; proton nuclear magnetic resonance