Synthesis of first ever 4-quinolone-3-carboxylic acid-appended spirooxindole-pyrrolidine derivatives and their biological applications.
A series of 4-quinolone-3-carboxylic acid-containing spirooxindole-pyrrolidine derivatives was synthesized via multicomponent 1,3-dipolar cycloaddition reactions of azomethine ylides with new (E)-4-oxo-6-(3-phenyl-acryloyl)-1,4-dihydroquinoline-3-carboxylic acids in good yields with high regioselectivity. The cycloadducts were characterized by analytical and spectral data including [Formula: see text], [Formula: see text], 2D NMR and mass spectroscopy. The structure of one of the compounds (8a) was investigated theoretically by computational techniques. DFT studies support the proposed mechanism for this cycloaddition reaction. Furthermore, antibacterial activities of the new compounds were evaluated against Gram-positive and Gram-negative bacterial strains. Compounds 8f, 8m and 8p showed potent inhibition activities against selected bacteria. The in vitro cytotoxicity of spirooxindole derivatives (8a-r) was evaluated against MCF-7 breast cancer cell line. Among the various compounds tested, compound 8f [Formula: see text] showed significant cytotoxic activity compared to the standard drug doxorubicin [Formula: see text].
School of Chemical Sciences, Bharathiar University, Coimbatore, Tamil Nadu, 641 046, India.|Department of Chemistry, Richardson College for the Environmental Science Complex, The University of Winnipeg, 599 Portage Avenue, Winnipeg, MB, R3B 2G3, Canada.
Thangaraj
T
Arasakumar
School of Chemical Sciences, Bharathiar University, Coimbatore, Tamil Nadu, 641 046, India.
Sadasivam
S
Mathusalini
Department of Chemistry, Richardson College for the Environmental Science Complex, The University of Winnipeg, 599 Portage Avenue, Winnipeg, MB, R3B 2G3, Canada. a.ata@uwinnipeg.ca.
Athar
A
Ata
Department of Physics, Bharathiar University, Coimbatore, Tamil Nadu, 641 046, India.
Ramasamy
R
Shankar
School of Chemical Sciences, Bharathiar University, Coimbatore, Tamil Nadu, 641 046, India.
Subashini
S
Gopalan
School of Chemical Sciences, Bharathiar University, Coimbatore, Tamil Nadu, 641 046, India.|DRDO-BU CLS, Bharathiar University, Coimbatore, Tamil Nadu, 641 046, India.
Krishnasamy
K
Lakshmi
DRDO-BU CLS, Bharathiar University, Coimbatore, Tamil Nadu, 641 046, India.
Pandiyarajan
P
Sakthivel
School of Chemical Sciences, Bharathiar University, Coimbatore, Tamil Nadu, 641 046, India. psmohan59@gmail.com.
Palathurai Subramaniam
PS
Mohan
D042462:4-Quinolones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D060326:Chemistry Techniques, Synthetic; D006801:Humans; D007211:Indoles / Q000737:chemistry*; D061986:MCF-7 Cells; D008958:Models, Molecular; D008968:Molecular Conformation; D000078183:Oxindoles; D011759:Pyrrolidines / Q000737:chemistry*; D011789:Quantum Theory; D013329:Structure-Activity Relationship
D042462:4-Quinolones; C576632:4-quinolone-3-carboxylic acid; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D002264:Carboxylic Acids; D007211:Indoles; D000078183:Oxindoles; D011759:Pyrrolidines; C022960:2-oxindole
Antibacterial activity; Cytotoxicity; DFT calculation; Multicomponent reaction; Quinolone; Spiropyrrolidine
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