Abstract
BackgroundA novel series of 5-(substituted aldehyde)-7-methyl-3-oxo-N-phenyl-2-((3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl)methylene)-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-6-carboxamide analogues (1–24) was synthesized using the Biginelli condensation.Results and discussionThe synthesized compounds were screened for their in vitro antimicrobial potential against Gram (positive and negative) bacterial and fungal strains by tube dilution technique. In the series, compound 15 exhibited significant antimicrobial activity against Candida albicans and Aspergillus niger with MIC value = 1.04 × 10−2 µM/ml and compound 2 was found to be most active antioxidant agent with IC50 value = 46.31 using DPPH assay. Anticancer activity results indicated that compound 23 displayed better anticancer activity against human breast cancer cell line (MCF-7) with GI50 value = 34.78 using SRB assay.ConclusionsAll synthesized derivatives exhibited good antimicrobial, antioxidant and anticancer activity using specific method and compared with standard drugs, especially compounds 2, 15 and 23 displayed more activity than reference drugs. Structure activity relationship demonstrated that presence of electron releasing groups of the synthesized compounds enhanced the antibacterial activity against Escherichia coli as well as antioxidant activity and electron withdrawing groups improved the antimicrobial as well as anticancer activity against human breast (MCF-7) cancer cell line.
Highlights
A novel series of 5-(substituted aldehyde)-7-methyl-3-oxo-N-phenyl-2-((3,4,5,6-tetrahydroxytetrahydro2H-pyran-2-yl)methylene)-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-6-carboxamide analogues (1–24) was synthesized using the Biginelli condensation
Structure activity relationship demonstrated that presence of electron releasing groups of the synthesized compounds enhanced the antibacterial activity against Escherichia coli as well as antioxidant activity and electron withdrawing groups improved the antimicrobial as well as anticancer activity against human breast (MCF-7) cancer cell line
Pyrimidine derivatives play a vital role in several biological activities i.e. antihypertensive, anticancer, antimicrobial, anti-inflammatory, antifungal, analgesic, antioxidant, anticonvulsant and antiviral [2]
Summary
Chemistry In the research work, we have synthesized new series of 5-(substituted aldehyde)-7-methyl-3-oxo-N-phenyl2-((3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl) methylene)-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-6-carboxamide analogues using the Biginelli condensation and synthetic steps of this series showing in Scheme 1. Compound 5 (7-Methyl-5-(3-nitrophenyl)-3-oxo-Nphenyl-2-((3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl)methylene)-1,2,3,5-tetrahydroimidazo[1,2-a] pyrimidine-6-carboxamide) IR: {3062 (C–H st.), 1597 (C=C st.), 693 (C–C st.) of aromatic ring}, 1630 (C=O st.,), 3307 (N–H st., 2° amide), {1630 (N=CH st.), 1330 (C–N st.) of pn}, 2779 (C–H st., cyclic ether), 1125 (C–O–C st., aryl ether), 3307 (O–H st., polyhydroxy), 1350 (NO2 st., phenyl nucleus), 841 (C–N st., C6H5NO2); 1H-NMR (DMSO-d6, δ ppm): 7.28–8.09 (m, 9H, Ar–H), 2.12 (s, 1H, NH), 8.10 (s, 1H, NH of 2o amide), 3.47–4.23 (m, 5H, CH of tetrahydropyran), 2.19 {s, 4H, (OH)4}; 13CNMR (DMSO-d6, δ ppm): 21.2, 72.3, 76.2, 98.5, 59.2, 120.3, 121.1, 125.4, 128.7, 128.9, 128.0, 129.1, 130.1, 133.3, 137.2, 144.2, 147.2, 152.3, 163.1; MS ES + (ToF): m/z 551 [M++1]. Amide), 6.69 (s, 1H, ethylene), 3.48–5.04 (m, 5H, CH of tetrahydropyran), 2.1 {s, 4H, (OH)4}, 6.16 {d, 1H,(CH)2; 6.51 (d, 1H, (CH)b of aliphatic chain}; 13C-NMR (DMSO-d6, δ ppm): 21.5, 73.4, 77.5, 79.3, 98.7, 122.5, 130.6, 162.3, 146.4, 163.4, 121.3, 123.4, 125.8, 137.4, 127.1, 128.8, 133.6, 136.5, 137.7 153.6, 119.3; MS ES + (ToF): m/z 532 [M++1]
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