Synthesis of new class of spirocarbocycle derivatives by multicomponent domino reaction and their evaluation for antimicrobial, anticancer activity and molecular docking studies

Sudhapriya, N.; Perumal, Paramasivan T.; Balachandran, C.; Ignacimuthu, S.; Sangeetha, M.; Doble, Mukesh

doi:10.1016/j.ejmech.2014.05.065

Cited by 36 publications

(35 citation statements)

References 41 publications

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“…Multicomponent reactions (MCRs), or one-pot reactions in which at least three different substrates join through the covalent bonds, have been of great interest in synthetic organic chemistry due to the efficiency of giving higher overall yields (Musonda et al, 2004;Dekamin et al, 2013a,b;Dekamin and Eslami, 2014;Rotstein et al, 2014;Sudhapriya et al, 2014;Oshiro et al, 2015;Aly, 2016;Aly et al, 2018). A literature survey reveals that numerous methods were developed for the synthesis of dihydropyrano[2,3-c]pyrazoles (Sudhapriya et al, 2014;Ambethkar et al, 2015;Pati Tripathi et al, 2017). In the beginning, we synthesized the reported pyrano-pyrazole 1 as a staring material by using ethylacetoacetate, hydrazine hydrate, 2-bromobenzaldehyde, and malononitrile, and the reaction was performed in ethanol using triethylamine as basic catalyst (Muramulla and Zhao, 2011).…”

Section: Chemistrymentioning

confidence: 99%

Novel Anticancer Fused Pyrazole Derivatives as EGFR and VEGFR-2 Dual TK Inhibitors

et al. 2020

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EGFR and VEGFR-2 represent promising targets for cancer treatment as they are very important in tumor development as well as in angiogenesis and metastasis. In this work, 6-amino-4-(2-bromophenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile 1 and (E)-4-(2-Bromobenzylidene)-5-methyl-2,4-dihydro-3H-pyrazol-3-one 11 were selected as starting materials to synthesize different fused pyrazole derivatives; dihydropyrano[2,3-c]pyrazole 1, 2, 7-9, and 15, pyrazolo[4 ′ ,3 ′ :5,6]pyrano[2,3d]pyrimidine 3-6, pyrazolo[3,4-d]pyrimidine 12 and 13, and pyrazolo[3,4-c]pyrazole 14 derivatives were synthesized to evaluate their anticancer activity against HEPG2 human cancer cell lines compared to erlotinib and sorafenib as reference drugs. Seven compounds 1, 2, 4, 8, 11, 12, and 15 showed nearly 10 fold higher activity than erlotinib (10.6 µM) with IC 50 ranging from 0.31 to 0.71 µM. In vitro EGFR and VEGFR-2 inhibitory activity were performed for the synthesized compounds, and the results identified compound 3 as the most potent EGFR inhibitor (IC 50 = 0.06 µM) and compound 9 as the most potent VEGFR-2 inhibitor (IC 50 = 0.22 µM). Moreover, compounds 9 and 12 revealed potent dual EGFR and VEGFR-2 inhibition, and these results were supported by docking studies of these two compounds within the active sites of both enzymes.

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Section: Chemistrymentioning

confidence: 99%

Novel Anticancer Fused Pyrazole Derivatives as EGFR and VEGFR-2 Dual TK Inhibitors

et al. 2020

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“…DNA is a good target for antimicrobial agents due to its base pairs with rich electrons. 40,41 Generally, bioactive molecules could bind to DNA in various modes such as electrostatic, groove and intercalative binding. Among them, the intercalative mode is the most important one, in which molecules could intercalate between the base pairs of double helix DNA, then greatly affect or even damage DNA.…”

Section: Molecular Docking Of Compound 6f and Dna Hexamer Duplexmentioning

confidence: 99%

Synthesis and bioactive evaluations of novel benzotriazole compounds as potential antimicrobial agents and the interaction with calf thymus DNA

Ren

Zhang

et al. 2015

J Chem Sci

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A novel series of benzotriazole derivatives were synthesized and characterized by NMR, IR and MS spectra. The bioactive assay manifested that most of the new compounds exhibited moderate to good antibacterial and antifungal activities against the tested strains in comparison to reference drugs chloromycin, norfloxacin and fluconazole. Especially, 2,4-dichlorophenyl substituted benzotriazole derivative 6f displayed good antibacterial activity against MRSA with MIC value of 4 μg/mL, which was 2-fold more potent than Chloromycin, and it also displayed 3-fold stronger antifungal activity (MIC = 4 μg/mL) than fluconazole (MIC = 16 μg/mL) against Beer yeast. The preliminary interactive investigations of compound 6f with calf thymus DNA revealed that compound 6f could effectively intercalate into DNA to form compound 6f-DNA complex which might block DNA replication to exert antimicrobial activities. Molecular docking experiments suggested that compound 6f projected into base-pairs of DNA hexamer duplex forming two hydrogen bonds with guanine of DNA. The theoretical calculations were in accordance with the experimental results.

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“…In this reaction, multiple C-C or C-H bonds are formed in the same vessel, including different reaction mechanisms to form complex molecules without the purification of intermediates. These reactions are often used in medical or combinatorial chemistry to synthesize complex active drug molecules (Sudhapriya et al, 2014;Tietze et al, 2014;Fu et al, 2013;Shestopalov et al, 2013;Zohreh & Alizadeh, 2013;Renault et al, 2007). Domino reactions are classified as homo-domino processes and hetero-domino processes (Nesi et al, 1999).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of 8-[7,8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid

Jacob

Sithambaresan²,

Kunjachan

et al. 2015

Acta Cryst E

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Synthesis of new class of spirocarbocycle derivatives by multicomponent domino reaction and their evaluation for antimicrobial, anticancer activity and molecular docking studies

Cited by 36 publications

References 41 publications

Novel Anticancer Fused Pyrazole Derivatives as EGFR and VEGFR-2 Dual TK Inhibitors

Novel Anticancer Fused Pyrazole Derivatives as EGFR and VEGFR-2 Dual TK Inhibitors

Synthesis and bioactive evaluations of novel benzotriazole compounds as potential antimicrobial agents and the interaction with calf thymus DNA

Crystal structure of 8-[7,8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid

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