Synthesis, characterization and anticancer screening of some novel piperonyl–tetrazole derivatives

Arshad, Mohammad; Bhat, Abdul Roouf; Pokharel, Smritee; Kim, Jieun; Lee, Eun Ju; Athar, Fareeda; Choi, Inho

doi:10.1016/j.ejmech.2013.11.008

Cited by 77 publications

(31 citation statements)

References 41 publications

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“…However, 1,5-disubstituted tetrazoles can be used as isosteres of cis-amide bond of peptides (May & Abell, 2001;May & Abell, 2002). Substances containing 1,5-disubstituted tetrazole fragment are being well studied as they exhibit anti-inflammatory (Rajasekaran & Thampi, 2004), antiviral, (Muraglia et al, 2006), antitubercular (Karabanovich et al, 2015), anticonvulsant, antimicrobial (Rostom, Ashour, Abd El Razik, Abd El Fattah, & El-Din, 2009), antiparasitic (Pedro et al, 2014), antiulcer (Uchida et al, 1989, antihypertensive (Ashton et al, 1992), antimalarial (Pandey et al, 2013), anticancer (Arshad et al, 2014), and COX-2 inhibitory (Al-Hourani et al, 2011) properties. 2,5-Disubstituted tetrazoles have been proved to exhibit antiviral (Chang et al, 2005), antimicrobial (Rostom, Ashour, Abd El Razik, Abd El Fattah, & El-Din, 2009), and glutamate receptor modulating (Vieira et al, 2005) properties.…”

Section: Introductionmentioning

confidence: 99%

Novel 5‐(1‐aryl‐1H‐pyrazol‐3‐yl)‐1H‐tetrazoles as glycogen phosphorylase inhibitors: An in vivo antihyperglycemic activity study

Kattimani

Somagond

Bayannavar

et al. 2019

Drug Development Research

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In this study, we report the ring transformation of 3‐arylsydnone into 1‐aryl‐1H‐pyrazole‐3‐carbonitriles via [3 + 2] cycloaddition with acrylonitrile. 1‐Aryl‐1H‐pyrazole‐3‐carbonitrile underwent [2 + 3] cycloaddition with sodium azide to afford 5‐(1‐aryl‐1H‐pyrazol‐3‐yl)‐1H‐tetrazoles which were further subjected to N‐alkylation with aryl/heteroaryl alkyl halides to afford 1,5‐ and 2,5‐disubstituted tetrazoles. Furthermore, the title compounds were screened for in vivo antihyperglycemic activity using albino Wistar rats of either sex. Compounds 4a, 6b, 7a, 7b, 8b, and 9b showed maximum fall in the blood glucose levels in streptozotocin‐induced diabetic rats after 5–7 days of administration. In support of antidiabetic activity, we also performed the experimental in vivo studies, namely, effect of compounds on enzymes (serum glutamic oxaloacetic transaminase, serum glutamic‐pyruvic transaminase, creatinine, urea, and total protein), antihyperlipidemic, and histopathology. Moreover, the molecular docking study has been performed for potent molecules among the series with glycogen phosphorylase as target enzyme, and this study corroborated the experimental in vivo results.

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Section: Introductionmentioning

confidence: 99%

Novel 5‐(1‐aryl‐1H‐pyrazol‐3‐yl)‐1H‐tetrazoles as glycogen phosphorylase inhibitors: An in vivo antihyperglycemic activity study

Kattimani

Somagond

Bayannavar

et al. 2019

Drug Development Research

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“…Further, tetrazole derivatives can be extensively used as synthons for the preparation of N ‐containing compounds in organic synthetic chemistry and in organocatalysis . The importance of the tetrazole‐containing materials as antitumor agents highlighted in literature survey …”

Section: Introductionmentioning

confidence: 99%

In situ green synthesis of Cu‐Ni bimetallic nanoparticles supported on reduced graphene oxide as an effective and recyclable catalyst for the synthesis of N‐benzyl‐N‐aryl‐5‐amino‐1H‐tetrazoles

Nasrollahzadeh

Sajjadi

Komber

et al. 2019

Applied Organom Chemis

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In the present work, for the first time we have designed a novel approach for the synthesis of N‐benzyl‐N‐aryl‐5‐amino‐1H‐tetrazoles using reduced graphene oxide (rGO) decorated with Cu‐Ni bimetallic nanoparticles (NPs). In situ synthesis of Cu/Ni/rGO nanocomposite was performed by a cost efficient, surfactant‐free and environmentally benign method using Crataegus azarolus var. aronia L. leaf extract as a stabilizing and reducing agent. Phytochemicals present in the extract can be used to reduce Cu2+ and Ni2+ ions and GO to Cu NPs, Ni NPs and rGO, respectively. Analyses by means of FT‐IR, UV–Vis, EDS, TEM, FESEM, XRD and elemental mapping confirmed the Cu/Ni/rGO formation and also FT‐IR, NMR, and mass spectroscopy as well as elemental analysis were used to characterize the tetrazoles. The Cu/Ni/rGO nanocomposite showed the superior catalytic activity for the synthesis of N‐benzyl‐N‐aryl‐5‐amino‐1H‐tetrazoles within a short reaction time and high yields. Furthermore, this protocol eliminates the need to handle HN3.

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“…Therefore, the discovery and development of new effective and selective anticancer drugs are of high importance in modern cancer research. Nitrogen‐based heterocycles such as triazoles and tetrazoles are five membered ring heterocyclic compounds and they have earned great interest in medicinal chemistry as anticancer agents . 1,2,4‐triazole, for example, has been found to inhibit the growth of various cancers including lung, colon, renal, ovarian, leukemia prostate, and breast .…”

Section: Introductionmentioning

confidence: 99%

“…1,2,4‐triazole, for example, has been found to inhibit the growth of various cancers including lung, colon, renal, ovarian, leukemia prostate, and breast . Tetrazole and its derivatives, on the other hand, exhibit a wide variety of biological properties including antibacterial, antimicrobial, anti‐inflammatory, antifungal, antiviral, antinociceptive, analgesic, cyclo‐oxygenase inhibition, and anticancer activities . Tetrazole derivatives exhibited anticancer activity against Hep G2, A 549, DU 145, and MCF‐7 cell lines …”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and anticancer activity of some azole‐heterocyclic complexes with gold(III), palladium(II), nickel(II), and copper(II) metal ions

Abdnoor

Alabdali

2019

J Chinese Chemical Soc

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Four new complexes of Au(III), Pd(II), Ni(II), and Cu(II) ions were synthesized, derived from a novel heterocyclic ligand (L) that has both triazole and tetrazole rings. The ligand synthesis was through successive steps to achieve both heterocyclic rings. The synthesized compounds were characterized using conventional techniques like infrared, ultra violet—visible and proton/carbon nuclear magnetic resonance spectroscopy, metal and thermal analyses, and molar conductivity. All complexes were suggested to have square planar geometry, gold, nickel, and palladium complexes were salts while copper neutral complexes have the chemical formulas; [AuL2]Cl.2H2O, [PdL2]Cl2.2H2O, [NiL2]Cl2.2H2O, and [CuL2]. The cytotoxic effect was studied on breast cancer cell line (MCF‐7 cell line) at different concentrations by using the 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide assay method, for the ligand (L) and complexes. The results showed that gold(III) and nickel(II) complexes have the highest cytotoxicity among all compounds against cancer cell lines.

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Synthesis, characterization and anticancer screening of some novel piperonyl–tetrazole derivatives

Cited by 77 publications

References 41 publications

Novel 5‐(1‐aryl‐1H‐pyrazol‐3‐yl)‐1H‐tetrazoles as glycogen phosphorylase inhibitors: An in vivo antihyperglycemic activity study

Novel 5‐(1‐aryl‐1H‐pyrazol‐3‐yl)‐1H‐tetrazoles as glycogen phosphorylase inhibitors: An in vivo antihyperglycemic activity study

In situ green synthesis of Cu‐Ni bimetallic nanoparticles supported on reduced graphene oxide as an effective and recyclable catalyst for the synthesis of N‐benzyl‐N‐aryl‐5‐amino‐1H‐tetrazoles

Synthesis, characterization, and anticancer activity of some azole‐heterocyclic complexes with gold(III), palladium(II), nickel(II), and copper(II) metal ions

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