Synthesis and biological evaluation of imidazo[2,1-b]thiazole-benzimidazole conjugates as microtubule-targeting agents

Baig, Mirza Feroz; Nayak, V. Lakshma; Budaganaboyina, Prasad; Mullagiri, Kishore; Sunkari, Satish; Gour, Jitendra; Kamal, Ähmed

doi:10.1016/j.bioorg.2018.02.005

Cited by 41 publications

(20 citation statements)

References 56 publications

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“…After washing, cells were stained with Annexin-V and propidium iodide using Annexin-V apoptosis detection kit (Sigma-Aldrich). Annexin V-FITC assay was performed as described earlier [39].…”

Section: Methodsmentioning

confidence: 99%

Comprehensive Analysis of Secondary Metabolites in Usnea longissima (Lichenized Ascomycetes, Parmeliaceae) Using UPLC-ESI-QTOF-MS/MS and Pro-Apoptotic Activity of Barbatic Acid

et al. 2019

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Considering the importance of ultra-performance liquid chromatography-electrospray ionization-quadrupole time of flight-tandem mass spectrometry (UPLC-ESI-QTOF-MS/MS) hyphenated techniques for analysis of secondary metabolites from crude extracts, the present study was aimed at identification of secondary metabolites in acetone extract of the lichen Usnea longissima. From our study, 19 compounds were tentatively identified through comparison of exact molecular masses from their MS/MS spectra, mass fragmentation studies and comparison with literature data. In addition, potent cytotoxic activity of U. longissima extract prompted us to isolate four compounds, 18R-hydroxy-dihydroalloprotolichesterinic acid (19), neuropogolic acid (20), barbatic acid (21), and usnic acid (22) from this extract which were adequately identified through mass spectrometry and NMR spectroscopy. All four compounds displayed cytotoxic activity. Barbatic acid (21) manifested doxorubicin equivalent activity against A549 lung cancer cell line with IC50 of 1.78 µM and strong G0/G1 accumulation of cells. Poly ADP-ribose polymerase (PARP) cleavage confirmed that it induced cytotoxic activity via apoptosis. Finally, our work has discerned the depside, barbatic acid (21) from crude extract as a candidate anti-cancer molecule, which induces cell death by stepping up apoptosis.

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Section: Methodsmentioning

confidence: 99%

Comprehensive Analysis of Secondary Metabolites in Usnea longissima (Lichenized Ascomycetes, Parmeliaceae) Using UPLC-ESI-QTOF-MS/MS and Pro-Apoptotic Activity of Barbatic Acid

et al. 2019

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“…Koudad and coworkers synthesised imidazothiazole derivatives via Claisen-Schmidt condensation of aldehyde and different methyl ketones. [32] The substituted acetophenone (5) and 2-aminothiazole (3) were the chosen substrates undergoing the reaction in presence of ethanol. The obtained product 4 followed by Vilsmeier-Haack reaction, in dimethylformamide (DMF) and phosphoryl chloride (POCl 3 ), provided the imidazothiazole-chalcones (6) (Scheme 2).…”

Section: From Aminothiazolesmentioning

confidence: 99%

“…Imidazothiazoles and its derivatives are synthesized by a plethora of reactions involving multicomponent reactions (MCRs), [24][25] biosynthesis of staphyloxanthin produced by staphylococcus aurease in the presence of dehydrosqualene synthase enzyme, [27] transition metal catalysed reactions, [28] visible light synthesis, [29] regioselective reaction, [30] Groebke-Blackburn-Bienayme-Reaction (GBBR) mechanism, [24,31] oxidative cyclisation, [32] Claisen-Schmidt condensation, [33] microwave assisted green synthesis [34] and ring-opening and ring-closing reconstruction reactions. [35] Multi-component reactions are reactions involving a combination of three or more substrates, which are carried out in a one-pot system to obtain the desired product.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Applications of Imidazothiazoles: An Overview

et al. 2020

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Imidazothiazoles and its derivatives have vital role in medicinal chemistry as they exhibit biological activities such as anti‐tumor, anti‐cancer, anti‐inflammatory, antibacterial, analgesic etc. This review summarises the various methodologies used to synthesise imidazothiazoles, its derivatives and applications covering literature upto 2020 and it emphasizes the synthesis of imidazothiazoles from 2‐aminothiazole, mercaptoimidazole and imidazothiadiazole.

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“…[15][16][17][18] In recent years, many research groups focused on the synthesis and anti-cancer properties of hybrid compounds of coumarin with other bio-active heterocyclic moieties such as pyrimidine, 19 chalcone, 20 βcarboline, 21 indole-triazole, 22 artemisinin, 23 thiazole, 24 and isooxazilones. 25 In the meantime, hybrid compounds of benzimidazole and their anticancer properties were reported with various heterocyclic moieties such as triazine, 26 ellipticine, 27 tetrazine, 28 deoxynucleosides, 29 thiazoles, 30 and chrysin. 31 However, according to our literature survey, coumarin-benzimidazole hybrids are very rare.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic effects of coumarin substituted benzimidazolium salts against human prostate and ovarian cancer cells

et al. 2019

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Coumarin and benzimidazole derivatives have individual biological activities including anticancer. In this study, we aimed to synthesize coumarin-benzimidazole hybrids in order to investigate their anticancer properties. For this purpose, six 6-substituted-4-chloromethylene coumarin derivatives were synthesized. Sixteen coumarin substituted benzimidazolium chlorides were synthesized by the reaction of 4-chloromethylene coumarin and N-benzylbenzimidazole derivatives. All of the synthesized compounds were characterized by 1 H and 13 C NMR, IR spectroscopic techniques and elemental analyses. Cytotoxicities of all compounds were tested by [3-(4,5-dimethylthiazole)-2-yl]-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay against human prostate (PC-3) and ovarian (A2780) cancer cells. All compounds performed significant cytotoxicities at 100 μM against both cancer cell lines. Moreover, some compounds performed significant activities at 1 μM against both cancer cell lines and the obtained results suggest that this type of compounds are promising candidates for the treatment of human prostate and ovarian cancers.

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Synthesis and biological evaluation of imidazo[2,1-b]thiazole-benzimidazole conjugates as microtubule-targeting agents

Cited by 41 publications

References 56 publications

Comprehensive Analysis of Secondary Metabolites in Usnea longissima (Lichenized Ascomycetes, Parmeliaceae) Using UPLC-ESI-QTOF-MS/MS and Pro-Apoptotic Activity of Barbatic Acid

Comprehensive Analysis of Secondary Metabolites in Usnea longissima (Lichenized Ascomycetes, Parmeliaceae) Using UPLC-ESI-QTOF-MS/MS and Pro-Apoptotic Activity of Barbatic Acid

Synthesis and Applications of Imidazothiazoles: An Overview

Cytotoxic effects of coumarin substituted benzimidazolium salts against human prostate and ovarian cancer cells

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