Synthesis and evaluation of novel imidazo[4,5-c]pyridine derivatives as antimycobacterial agents against Mycobacterium tuberculosis

Madaiah, M.; Prashanth, M.K.; Revanasiddappa, H. D.; Veeresh, Bantal

doi:10.1039/c6nj02069k

Cited by 28 publications

(6 citation statements)

References 21 publications

(22 reference statements)

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“…The in vitro activity of imidazole derivatives along with the references against Mycobacterium tuberculosis (ATCC 35801) were performed as previously described . Briefly, MIC for the compounds was determined by an agar dilution method.…”

Section: Methodsmentioning

confidence: 99%

MoS₂–Calix[4]arene Catalyzed Synthesis and Molecular Docking Study of 2,4,5-Trisubstituted Imidazoles As Potent Inhibitors of Mycobacterium tuberculosis

Raghu¹,

Kumar²,

Prasad³

et al. 2020

ACS Comb. Sci.

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A MoS2-supported-calix[4]arene (MoS2-CA4) nanocatalyst was used for efficient synthesis of 2,4,5-trisubstituted imidazole derivatives from 1-(4-nitrophenyl)-2-(4-(trifluoromethyl)phenyl)ethane-1,2-dione, aldehydes and ammonium acetate under solvent-free conditions. Reusability of the catalyst up to five cycles without any significant loss in the yields of the product is the unique feature of this heterogeneous solid catalysis. Furthermore, the noteworthy highlights of this method are safe reaction profiles, broad substrate scope, excellent yields, economical, solvent-free, and simple workup conditions. All synthesized compounds were evaluated for their in vitro antitubercular (TB) activity against Mycobacterium tuberculosis (Mtb) H37Rv. Among the screened compounds 3c, 3d, 3f, 3m, and 3r had MIC values of 2.15, 2.78, 5.75, 1.36, and 0.75 μM, respectively, and exhibited more potency than the reference drugs pyrazinamide (MIC: 3.12 μM), ciprofloxacin (MIC: 4.73 μM), and ethambutol (7.61 μM). Besides, potent compounds (3c, 3d, 3f, 3m, and 3r) have been tested for inhibition of MabA (β-ketoacyl-ACP reductase) enzyme and cytotoxic activity against mammalian Vero cell line. A molecular docking study was carried out on the MabA (PDB ID: 1UZN) enzyme to predict the interactions of the synthesized compounds. The results of the in vitro anti-TB activity and docking study showed that synthesized compounds have a strong anti-TB activity and can be adapted and produced more effectively as a lead compound.

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Section: Methodsmentioning

confidence: 99%

MoS₂–Calix[4]arene Catalyzed Synthesis and Molecular Docking Study of 2,4,5-Trisubstituted Imidazoles As Potent Inhibitors of Mycobacterium tuberculosis

Raghu¹,

Kumar²,

Prasad³

et al. 2020

ACS Comb. Sci.

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“…After primary screening of the toxicity studies, compounds 83a and 93b appeared to be the best potent molecule with minimum cytotoxicity. Prashanth et al synthesized imidazo[4,5-c]pyridine derivatives and evaluated their antimicrobial activity (Madaiah et al, 2016). The synthesis of the desired compound involved a series of reactions initiating from the chlorination of 2,6dichloropyridine 94 in the presence of trifluoroacetic acid, H 2 O 2 and POCl 3.…”

Section: Scheme 28mentioning

confidence: 99%

Synthetic approaches to potent heterocyclic inhibitors of tuberculosis: A decade review

Dasmahapatra

Chanda

2022

Front. Pharmacol.

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Tuberculosis (TB) continues to be a significant global health concern with about 1.5 million deaths annually. Despite efforts to develop more efficient vaccines, reliable diagnostics, and chemotherapeutics, tuberculosis has become a concern to world health due to HIV, the rapid growth of bacteria that are resistant to treatment, and the recently introduced COVID-19 pandemic. As is well known, advances in synthetic organic chemistry have historically enabled the production of important life-saving medications that have had a tremendous impact on patients’ lives and health all over the world. Small-molecule research as a novel chemical entity for a specific disease target offers in-depth knowledge and potential therapeutic targets. In this viewpoint, we concentrated on the synthesis of a number of heterocycles reported in the previous decade and the screening of their inhibitory action against diverse strains of Mycobacterium tuberculosis. These findings offer specific details on the structure-based activity of several heterocyclic scaffolds backed by their in vitro tests as a promising class of antitubercular medicines, which will be further useful to build effective treatments to prevent this terrible illness.

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“…[4,5] Furthermore, several thiazolidine derivatives have been reported for a variety of biological activities apart from synthetic interests, [6][7][8][9] antibacterial, [10] anti-inflammatory, cardiovascular, hypoglycemic, lipid lowering, [11,12] and anti-oxidant activity. [13] In addition, a series of heterocyclic compounds bearing a pyridine moiety observed that the pyridine ring plays a vital role in many biological activities such as antimicrobial, [14][15][16] antiviral, [17,18] anti-convulsant, [19] and anti-mycobacterial. [20] Polysubstituted pyridine containing cyano group exhibited antitumor activity in numerous publications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antitumor evaluation of some new thiazolopyridine, nicotinonitrile, pyrazolopyridine, and polyhydroquinoline derivatives using ceric ammonium nitrate as a green catalyst

Raslan

Hessein

Fouad

et al. 2021

Journal of Heterocyclic Chem

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A novel series of thiazolo[5,4‐b]pyridine, polysubstituted pyridines, pyrazolo [3,4‐b] pyridine‐5‐carbonitriles, and polyhydroquinoline were synthesized via one‐pot reaction of 2‐iminothiazolidin‐5‐one, acetyl pyridine, pyrazolone, and/or cyclohexanone with various aldehydes, some active methylene and ammonium acetate in the presence of ceric ammonium nitrate (CAN). The resulting compounds were generated in high yields in a short amount of time, and the structures of the novel compounds were confirmed using IR, 1H NMR, 13C‐NMR, and mass spectra. The cytotoxic activity of 15 substances was tested in vitro against HePG‐2 and Caco‐2 cell lines. The results of antitumor assay confirmed that quinoline 12d compounds possess higher cytotoxic activity against two cell lines closed to doxorubicin, which is used as a standard anticancer drug. Also, 12c compounds are more efficient antitumor against the 2‐cell lines. While compounds 1 showed moderate activity toward Caco‐2. On the other hand, most of the tested compounds exhibited moderate to low cytotoxic activity toward the two cell lines. Based on the results, some of the newly synthesized derivatives showed excellent antitumor activity that qualified them for biomedical applications.

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Synthesis and evaluation of novel imidazo[4,5-c]pyridine derivatives as antimycobacterial agents against Mycobacterium tuberculosis

Abstract: Novel imidazo[4,5-c]pyridine derivatives showed cytotoxicity and decreased the bacterial load in lung and spleen tissues in the in vivo animal model.

Cited by 28 publications

References 21 publications

MoS₂–Calix[4]arene Catalyzed Synthesis and Molecular Docking Study of 2,4,5-Trisubstituted Imidazoles As Potent Inhibitors of Mycobacterium tuberculosis

MoS₂–Calix[4]arene Catalyzed Synthesis and Molecular Docking Study of 2,4,5-Trisubstituted Imidazoles As Potent Inhibitors of Mycobacterium tuberculosis

Synthetic approaches to potent heterocyclic inhibitors of tuberculosis: A decade review

Synthesis and antitumor evaluation of some new thiazolopyridine, nicotinonitrile, pyrazolopyridine, and polyhydroquinoline derivatives using ceric ammonium nitrate as a green catalyst

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Synthesis and evaluation of novel imidazo[4,5-c]pyridine derivatives as antimycobacterial agents against Mycobacterium tuberculosis

Abstract: Novel imidazo[4,5-c]pyridine derivatives showed cytotoxicity and decreased the bacterial load in lung and spleen tissues in the in vivo animal model.

Cited by 28 publications

References 21 publications

MoS2–Calix[4]arene Catalyzed Synthesis and Molecular Docking Study of 2,4,5-Trisubstituted Imidazoles As Potent Inhibitors of Mycobacterium tuberculosis

MoS2–Calix[4]arene Catalyzed Synthesis and Molecular Docking Study of 2,4,5-Trisubstituted Imidazoles As Potent Inhibitors of Mycobacterium tuberculosis

Synthetic approaches to potent heterocyclic inhibitors of tuberculosis: A decade review

Synthesis and antitumor evaluation of some new thiazolopyridine, nicotinonitrile, pyrazolopyridine, and polyhydroquinoline derivatives using ceric ammonium nitrate as a green catalyst

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MoS₂–Calix[4]arene Catalyzed Synthesis and Molecular Docking Study of 2,4,5-Trisubstituted Imidazoles As Potent Inhibitors of Mycobacterium tuberculosis

MoS₂–Calix[4]arene Catalyzed Synthesis and Molecular Docking Study of 2,4,5-Trisubstituted Imidazoles As Potent Inhibitors of Mycobacterium tuberculosis