Preparation, biological evaluation and molecular docking study of imidazolyl dihydropyrimidines as potential Mycobacterium tuberculosis dihydrofolate reductase inhibitors

Desai, N. C.; Trivedi, Anjali; Khedkar, Vijay M.

doi:10.1016/j.bmcl.2016.06.082

Cited by 27 publications

(9 citation statements)

References 54 publications

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“…The scientists also evaluated their cytotoxic effect in VERO cells and found that several compounds had low level of cytotoxicity. The IC 50 value of Compound 33 was 9.4 μM, and the selectivity index value of it was 24.10 (Desai, Trivedi, & Khedkar, ; Fan et al, ).…”

Section: Five‐membered Ring Compoundsmentioning

confidence: 99%

Opportunities and challenges of using five‐membered ring compounds as promising antitubercular agents

Wang

et al. 2020

Drug Development Research

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Tuberculosis (TB), a chronic infectious disease, is one of the greatest risks to human beings and 10 million people were diagnosed with TB and 1.6 million died from this disease in 2017. In addition, with the emergence of multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB), the TB situation has become even worse, which has aggravated the mortality and spread of this disease.To overcome this problem, research into novel antituberculosis agents with enhanced activities against MDR-TB, reduced toxicity, and shortened duration of therapy is of great importance. Fortunately, many novel potential anti-TB drug candidates with five-membered rings, which are most likely to be effective against sensitive and resistant strains, have recently entered clinical trials. Different five-membered rings such as furans, pyranoses, thiazoles, pyrazolines, imidazoles, oxazolidinone, thiazolidins, isoxazoles, triazoles, oxadiazoles, thiadiazoles, and tetrazoles have been designed, prepared, and evaluated for their antimycobacterial activity against Mycobacterium tuberculosis. In this article, we highlight the recent advances made in the discovery of novel five-membered ring compounds and focus on their antitubercular activities, toxicity, structure-activity relationships, and mechanisms of action. K E Y W O R D Santi-TB drug, antitubercular activities, five-membered ring, MDR-TB, tuberculosis

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Section: Five‐membered Ring Compoundsmentioning

confidence: 99%

Opportunities and challenges of using five‐membered ring compounds as promising antitubercular agents

Wang

et al. 2020

Drug Development Research

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“…The preparation of 3,4‐dihydropyrimidin‐2(1 H )‐ones (DHPMs) and their derivatives have attracted considerable attention due to the pervasiveness of these compounds in pharmaceutical products such as antiviral, antitumor, anti‐inflammatory as well as calcium channel blockers and backbones of anticancer drugs . Until now, three‐component Biginelli condensation is the most common method for the synthesis of dihydropyrimidine derivatives .…”

Section: Figurementioning

confidence: 99%

Au Nanorod: An Efficient Catalyst for One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2(1H)‐ones via the Multicomponent Biginelli Reaction.

Nguyen

et al. 2017

ChemistrySelect

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Gold nanoparticle catalysts have attracted much attention due to their catalytic efficiency under mild conditions. We report here the synthesis of a series of shapes of gold nanocrystals by simple reduction of HAuCl4⋅3H2O and application them as the catalysts for multicomponent Biginelli reaction. Amongst these, unsupported gold nanorods show the best catalytic activity. Its efficiency allows one‐pot synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones to proceed in high yield under mild conditions.

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“…In past decades, dihydropyrimidinones (DHPMs) and their derivatives have attracted considerable interest due to their heterocyclic scaffold and interesting pharmacological properties such as antiviral, antitumor, anti inflammatory as well their applications as calcium channel blockers and anticancer drugs (Ali et al, 2016;Desai et al, 2016;Xue et al, 2016;Dalil et al, 2016;Dhumaskar et al, 2014;Jetti et al, 2014). Different strategies have been used for the modification of 3,4-dihydropyrimidine-2(1H)-ones.…”

Section: Structure Descriptionmentioning

confidence: 99%

5-Acetyl-6-methyl-4-phenyl-1-(prop-2-ynyl)-3,4-dihydropyrimidin-2(1H)-one

Kaoukabi¹,

Taourirte²,

Lazrek³

et al. 2017

IUCr Data

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The 4-dihydropyrimidin-2(1H)-one moiety of the title molecule, C16H16N2O2, displays a half-chair conformation. The least-squares mean plane through this heterocycle is almost perpendicular to the aromatic ring [dihedral angle = 89.52 (8)°] and to the prop-2-ynyl chain [C—C—N—C torsion angle of −73.2 (2)°]. The mean plane through the acetyl group makes a dihedral angle of 30.93 (10)° with the mean plane of the heterocycle. There is an intramolecular C—H...O hydrogen bond forming anS(6) ring motif. In the crystal, molecules are linked by pairs of N—H...O hydrogen bonds forming inversion dimers.

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Preparation, biological evaluation and molecular docking study of imidazolyl dihydropyrimidines as potential Mycobacterium tuberculosis dihydrofolate reductase inhibitors

Cited by 27 publications

References 54 publications

Opportunities and challenges of using five‐membered ring compounds as promising antitubercular agents

Opportunities and challenges of using five‐membered ring compounds as promising antitubercular agents

Au Nanorod: An Efficient Catalyst for One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2(1H)‐ones via the Multicomponent Biginelli Reaction.

5-Acetyl-6-methyl-4-phenyl-1-(prop-2-ynyl)-3,4-dihydropyrimidin-2(1H)-one

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