Synthesis, antibacterial and antifungal evaluation of novel 1,4-dihydropyridine derivatives

Abu-Melha, Hanaa

doi:10.1016/j.saa.2012.12.069

Cited by 22 publications

(13 citation statements)

References 14 publications

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“…2). According to the results of Albu Mehal [21], 1,4-DHP derivatives showed better activity against Gram-positive than against Gram-negative bacteria, as also confirmed in our work.…”

Section: Resultssupporting

confidence: 90%

Antimicrobial Activity of Novel C2-Substituted 1,4-Dihydropyridine Analogues

et al. 2014

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The antimicrobial activity of 3-methyl-5-isopropyl (or ethyl) 6-methyl-4-nitrophenyl-1,4-dihydropyridine-3,5-dicarboxylate derivatives was evaluated. Prokaryotes (bacteria) appeared to be more sensitive to their antimicrobial activity than were eukaryotes (filamentous fungi). The best antibacterial activity was shown by derivative 33, which was able to inhibit the growth of Mycobacterium smegmatis (MIC33 = 9 μg.ml−1), Staphylococcus aureus (MIC33 = 25 μg.ml−1), and Escherichia coli (MIC33 = 100 μg.ml−1). In addition, derivative 4 demonstrated its antibacterial power on the acid-fast bacterial species M. smegmatis and on Gram-positive S. aureus. Focusing on the structure-activity relationship, it appears that the increase in the substituent bulk at the C2 position improved the antibacterial activity of the set of compounds studied. Derivatives 33 and 4, carrying 2-cyano-3-oxo-3-phenylprop-1-en-1-yl and allyliminomethyl groups, respectively, showed significantly higher inhibition activities on all tested microorganisms in comparison with the rest of the derivatives. This enhancement was also in good correlation with different log P values (lipophilicity parameter).

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“…2). According to the results of Albu Mehal [21], 1,4-DHP derivatives showed better activity against Gram-positive than against Gram-negative bacteria, as also confirmed in our work.…”

Section: Resultssupporting

confidence: 90%

Antimicrobial Activity of Novel C2-Substituted 1,4-Dihydropyridine Analogues

et al. 2014

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“…The polyhydroquinoline moiety is a fertile source of biologically and pharmacologically important molecules such as vasodilator, bronchodilator, anti-atherosclerotic, hepto-protective, anti-tumor, anti-mutagenic, geroprotective, anti-diabetic agents, HIV protease inhibition and most importantly as calcium channel blockers. [8][9][10][11][12][13][14][15] All mentioned cases demonstrate clearly the remarkable potential of the polyhydroquinoline derivatives as a source of valuable drugs. 16,17 In continuation of our investigation on the use of nano-g-Fe 2 O 3 -SO 3 H as catalyst for MCRs and our interest in synthesis of heterocycles containing a nitrogen atom, 18,19 we report an efficient and facile synthesis of hexahydroquinolines under solvent-free conditions (Scheme 1).…”

Section: Introductionmentioning

confidence: 75%

A solvent-free synthesis of polyhydroquinolines via Hantzsch multicomponent condensation catalyzed by nanomagnetic-supported sulfonic acid

Otokesh¹,

Koukabi²,

Kolvari³

et al. 2015

S.Afr.j.chem

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A simple and efficient procedure for the synthesis of polyhydroquinolines was developed, involving a one-pot four-component Hantzsch condensation of aromatic aldehydes, 1,3-cyclohexanediones, alkyl acetoacetate and ammonium acetate in the presence of a catalytic amount of nanomagnetic-supported sulfonic acid under solvent-free conditions. The method offers several advantages including high yields, short reaction times, a simple work-up procedure and catalyst reusability for several runs. Furthermore, easy isolation of the catalyst from the reaction mixture was enabled by use of an external magnet.

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“…Synthesized compounds ( Figure S3, Supporting Information ) were assessed for their in vitro antibacterial activity against Gram‐positive bacteria ( B. subtilis ), Gram‐negative bacteria ( P. vulgaris ) and fungi ( C. albicans ). The following reason for the antibacterial activity of dihydropyridine compound: (a) existence of an unsaturated dihydropyridine basic ring with no substitution at the N1 atom, (b) low molecular weight substituents (alkyl groups) at the C2 and C6 positions, (c) ester groups at the C3 and C5 positions, and a phenyl ring at the C4 position, and (d) the ester groups at C3 and C5 should be non‐identical, representing the fact that the C4 carbon becomes chiral, Kirby‐Bauer antibiotic testing was applied to the determination of preliminary antibacterial and antifungal activity, their images shown in Figure . During this test, wafers including antibiotics were placed on an agar plate where bacteria have been located, and the plate is left to incubate.…”

Section: Resultsmentioning

confidence: 99%

Polybenzimidazole-Triphenylphosphene-Catalyzed One-Pot Synthesis and Evaluation of Dihydropyridine Derivative as Antibiotics and Antifungals

et al. 2017

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Dihydropyridines derivative have been synthesized by one‐pot multicomponent cyclocondensation reaction using PBI‐PPh3 catalyst. This catalyst is characterized by the solid state of 13C‐NMR, 15N‐NMR, and 31P‐NMR spectrum, FT‐IR, cyclic voltammetry, and XRD analysis. The selection of catalyst is quite interesting because of its affordability, toxic free nature and high stability. Functional groups of all dihydropyridines confirms by H1‐NMR and FTIR spectra. Synthesized compounds show exceptional yields of 96–99 %. Synthesized compounds has evaluated for their invitro antibacterial activity against B. subtilis, and P. vulgaris (ATCC 49565) and C. albicans (ATCC 90028). Synthesized dihydropyridines showed promising antibacterial and antifungal activities, in particularly, ethyl‐4‐(4‐methylphenyl)‐2,7,7‐trimethyl‐5‐oxo‐1,4,5,6,7,8‐hexadihydropyridine‐3‐carboxylate are exhibiting a higher inhibition zone of 66.7 % against bacteria. Our method may help to drug chemists for design more interesting, useful, and sustainable reactions in the near future.

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Synthesis, antibacterial and antifungal evaluation of novel 1,4-dihydropyridine derivatives

Cited by 22 publications

References 14 publications

Antimicrobial Activity of Novel C2-Substituted 1,4-Dihydropyridine Analogues

Antimicrobial Activity of Novel C2-Substituted 1,4-Dihydropyridine Analogues

A solvent-free synthesis of polyhydroquinolines via Hantzsch multicomponent condensation catalyzed by nanomagnetic-supported sulfonic acid

Polybenzimidazole-Triphenylphosphene-Catalyzed One-Pot Synthesis and Evaluation of Dihydropyridine Derivative as Antibiotics and Antifungals

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