Design, synthesis, in vitro evaluation of tetrahydropyrimidine–isatin hybrids as potential antibacterial, antifungal and anti-tubercular agents

Akhaja, Tarunkumar Nanjibhai; Raval, Jignesh P.

doi:10.1016/j.cclet.2012.01.040

Cited by 58 publications

(13 citation statements)

References 20 publications

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“…and appropriate diaminoalkanes 2a-e (2 eq.) in absolute ethanol are refluxed for [16][17][18][19][20][21][22] 2c-e 4a-c …”

Section: Resultsmentioning

confidence: 99%

“…Recently, much attention has been paid to derivatives of pyrimidine, including their hydrogenation products. This class of compounds displays wide ranges of biological and pharmacological properties such as anti-inflammatory [14], analgesic [15], antitumor [16], antidepressant [17], antibacterial, antifungal, and antitubercular effects [18][19][20].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of New Imidazolidine and Tetrahydropyrimidine Derivatives

Beyzaei

Aryan

Keshtegar

2014

Advances in Chemistry

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Synthesis of new imidazolidine and tetrahydropyrimidine derivatives 3a, b and 4a-c as cyclic 1,3-diamines under two reaction conditions (A and B) is described. Under reaction conditions-A, a suspension of (E)-2-cyano-2-(oxazolidin-2-ylidene)ethanethioamide 1 (1 eq.) and diaminoalkanes 2a-e (2 eq.) in absolute ethanol is heated under reflux for 16-22 h to afford 3a, b and 4a-c. Alternatively, under reaction conditions-B, a solution of thioamide 1 (1 eq.) in diaminoalkanes 2a-e (3 eq.) is stirred under solvent-free conditions at room temperature for 3 days to give desired products. Reaction conditions-A for having higher yields, shorter reaction times, and required less diamines is more effective than reaction conditions-B. Oxazolidine ring opening is observed by reacting compound 1 with all of the diamines 2a-e, but the thioamide group only reacts with nonbulky diamines 2a, b. The chemical structures of novel compounds were confirmed by 1 H NMR, 13 C NMR, elemental analysis, and FT-IR spectrometry.

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“…and appropriate diaminoalkanes 2a-e (2 eq.) in absolute ethanol are refluxed for [16][17][18][19][20][21][22] 2c-e 4a-c …”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of New Imidazolidine and Tetrahydropyrimidine Derivatives

Beyzaei

Aryan

Keshtegar

2014

Advances in Chemistry

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“…In recent years, growing attention has been paid to the synthesis of N-heterocycles due to diverse biological and pharmaceutical applications [1][2][3]. In this respect, the presence of pyrrol-2-ones (5-lactams or γ-lactams) in pharmaceuticals and natural products has continued to stimulate a great deal of interest in the development of new methodologies for their synthesis [4][5][6].…”

Section: Introductionmentioning

confidence: 99%

Trifluoroacetic Acid Catalyzed One-Pot Four-Component Domino Reaction for the Synthesis of Substituted Dihydro 2-Oxypyrroles

Lashkari

Maghsoodlou

Karima

et al. 2018

J. Chil. Chem. Soc.

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Trifluoroacetic acid was applied as an efficient catalyst for the one-pot four-component synthesis of N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates via the domino reaction of amines, formaldehyde and dialkyl acetylenedicarboxylates at ambient temperature in methanol. This methodology includes number of advantages such as: short reaction time, clean work-up, use of inexpensive catalyst, high yields and clean work-up. The work-up of this reaction involves only a filtration and a simple washing step with MeOH, and there is no need for column chromatography.

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“…It have wide range of biological activities 1,2 . Such as, anti-leishmanial 3 , anti-tuberculosis 4 , analgesic, anti-inflammatory [5][6][7] , antimicrobial 8 , antifungal 9 anti-emetic 10 and antitumor properties 11 . The nonlinear optical active molecules with p _ conjugated backbones, electron donating, electron withdrawing moieties are important class of materials in modern technologies, such as telecommunication and optoelectronics 12 ,multiphoton microscopy 13 , Organic light-emitting diodes (OLED) 14 , organic field effect transistors (OFET) 15 and to achieve hierarchical self-assembly in "all-organic" photovoltaic devices 16 Here, we report synthesis of a new nonlinear molecule ethyl ethyl 4-(3-(2,3-dihydrobenzofuran-5-carboxamido)phenyl)-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-5-carboxylate(DFOC).…”

Section: Introductionmentioning

confidence: 99%

Spectral Characterization and Vibrational Assignments of Ethyl 4-(3-(2,3-Dihydrobenzofuran-5-Carboxamido)Phenyl) -6-Methyl-2-Oxo-1,2,3,4-Tetrahydropyrimidine-5- Carboxylate by Ab Initio Density Functional Method

Adaikalaraj¹,

Manivarman²,

Bose³

2017

Orient. J. Chem

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In the present investigation, then novel compound ethyl 4-(3-(2,3-dihydrobenzofuran5carboxamido)phenyl-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-5-carboxylate(DFOC) were synthesized .The synthesized compound have been characterized by using UV-visible, FT-IR, FT-Raman, 1 H-NMR and 13 CNMR spectral studies. The harmonic vibrational frequencies, optimized molecular geometry have been carried out with the help of B3LYP density functional theory method. The stability of the molecule was analyzed by means natural bond orbital analysis and delocalized p-p* interactions. Moreover, the frontier molecular orbital analysis, molecular electrostatic potential surface and thermodynamic properties of DFOC were investigated using DFT calculations.keywords: DFOC, NBO, NLO HOMO-LUMO and DFT.

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Design, synthesis, in vitro evaluation of tetrahydropyrimidine–isatin hybrids as potential antibacterial, antifungal and anti-tubercular agents

Cited by 58 publications

References 20 publications

Synthesis of New Imidazolidine and Tetrahydropyrimidine Derivatives

Synthesis of New Imidazolidine and Tetrahydropyrimidine Derivatives

Trifluoroacetic Acid Catalyzed One-Pot Four-Component Domino Reaction for the Synthesis of Substituted Dihydro 2-Oxypyrroles

Spectral Characterization and Vibrational Assignments of Ethyl 4-(3-(2,3-Dihydrobenzofuran-5-Carboxamido)Phenyl) -6-Methyl-2-Oxo-1,2,3,4-Tetrahydropyrimidine-5- Carboxylate by Ab Initio Density Functional Method

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