EFFECTIVE MICROWAVE SYNTHESIS OF BIOACTIVE THIENO[2,3-d]PYRTMIDINES

Khatri, Taslimahemad T.; Shah, V. H.

doi:10.4067/s0717-97072017000100010

Cited by 10 publications

(8 citation statements)

References 17 publications

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“…The 2-aminothiophene derivatives 3a and 3b were easily accessible via the Gewald's reaction between N-aryl-3-oxobutanamide derivatives 1, elemental sulfur, and malononitrile (2) according to the method prescribed in literature [37] (Scheme 1). The structures of compounds 3a and 3b were secured by their compatible IR, 1 H NMR, and 13 C NMR analyses.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of some new thiophene-based compounds and evaluations of their cytotoxic activities

Mehdhar¹,

Alzahrani²,

Abdel‐Galil³

et al. 2022

Bull. Chem. Soc. Eth.

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ABSTRACT. A series of new thiophene derivatives was prepared through nucleophilic substitution reactions of the precursor N-(4-substituted-phenyl)-5-(2-chloroacetamido)-4-cyano-3-methylthiophene-2-‎carboxamides 4a and 4b with different sulfur and/or nitrogen nucleophilic reagents (namely; mercaptoacetic acid, 2-mercaptobenzothiazole, 5-(phenylamino)-1,3,4-thiadiazole-2-thiol, 2-mercapto-4,6-dimethylnicotinonitrile, 3-arylazo-4-mercapto-4-(phenylamino)-but-3-en-one derivatives, ammonium thiocyanate, piperidine and/or morpholine). The structures of the prepared thiophene compounds were characterized by spectral analysis. Their cytotoxicity was evaluated against two human cancer cell lines (HepG2 and MCF-7) and indicated promising results. Pretreatment of HepG2 cells with the tested compound 4b sensitized the cells to the cytotoxicity of sorafenib, leading to a significant decrease in the IC50 from 3.9 to 0.5 µM. KEY WORDS: N-(Thienyl)-2-chloroacetamide, Bis-thiophene, Thieno[2,3-d]pyrimidine, Ammonium thiocyanate, Cytotoxicity Bull. Chem. Soc. Ethiop. 2023, 37(2), 373-389. DOI: https://dx.doi.org/10.4314/bcse.v37i2.10

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Section: Resultsmentioning

confidence: 99%

Synthesis of some new thiophene-based compounds and evaluations of their cytotoxic activities

Mehdhar¹,

Alzahrani²,

Abdel‐Galil³

et al. 2022

Bull. Chem. Soc. Eth.

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“…The compound (Fig. 18) was found to be exhibited significant antimicrobial activity [27]. Anti-microbial activity of the synthesized compounds was tested against seven microbial strains (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Shigella sp, Candida albicans, Aspergillus niger, Alternaria alternate) using the agar well diffusion method.…”

Section: Jadhav and Baravkarmentioning

confidence: 99%

Recent Advances in Antimicrobial Activity of Pyrimidines: A Review

JADHAV¹,

BARAVKAR²

2021

Asian J Pharm Clin Res

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Over the past era, development of small heterocycles as potential therapeutics has been a zone of major interest. A large number of pyrimidine derivatives are of considerable biological and chemical interest. Pyrimidine derivatives have shown numerous biological activities such as antimicrobial, antitubercular, anticancer, anticonvulsant, antidiabetic, antiviral, and anti-inflammatory. Being a heterocyclic compound, Pyrimidine finds its use for designing synthesis of newer biologically active structures, as its aromaticity makes it relatively stable, also reactive sites which allow for functionalization. Several amino derivatives of nitrogen-containing heterocycles such as pyrimidine, pyridine possess an antimicrobial activity. In this review, recent advancements in the antimicrobial activity of pyrimidine derivatives have been reported.

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“…All these factors motivate the research and development of the novel classes of small molecules suitable as antimicrobials. According to the results of the recent studies of thieno [2,3-d]pyrimidine derivatives, which showed the antimicrobial activity against both Gram-negative and Gram-positive bacteria [2][3][4][5], the molecules bearing this heterocyclic fragment are good candidates for the promising novel class of antibacterials.…”

Section: Introductionmentioning

confidence: 99%

“…Gram-negative and Gram-positive bacteria [2][3][4][5], the molecules bearing this heterocyclic fragment are good candidates for the promising novel class of antibacterials.…”

Section: Introductionmentioning

confidence: 99%

“…Other reports have shown some examples of successful modifications of other positions of the thieno [2,3-d]pyrimidine system as well as fusion of this ring system with different heterocycles (which led to the effective antimicrobials). The examples tetrahydrobenzo [4,5]thieno [2,3-d]pyrimidine derivatives [12,13], 5-furyl [14] and 2-thienyl theinopyrimidines fused with triazole [15] or pyrimidine cycles can also be mentioned [16].…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis and In Vitro Antimicrobial Activity of 6-(1H-Benzimidazol-2-yl)-3,5-dimethyl-4-oxo-2-thio-3,4-dihydrothieno[2,3-d]pyrimidines

et al. 2021

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The rapid development in bacterial resistance to many groups of known antibiotics forces the researchers to discover antibacterial drug candidates with previously unknown mechanisms of action, one of the most relevant being the inhibition of tRNA (Guanine37-N1)-methyltransferase (TrmD). The discovery of selective TrmD inhibitors in the series of carboxamide derivatives of thienopyrimidines became a background for further modification of the similar structures aimed at the development of promising antibacterial agents. As part of this research, we carried out the construction of heterocyclic hybrids bearing the moieties of thieno[2,3-d]pyrimidine and benzimidazole starting from 3,5-dimethyl-4-oxo-2-thioxo-1H-thieno[2,3-d]pyrimidine-6-carboxylic acid, which was used as the pivotal intermediate. The hybrid molecule of 6-(1H-benzimidazol-2-yl)-3,5-dimethyl-2-thioxo-1H-thieno[2,3-d]pyrimidin-4-one prepared via condensation of the carboxylic acid with ortho-phenylenediamine was further alkylated with aryl/hetaryl chloroacetamides and benzyl chloride to produce the series of S-alkyl derivatives. The results of molecular docking studies for the obtained series of S-alkyl benzimidazole-thienopyrimidines showed their high affinity to the TrmD isolated from the P. aeruginosa. The results of antimicrobial activity screening revealed the antimicrobial properties for all of the studied molecules against both Gram-positive and Gram-negative bacteria and the Candida albicans fungal strain. The highest antimicrobial activity was determined for 2-{[6-(1H-benzimidazol-2-yl)-3,5-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl]thio}-N-(4-isopropylphenyl)acetamide, which also had the highest affinity to the TrmD inhibitor’s binding site according to the docking studies results.

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EFFECTIVE MICROWAVE SYNTHESIS OF BIOACTIVE THIENO[2,3-d]PYRTMIDINES

Cited by 10 publications

References 17 publications

Synthesis of some new thiophene-based compounds and evaluations of their cytotoxic activities

Synthesis of some new thiophene-based compounds and evaluations of their cytotoxic activities

Recent Advances in Antimicrobial Activity of Pyrimidines: A Review

Design, Synthesis and In Vitro Antimicrobial Activity of 6-(1H-Benzimidazol-2-yl)-3,5-dimethyl-4-oxo-2-thio-3,4-dihydrothieno[2,3-d]pyrimidines

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