A one pot, two-step synthesis of 5-arylpyrrolo[2,3- d ]pyrimidines and screening of their preliminary antibacterial properties

Saikia, Lakhinath; Roudragouda, P.; Thakur, Ashim Jyoti

doi:10.1016/j.bmcl.2015.12.047

Cited by 12 publications

(6 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Yield 2-(7-(4-Phenoxyphenyl)-5-(thiophen-2-yl)-2,3-dihydro-5Hthiazolo[3,2-a] pyrimidin-6-yl)acetyl azide (11).…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Some Novel Thiazolo[3,2‐a]pyrimidine and Pyrimido[2,1‐b][1,3]thiazine Derivatives and their Antimicrobial Evaluation

Behalo

2018

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

A 2‐(2‐Mercapto‐4‐(4‐phenoxyphenyl)‐6‐(thiophen‐2‐yl)‐1,6‐dihydropyrimidin‐5‐yl) acetic acid was used as a reactive key precursor to design various pyrimidine derivatives such as thiazolo[3,2‐a]pyrimidines and pyrimido[2,1‐b][1,3]thiazines. The chemical structures of the newly synthesized products were confirmed by their elemental analyses and spectral data (IR, 1H NMR, 13C NMR, and mass spectra). The antibacterial and antifungal activities of some of the synthesized products were also evaluated, and it was found that compounds 3, 5, 9, and 11 exhibited potent activity against tested microorganisms in comparison with standard drugs.

show abstract

“…Yield 2-(7-(4-Phenoxyphenyl)-5-(thiophen-2-yl)-2,3-dihydro-5Hthiazolo[3,2-a] pyrimidin-6-yl)acetyl azide (11).…”

Section: Methodsmentioning

confidence: 99%

“…They exhibited anticancer [1][2][3][4][5], antioxidant [6][7][8], antifungal [9,10], and antibacterial activities [11][12][13][14]. They exhibited anticancer [1][2][3][4][5], antioxidant [6][7][8], antifungal [9,10], and antibacterial activities [11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some Novel Thiazolo[3,2‐a]pyrimidine and Pyrimido[2,1‐b][1,3]thiazine Derivatives and their Antimicrobial Evaluation

Behalo

2018

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…Screening of the amount of catalyst showed that 10 mol% of L-proline was sufficient to push the reaction forward successfully (entries 2, 9 and 10). Next, we repeated the model reaction in various solvents (Table 1, entries [11][12][13][14][15][16][17][18], and we found that reactions in protic solvents gave higher yields than did those in nonprotic solvents and that the reaction in water gave the highest yield (entry 2). The same model reaction was then carried out at temperatures of 60, 80, and 100 °C for two hours.…”

Section: Syn Lettmentioning

confidence: 99%

“…17 Recently, Thakur and co-workers reported the synthesis of 5arylpyrrolo[2,3-d]pyrimidines in a one-pot two-step manner from an aminopyrimidine and nitrostyrenes. 18 Despite these advances, most of these approaches suffer from one or more drawbacks such as the need for a transition-metal catalyst, the use of a strong base or acid, the use of hazardous or expensive reagents, multistep sequences, or the need…”

mentioning

confidence: 99%

l-Proline-Catalyzed Cyclization of 6-Aminopyrimidine-4(3H)-ones with Nitroolefins: Synthesis of Polysubstituted 5-Arylpyrrolo[2,3-d]pyrimidin-4-ones

Zhang

2017

Synlett

View full text Add to dashboard Cite

A simple and efficient one-pot procedure for the synthesis of new pyrrolo[2,3-d]pyrimidine derivatives has been established through an l-proline-catalyzed cyclization of 6-aminopyrimidine-4(3H)-one with nitroolefins in water. The reaction at 80 °C in water gives various highly substituted pyrrolo[2,3-d]pyrimidines in good to excellent yields. This procedure has the advantages of environmental friendliness, good yields, and convenient operation.

show abstract

“…Pyrimidine is an important class of heterocyclic compounds with wide applications in medicine and pesticides research due to their remarkable biological and pharmacological properties, such as antibacterial [23][24][25], antiviral [26,27], insecticide [28,29], anticancer [30,31], antimalaria [32], herbicida [33] and other biological activities [34]. In 2019, Zhang reported a series of derivatives containing pyrimidine ethers were synthesized, which have a good control effect on cucumber downy mildew [35].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Antibacterial Activity of Novel Pyrimidine‐Containing 4H‐Chromen‐4‐One Derivatives**

Chen

Tang

et al. 2021

Chemistry & Biodiversity

View full text Add to dashboard Cite

A series of pyrimidine-containing 4H-chromen-4-one derivatives were designed and synthesized by combining bioactive substructures. All compounds were characterized using 1 H NMR, 13 C NMR, 19 F NMR and HRMS. Preliminary biological activity results showed that most of title compounds displayed signi cant inhibitory activity against Xanthomonas axonopodis pv. Citri (Xac), Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (Rs). In particular, compound 4c demonstrated a good inhibitory effect against Xac and Xoo, with half-maximal effective concentration(EC 50 ) values of 15.5 and 14.9 μg/mL respectively, and that of compound 4h showed the best antibacterial activity against Rs with an EC 50 value of 14.7 μg/mL, These results were better than both bismerthiazol (BT, 51.7, 70.1 and 52.7 μg/mL, respectively) and thiodiazole copper (TC, 77.9, 95.8 and 72.1 μg/mL respectively). In vivo antibacterial activity results indicated that compound 4c displayed better curative(42.4%) and protective (49.2%) activities for reducing rice bacterial leaf blight than both BT (35.2, 39.1%) and TC (30.8, 27.3%). The mechanism of compound 4c against Xoo was analysed through scanning electron microscopy (SEM). Results showed that the compound destroied the bacterial cell membrane structure. These results indicated that pyrimidine-containing 4H-chromen-4-one derivatives are valuable in the research of new agrochemicals.

show abstract

A one pot, two-step synthesis of 5-arylpyrrolo[2,3- d ]pyrimidines and screening of their preliminary antibacterial properties

Cited by 12 publications

References 38 publications

Synthesis of Some Novel Thiazolo[3,2‐a]pyrimidine and Pyrimido[2,1‐b][1,3]thiazine Derivatives and their Antimicrobial Evaluation

Synthesis of Some Novel Thiazolo[3,2‐a]pyrimidine and Pyrimido[2,1‐b][1,3]thiazine Derivatives and their Antimicrobial Evaluation

l-Proline-Catalyzed Cyclization of 6-Aminopyrimidine-4(3H)-ones with Nitroolefins: Synthesis of Polysubstituted 5-Arylpyrrolo[2,3-d]pyrimidin-4-ones

Design, Synthesis and Antibacterial Activity of Novel Pyrimidine‐Containing 4H‐Chromen‐4‐One Derivatives**

Contact Info

Product

Resources

About