Heteroannelation of Cyclic Ketones: Synthesis, Characterization and Antitumor Evaluation of Some Condensed Azine Derivatives

Soylem, Essam A.; Assy, M. G.; Morsi, Ghania M

doi:10.17344/acsi.2016.2297

Cited by 8 publications

(3 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Condensation reaction of compound 3 with some 1,3‐binucleophiles was investigated in different catalyzed reaction media. Reaction of thiourea with chalcone 3 can be either acid or base catalyzed . Treatment of an ethanolic solution of compund 3 with thiourea in the presence of catalytic amount of pipridine afforded pyrimidinethione derivative 6 in 85% yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of some Functionalized Heterocycles Derived from Novel Quinolinyl Chalcone

Hassan

Farouk

2017

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

The reaction of 3‐acetyl‐4‐hydroxyl‐1‐methylquinolin‐2(1H)‐one (1) with 10‐oxo‐4,6,7,8,9,10‐hexahydropyrazolo[1,5‐a][1]benzothieno[2,3‐d]pyrimidine‐3‐carbaldehyde (2) afforded the novel enone system 3. The latter compound was reacted with some 1,2‐binucleophilic reagents to give pyrazoline derivative 4 and isoxazoline derivative 5. Treatment of chalcone 3 with 1,3‐binucleophilic reagents afforded pyrimidine and thiazine derivatives 6–8. Moreover, reaction of compound 3 with active methylene reagents furnished pyridine, pyran, and cyclohexanone derivatives 9–12. Cyclization of compound 12 by using hydrazine hydrate yielded indazol‐3‐one derivative 13. On the other hand, the cyclocondensation of the enone 3 with 1,4‐dinucleophilic reagents yielded diazepine derivative 14 and triazolothiadiazepine derivative 15.The characterization of the newly synthesized heterocyles were confirmed on the basis of their elemental analysis and spectral data (IR, NMR, and MS). These compounds were also screened for their antibacterial activities.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of some Functionalized Heterocycles Derived from Novel Quinolinyl Chalcone

Hassan

Farouk

2017

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…Many of such compounds have shown relevant medicinal properties and have inspired the synthesis and investigation of the biological activities of a variety of compounds presenting a pyran ring as a structural feature, including 2-amine-4H-pyran-3-carbonitriles. A series of works have shown that 2-amine-4H-pyran-3-carbonitriles exhibit a broad spectrum of biological effects of pharmaceutical interest, such as anticancer, anti-microbial, antihemolytic, and antioxidant activities [1][2][3][4][5][6][7][8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Daylight LED promotes photochemical ring contraction of 2-amine-4H-pyran-3-carbonitriles with consequent loss of their antifungal activity

Silva

Sousa

Ferreira

et al. 2021

Photochem Photobiol Sci

View full text Add to dashboard Cite

The initial objective of our work was to synthesize a series of 2-amino-4H-pyran-3-carbonitriles to be tested for their antifungal activities against economically relevant phytopathogenic fungi. Fourteen compounds were prepared in up to 94% yield and shown percentages of Botrytis cinerea inhibition above 70%. Despite the promising biological results, we observed that stock solutions prepared for biological tests showed color changing when kept for a few days on the laboratory bench, under room conditions, illuminated by common LED daylight tubes (4500-6000 k). This prompted us to investigate the possible photo-induced degradation of our compounds. FT-IR ATR experiments evidenced variations in the expected bands for functional of -amino-4H-pyran-3-carbonitriles stored under LED daylight. Following, HPLC-UV analysis showed reductions in the intensity of chromatographic peaks of 2-amino-4H-pyran-3-carbonitriles, and but not for solutions kept in the dark. A solution of (E)-2-amino-8-(4-nitrobenzylidene)-4-(4-nitrophenyl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile underwent 84.4% of conversion after 72 h of exposure to continuous LED daylight in a BOD chamber, and the reaction product was isolated in 36% yield and characterized as (E)-7-cyano-5-(4-nitrobenzylidene)-8-(4-nitrophenyl)bicyclo[4.2.0] oct-1(6)-ene-7-carboxamide (7*). Despite freshly prepared solutions of 2-amino-4H-pyran-3-carbonitriles produced antifungal activities, these solutions lost biological activity when left on the bench for a week. Besides, compound 7* formed from photo-induced degradation of 7 also showed no antifungal activity. With this, we hope to bring two contributions:(1) production of cyclobutenes through photochemical reactions of 2-amino-4H-pyran-3-carbonitriles can be carried out through exposure to simple white LED daylight; (2) biological applications of such 2-amino-4H-pyran-3-carbonitriles may be impaired by their poor photostability.

show abstract

“…[31] Changes in their structure have offered a high degree of diversity that has proven useful for the development of new therapeutic agents having improved potency and lowered toxicity. Based on the above considerations and in continuation of our research on biologically potent heterocyclic derivatives, [32][33][34][35][36][37][38] herein, we report the synthesis, structural elucidation and antidiabetic activity of some new azoles and azines prepared from commercially available reagents.…”

Section: Introductionmentioning

confidence: 99%

Michael Cyclization of Polarized Systems: Synthesis and in vitro Anti-Diabetic Evaluation of Some Novel Pyrimidine, Pyridine, Pyrazole and Pyrazolo[3,4-b ]pyridine Derivatives

2017

View full text Add to dashboard Cite

Various interesting heterocycle skeletons were synthesized via Michael type addition reaction with 1,2; 1,3-bidentate nitrogen and carbon nucleophiles. Cycloaddition of different α,β-unsaturated systems afforded bromopyrimidinone 3/5, bromothiazine 4 and bromopyrazole 6a/6b pyrazole-1-carboxylate 8, pyridinylmethanone 9, nicotinonitrile 10, pyrazolopyridine 11a/11b, pyran-3-carbonitrile 12/13, chromenopyridine 14 and N-butyrylpyrazolyl-1-butanone 15 derivatives. The structures of the synthesized compounds were elucidated based on IR, NMR and mass spectral analyses. Group of the newly synthesized compounds were screened for their anti-diabetic activities, whereas compounds 8 and 11b exhibited promising anti-diabetic activities at micro molar concentration against α-glucosidase inhibitor with IC50 values ranging between 13.80-500 μM. On the other hand compound 10 showed a week effect as compared to the standard anti-diabetic agent.

show abstract

Heteroannelation of Cyclic Ketones: Synthesis, Characterization and Antitumor Evaluation of Some Condensed Azine Derivatives

Cited by 8 publications

References 32 publications

Synthesis and Antimicrobial Evaluation of some Functionalized Heterocycles Derived from Novel Quinolinyl Chalcone

Synthesis and Antimicrobial Evaluation of some Functionalized Heterocycles Derived from Novel Quinolinyl Chalcone

Daylight LED promotes photochemical ring contraction of 2-amine-4H-pyran-3-carbonitriles with consequent loss of their antifungal activity

Michael Cyclization of Polarized Systems: Synthesis and in vitro Anti-Diabetic Evaluation of Some Novel Pyrimidine, Pyridine, Pyrazole and Pyrazolo[3,4-b ]pyridine Derivatives

Contact Info

Product

Resources

About