Synthesis of Chromen-2-one, Pyrano[3,4-c]chromene and Pyridino[3,4-c]chromene Derivatives as Potent Antimicrobial Agents

Fouad, Sawsan A.; Hessein, Sadia A.; Abbas, Samir Y.; Farrag, Ayman A.; Ammar, Yousry A.

doi:10.5562/cca3266

Cited by 23 publications

(10 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Another interesting structural core is the chromen ring. Chromen derivatives were also reported to display a wide range of biological activities such as antioxidant [ 36 , 37 ], anti-inflammatory [ 38 , 39 ], antimicrobial [ 40 , 41 , 42 , 43 , 44 , 45 ], anti-HIV [ 46 , 47 ] and others [ 48 , 49 ].…”

Section: Introductionmentioning

confidence: 99%

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

et al. 2021

View full text Add to dashboard Cite

Herein we report the synthesis of some new 1H-1,2,4-triazole functionalized chromenols (3a–3n) via tandem reactions of 1-(alkyl/aryl)-2-(1H-1,2,4-triazole-1-yl) with salicylic aldehydes and the evaluation of their antifungal activity. In silico prediction of biological activity spectra with computer program PASS indicate that the compounds have a high novelty compared to the known antifungal agents. We did not find any close analog among the over 580,000 pharmaceutical agents in the Cortellis Drug Discovery Intelligence database at the similarity cutoff of 70%. The evaluation of antifungal activity in vitro revealed that the highest activity was exhibited by compound 3k, followed by 3n. Their MIC values for different fungi were 22.1–184.2 and 71.3–199.8 µM, respectively. Twelve from fourteen tested compounds were more active than the reference drugs ketoconazole and bifonazole. The most sensitive fungus appeared to be Trichoderma viride, while Aspergillus fumigatus was the most resistant one. It was found that the presence of the 2-(tert-butyl)-2H-chromen-2-ol substituent on the 4th position of the triazole ring is very beneficial for antifungal activity. Molecular docking studies on C. albicans sterol 14α-demethylase (CYP51) and DNA topoisomerase IV were used to predict the mechanism of antifungal activities. According to the docking results, the inhibition of CYP51 is a putative mechanism of antifungal activity of the novel chromenol derivatives. We also showed that most active compounds have a low cytotoxicity, which allows us to consider them promising antifungal agents for the subsequent testing activity in in vivo assays.

show abstract

Section: Introductionmentioning

confidence: 99%

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

et al. 2021

View full text Add to dashboard Cite

show abstract

“…The classical CA inhibitors (CAIs) are the primary sulfonamides, which coordinate the zinc ion with their terminal deprotonated nitrogen atom and have been in clinical use for more than 70 years as diuretics and systemically acting antiglaucoma drugs [ 10 ]. Chromenes have attracted the interest of the scientific community due to their wide range of biological activities, such as antimicrobial [ 11 , 12 ], anticancer [ 13 , 14 ], anti-inflammatory [ 15 , 16 ], and CA inhibitors [ 17 , 18 , 19 , 20 , 21 ], nematicidal [ 22 ], antiallergic [ 23 ] Some sulfonamides also show antimicrobial [ 24 , 25 ], anticancer [ 26 , 27 ], antidiabetic [ 28 ], anti-inflammatory [ 15 , 29 ], and antitubercular [ 30 ] activities. Taking into account all of the above-mentioned, here we report the synthesis of (4-sulfamoylphenyl)-4 H -chromene-2-carboxamide derivatives for its incorporation into one scaffold chromene and sulfonamide moieties.…”

Section: Introductionmentioning

confidence: 99%

Chromene-Containing Aromatic Sulfonamides with Carbonic Anhydrase Inhibitory Properties

Angeli

Карцев²,

Petrou

et al. 2021

IJMS

View full text Add to dashboard Cite

Carbonic anhydrases (CAs, EC 4.2.1.1) catalyze the essential reaction of CO2 hydration in all living organisms, being actively involved in the regulation of a plethora of patho/physiological conditions. A series of chromene-based sulfonamides were synthesized and tested as possible CA inhibitors. Their inhibitory activity was assessed against the cytosolic human isoforms hCA I, hCA II and the transmembrane hCA IX and XII. Several of the investigated derivatives showed interesting inhibition activity towards the tumor associate isoforms hCA IX and hCA XII. Furthermore, computational procedures were used to investigate the binding mode of this class of compounds, within the active site of hCA IX.

show abstract

“…It is especially effective in treating Tinea versicolor. Chromene nucleus are of great interest for their various biological and medicinal activities as well as their therapeutical applications [21][22][23][24][25]. Chromene nucleus is naturally occurring and they are found in commercially available antimicrobial drugs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial evaluation of new 2‐pyridinone and 2‐iminochromene derivatives containing morpholine moiety

Salem

Abbas

Hammami

2021

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

As trail to overcome on the antimicrobial drug-resistance problems, new functionalized 2-pyridinone and 2-iminochromene derivatives bearing morpholine moiety were designed and synthesized. The 2-pyridinone derivatives were obtained through the cyclization of cyanoacetohydrazone of 4-morpholinylacetophenone with 1,3-dicarbonyl compounds, α,β-unsaturated nitriles or 2-(arylidene) malononitriles. The 2-iminochromene derivatives were synthesized through the ring closure of cyanoacetohydrazonewith salicylaldehyde derivatives. The antibacterial and antifungal activities for the synthesized 2-pyridinone and 2-iminochromene derivatives were investigated. Most of the tested compounds showed moderate activity against P. vulgaris. Compounds 4a,b and 5a,b showed moderate activity against G Àve bacteria. All iminochromene derivatives showed moderate activity against C. albicans. Compound 8c was the most active compound.

show abstract

Synthesis of Chromen-2-one, Pyrano[3,4-c]chromene and Pyridino[3,4-c]chromene Derivatives as Potent Antimicrobial Agents

Cited by 23 publications

References 13 publications

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

Chromene-Containing Aromatic Sulfonamides with Carbonic Anhydrase Inhibitory Properties

Synthesis and antimicrobial evaluation of new 2‐pyridinone and 2‐iminochromene derivatives containing morpholine moiety

Contact Info

Product

Resources

About