Multicomponent synthesis of pyranonicotinonitrile and chromene-3-carbonitrile: Studies on bioactivities and molecular docking

Siziani, Dhaouya; Ziani, Borhane E.C.; Abdi, Yamina; Bensouilah, Nadjia; Boutemeur-Kheddis, Baya; Ziani, Chaïma; Boukkena, Leila; Hamdi, Maâmar; Talhi, Oualid; Bachari, K.; Silva, Artur M. S.

doi:10.1016/j.molstruc.2022.133236

Cited by 8 publications

(3 citation statements)

References 60 publications

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“…Pyrano[3,2-c]chromene derivatives enjoy attention from researchers due to their pharmacological activity (Siziani et al, 2022;Tashrifi et al, 2020), heavy metal chemisensing (Mohajer et al, 2022), semiconductivity (Mal et al, 2022), etc. As part of our studies in this area, the crystal structure of the 1:1 co-crystal of 2-amino-4-(4-methoxyphenyl)-5oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile and acetic acid is now reported.…”

Section: Structure Descriptionmentioning

confidence: 99%

2-Amino-4-(4-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile acetic acid monosolvate

Chakraborty,

Paul,

Anwar

et al. 2023

IUCr Data

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Section: Structure Descriptionmentioning

confidence: 99%

2-Amino-4-(4-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile acetic acid monosolvate

Chakraborty,

Paul,

Anwar

et al. 2023

IUCr Data

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“…Siziani et al reported a microwave‐assisted synthesis of some novel heterocyclic compounds based on DHA‐scaffold and studied their in vitro antioxidant and antimicrobial activities. [ 42 ] Among the tested compounds, 3 showed the best 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) scavenging activity with an IC 50 value of 1.12 mg/L. In contrast, the best antibacterial and antifungal activity was for compound 4 with ZOI of 20 mm and 40.9 mm for Staphylococcus aureus and Pneumocystis jirovecii , respectively.…”

Section: Biological Activities Of Dha‐based Compoundsmentioning

confidence: 99%

Dehydroacetic acid a privileged medicinal scaffold: A concise review

Grover,

Kumar,

Tittal

et al. 2023

Archiv der Pharmazie

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From the last decade, research on dehydroacetic acid (DHA) and its derivatives has increased immensely due to its significant role in various fields, including medicine, cosmetics, food industry, and so on. In the medicinal area, DHA plays an essential role in developing novel action‐based drugs, which are helpful for treating various diseases. Besides its plethora of biological applications, its chelating ability offers the easiest synthetic route for synthesizing more active metal complexes. DHA derivatives along with their metal complexes show a number of biological activities and also exhibit various interactions with multiple biological targets. This article summarizes recent medicinal applications (2000‐onwards) of DHA‐based compounds and their analogs, along with their structure–activity relationship (SAR) analysis. Their interactions with different target enzymes are also discussed. This information derived from SAR analysis would be helpful for medicinal chemists working on the development of drugs based on heterocyclic frameworks, particularly those based on the DHA scaffold.

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“…Pyran backbones have become one of quite important bioactive fragments. New compounds with pyran backbones as potential fungicides are constantly discovered. − …”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Bioactive Evaluation, and Molecular Dynamics Simulation of Novel 4H-Pyrano[3,2-c]pyridine Analogues as Potential Sterol 14α-Demethylase (CYP51) Inhibitors

Bao,

Jiang,

Xie

et al. 2024

J. Med. Chem.

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To discover potential sterol 14α-demethylase (CYP51) inhibitors, thirty-four unreported 4H-pyrano[3,2-c]pyridine derivatives were designed and synthesized. The assay results indicated that most compounds displayed significant fungicidal activity against Sclerotinia sclerotiorum, Colletotrichum lagenarium, Botrytis cinerea, Penicillium digitatum, and Fusarium oxysporum at 16 μg/mL. The half maximal effective concentration (EC50) values of compounds 7a, 7b, and 7f against B. cinerea were 0.326, 0.530, and 0.610, respectively. Namely, they had better antifungal activity than epoxiconazole (EC50 = 0.670 μg/mL). Meanwhile, their half maximal inhibitory concentration (IC50) values against CYP51 were 0.377, 0.611, and 0.748 μg/mL, respectively, representing that they also possessed better inhibitory activities than epoxiconazole (IC50 = 0.802 μg/mL). The fluorescent quenching tests of proteins showed that 7a and 7b had similar quenching patterns to epoxiconazole. The molecular dynamics simulations indicated that the binding free energy of 7a and epoxiconazole to CYP51 was −35.4 and −27.6 kcal/mol, respectively.

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Multicomponent synthesis of pyranonicotinonitrile and chromene-3-carbonitrile: Studies on bioactivities and molecular docking

Cited by 8 publications

References 60 publications

2-Amino-4-(4-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile acetic acid monosolvate

2-Amino-4-(4-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile acetic acid monosolvate

Dehydroacetic acid a privileged medicinal scaffold: A concise review

Design, Synthesis, Bioactive Evaluation, and Molecular Dynamics Simulation of Novel 4H-Pyrano[3,2-c]pyridine Analogues as Potential Sterol 14α-Demethylase (CYP51) Inhibitors

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