An efficient, catalyst-free, one-pot synthesis of 4H-chromene derivatives and investigating their biological activities and mode of interactions using molecular docking studies

Basit Öğe Kaydı
dc.contributor.authorDinparast, Leila
dc.contributor.authorHemmati, Salar
dc.contributor.authorAlizadeh, Ali Akbar
dc.contributor.authorZengin, Gökhan
dc.contributor.authorKafil, Hossein Samadi
dc.contributor.authorBahadori, Mir Babak
dc.contributor.authorDastmalchi, Siavoush
dc.date.accessioned2020-03-26T20:20:07Z
dc.date.available2020-03-26T20:20:07Z
dc.date.issued2020
dc.departmentSelçuk Üniversitesi, Fen Fakültesi, Biyoloji Bölümüen_US
dc.description.abstractIn the present study, the design and development of an efficient and green method for the synthesis of dialkyl 4-hydroxy-4H-chromene-2,3-dicarboxylate derivatives together with their biological evaluation are reported. A series of 4H-chromenes were synthesized in the presence of 1-hexyl-3-methylimidazolium bromide ([HMIM]Br) as an environmentally friendly media, without using any organic and toxic solvent and catalyst. The reaction was rapid and was conducted at room temperature with high-to-excellent yields. The antiproliferative potential of the synthesized compounds was evaluated against human lung (A549), breast (MCF-7), and colon (HT-29) cancerous cell lines by adopting MTT method. The tested chromenes showed cytotoxicity in the range of 8.8-82.3% against A549 cells at 200 mu g/mL. Also, chromene derivatives were assessed for tyrosinase and alpha-glucosidase inhibitory activities. Based on IC50 values (2.99-4.39 mM), all chromenes exhibited significant alpha-glucosidase inhibition compared with acarbose (IC50 = 7.90 mM). Furthermore, the ability of the studied compounds to inhibit tyrosinase was evaluated and found to be moderate (IC50 = 3.50-12.20 mM). In silico studies were performed to explore the binding modes of the chromenes at the binding site of alpha-glucosidase and tyrosinase. Molecular docking results revealed the importance of hydrogen bonding, hydrophobic, pi-pi stacking, pi-cation, and metal interactions between the target enzymes and the synthesized compounds. Collectively, the results obtained in the current work indicated that the studied chromenes may be regarded as lead compounds for designing new chemicals potentially effective in conditions such as skin disorders and diabetes mellitus. (C) 2019 Elsevier B.V. All rights reserved.en_US
dc.description.sponsorshipMinistry of Health and Medical Education; Biotechnology Research Center at Tabriz University of Medical Sciencesen_US
dc.description.sponsorshipThe authors would like to acknowledge the Ministry of Health and Medical Education, and also, Biotechnology Research Center at Tabriz University of Medical Sciences for the financial support.en_US
dc.identifier.citationDinparast, L., Hemmati, S., Alizadeh, A. A., Zengin, G., Kafil, H. S., Bahadori, M. B., Dastmalchi, S. (2020). An Efficient, Catalyst-Free, One-Pot Synthesis of 4H-Chromene Derivatives and Investigating Their Biological Activities and Mode of Interactions Using Molecular Docking Studies. Journal of Molecular Structure, 1203, 1-10.
dc.identifier.doi10.1016/j.molstruc.2019.127426en_US
dc.identifier.endpage10
dc.identifier.issn0022-2860en_US
dc.identifier.issn1872-8014en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage1
dc.identifier.urihttps://dx.doi.org/10.1016/j.molstruc.2019.127426
dc.identifier.urihttps://hdl.handle.net/20.500.12395/38505
dc.identifier.volume1203en_US
dc.identifier.wosWOS:000504448700055en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.institutionauthorZengin, Gökhan
dc.language.isoenen_US
dc.publisherELSEVIERen_US
dc.relation.ispartofJOURNAL OF MOLECULAR STRUCTUREen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.selcuk20240510_oaigen_US
dc.subjectChromeneen_US
dc.subjectIonic liquiden_US
dc.subjectGreen chemistryen_US
dc.subjectCytotoxicityen_US
dc.subjectMolecular dockingen_US
dc.subjectEnzyme inhibitionen_US
dc.titleAn efficient, catalyst-free, one-pot synthesis of 4H-chromene derivatives and investigating their biological activities and mode of interactions using molecular docking studiesen_US
dc.typeArticleen_US

Dosyalar

Orijinal paket
Listeleniyor 1 - 1 / 1
Küçük Resim
İsim:
Leila Dinparast.pdf
Boyut:
1.75 MB
Biçim:
Adobe Portable Document Format
Açıklama:
Full Text Access
İndir

Koleksiyon

WoS İndeksli Yayınlar Koleksiyonu
Biyoloji/Makale Koleksiyonu
Scopus İndeksli Yayınlar Koleksiyonu