Propargylated monocarbonyl curcumin analogues: synthesis, bioevaluation and molecular docking study
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Medicinal Chemistry Research https://doi.org/10.1007/s00044-020-02611-7
ORIGINAL RESEARCH
Propargylated monocarbonyl curcumin analogues: synthesis, bioevaluation and molecular docking study Amol A. Nagargoje1,2 Satish V. Akolkar1 Dnyaneshwar D. Subhedar1 Mubarak H. Shaikh1,3 Jaiprakash N. Sangshetti4 Vijay M. Khedkar5 Bapurao B. Shingate 1 ●
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Received: 21 April 2020 / Accepted: 31 July 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract In the current experimental study, we have synthesised new monocarbonyl curcumin analogues bearing propargyl ether moiety in their structure and evaluated for in vitro antifungal and radical scavenging activity. The antifungal activity was carried out against five human pathogenic fungal strains such as Candida albicans, Fusarium oxysporum, Aspergillus flavus, Aspergillus niger and Cryptococcus neoformans. Most of the curcumin analogues displayed excellent to moderate fungicidal activity when compared with standard drug Miconazole. Also, synthesised analogues exhibited potential radical scavenging activity as compared with standard antioxidant Butylated hydroxyl toluene (BHT). Based on biological data, structureactivity relationship (SAR) were also discussed. Furthermore, in silico computational study was carried out to know binding interactions of synthesised analogues in the active sites of enzyme sterol 14α-demethylase (CYP51). Graphical Abstract
Keywords Monocarbonyl curcumin analogues Antifungal activity Antioxidant activity SAR Molecular docking study ●
Introduction Curcumin is the principal curcuminoid of the turmeric plant of the family Zingiberaceae. It has been used to treat many health conditions in India and other parts of Asia since
Supplementary information The online version of this article (https:// doi.org/10.1007/s00044-020-02611-7) contains supplementary material, which is available to authorized users. * Bapurao B. Shingate [email protected] 1
Department of Chemistry, Dr Babasaheb Ambedkar Marathwada University, Aurangabad 431004, India
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Department of Chemistry, Khopoli Municipal Council College, Khopoli 410203, India
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ancient times. According to recent literature, curcumin is the multi-target pleiotropic agent displaying a wide spectrum of biological activities (Goel et al. 2008; Marchiani et al. 2013; Bairwa et al. 2014; Shetty et al. 2015). Curcumin has been evaluated in clinical trials for the treatment of various diseases like cancer, liver diseases, infectious diseases and rheumatoid arthritis (Hatcher et al. 2008; Bairwa et al. 2014). However, clinical use of the curcumin is restricted due to poor bioavailability, poor 3
Department of Chemistry, Radhabai Kale Mahila Mahavidyalaya, Ahmednagar 414001, India
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Department of Pharmaceutical Chemistry, Y. B. Chavan College of Pharmacy, Rafiq Zakaria Campus, Aurangabad 431001, India
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Department of Pharmaceutical Chemistry, School of Pharmacy, Vishwakarma University, Pune 411048, India
Medicinal Chemistry R
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