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Biological Potentials of Hymecromone-Based Derivatives: a Systematic Review

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Biological Potentials of Hymecromone-Based Derivatives: a Systematic Review Sys Rev Pharm 2020;11(11):438-452 BA miulotifacleotedgreviewcjaourlnalpin tohe ftieled ofnphtarmiacyls of Hymecromone-based derivatives: A systematic review *, PYhaassrmeraFceauktrici aMl uCshteamfaistNryooDreapTarhtammenetr, ACbodllueglaezoizf Pharmacy, Mosul University, Nineveh, Iraq. Corresponding Author: [email protected] ABSTRACT Keywords: Coumarin-based derivatives occupy a prominent position in many fields Hymecromone, Antimicrobial, Antioxidant, Anti-inflammatory, related to medicine and industry. This can be attributed to their multilateral Canotritruemsopro, anndtievnircael, cardio protective. biological activities and diversity of chemical features. Among coumarin-based Yasser Fakri Mustafa derivatives, hymecromone (7-hydroxy-4-methylcoumarin) has attracted great : attention from the medicinal chemists. In addition to its ease preparation, this synthetic coumarin, which is known chemically as 7-hydroxy-4-methyl-2H- Pharmaceutical Chemistry Department, College of Pharmacy, Mosul chromen-2-one, possesses a phenolic hydroxyl group that considers as one of University, Nineveh, Iraq. the most derivatiable functional groups. In the literature, many scientific [email protected] papers described the synthesis and biological activities of hymecromone- *Corresponding author: Yasser Fakri Mustafa email-address: based derivatives. This systematic review focused on the synthesis of these derivatives and description of their biological potentials, especially those related to the antimicrobial, antioxidant, antitumor, antiviral, anti-Alzheimer, anti-inflammatory, and cardio-protective effects. The authors proposed that this review may guide the medicinal chemists to select the proper functional groups and their substitutional positions on hymecromone nucleus for the development of new therapeutic agents. INTRODUCTION Coumarins are a respectable family of oxygen-based antioxidant (8), anti-diabetic (9), anti-Alzheimer (10), heterocycles that have widely used in pharmaceutical (1) antitumor (11), antimicrobial (12), antiparasitic (13), and industrial intentions (2). The prototype of this family, anti-inflammatory (14), anticonvulsant (15), coumarin, has historically been isolated via Vogel from antipsychotic (16), analgesic F(1ig7u),raen1ticoagulant (18), and Tonka bean, from which the name of coumarin has driven antiviral (19) activities. (3). Although the coumarins are sharing a benzo-α- Hymecromone, as shown in , is one of the most pyrone skeleton, they differ in the presence of prepared and investigated coumarins. Products with substituents and their positions (4). This variation affords chemical structures based on hymecromone have widely a wide range of properties, some of them related to been synthesized (20), and their biological activities biological activities (5), and the others may be useful for attracted great attention (21). This motivated the work industry (6). Until now, there is a high number of isolated team to report the biological potentials of the natural and coumarins and those synthesized in the laboratory (7). synthetic coumarins with chemical structures based on Most of the investigated natural and synthetic coumarins hymecromone. have exhibited one or more medicinal potentials such as Figure 1: Chemical structure of hymecromone. Antimicrobial potential et al. N1 N2 Nst5arting material, and showed a promising antibacterial Jogi have rNe1poNrt6ed the synthesis and antibacterial activity against the test bacteria. Compounds , , and Facigtiuvritey 2of six novel coumarin-based azo compounds, have been found to possess an antibacterial activity herein termed - . These products, as shown in similar to those of ampicillin and streptomycin (22). , were synthesized by using hymecromone as a 438 Systematic Reviews in Pharmacy Vol 11, Issue 11, Nov-Dec 2020 Sys Rev Pharm 2020;11(7):1-6 439 A multifaceted review journal in the field of pharmacy Figure 2: Coumarin-based azo compounds with an antibacterial activity developed by Jogi et al. et al. Zayane have reporStecdhetmhee sy1nthesis of four novel activity versus the test fungi. The authors have concluded coumarin estersN7uNsi1n0g hymecromone as a starting that the pyrrole and pyrazole rings may play a significant material, as shown in . These compounds, role in this activity (23). herein termed - , exhibited a potent antifungal Scheme 1: The synthetic plan followed by Zayane et al. to synthesize four novel coumarin esters. 439 Systematic Reviews in Pharmacy Vol 11, Issue 11, Nov-Dec 2020 Sys Rev Pharm 2020;11(7):1-6 440 A multifaceted review journal in the field of pharmacy et al. Scheme 2 N11 N17 Hussein have prepared many new derivatives of resulting in the formation of several aromatic- and amino hymecromone, as shown in , by oxidizing the acid-containing Schiff bases, herein termeNd16 - . carbon atom substituted at position 4. The resulted These bases revealed a significant antibacterial activity aldehyde-containing coumarin was condensed versus the test bacteria, among these bases, was the individually with different amine-based compounds best (24). Scheme 2: Synthetic outline of some Schiff base-containing coumarins reported by Hussein et al. et al. Pseudomonas fBluaonrseusrciens have tested hymecromone itself as an chemical structures of the coumarins belong to the antibacterial agent versus 10 isolates of second series have the backbone of 7-methoxy-4- acquired from the soil of Gujarat state in India. methylcoumarin. The antimicrobial activity of the The authors concluded that hymecromone has a potent prepared coumarins has been investigated versus many activiteyt vael.rsus 7 isolates and mild activity versus the bacterial and fungal strains. The authors concluded that others (25). the coumarins of the first series have better antimicrobial SAcmhienme 3 have reported the synthesis of two series of activity versus the test microbes than those of the second thiosemicarbazone-containing coumarins, as shown in series (26). Coumarins of the first series were based in their chemical structures on hymecromone, while the Scheme 3: The synthetic pathway for the thiosemicarbazone-containing coumarins as reported by Amin et al. 440 Systematic Reviews in Pharmacy Vol 11, Issue 11, Nov-Dec 2020 Biological potentials of Hymecromone-based derivatives: A systematic review Antioxidant potential et al. Scheme 4 capability of these new coumarins was tested versus 2,2- Šarkanj N18 hNa2v2e reported the synthesis of two series, as diphenyl-1-picrylhydrazyl (DPPH) and galvinoxyl free shown in , of new five hybrid coumarins, herein radicals. The authors concluded that the hybridized termed - , starting from hymecromone. In the coumarins of the first series showed bettNe2r 0antioxidNa2n1t first series, hymecromone was hybridized with activity than those of the second one. Also, the best thiosemicarbazides, while it was hybridized with 4- activity was contributed to compounds and thiazolidinones in the second series. The chain-breaking (27). Scheme 4: The synthetic outline of the coumarins prepared by Šarkanj et al. et al. N30 N34 Scheme 5 Molnar have prepared 26 new coumariNn2y3l-SNch4i8ff that coumarin derivatives - that possess bases, as shown in , using hymecromone as a dihydroxyphenyl moiety in their chemical structures building block. These products, herein termed - , exhibited the best antioxidant activity among the others were examined for their antioxidant potential against (28). galvinoxyl and DPPH free radicals. The authors concluded Scheme 5: New coumarins prepared by Molnar et al. 441 Systematic Reviews in Pharmacy Vol 11, Issue 11, Nov-Dec 2020 Sys Rev Pharm 2020;11(7):1-6 442 A multifaceted review journal in the field of pharmacy et al. Scheme 6 Al-Amiery have synthesized six new antioxidant activity versus hydrogen peroxide radicals. hymercromone-baNse4d9dNe5ri4vatives, as shown in , The authors concluded that the new derivatives have via a microwave-assisted method. These derivatives, higher trapping activity versus hydrogen peroxide herein termed - , were scanned for their radicals than that of ascorbic acid (29). Scheme 6: The outline for the synthesis of new hycromone-based derivatives as depicted by Al-Amiery et al. et al. N53 N66 Šeršeň and Lácová have investigated the antioxidant Tyagi have synthesized 14 hymecromone-based activity of 19 previously prepared coumarins including derivatives, herein termed - . Their influences on hymecromone versus DPPH, hydroxyl, and superoxide the NADPH-dependent hepatic microsomal lipid free radicals. The authors concluded that the antioxidant peroxidation and the antiradical activity versus DPPH activity of these coumarins versus the test free radicals were investigated. This study aimed to highlight some was related to the number of the substituted phenolic issues conceFringiunrgeth3e structure-activity relationship (SAR) hydroxyl groups and their positions on the benzene of these derivatives that have the chemical structures component of the coumarin skeleton. Accordingly, the shown in . The authors concluded that the derivatives without this type of functional group showed presence of a carboxylic acid group reduces the very poor activity. Furthermore, the highest antioxidant antioxidant activity of the hydroxycoumarins, primarily potential was attributed to the coumarins substituted on due to the hydrogen bonding (31). positions 7 and 8 with phenolic hydroxyl groups (30). 442 Systematic Reviews in Pharmacy Vol 11, Issue 11, Nov-Dec 2020 Sys Rev Pharm 2020;11(7):1-6 443 A multifaceted review
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