Int J Curr Pharm Res, Vol 13, Issue 4, 1-5Reviewl Article


MEDICINAL SIGNIFICANCE OF NOVEL COUMARINS: A REVIEW

SHARANABASAPPA B. PATIL*, GOURAMMA P., SHIVAKUMAR S. JALDE

*Department of Chemistry, Ramaiah Institute of Technology, Bangalore 560054, Department of Chemistry, S B College of Science, Kalaburagi 585102, Karnataka, India, Department of Medicinal Chemistry, Jungwon University Goesan 28024, Republic of Korea
Email: sbp7910@gmail.com

Received: 02 May 2021, Revised and Accepted: 24 Jun 2021

ABSTRACT

Coumarone is a chemical compound found in many plants. Coumarone having diverse pharmacological properties popularly known as an antimicrobial, Analgesic anti-inflammatory, Anticancer, Antiviral, anticoagulant, antihypertensive, anticonvulsant, antihyperglycemic, antioxidant, activities. Coumarone was also observed in all green color veggies, and also in fruits and their seeds, dark coffee, tea leafs, further it is used for herbal remedies due to having less toxicity, very cheaper. The most useful method for the synthesis of Coumarone is from phenol and ethyl acetate and also by using catalyst. In this paper we tried to update the observations of authors towards the biological and medicinal significance of novel the natural and synthetic coumarone derivatives.

Keywords: Coumarone derivatives, Biological and Pharmacological activities

© 2021 The Authors. Published by Innovare Academic Sciences Pvt Ltd. This is an open access article under the CC BY license (https://creativecommons.org/licenses/by/4.0/)
DOI: https://dx.doi.org/10.22159/ijcpr.2021v13i4.42733 Journal homepage: https://innovareacademics.in/journals/index.php/ijcpr

INTRODUCTION

Coumarone consists the huge class of phenolic compounds [1, 2]. Coumarone were initially observed in Tonka bean and having thirty different families [3-9]. Coumarone also observed in some of the oils such as cassia oil [10], cinnamon oil [11-16] etc.

Fig. 1: Coumarin or benzpyrone

As coumarin having the properties of blood thinning and antitumour properties, so it should not be taken while using anticoagulant. In view of these literature surveys, several natural and synthetic coumarin (2-oxo-2H-chromene) derivatives showed various medicinal and pharmacological activities [17-21]. Coumarins are also widely used as therapeutic agents and malignancies [22, 23].

Medicinal applications

Steffen et al. [24] synthesized hydroxycoumarin derivatives and screened on human tumor cells. Egan and his team [25, 26] was observed cytostatic and cytotoxic nature of nitro substituted hydroxycoumarin. Warfarin, a coumarin analog was more or less cytotoxic against tumor cells [27]. Warfarin was reported to inhibit rat mammary carcinoma.

Fig. 2: Warafarin

Akmal and team [28, 29] observed synergistic cytotoxicity activity [30].

Fig. 3: 3,3’-Benzylidene-bis (4-hydrpxycoumanin)

The following coumarone complex derivatives showed good anticoagulant action.

Fig. 4: 3-Sulfo-4-hydroxycoumarin

Fig. 5: Bis-(4hydroxy-3-coumarinyl)-acetic acid

Kerr et al. [31-37] synthesized compounds that inhibit the Vitamin K and Kam et al. [38] sythesisezed various isocoumarin derivatives.

Fig. 6: 7-Amino-4-chloro-3-(3-isothioureidopropoxy) isocoumarin

Smirnova and team reported various coumanrone derivatives [39]. Wallin et al. [40] and Hart et al. [40] have studied the synthesis and anticoagulant activity of coumarin derivatives. Yamada [42, 43] and team observed the spasmolytic activity of several coumarin compounds. Aminov and team [44]. Observed spasmolytic and hypotensive activities. Brhamabhatt et al. [45] have synthesized various derivatives. Bhosale et al. [46] have reported the synthesis and antipsychotic activity of new coumarinoacetamides.

Fig. 7: Bis(4-hydroxy-2-oxo-2H-chromen-3-yl)-(1H-pyrazol-3-yl)-methane

Irena K et al. [47] sythesised the various coumarin complexes. Recently, Antigoni Kotali et al.[48] observed the antileucemic activity of coumarin benzoylhyrozone derivatives.

Fig. 8: 7- Hydroxy-8-acetylcoumarin benzoy 1hydrazone

Shingare et al. [49] have reported a new methodology for the synthesis of coumarinophosphorothioates from 7-hydroxy coumarin derivatives using O, O-diethyl phosphorochloridothiate in presence of sodium hydroxide and aliquat 336 as catalyst.

Biological activities

Desai et al. have mentioned ecofriendly microwave synthesis of imidazole derivatives containing coumarin moiety and their antimicrobial activity.

Fig. 9: 3-(1-(Benzo[d]thiazol-2-yl)-2-mercapto-1H-imidazol-4-yl)-2H-benzpyra-2-one

Sandeep et al. [50, 51] observed significant antimicrobial and anti-inflammatory activities.

Fig. 10: 7Methoxy-4-methyl-8-[5-arylisoxazol-3-yl]-2H-benzopyran-2-one

Rafat M. and team [52] observed antifungal and antibacterial activities.

Fig. 11: 8-Methyl-9H-pyreno[l,2-6]pyran-9-one

Fig. 12: 3-Methyl 2H-anthra[l,2-b]pyran-2-one

Novobiocin, Coumermycin and clorobiocin are potent antibiotics.

Fig. 13: R=H, Na

Fig. 14: Cloromycin

Fig. 15: Coumermycin

Coumarone derivatives showed strong coronary vasodilating activity.

Fig. 16: 7-Oxycoumarin skeleton

Recently, the Synthetic 7-hydroxy coumarone derivative observed as an antianginal drug.

Fig. 17: 3β-Diethylaminoethyl-4-methylcoumarin-7-ethyloxyacetate

A number of naturally occurring as well as synthetic furocoumarins such as psoralen etc are well known for their dermal photosensiting, estrogenic, antibacterial, antifungal, antiviral and insectisidal activities. Marked anti-fertility activity of a number of diphenyl furocoumarins is also attributed to a triaryl ethylene pattern.

Fig. 18: 5-Methoxy psoralen

Fig. 19: 8-Methoxy psoralen

Fig. 20: 4, 5΄,8-Trimethoxy psoralen

Various pyrano benzopyrans are known for their biological activities. Some pyrono benzopyran 2,5 diones are well known for their anticoagulant activity, CNS activity and anti-HIV agents.

Other known antioxidants include curcumin found in turmeric and ginger.

Fig. 21: α-Tocopherol

Fig. 22: Retinal

Fig. 23: 2,2,5,7,8,-Pentamethyl-6-chromanol

The benzofurano (3,2-b) pyridines and tetra hydropyridines have been reported as potential anti-allergic agents and potential antidepressants.

Fig. 24: Thymine dimer photosensitiser

Pyridine–fused coumarins and benzofuran

Fig. 25: Novel angularly fused pentacyclic heterocycles

Fig. 26: Diversified coumarin

3-carboxyl coumarin derivatives useful as GPR35 agonists observed by Liang, Xinmiao et al. and Li, Xue was observed antiplatelet aggregation activity.

Derivaties of (coumarin-4-yl) aminocarboxylic acids, (thiocoumarin-4-yl) aminocarboxylic acids and (2-oxo-1,2-dihydroquinolin-4-yl) aminocarboxylic acids (I) (R1 is a hydrogen or a nitro group; X is O, S or NH; Y is OH, OCH3, OC2H5, NH2 or NHCH3; n = 3, 4, 5, 6) were showed as anticonvulsants observed by Mokrov, G. V

Following Coumarone derivatives synthesized in our laboratory

Naganna M. Goudgaon et al. [53] synthesized and observed antimicrobial activites of a series of some innovative substituted coumarone derivatives.

Sharanabasappa B. Patil et al. [54]., synthesized and observed antimicrobial activity of 6-bromo-3-((E)-3-(3-(Aryl)-1-phenyl-1H-pyrazol4-yl)acryloyl)-2H-chromen-2-ones, 6-bromo-3-(1,2,5,6-tetrahydro-6-(3-(Aryl)-1-phenyl1H-pyrazol-4-yl)-2-thioxopyrimidin-4-yl)-2Hchhromen-2-ones, 4-(6-bromo-2-oxo-2Hchromen-3-yl)-5, 6-dihydro-6-(3-(Aryl)-1-phenyl1H-pyrazol-4-yl) pyrimidin-2(1H)-ones and 6-bromo-3-(4, 5-dihydro-5-(3-(Aryl)-1-phenyl-1H.

CONCLUSION

The natural and Synthetic Coumarone derivatives showed potent biological properties. (such as anti-inflammatory, anticoagulant, antimicrobial, antiviral, anticancer, antihypertensive, antitubercular, anticonvulsant, antiadipogenic, antihyperglycemic, antioxidant, and neuroprotective).

FUNDING

Nil

AUTHORS CONTRIBUTIONS

All the authors have contributed equally.

CONFLICT OF INTERESTS

Declared none

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