STRUCTURE BASED ANTIBACTERIAL ACTIVITY OF 1,3-DIARYL-2-PROPEN-1-ONES AND THEIR RECENT PHARMACOLOGICAL INTERESTS

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ABOUT AUHTORS
Nisha Sharma, Mahroz, Deepak Chowrasia*
University Institute of Pharmacy,
Chhatrapati Shahu Ji Maharaj University, Kanpur, U.P.,  India

chowrasia.deepak@gmail.com

ABSTRACT
Chemically chalcones are 1,3–diphenyl-2-propene-1-one, containing dual aromatic rings which are linked to each other via carbon bridge system enveloping keto-ethylenic core structure. Owing to the presence of conjugated double bond and electron dense aromatic ring system, the molecule posses less redox potential; thus greater probability for characteristic electron transfer reactions. Naturally, conjugated systems of these types are abundantly present in edible plants and are considered to be precursors of bioactive flavonoids and bioflavonoids. Chalcones and their derivatives find numerous industrial applications such as artificial sweeteners, scintillator, polymerization catalyst, fluorescent whitening agent, organic brightening agent, stabilizer against heat, visible light, and ultraviolet radiation.  As a chemo-identifying agent, chalcones have been found useful in elucidating structure of natural products like hemlock, tannin, cyanomaclurin, ploretin, eriodictyol and homoeriodictyol, and naringenin. Pharmacologically, the same molecule acts as a versatile and universally accepted moiety for design and development of numerous bioactive synthetic analogues in search of ideal medicine to conquer human pathological conditions.  The present paper thus designs to explore and study various prospective of chalcones and their derivatives in terms of recent developments and pharmacological importance.

REFERENCE ID: PHARMATUTOR-ART-2458

PharmaTutor (ISSN: 2347 - 7881)

Volume 5, Issue 1

Received On: 22/08/2016; Accepted On: 16/09/2016; Published On: 01/01/2017

How to cite this article: Sharma N, Mahroz, Chowrasia D; Structure based Antibacterial Activity Of 1,3-Diaryl-2-Propen-1-Ones And Their Recent Pharmacological Interests; PharmaTutor; 2017; 5(1); 42-47

INTRODUCTION
Chalcones are excellent scaffolds not only for synthetic manipulations but also act as a unique template responsible for numerous pharmacological activities1. Biphenylic bridged core structure of chalcone provides firm backbone for generation of potential pharmacophore when derivatized2-3 yields multiple potent and highly selective medicinal active compounds with differential biological activities4-14. Chalcones are the close conger of naturally occurring bioactive flavonoid, isoflavonoids & their analogues but differ from them in having dual (instead of triple) ring system. Xanthohumol, cardamonin, and flavokawains A, B, C are only few bioactive naturally occurring chalcones derivatives that posses potent anticancer, vasorelaxant and anti-inflammatory properties15-17. However, occurs naturally isolation of chalcones employs tedious multi-step time-consuming complicated methodologies which rarely compatible & comparable with end product yield. 

Chemistry of Chalcones
Chalcone (1,3-diaryl-2-propen-1-ones) also termed as benzalacetophenone or benzylidene acetophenone was initially named by Kostanecki and Tambor18. These compounds contain two aromatic ring systems A and B linked by highly reactive keto-ethylenic group –CO-CH=CH- (See figure 01) endowed with potent pharmacological activity such as antioxidant and antimicrobial, but also contribute towards efficient chromogenic property of this molecule. The conjugated double bonded carbon bridge and completely delocalized pi-electrons of dual aromatic ring system ultimately not only fulfilled its criteria for relative low redox potential but bequeath the molecule with higher possibility of easier electron transfer aromatic substitution reactions. This thus makes molecule prone for laboratory derivatization and subsequent molding into differential scaffold by interchanging the position of various substituent on aromatic rings intra-molecularly. Besides having induced chemical differentiability they act as key intermediate for synthesis of heterocyclic ring system19-22 with well defined diversified biological activities. Numerous methods are available for the synthesis of chalcones, the most convenient and popular method is the Claisen-Schmidt reaction (figure-12), relay on base assisted condensation of equimolar quantities of arylmethlketone with aryl aldehyde in the presence of absolute alcohol. The limiting factor for reaction is concentration of alkali, which usually ranges from 10-60 %. Rather than alkali other condensing agents such as amino acid, aqueous solution of borax, perchloric acid, Pepperdine, boron trifloride, alkali metal alkoxide, and magnesium tert-butoxide.

Recent developments
Chalcones are precursor for biosynthesis flavonoids. Literatures are surplus with compounds reported to having backbone analogues to that of chalcone and their multidisciplinary pharmacological action23,4-14 including antiviral, antibacterial, antifeedant, antimycobacterial, antiinvasive, antiplatelet, cytotoxic, anti-HIV, antihyperlipidemic, hypoglycemic agent, antiulcerative, antiprotozoal, antioxidant, antimalarial, analgesic, anti-inflammatory, cytoprotective, antitumor, antileishmanial, antihistamine  etc. Although other related compounds also posses these activity but not to an extent comparable with this (chalcone). Thus chalcones attract considerable attention globally from scientific community to explore this molecule further in order to improve activity of existing molecule, but also search for novel derivatized chalcone based lead moiety which may in future leads to a potential therapeutic agent. Here is the brief discussion on some of the well defined chalcone based pharmacophore responsible for antimicrobial activity.

Prasad et. al.25 synthesize benopyran-2-one substituted chalcone (figure 02) based antimicrobial agent against E.coli and B. subtilis and reveals activity of these compound in a manner proportional to electron releasing group on ring.

Nielsen et al.26 studied bioisosteric effect & hydrophilicity of various substitution on aromatic ring of chalcone and their derivatives and find out that substitution of halogen atom on ring increase not only the solubility

Prasad et. al.27 synthesize naphthalene based chalcone derivative and studied its antimicrobial and antifungal property.

Rao et al.28 syntheise halogen based chalcone derivative and elucidate its antimicrobial action predominantly against E. Coli.

Nowakowska et al.29 synthesized a series of substituted chalcones and tested for their antibacterial and antifungal activities.

Okunade et al.30 synthesized dihydrochalcones having antibacterial activity.

Boeck et al.31 synthesized novel xanthoxylin-derived chalcones showing antifungal activity.

Sohly et al.32 isolated prenylated chalcones from the leaves of Malclura tinctoria possessing antifungal activity.

Stevaz et al.33 isolated a 2',4'-dihydroxy-3'-methoxychalcone from the methanolic extract of Zuccagnia punctata which exhibited antifungal activity.

Tsuchiya et al.34 synthesized hydroxychalcones which exhibited antifungal activity.

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