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Flavanone: a Versatile Heterocyclic Nucleus

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Flavanone: a Versatile Heterocyclic Nucleus International Journal of ChemTech Research CODEN (USA): IJCRGG ISSN : 0974-4290 Vol.6, No.5, pp 3160-3178, Aug-Sept 2014 Flavanone: A Versatile Heterocyclic Nucleus Yogesh Murti* and Pradeep Mishra Institute of Pharmaceutical Research, GLA University, Mathura-281406 (U.P.), India *Corres.author: [email protected] Mobile: +91-8006240340, Fax No. +91-5662-241687 Abstract: The chemistry of heterocyclic compounds has been an interesting field of study for a long time. The present review article highlights different synthetic approaches to synthesize flavanone nucleus, natural and synthetic flavanones as well as recently synthesized flavanone possessing important biological activities. It was found that among the important pharmacophores responsible for various activities, flavanone also plays an important role in various medicines. Keywords: Chalcone, Flavanone, Heterocyclic compounds, Natural Flavanone, Synthetic flavanone, Biological activity. Introduction Flavonoids are extensive group of compounds occurring in plants. They are prominent plant secondary metabolites that have been found in dietary components including fruits, vegetables, olive oil, tea, and red wine. It has been observed that even a high take of plant based dietary flavonoids is safe and not associated with any adverse health effect. The basic flavanoid structure is a flavone nucleus, In nature, they are available as flavone, flavonol, flavanone, isoflavone, chalcone and their derivatives[1]. Figure 1: Molecular structure of the flavone backbone (2-Phenyl-1,4-benzopyrone ) Over 5000 naturally occurring flavonoids have been characterized from various plants. They have been classified according to their chemical structure, and are usually subdivided into the following subgroups[2] (Table: 1). Natural and synthetic flavanoids and flavanones have attracted considerable attention because of their interesting biological activity including antimycobacterial[3], antimicrobial[4,5], anti-lung cancer[6], antibacterial[7], antiproliferative[8], anti-tuberculosis[9], antifungal[10], antiarrhythmic[11], antiviral[12], antihypertensive, antioxidant and anti-inflammatory[13]. http://www.sphinxsai.com/framesphinxsaichemtech.htm Yogesh Murti et al /Int.J. ChemTech Res.2014,6(5),pp 3160-3178. 3161 Table 1: Classification of Flavones[14] Group Skeleton Examples Description Functional groups Structural formula 3- 2,3- Hydroxyl Dihydro Flav one 2- ✗ ✗ Luteolin, phenylchromen- Apigenin, 4-one Tangeritin Flav on ol 3-hydroxy -2- ✓ ✗ Quercetin, or phenylchromen- Kaempferol, 3-hydroxy flav one 4-one Myricetin, Fisetin, Isorhamnetin, Pachypodol, Rhamnazin Flav an one 2,3-dihydro -2- ✗ ✓ Hesperetin, phenylchromen- Naringenin, 4-one Eriodictyol, Homoeriodictyol Flav an on ol 3-hydroxy -2,3- ✓ ✓ Taxifolin or dihydro -2- (Dihydroquercetin), 3- phenylchromen- Dihydrokaempferol Hydroxy flav an one 4-one or 2,3- dihydro flav on ol Properties of 2,3-Dihydro-2-Phenylchromen-4-one Nucleus[15] The flavanones are a type of flavonoids. They are generally glycosylated by a disaccharide at position seven to give flavanone glycosides. Being naturally occurring compounds, flavanones have high availability and good pharmacological profile. It shows many biological activities in the body. Molecular structure: 3D Structure: Yogesh Murti et al /Int.J. ChemTech Res.2014,6(5),pp 3160-3178. 3162 Chemical Name: Flavanone Phase: Solid (White crystals) Chemical formula: C15 H12 O2 Melting point: 77 ºC Molecular weight: 224.255 Boiling Point: 356 ºC IUPAC Name: 2-Phenyl-2,3-dihydro-4H-chromen- Solubility: In methanol 4-one Synthesis of Flavanone Nucleus 1. Chalcone method: The appropriate 2-hydroxyacetophenone is considered with benzaldehyde or hydroxybenzaldehyde to give chalcone. The chalcone can be converted into flavanone[16]. OH OH O C6H5 CH.C H + NaOH 6 5 OHC.C6H5 CH3 HCl O O O 2. Algar-Flynn-Oyamada method: 2-Hydroxychalcone, prepared by the interaction of 2- hydroxyacetophenone and benzaldehyde in presence of alkali, is treated with alkaline hydrogen peroxide to form 3-hydroxy flavanone by oxidative cyclization[17]. OH OH O C6H5 CH.C H + NaOH 6 5 OHC.C6H5 CH3 H2O2 OH O O O 3. Conversion of 2-hydroxychalcones to flavanones catalysed by cobalt Schiff base complex: Co (salpr) catalyzes the conversion of 2-hydroxychalcones to flavanones in methanol under oxygen. Base catalysis by Co (salpr) (OH) produced in situ is responsible for the reaction, which is found to proceed reversibly[18]. OH - O CoIII (L1) III 1 + Co (L ) (OH) + H2O O O O CH3OH O III 1 Co (L ) (OCH3) + - O CoIII (L1) O 4. Cyclization of 2-hydroxy-4-methoxychalcone to 4-methoxyflavanone: The cyclization of 2-hydroxy-4- methoxychalcone to 4-methoxyflavanone was done by refluxing the corresponding chalcone in acetic acid for 72 hours, although in moderate yield (55%)[19]. Yogesh Murti et al /Int.J. ChemTech Res.2014,6(5),pp 3160-3178. 3163 OCH3 OH OCH3 O AcOH, 72 h, reflux 55 % O O 5. Isomerisation of 2-hydroxychalcones to flavanones: An isomerisation of 2-hydroxychalcones into the corresponding flavanones in ethanol in the presence of triethylamine[20]. R3 R4 OH R2 R4 O Et3N R3 R1 EtOH R2 R1 O R O R 6. Heterogeneous synthesis of Flavanone over MgO catalyst: The effect of several solvents on the heterogeneous synthesis of flavanone from benzaldehyde and 2-hydroxyacetophenenone over a solid MgO catalyst was examined. Among the different high-boiling-point solvents examined for the synthesis of flavanone from benzaldehyde and 2-hydroxyacetophenone over a MgO catalyst, the use of dimethyl sulfoxide (DMSO) was found to significantly promote the yield of flavanone[21]. OH MgO O DMSO O O 7. Microwave accelerated solvent-free synthesis of flavanones: A study of the microwave-accelerated synthesis of flavanones using an unmodified household microwave oven was undertaken. The use of trifluoroacetic acid (TFA) in refluxing chloroform almost doubled the conversion achieved previously in refluxing acetic acid[22]. R6 R5 R6 R2 OH R5 R2 O TFA 30% / Silica gel R4 Microwave, 9 min. 69-80% R3 R4 O O R R 1 3 R1 The cyclization of 2’-hydroxychalcones in the presence of triethylamine, a mild base, using Microwave irradiation resulted in a “green-chemistry” procedure with improved yields for the preparation of flavanones[23]. R3 R3 R 4 R4 R OH 2 MW, 20-50 sec R2 O R5 R5 R1 R (C2H5)3N, EtOH 1 O O Yogesh Murti et al /Int.J. ChemTech Res.2014,6(5),pp 3160-3178. 3164 8. Synthesis of flavanones catalysed by L-proline: L-proline is utilized as an efficient organocatalyst for the synthesis of substituted flavanones and chalcones in good yields[24]. R R R OH O O 2 L-Proline + R2 H DMF, 80oC R1 18 h R1 O O 9. Catalytic enantioselective synthesis of flavanones: The enantioselective synthesis of flavanones and chromanones is described. Bifunctional thiourea catalysts promote an asymmetric oxo-conjugate addition to a β-ketoester alkylidene in high yields with excellent enantioselectivity (80−94% ee) for aryl and alkyl substrates. Decarboxylation of the β-ketoester proceeds smoothly in a one-pot procedure to afford the enantioenriched flavanones and chromanones[25]. Chiral OH O R thiourea O O catalyst CO2t-Bu CO2t-Bu O R O R favors cyclization R=aryl, alkyl 80-94 % ee Single flask 10. Catalytic synthesis of flavanone using Zn-Al hydrotalcite adhere ionic liquid: The Claisen-Schmidt condensation of 2-hydroxy acetophenone and benzaldehyde to chalcone and flavanone show that calcined Zn- Al hydrotalcite is active for synthesis. The activity of this catalyst can be further increased by about 1.5 times by coating ionic liquid triethoxysilane-3-methyl imidazolium chloride on calcined hydrotalcite[26]. O O OH H O + CHTlc Zn-Al OH O O R R R 11. Synthesis of flavanone using environmental friendly catalyst H[bimBF4]: A high yielding and fast method for smooth conversion of substituted α,β-unsaturated carbonyl compounds chalcones to corresponding substituted 2-phenylchroman-4-one i.e. flavanone by grinding at room temperature using ionic liquid H[bimBF4] which is recyclable[27]. O O H[bimBF4] Grinding/ 10-15 min. O R1 R1 R 2 R2 12. Synthesis of flavanone with boracic acid and ethylene glycol: A series of new flavanone derivatives of farrerol was synthesized by convenient method. In a typical synthetic procedure, substituted 2- hydroxyacetophenone was reacted with substituted benzaldehydes, and boracic acid in ethylene glycol at 130ºC to yield the product[28]. Yogesh Murti et al /Int.J. ChemTech Res.2014,6(5),pp 3160-3178. 3165 CH3 CH3 HO OH HO O R Ethylene glycol + RCHO CH3 o Boracic acid, 130 C, 3h H3C H3C OH O OH O 13. Synthesis of flavanone with phosphoric acid: Flavanones were prepared by refluxing the corresponding chalcones with phosphoric acid in alcohols for 2-3 days[29]. Y X Y X O H3PO4 O O 14. Synthesis of flavanone via the isoxazoline route: The parent flavanone was prepared by selective chlorination of salicyaldehyde oxime to salicylhydroxamoyl chloride, which was cycloadded to styrene. Reductive cleavage of the isoxazoline ring to the β-hydroxy ketone and acid catalyzed cyclization gave parent flavanone[30]. OH O CHO i. NH2OH N ii. NCS O i. Raney-Ni, H2 + iii. Styrene, KHCO3 ii. H OH O 15. Synthesis of flavanones from 2-methoxybenzoic acids: Flavanones can be synthesized via 1-(2’-methoxy- phenyl)-1-oxo-propan-3-phenyl-3-ols from 2’-methoxy-acetophenones which were synthesized by treatment of 2-methoxy benzoic acids with 2 equiv of methyl lithium in THF for 0.5-2 h at -78ºC in 88-93% yields as a new synthetic route[31]. R1 R1 i.1 eq LiN(i-Pr)2/THF H O+ R2 OCH3 R2 OCH3 3 i. 2 eq CH3Li/THF ii. p-R4-C H CHO pH=4 + 6 4 OH ii. H3O CH3 R R3 3 O O R1 R4 R1 R2 OCH3 R4 B R O 2 eq HBr/HOAc 2 A o R3 100 C, 5 h R3 O OH O Yogesh Murti et al /Int.J.
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