A REVIEW ARICLE ON SYNTHESIS AND BIOLOGICAL PROPERTY OF SOME NOVEL BUTENOLIDE DERIVATIVES

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About Authors:
Rajender Kumar1*,Dr.Sukhbir L.Khokara2,
1Department of Pharmacy, Manav Bharti University, Solan (H.P.) 173229
2Institute of pharmaceutical sciences, Kurukshetra University,
Kurukshetra, Harayana-136119
*rajkaushal13@gmail.com

ABSTRACT
Butenolides (furanones) consist of unsaturated γ- lactone which occur in plants as glycosides. There is a group of steroids which contain α,β unsaturated butenolide ring in the side chain such steroids are known as cardenolides. The  presence of γ - lactone ring contain natural products like Goniobutenolides A & B ,Digitoxigenin and  lignans. These compound have biological properties like antibiotic, antitumor, anticonvulsant, antimicrobial and medicinal uses like fungicides, bactericides and allergic inhibitor.

Reference Id: PHARMATUTOR-ART-1401

1.INTRODUCTION
Butenolides derivatives are a group of important compounds containing inique carbon skeleton of 2(5H) & 2(3H) furanone and may be regarded as furan dv. i.e. 2,3 and 2,5 di hydro furan-2-one(l-3) (I) and (II) and the term “butenolide” was first time used by Klobb(4).

        

They are also known as butenolactones / crotonolactones / (α,β)-angelica lactones(5’6). They are also represented by the term “Furanones”(7)  hence?β,γ-butenolides are 2(3H)-furanones and ?α,β-

They are also known as butenolactones / crotonolactones / (α,β)-angelica lactones(5’6). They are 2(5H)-furanones. Hydrolysis of these compoimds & Hydrogenation of the double bond in their structure, results the loss of activity of these compounds. There is a group of steroids which contain α,β unsaturated butenolide ring in the side chain such steroids are known as cardenolides(8-10).

 

2.AVAILABILITY IN NATURE
Butenolides consist of unsaturated γ- lactone which is widely present in many natural products(11)Some of them occur in plants as glycosides. The γ - lactone ring is a part of varity of natural products like Goniobutenolides A & B (llla, IIIb) (l2`14) Digitoxigenin (IV), lignans like Podophyllotoxin W), Ascorbic acid (VI), Sesquiterpene, antibiotic like patulin(l5). They also exist naturally like fissohamione (VII) from Fissistigma oldhamii(16)

3.METHODS OF PREPARATION

3.1.Synthesis of ?β,r-butenolides [2(3H) furanones]
I.          γ-keto acid such as levulinic acid give ?β,γ- butenolides(17’18). Succinic anhydride with               dichloroalurninoethyl (C2H5A1Cl2) gives compound (VIII) (R=C2H5)(l9,20), which on cyclization by heating with orthophosphoric acid  gives ?β,γ - butenolides(21) (IX).

γ –Aryl-?β,γ -butenolides can be prepared by acetic anhydride cyclisation of β-aroylpropionic acid(22'25) while cyclization of β -benzoylpropionic acid give γ -phenyl-?β,γ - butenolides which has been studied extensively (26).

II.        2-Trimethylsilyloxy furan and Morita- Baylis- Hillman acetate (X) in the presence of chiral  phosphines (cata1yst)(27) and THF as a solvent results in corresponding syn-γ-butenolides (XI) (28).

III.       α-Aryl-β-aroyl propoinic acid (XII) on heating with acetyl chloride(29) or acetic  anhydride(30) above their melting points reported to yield α-y-diaryl ?β,γb butenolides(XIII).

IV.       Cyclization of alkanoate ester (XIV) in the presence of bases gives furanone (3l)(XV)

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A multistep synthesis of butenolides (XVII) starting from methyl benzoate (XVI) has been reported(32).

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