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Synthesis and Cytotoxicity Studies of Some Furanone Derivatives

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Synthesis and Cytotoxicity Studies of Some Furanone Derivatives id7079828 pdfMachine by Broadgun Software - a great PDF writer! - a great PDF creator! - http://www.pdfmachine.com http://www.broadgun.com OOrrggaanniicc ISSN: 0974 - 7516 Volume 8 Issue 2 CCHHEEMMAn IIInSSdiTTan RRJouYrYnal Trade Science Inc. Full Paper OCAIJ, 8(2), 2012 [60-64] Synthesis and cytotoxicity studies of some furanone derivatives C.V.Sindhu Ramachandran1*, P.K.Sreekumar2, P.Madhavan Pillai3, P.Balaram4 1Department of Chemistry, NSS College, Manjeri, Calicut University, Kerala, (INDIA) 2Department of Chemistry, NSS College, Pandalam, KeralaUniversity, Kerala, (INDIA) 3Department of Applied Chemistry, Cochin University of Science and Technology, Kerala, (INDIA) 4Research Division, Regional Cancer Centre, Thiruvananthapuram, Kerala, (INDIA) E-mail: [email protected] Received: 29th May, 2011 ; Accepted: 29th June, 2011 ABSTRACT KEYWORDS A series of 2(5H)-Furanone derivatives were prepared starting from 3,4- Mucohalic acid; - - - - dibromocrotonolactone, which was obtained from highly functionalized 3,4 dibromo 5 hydroxy - mucobromic acid. Lactone on treatment with various nucleophiles gave 4- 2(5H) furanone; - - - substituted-3-bromo-furanone derivatives. These derivatives were tested 2,3 dibromo 3 formyl for their short term cytotoxic activity and three of them were found active. acrylic acid; -d - -o - Compound 4-(2-Aminoanilino)-3-bromo-2(5H)-furanone 5 was found to be 2,3 ibromo 4 xo -b most active against DLA and HeLa cell lines. 2 utenoic acid. 2012 Trade Science Inc. - INDIA INTRODUCTION Under basic conditions the reactions proceeded with the substitution of the chlorine atom(s) by 2(5H)-Furanone derivatives are a large family of arylthiogroup(s), while in an acidic medium the hydroxyl heterocycles that include synthetically useful com- group at C5 was substituted. Different types of new pounds, several natural products and drugs with diverse sulphur-containing products of di- and tri substitution biological activities ranging from antibiotic, cytotoxic, on the basis of mucochloric acid were obtained[8]. To antitumor and inhibition of cholesterol biosynthesis[1-4] study the reactivity of the system towards nucleophiles, Mucobromic acid or 3,4-dibromo-5-hydroxy-2(5H)- the first series of reaction was carried out with hydra- furanone is a highly functionalised, inexpensive starting zine and its derivatives and it was found that pyridazone material which can provide a simple and convenient entry derivatives were the products[9]. to a wide variety of interesting organic compounds. Reactions of mucohalic acid series with dl penicillamine EXPERIMENTAL ã-lactam thiazolidines and its methyl ester gave the fused ’s which are structurally related to penicillin [5]. Melting points were determined on a Neolab cap- Mucobromic acid was prepared from furanoic acid by illary melting point apparatus and are uncorrected. UV treatment with bromine in 60-70% yield or it may be spectra were obtained with a Schimadzu 160-A spec- prepared from furfural with bromine[6,7]. Stable reac- trophotometer. IR spectra (KBr) were recorded on a tion products of mucohalic acid with aromatic and het- Schimadzu DR8001FT-IR. 1H NMR spectra were erocyclic thiols were synthesized and characterized. obtained on a Jeol GSX 400NBFT-NMR spectrom- OCAIJ, 8(2) 2012 C.V.Sindhu Ramachandran et al. 61 Full Paper eter operating at 400 MHz. Chemical shifts were re- mixture (99:1). ä units ported in (ppm) relative to (CH ) Si as internal Yield 90mg (60%), mp 178OC; Uv(CH OH): 3 4 ëmax(å), 258nm(19560); Ir (KBr) 3 standard. Mass spectra were recorded on a Finnigan cm-1: 3300,3456 Mat 8230 mass spectrometer. Elemental analyses (C, (NH2), 1750 (C=O), 1649 (C=C); 1H NMR (TMS) ä + H, N) for final compounds were performed on a Carlo ppm :4.73(s, 2H, CH2), 4 (s, 2H, NH2); MS: 268(M ), Erba Model 1106 analyzer. Thin layer chromatography 270(M+2). Anal. Calcd. for C4H4BrNO2: C 28.51; H (TLC) was carried out on Silica gel G plates. The prod- 2.06; N 7.90. Found: C 28.39; H 2.23; N 7.84. ucts were separated by column chromatography on 4-(2-Amino)anilino-3-bromo-2(5H)-furanone (5) silica gel of 60-120 mesh size. To a solution of 2(200mg, 0.0008mol) in DMF 3,4-Dibromo-2(5H)-furanone (2) (1mL) was added o-phenylene diamine (80mg, To a mixture of mucobromic acid in water (1g, 0.00075mol) and stirred for 3h. It was poured into 0.0039mol) was added sodium borohydride (0.15g, crushed ice and the solid separated was filtered, dried 0.0018mol) with stirring. The mixture frothed and turned and recrystallised from ethyl acetate-hexane mixture yellow. After stirring for 1h at room temperature it was (99:1). diluted with 2N HCl (20mL) and cooled. The solid Yield 100mg (50%), mp 145OC; UV(CH OH): ëmax(å), 267nm(14870), 240nm(13320), ; I 3 separated was collected, dried and recrystallised from R(KBr) -1 hexane. cm : 3366,3347,3312 (NH and NH2), 1736 (C=O), o ä Yield 0.65g (65%), mp 89 C; UV(CH3OH): 1640 (C=C); 1H NMR (TMS) ppm: 9(s, 1H, NH), ëmax(å), 237nm(7000); -1 IR(KBr) cm : 1790 (C=O), 6.45-7.1(m,4H,Ar,), 5.2(s, 2H, CH2), 4.67(s, 2H, ä + 1610 (C=C), 1215 (C-O); 1H NMR (TMS) ppm : NH2); MS: 268(M ), 270(M+2). Anal. Calcd. for + 4.92(s, 2H, CH2); MS: 240 (M ),242(M+2). C10H9BrN2O2: C 44.77; H 3.35; N 10.44. Found: C 4-Azido-3-bromo-2(5H)-furanone (3) 44.05; H 3.13; N 10.40. 3-Bromo-4-(2-hydroxy)anilino-2(5H)-furanone (6) To an ice cold solution of NaN3 (100mg, .0016mol) in CH3CN (10mL) was added 3,4-dibromo- To a solution of 3,4-dibromocrotonolactone crotonolactone (200mg,0.0008mol) in CH3CN (5mL) (500mg, 0.002mol) in CH3OH (5mL) was added o- and stirred overnight at room temperature. It was di- aminophenol (200mg, 0.002mol) and two drops of py- luted with water (10mL) and then extracted with ether ridine. The mixture was refluxed for 3h on a water bath (50mL). The ether layer was washed with 5% Na2S2O3 and poured over crushed ice. The solid separated was ad then with water. The ether layer was dried and filtered and dried. Further purification was done on a evaporated to give needle shaped crystals which was silica column with CHCl3-CH3OH (99:1) as eluent. purified by crystallization from hexane. Yield 350mg (70%), mp 171OC; UV(CH OH): ëmax(å), 280nm( 3 Yield 100mg (50%), mp 60OC; UV(CH OH): 23000),; IR(KBr) cm-1: 3088,3341 ëmax(å), 268nm( 3 11500); IR(KBr) cm-1: 2131 (N ), (OH and NH), 1716 (C=O), 1626 (C=C), 1230 (C- 3 ä 1750 (C=O),1625 (C=C), 1230 (C-O); 1H NMR O); 1H NMR (TMS) ppm :10.01(s, 1H, OH), 8.9(s, ä + (TMS) ppm: 5.19(s, 2H, CH2); MS: 203(M ), 1H, NH), 6.8-7.1(m,4H,Ar,), 4.8 (s, 2H, CH2),; MS: + 205(M+2). 269(M ), 271(M+2). Anal. Calcd. for C10H8BrNO3: 3-Amino-3-bromo-2(5H)-furanone (4) C 44.60; H 2,79; N 5.20. Found: C 44.32; H 2.80; N 5.14. A mixture of 2 (150mg, 0.0006mol) and NaN 3 ’ N,N -Bis(3-bromocrotonolactonyl) hydrazine (7) (80mg, 0.0012mol) in CH3CN (10mL) was refluxed for 4h on a water bath. The mixture was diluted with To a solution of hydrazine hydrate water (15mL) and extracted with ether (100mL). The (0.2mL.0.004mol) in CH3OHwas added 3,4- ether layer was washed with water, dried and con- dibromocrotonolactone (500mg, 0.002mol) and stirred centrated under reduced pressure and the residue ob- overnight. The reaction mixture was diluted with water tained was recrystallised from ethylacetate-hexane (25mL) and extracted with CH2Cl2(150mL). The com- Organic CHEAMn InIdiSanT JoRurnYal 62 Synthesis and cytotoxicity studies of some furanone derivatives OCAIJ, 8(2) 2012 Full Paper pound was purified by a silica column with CH2Cl2 as (3mL) The reaction mixture was stirred until the spot of eluent and further recrystallisation from CHCl3-CH3OH lactone on TLC (methylene chloride) disappeared. The to give the product. volume was reduced and diluted with water (25mL), Yield 250mg (50%), mp 150OC; UV(CH OH): extracted with chloroform (100mL). The solvent was ëmax(å), 320nm(23460), 2 3 76nm(22390; Ir (KBr) cm-1: removed and the component was separated by silica 3300 (NH), 1749 (C=O), 1626 (C=C), 1219 (C-O); column using CHCl -CH OH (99:1) mixture as eluent. ä 3 3 H NMR (TMS) ppm: 8.5(s, 1H, NH), 5.29 (s, 2H, Yield 300mg (60%), mp 135OC; UV(CH OH): 1 ëmax(å), 277nm(12360); I 3 CH ),; MS: 269(M+), 271(M+2). Anal. Calcd. for R (KBr) cm-1: 1732 (C=O), 2 äppm C8H6Br2N2O4: C 27.27; H 1.70; N 7.95. Found: C 1650 (C=C), 1259 (C-O); 1H NMR (TMS) : 27.9; H 1.65; N 8.01 4.7 (s, 2H, CH2), 3.3(m,4H, 2CH2) 2.1(m, 4H, + 4-Anilino-3-bromo-2(5H)-furanone (8) 2CH2),; MS: 231(M ), 233(M+2). Anal. Calcd. for C H BrNO : C 41.55; H 4.32; N 6.06. Found: C 42; To a cold solution of 3,4-dibromocrotonolactone 8 10 2 H 4.46; N 5.60. 2 (100mg, 0.0004mol) in absolute ethanol(1mL) was added aniline (0.07mL, 0.0008mol) in 1mL alcohol. DISCUSSION The mixture was cooled overnight, when a solid was formed, The solid was separated and recrystallised from Here we are reporting some furanone derivatives CHCl .
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