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and an NH signal as broad singlet at 11.33 ppm(which disappeared in D 2O exchange) in additionto the disappearance of the signal corresponding

to the CH 2 group. Moreover, the mass spectrumof this compound showed the molecular ion peakat m/z 357 ([MH] +, 66%), which is in accordancewith its molecular formula. On the other hand,when the thiazolidine deri vatives 2ad were al-lowed to react with the aromatic aldehydes 7ad in the presence of acetic acid in ethanol at reuxtemperature, the cor responding (2 E ,5E )-4-subs-tituted arylidene-2-[( E )-(4-ary lidene)hydrazono]

thiazolidin-4-ones 8ad were obtained in 78 80%yields. The IR spectra of the disubstituted 2,5-thi-azolidinone derivatives showed the presence of

characteristic absorption bands at 3325, 1682 and1605 cm 1 corresponding to NH, C=O, and C=N,respectively. The 1H NMR spectrum of compound8a showed signals of the aromatic protons at 6.88 8.05 ppm in addition to an NH signal at 10.55 ppm. The disappearance of the singlet peakof the CH 2 group also conrmed the assignedstructure.

R

NNH

NH2

S

R

NN

NH

S

O

R

NN

NH

S

O

NN

R

NN

NH

S

O

NN

N

S

1a - d

2a - d 6a - d

NN

N

S

Cl

5

NNCl

3

ii

iii

i

iv

4a - d

R

NN

NH

S

O R8a - d

1

2

1 1

11

R

CHO

2

7a - d

Compound R 1 R 2

1a H 1b Cl 1c Br 1d N(CH 3)2 2a H 2b Cl 2c Br 2d N(CH 3)2 4a H 4b Cl 4c Br 4d N(CH 3)2

Compound R 1 R 2

6a H 6b Cl 6c Br 6d N(CH 3)2 7a H7b Cl7c Br7d N(CH 3)2 8a Br H8b Br Cl8c Br Br8d Br N(CH 3)2

Fig. 1. Synthesis of 2,4-disubstituted thiazolidinone derivatives. (i) ClCH 2COOEt, EtOH, reux; (ii) 3, KOH/H 2O;(iii) 5, KOH/H 2O; (iv) 7ad , EtOH/reux

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Abdel-Rahman A. A.-H., El-Sayed W. A., Abdel-BaryH. M., Abdel-Megied A. E.-S., and Morcy E. M.(2008), Amino acid derivatives, VIII [1]: synthesisand antimicrobial evaluation of -amino acid estersbearing an indole side chain. Monatsh. Chem. 139 ,1095 1101.

Andreani A., Rambaldi M., Locatelli A., Leoni R.,Bossa M., Chiericozzi I., Galatulas G., and SalvatoreA. (1993), Synthesis of lactams with potential cardio-tonic activity. Eur. J. Med. Chem. 28, 825 829.

Brown F. G. (1961), 4-Thiazolidinones. Chem. Rev. 61,463 521.

Chen H., Fan Y.-H., Natarajan A., Guo Y., Iyasere J.,Harbinski F., Luis L., Christ W., Aktas H., and Halp-erin J. (2004), Synthesis and biological evaluationof thiazolidine-2,4-dione and 2,4-thione derivativesas inhibitors of translation initiation. Bioorg. Med.Chem. Lett. 14, 5401 5405.

DeLima M. C. A., Costa D. L. B., Goes A. J. S., GaldinoS. L., Pitta I. R., and Luu-Duc C. (1992), Synthseet activit antimicrobienne de drivs chlorobenzylbenzylidne imidazolidinediones et thiazolidinedi-

ones substitues. Pharmazie 47, 182 184.El-Feky S. A. H. (1993), Synthesis and anticonvulsantproperties of some quinazolinone thiazolidine and4-thiazolidinone derivatives. Pharmazie 48, 894 896.

El-Sayed W. A., Ramiz M. M. M., and Abdel-RahmanA. A.-H. (2008) C -Furyl glycosides, I: Synthesis andantimicrobial evaluation of C -furyl glycosides andchalcones derived therefrom. Monatsh. Chem. 139 ,1499 1505.

El-Sayed W. A., Nassar I. F., and Abdel-Rahman A. A.-H. (2009), C -Furyl glycosides, II: Synthesis and an-timicrobial evaluation of C -furyl glycosides bearingpyrazolines, isoxazolines, and 5,6-dihydropyrimidine-2(1H )-thiones. Monatsh. Chem. 140 , 365 370.

Geronikaki A., Hadjipavlou-Litina D., ChatziopoulosC., and Soloupis G. (2003), Synthesis and biologicalevaluation of new 4,5-disubstituted-thiazolyl amides,derivatives of 4-hydroxy-piperidine or of 4- N -methylpiperazine. Molecules 8, 472 479.

Greenwood D. (2000), Antimicrobial Chemotherapy,4th ed. Oxford University Press, New York, p. 114.

Janssen A. M., Scheffer J. J., and Svendsen A. B. (1987),Antimicrobial activity of essential oils; a 1976 1986literature review. Planta Med. 53, 395 400.

Jorgensen J. H., Jurnide J. D., and Washington J. A.(1999), Antimicrobial susceptibility tests. In: Man-ual of Clinical Microbiology, 7th ed. (Muarry P. R.,Baron E. J., and Yolken R. C., eds.). American So-ciety for Microbiology, Washington, DC, USA, pp.1526 1543.

Kearney P. C., Fernandz M., and Flygare J. A. (1988),Solid-phase synthesis of 2-aminothiazoles. J. Org.Chem. 63, 196 200.

Kirsi J. J., North J. A., McKernan P. A., Murray B. K.,Canonico P. G., Huggins J. W., Srivastava P. C., andRobins R. K. (1983), Broad-spectrum antiviral activ-ity of 2- -D-ribofuranosylselenazole-4-carboxamide, anew antiviral agent. Antimicrob. Agents Chemother.24, 353 361.

Labouta I. M., Salama H. M., Eshba N. H., Kader O.,and El-Chrbini E. (1987), Potential anti-microbial:syntheses and in vitro anti-microbial evaluation ofsome 5-arylazo-thiazolidones and related compounds.Eur. J. Med. Chem. 22, 485 489.

Lpez-Garca B., Veyrat A., Prez-Pay E., Gonzlez-Candelas L., and Marcos J. F. (2003), Comparisonof the activity of antifungal hexapeptides and thefungicides thiabendazole and imazalil against post-harvest fungal pathogens. Int. J. Food Microbiol. 89,163 170.

Mgonzo R., Geronikaki A., and Kourounakis P. N. (1995),Synthesis and antiinammatory activity of some newthiazole derivatives. Pharmazie 50, 505 506.

Milne G. W. A. (ed.) (2000), Ashgate Handbook of An-tineoplastic Agents. Gower, London, UK.

Motomura W., Okumura T., Takahashi N., Obara T.,and Kohgo Y. (2000), Activation of peroxisomepoliferator-activated receptor by troglitazone in-hibits cell growth through the increase of p27Kip1in human pancreatic carcinoma cells. Cancer Res. 60,5558 5564.

Nasr M. N., Gineinah M. M., and El-Bendary E. R.(2003), Synthesis and in vitro antibacterial evalu-ation of novel imidazo[2,1:5,1]-1,2,4-triazolo[4,3-c]-quinazoline derivatives of 5-thioxo-1,2,4-triazole,4-oxothiazolidine, and their open-chain counterparts.Arch. Pharm. 336 , 560 566.

Sato H., Ishihara S., Kawashima K., Moriyama N., Suet-sugu H., Kazumori H., Okuyama T., Rumi M. A. K.,Fukuda R., Nagasue N., and Kinoshita Y. (2000), Ex-pression of peroxisome proliferator-activated recep-tor (PPAR) in gastric cancer and inhibitory effectsof PPAR agonists. Br. J. Cancer 83, 1394 1400.

Singh S. P., Parmar S. S., Raman K., and Stenberg V. I.(1981), Chemistry and biological activity of thiazo-lidinones. Chem. Rev. 81, 175 203.

Srivastava P. C., Pickering M. V., Allen L. B., StreeterD. G., Campbell M. T., Witkowski J. T., Sidwell R. W.,and Robins R. K. (1977), Synthesis and antiviral ac-tivity of certain thiazole C -nucleosides. J. Med. Chem.20, 256 261.

Takahashi N., Okumura T., Motomura W., FujimotoY., Kawabata I., and Kohgo Y. (1999), Activationof PPAR inhibits cell growth and induces apop-tosis in human gastric cancer cells. FEBS Lett. 455 ,135 139.

Tsuji K. and Ishikawa H. (1994), Synthesis and anti-pseudomonal activity of new 2-isocephems with a di-hydroxypyridone moiety at C-7. Bioorg. Med. Chem.Lett. 4, 1601 1606.

Unangst P. C., Connor D. T., Cetenko W. A., SorensonR. J., Sircar J. C., Wright C. D., Schrier D. J., and DyerR. D. (1993), Oxazole, thiazole, and imidazole deriva-tives of 2,6-di- tert -butylphenol as dual 5-lipoxygenaseand cyclooxygenase inhibitors. Bioorg. Med. Chem.Lett. 3, 1729 1734.

Vagdevi H. M., Vaidya V. P., Latha K. P., and PadmashaliB. (2006), Synthesis and pharmacological examinationof some thiazolidinone derivatives of naphtho[2,1- b ]-furan. Indian J. Pharm. Sci. 68, 719 725.