Synthesis and Antimicrobial Evaluation of N-Substituted-5- Benzylidene-2,4-Thiazolidinedione Derivatives Synthesis of N-substituted-5-benzylidene-2,4-thiazolidinediones
Iranian Journal of Pharmaceutical Sciences,
Vol. 8 No. 3 (2012),
1 July 2012
,
Page 209-214
https://doi.org/10.22037/ijps.v8.40948
Abstract
A series of N-substituted-2,4-thiazolidinedione derivatives (TZDs) were prepared via N-alkylation of 2,4-TZD at position 3 using substituted benzyl halides. Synthesized N-substituted-2,4-TZD was then substituted at position 5 with substituted aromatic aldehyde according to Knoevenagel condensation method. Structures of the compounds were elucidated using various spectral techniques viz. IR, 1HNMR. The synthesized compounds were evaluated for their antimicrobial activity.
Keywords:
- Antimicrobial activity
- Knoevenagel condensation
- Thiazolidinedione
How to Cite
Neeru Malik, & D.N. Prasad. (2012). Synthesis and Antimicrobial Evaluation of N-Substituted-5- Benzylidene-2,4-Thiazolidinedione Derivatives: Synthesis of N-substituted-5-benzylidene-2,4-thiazolidinediones. Iranian Journal of Pharmaceutical Sciences, 8(3), 209–214. https://doi.org/10.22037/ijps.v8.40948
References
[1] Labouta IM, Salma HM, Ehsba O, Kader E, El-Churbini. Potential anti-microbial: synthesis and in vitro anti-microbial evaluation of some 5-arylazo-thiazolidones and related compounds.Eur J Med Chem 1987; 22: 485-89.
[2] Goes AJS, DeLima MCA, Galdino SL, Pitta IR, Luu-Ducc C. Synthese et activite antifongique des chlorobenzyl benzylidene thiazolidinediones et imidazolidinediones substituees. Ann Pharm Francaises 1991; 49: 92-8.
[3] DeLima MCA, Costa DLB, Goes AJS, Galdino SL, Pitta IR, Luu-Ducc C. Synthese et activite antimicrobienne dederives chlorobenzyl benzylidene imidazolidinediones et thiazolidinediones substituees. Pharmazie 1992; 47: 182-4.
[4] Cantello BCC, Cawthorne MA, Cottam GP, Duff PT, Haigh D, Hindley RM Lister CA, Smith SA, Thurlby PL. [[ω-(Heterocyclylamino)alkoxy] benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents. J Med Chem 1994; 37:3977-85.
[5] Andreani A, Rambaldi M, Locatelli A, Leoni A, Bossa R, Chiericozzi M, Galatulas I, Salvatore G. Synthesis of lactams with potential cardiotonic activity. Eur J Med Chem 1993; 28: 825-9.
[6] Eel-Feky SAH. Synthesis and anticonvulsant properties of some novel quinazolinone thiazolidine and 4-thiazolidine derivatives. Pharmazie 1993; 48: 28-34.
[7] Timothy M, Peter J, Brown, Daniel DS, Brad RH. The PPARs: from orpharn receptors to drug discovery. J Med Chem 2000; 43: 527-50.
[8] Shiva PS, Surinder SP. Chemistry and biological activity of thiazolidinediones. Chem Rev 1981; ISSUE NUMBER: 175-203.
[9] Kucukguzel GS, Oruc E, Sevim R, Sahin F, Ozbek A. Synthesis, characterization and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Eur J Med Chem 2002; 37:197-206.
[10] Frances CB. 4-thiazolidinones. Chem Rev 1961; ISSUE NUMBER: 464-521.
[11] Pattan SR, Kerkare P, Nikalje A, Hole MB. Synthesis and evaluation of some new thiazolidinedione derivatives for their antidiabetic activity. Asian J Res Chem 2009; 2: 123-6.
[12] Pattan SR, Khade AB, Pawar PD, Tarnalli AD,Kittur BS, Borkar SD. Synthesis of 2-amino [5'-(4-sulphonyl benzylidene)-2,4-thiazolidinedione]-6-fluro benzothiazoles as anti-inflammatory agents. Indian J Heterocyclic Chem 2007; 16: 299-300.
[13] Pattan SR, Suresh Ch, Pujar VD, Reddy VVK, Rasal VP, Koti BC. Synthesis and antidiabeticactivity of 2-amino[5(4-sulphonylbenzylidine) -2,4-thiazolidinedione]-7-chloro-6-fluorobenzothiazole.Indian J Chem 2005; 44B: 2404-8.
[14] Shelke KF, Sapkal SB, Shingare MS. Ionic liquid promoted efficient synthesis of 5-arylidene-2, 4-thiazolidinedione. Bulletin Catalysis Society India 2009; 8: 30-4.
[2] Goes AJS, DeLima MCA, Galdino SL, Pitta IR, Luu-Ducc C. Synthese et activite antifongique des chlorobenzyl benzylidene thiazolidinediones et imidazolidinediones substituees. Ann Pharm Francaises 1991; 49: 92-8.
[3] DeLima MCA, Costa DLB, Goes AJS, Galdino SL, Pitta IR, Luu-Ducc C. Synthese et activite antimicrobienne dederives chlorobenzyl benzylidene imidazolidinediones et thiazolidinediones substituees. Pharmazie 1992; 47: 182-4.
[4] Cantello BCC, Cawthorne MA, Cottam GP, Duff PT, Haigh D, Hindley RM Lister CA, Smith SA, Thurlby PL. [[ω-(Heterocyclylamino)alkoxy] benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents. J Med Chem 1994; 37:3977-85.
[5] Andreani A, Rambaldi M, Locatelli A, Leoni A, Bossa R, Chiericozzi M, Galatulas I, Salvatore G. Synthesis of lactams with potential cardiotonic activity. Eur J Med Chem 1993; 28: 825-9.
[6] Eel-Feky SAH. Synthesis and anticonvulsant properties of some novel quinazolinone thiazolidine and 4-thiazolidine derivatives. Pharmazie 1993; 48: 28-34.
[7] Timothy M, Peter J, Brown, Daniel DS, Brad RH. The PPARs: from orpharn receptors to drug discovery. J Med Chem 2000; 43: 527-50.
[8] Shiva PS, Surinder SP. Chemistry and biological activity of thiazolidinediones. Chem Rev 1981; ISSUE NUMBER: 175-203.
[9] Kucukguzel GS, Oruc E, Sevim R, Sahin F, Ozbek A. Synthesis, characterization and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Eur J Med Chem 2002; 37:197-206.
[10] Frances CB. 4-thiazolidinones. Chem Rev 1961; ISSUE NUMBER: 464-521.
[11] Pattan SR, Kerkare P, Nikalje A, Hole MB. Synthesis and evaluation of some new thiazolidinedione derivatives for their antidiabetic activity. Asian J Res Chem 2009; 2: 123-6.
[12] Pattan SR, Khade AB, Pawar PD, Tarnalli AD,Kittur BS, Borkar SD. Synthesis of 2-amino [5'-(4-sulphonyl benzylidene)-2,4-thiazolidinedione]-6-fluro benzothiazoles as anti-inflammatory agents. Indian J Heterocyclic Chem 2007; 16: 299-300.
[13] Pattan SR, Suresh Ch, Pujar VD, Reddy VVK, Rasal VP, Koti BC. Synthesis and antidiabeticactivity of 2-amino[5(4-sulphonylbenzylidine) -2,4-thiazolidinedione]-7-chloro-6-fluorobenzothiazole.Indian J Chem 2005; 44B: 2404-8.
[14] Shelke KF, Sapkal SB, Shingare MS. Ionic liquid promoted efficient synthesis of 5-arylidene-2, 4-thiazolidinedione. Bulletin Catalysis Society India 2009; 8: 30-4.
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