Synthesis of highly potent piperazine-linked benzothiazolyl-4-thiazolidinones via catalytic N-formylation: Antibacterial drug design

Medicinal Chemistry Research

Volumn 23, Issue 9, 2014, Pages 4099-4107

  Patel, Rahul V ^a   Park, Se Won ^a  

^a Konkuk University   (South Korea)

Author keywords

4 Thiazolidinones; Antibacterial activity; Benzothiazole; N Formylation; Piperazine; Schiff base

Indexed keywords

EID: 84895916206     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-014-0987-z     Document Type: Article

References (34)

1. Altintas H, Ates O, Kocabalkanli A, Birteksoz S, Otuk G (2005) Synthesis, characterization and evaluation of antimicrobial activity of Mannich bases of some 2-[(carbethoxymethylthiazole-2-yl)imino]-4-thiazolidinones. Ind J Chem 44B:585-590
2. Bhojegowd M, Nizam A, Pasha M (2010) Amberlite IR-120: a reusable catalyst for N-formylation of amines with formic acid using microwaves. Chin J Catal 31:518-520
3. Chandra Shekhar A, Ravi Kumar A, Sathaiah G, Luke Paul V, Sridhar M, Shanthan Rao P (2009) Facile N-formylation of amines using Lewis acids as novel catalysts. Tetrahedron Lett 50:7099-7101
4. Chavan AA, Pai NR (2007) Synthesis and antimicrobial screening of 5-arylidene-2-imino-4-thiazolidinone. ARKIVOC 16:148-155
5. Chen FMF, Benoiton NL (1979) A general method for formylating sensitive amino acid esters. Synthesis 9:709-714
6. Duezek W, Deutsch J, Vieth S, Niclas HJ (1996) A simple and convenient synthesis of N-formyl amino acid esters under mild conditions. Synthesis 1:37-38
7. Gillespie SH (1994) Medical microbiology - illustrated. Butterworth-Heinemann, Dunfermline, pp 234-247
8. Green TW, Wuts PGM (1999) Protective groups in organic synthesis, 3rd edn. Wiley, New York, p 116
9. Hawkey PM, Lewis DA (1994) Medical bacteriology - a practical approach. Oxford University Press, Oxford, pp 181-194
10. Hosseini-Sarvari M, Sharghi H (2006) ZnO as a new catalyst for N-formylation of amines under solvent-free conditions. J Org Chem 71:6652-6654
11. Jain AK, Vaidya A, Ravichandran V, Kashaw SK, Agrawal RK (2012) Recent developments and biological activities of thiazolidinone derivatives: a review. Bioorg Med Chem 20:3378-3395
12. Kim JG, Jang DO (2010a) Indium-catalyzed N-formylation of amines under solvent-free conditions. Synlett 8:1231-1234
13. Kim JG, Jang DO (2010b) Facile and highly efficient N-formylation of amines using a catalytic amount of iodine under solvent-free conditions. Synlett 14:2093-2096
14. 25 or sulfated titania. J Mol Catal A 334:98-102
15. Luca LD, Giacomelli G, Porcheddu A, Salaris M (2014) A new, simple procedure for the synthesis of formyl amides. Synlett 14:2570-2572
16. 3 nanocrystallites as a magnetically Bronsted acid for N-formylation of amines. Appl Catal A 377:64-69
17. 3-promoted synthesis of formamide derivatives via dichlorocarbene generated from chloroform. Synthesis 15:2317-2320
18. Nagarajan AS, Kamalraj S, Muthumary J, Reddy BSR (2009) Synthesis of biologically active benzothiazole substituted thiazolidinone derivatives via cyclization of unsymmetrical imines. Ind J Chem 48B:1577-1582
19. Pareek D, Chaudhary M, Pareek PK, Kant R, Ojha KG, Pareek R, Iraqia SMU, Pareeka A (2010) Synthesis of some bioactive 4-thiazolidinone derivatives incorporating benzothiazole moiety. Der Chem Sin 1:22-35
20. Patel NB, Patel SD (2010) Synthesis and antimicrobial study of fluoroquinolone based 4-thiazolidinones. Med Chem Res 19:757-770
21. Patel NB, Shaikh FM (2010) Synthesis and antimicrobial activity of new 4-thiazolidinone derivatives containing 2-amino-6-methoxybenzothiazole. Saudi Pharm J 18:129-136
22. Patel RV, Kumari P, Rajani DP, Chikhalia KH (2011) Synthesis and studies of novel 2-(4-cyano-3-trifluoromethylphenyl amino)-4-(quinoline-4-yloxy)-6-(piperazinyl/piperidinyl)-s-triazines as potential antimicrobial, antimycobacterial and anticancer agents. Eur J Med Chem 46:4354-4365
23. Patel D, Kumari P, Patel NB (2012a) Synthesis and biological evaluation of some thiazolidinones as antimicrobial agents. Eur J Med Chem 48:354-362
24. Patel RV, Kumari P, Rajani DP, Chikhalia KH (2012b) A new class of 2-(4-cyanophenyl amino)-4-(6-bromo-4-quinolinyloxy)-6-piperazinyl(piperidinyl)-1,3,5-triazine analogues with antimicrobial/antimycobacterial activity. J Enzyme Inhib Med Chem 27:370-379
25. Patel RV, Kumari P, Rajani DP, Pannecouque C, De Clercq E, Chikhalia KH (2012c) Antimicrobial, anti-TB, anticancer and anti-HIV evaluation of newer s-triazine based heterocycles. Future Med Chem 4:1053-1065
26. Patel RV, Patel PK, Kumari P, Rajani DP, Chikhalia KH (2012d) Synthesis of benzimidazolyl-1,3,4-oxadiazol-2ylthio-N-phenyl(benzothiazolyl) acetamides as antibacterial, antifungal and antituberculosis agents. Eur J Med Chem 53:41-51
27. Patel RV, Kumari P, Chikhalia KH (2013a) New quinolinyl-1,3,4-oxadiazoles: synthesis, in vitro antibacterial, antifungal and antituberculosis studies. Med Chem 9(2013):596-607
28. Patel RV, Patel JK, Nile SH, Park SW (2013b) Copper (II) triflate promoted multicomponent catalytic clubbing of piperazinyl-thiazoloquinolines and thiazolocoumarins as antimicrobials. Arch Pharm Chem Life Sci 346:221-231
29. Pathare SP, Sawant RV, Akamanchi KG (2012) Sulfated tungstate catalyzed highly accelerated N-formylation. Tetrahedron Lett 53:3259-3263
30. Sawhney SN, Boykin DW (1979) Transmission of substituent effects in heterocyclic systems by carbon-13 nuclear magnetic resonance: benzothiazoles. J Org Chem 44:1136-1142
31. Shingade SG, Bari SB (2013) Synthesis and antimicrobial screening of 4-thiazolidinone and 2-azetidinone derivatives of piperazine. Med Chem Res 22:699-706
32. Verma A, Saraf SK (2008) 4-Thiazolidinone - a biologically active scaffold. Eur J Med Chem 43:897-905
33. Waki J, Meinhofer J (1997) Efficient preparation of Nα-formylamino acid tert-butyl esters. J Org Chem 42:2019-2021
34. World Health Organization (WHO) (2013) Infectious diseases. http://www.who.int/topics/infectious-diseases/en/. Accessed 5 Oct 2013