Synthesis and antimicrobial screening of 4-thiazolidinone and 2-azetidinone derivatives of piperazine

Medicinal Chemistry Research

Volumn 22, Issue 2, 2013, Pages 699-706

  Shingade, Sunil G ^a   Bari, Sanjaykumar B ^a  

^a R C PATEL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH   (India)

Author keywords

2 Azetidinone; 4 Thiazolidinone; Antimicrobial activity; Piperazine; Schiff bases

Indexed keywords

2 (3 HYDROXY 4 METHOXYPHENYL) 3 (2 PIPERAZIN 1 YLETHYL) 1,3 THIAZOLIDIN 4 ONE; 2 [[(2 PIPERAZIN 1 YLETHYL)IMINO]METHYL]PHENOL; 2 AZETIDINONE DERIVATIVE; 2 METHOXY 4 [[(2 PIPERAZIN 1 YLETHYL)IMINO]METHYL]PHENOL; 2 METHOXY 5 [[(2 PIPERAZIN 1 YLETHYL)IMINO]METHYL]PHENOL; 3 [[(2 PIPERAZIN 1 YLETHYL)IMINO]METHYL]PHENOL; 4 [[(2 PIPERAZIN 1 YLETHYL)IMINO]METHYL]PHENOL; 4 THIAZOLIDINONE DERIVATIVE; ANTIINFECTIVE AGENT; N [(4 METHOXYPHENYL)METHYLIDENE] 2 PIPERAZIN 1YLETHANAMINE; N [FURAN 2 YLMETHYLIDENE] 2 PIPERAZIN 1 YLETHANAMINE; N [PHENYLMETHYLIDENE] 2 PIPERAZIN 1 YLETHANAMINE; PIPERAZINE DERIVATIVE; SCHIFF BASE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84873992855     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0063-5     Document Type: Article

References (29)

1. Abdel-Aziz HA, El-Zahabi HSA, Dawood KM (2010) Microwave-assisted synthesis and in vitro anti-tumor activity of 1,3,4-triaryl-5-N-arylpyrazole- carboxamides. Eur J Med Chem 30:1-6
2. Arnould JC, Boutron P, Pasquet MJ (1992) Synthesis and antibacterial activity of C4 substituted monobactams. Eur J Med Chem 27:131-140
3. Bali A, Malhotra S, Dhir H, Kumar A, Sharma A (2009) Synthesis and evaluation of 1-(quinoliloxypropyl)-4-aryl piperazines for atypical antipsychotic effect. Bio Med Chem Lett 19:3041-3044
4. Bali A, Sharma K, Bhalla A, Bala S, Reddy D, Singh A, Kumar A (2010) Synthesis, evaluation and computational studies on a series of acetophenone based 1-(aryloxypropyl)-4-(chloroaryl) piperazines as potential atypical antipsychotics. Eur J Med Chem 30:1-7
5. Bhandari SV, Bothara KG, Patil AA, Chitre TS, Sarkate AP, Gore ST, Dangre SC, Khachane CV (2009) Design, synthesis and pharmacological screening of novel antihypertensive agents using hybrid approach. Bio Med Chem 17:390-400
6. Chandra JNNS, Sadashiva CT, Kavitha CV, Rangappa KS (2006) Synthesis and in vitro antimicrobial studies of medicinally important novel N-alkyl and N-sulfonyl derivatives of 1-[bis(4-fluorophenyl)-methyl]piperazine. Bio Med Chem 14:6621-6627
7. Chaudhary P, Kumar R, Verma AK, Singh D, Yadav V, Chhillar AK, Sharmab GL, Chandra R (2006) Synthesis and antimicrobial activity of N-alkyl and N-aryl piperazine derivatives. Bio Med Chem 14:1819-1826
8. Chen H, Bai J, Jiao L, Guo Z, Yin Q, Li X (2009) Design, microwave-assisted synthesis and HIV-RT inhibitory activity of 2-(2,6-dihalophenyl)-3-(4,6-dimethyl-5-(un)substituted-pyrimidin-2-yl) -thiazolidin-4-ones. Bioorganic Med Chem 17:3980-3986
9. Choo HP, Chung B, Chung S (1999) Synthesis of piperazine derivatives and evaluation of their antihistamine and antibradykinin effects. Bio Med Chem Lett 9:2727-2730
10. Cunico W, Gomes CRB, Moreth M, Manhanini DP, Figueiredo IH, Penido C, Henriques MGMO, Varotti FP, Krettli AU (2009) Synthesis and antimalarial activity of hydroxyethylpiperazine derivatives. Eur J Med Chem 44:1363-1368
11. Foroumadi A, Ghodsi S, Emami S, Najjari S, Samadi N, Faramarzi MA, Beikmohammadi L, Shirazi FH, Shafiee A (2006) Synthesis and antibacterial activity of new fluoroquinolones containing a substituted N-(phenethyl) piperazine moiety. Bio Med Chem Lett 16:3499-3503
12. Foroumadi A, Emami S, Mansouri S, Javidnia A, Saeid-Adeli N, Shirazi FH, Shafiee A (2007) Synthesis and antibacterial activity of levofloxacin derivatives with certain bulky residues on piperazine ring. Eur J Med Chem 42:985-992
13. Halve AK, Bhadauria D, Dubey R (2007) N/C-4 substituted azetidin-2-ones: synthesis and preliminary evaluation as new class of antimicrobial agents. Bio Med Chem Lett 17:341-345
14. Keri RS, Hosamani KM, Shingalapur RV, Reddy HRS (2009) 2-Azetidinone derivatives: design, synthesis, in vitro anti-microbial, cytotoxic activities and DNA cleavage study. Eur J Med Chem 44:5123-5130
15. Kimura M, Masuda T, Yamada K, Kawakatsu N, Kubota N, Mitani M, Kishii K, Inazu M, Kiuchi Y, Oguchid K, Namikia T (2004) Antioxidative activities of novel diphenylalkyl piperazine derivatives with high affinities for the dopamine transporter. Bio Med Chem Lett 14:4287-4290
16. Lv P, Zhou CF, Chen J, Liu PG, Wang KR, Mao WJ, Li HQ, Yang Y, Xiong J, Zhu HL (2010) Design, synthesis and biological evaluation of thiazolidinone derivatives as potential EGFR and HER-2 kinase inhibitors. Bio Med Chem 18:314-319
17. Martyn DC, Cortese JF, Tyndall E, Dick J, Mazitschek R, Munoz B, Clardy J (2010) Antiplasmodial activity of piperazine sulphonamides. Bio Med Chem Lett 20:218-221
18. Papadopoulou C, Geronikaki A, Hadjipavlou-Litina D (2005) Synthesis and biological evaluation of new thiazolyl/benzothiazolyl-amides, derivatives of 4-phenyl-piperazine. Il Farmaco 60:969-973
19. Rao A, Balzarini J, Carbone A, Chimirri A, Clercq ED, Monforte AM, Monforte P, Pannecouque C, Zappala M (2004) 2-(2,6-Dihalophenyl)-3-(pyrimidin-2- yl)-1,3-thiazolidin-4-ones as non-nucleoside HIV-1 reverse transcriptase inhibitors. Antiviral Res 63:79-84
20. Rawal RK, Prabhakar YS, Kattia SB, Clercq ED (2005) 2-(Aryl)-3-furan-2- ylmethyl-thiazolidin-4-ones as selective HIV-RT inhibitors. Bio Med Chem 13:6771-6776
21. Ryckebusch A, Deprez-Poulain R, Debreu-Fontaine M, Vandaele R, Mouray E, Grellier P, Sergheraert C (2003) Synthesis and antimalarial evaluation of new 1,4-bis(3-aminopropyl)piperazine derivatives. Bio Med Chem Lett 13:3783-3787
22. 1-(7-chloro-4-quinolyl)-1,4-bis(3-aminopropyl)-piperazine derivatives. Bio Med Chem Lett 15:297-302
23. Shingade SG, Bari SB, Waghmare UB (2011) Synthesis and antimicrobial activity of 5-chloroindoline-2,3-dione derivatives. Med Chem Res. doi: 10.1007/s00044-011-9644-y
24. Soleiman HA (2011) Some fused/isolated heterocyclic of pyrimidine, β-lactam, thiazolidine and triazine derivatives. Open Catal J 4:18-26
25. Srinivas K, Srinivas U, Bhanuprakash K, Harakishore K, Murthy USN, Rao VJ (2006) Synthesis and antibacterial activity of various substituted s-triazines. Eur J Med Chem 41:1240-1246
26. Terzioglu N, Rijn RMV, Bakker RA, Esch IJPD, Leurs R (2004) Synthesis and structure-activity relationships of indole and benzimidazole piperazines as histamine H4 receptor antagonists. Bio Med Chem Lett 14:5251-5256
27. Tomar V, Bhattacharjee G, Kamaluddin, Kumar A (2007) Synthesis and antimicrobial evaluation of new chalcones containing piperazine or 2,5-dichlorothiophene moiety. Bio Med Chem Lett 17:5321-5324
28. Vicini P, Geronikaki A, Incerti M, Zani F, Deardenc J, Hewitt M (2008) 2-Heteroarylimino-5-benzylidene-4-thiazolidinones analogues of 2-thiazolylimino-5-benzylidene-4-thiazolidinones with antimicrobial activity: Synthesis and structure-activity relationship. Bio Med Chem 16:3714-3724
29. 2A receptor antagonists. Bio Med Chem 18:1665-1675