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Synthesis and antioxidant activity of some novel derivatives of bis-2-azetidinones and bis-4-thiazolidinones

Year 2015, Volume: 2 Issue: 4, 22 - 31, 24.04.2015
https://doi.org/10.18596/jotcsa.24082

Abstract

In present study, several bis-2-azetidinones 2a-g and bis-4-thiazolidinones 3a-g have been synthesized from ethylenediaminebis-Schiff bases using conventional as well as microwave techniques. The newly synthesized compounds were established on the basis of spectroscopic techniques. Further, all compounds were screened for antioxidant activity; most of the titled compounds show potent activity.

References

  • Dave TK, Purohit DH, Akbari JD, Joshi SH. Synthesis and pharmacological study of thiazolidinones and mannich bases of 4-amino-3-mercapto-5-pyridin-3'-yl-[1,2,4]triazole. Indian J. Chem. 2007, 46B, 352-356.
  • Patel RB, Chikhalia, KH. Synthesis and biological activity of some 2,4,6-trisubstituted- 1,3,5-s-triazines J. Indian Chem. Soc. 2003, 80, 138.
  • Kumar VM, Nagraja TS, Shameer H, Jayachandran E, Sreenivasa GM. N – Substituted–3 –chloro– V, Nagaraja 2-azetidinones: Synthesis and characterization of new novel anti-inflammatory agents. J. Pharm. Sci. Res. 2009,1, 83-92.
  • Udupi RH, Kasinath NM, Bhat AR. Synthesis and biological activity of some 2-(6-methoxy Napthyl) propionamido azetidine-2-ones. Indian J. Heterocycl. Chem. 1998, 17, 221-224.
  • Samadhiya P, Sharma R, SrivastavaSK, Srivastava SD. Synthesis and biological evaluation of 4-thiazolidinone derivatives as antitubercular and antimicrobial agents. Arebian J. chem.2014,7,657-665
  • Chavan AA, Pai NR. Synthesis and Biological Activity of N-Substituted-3-chloro-2-azetidinones Molecules 2007, 12, 2467-2477.
  • Havaldar FH, Mishra SJ. Azetidin-2-ones and thiazolidin-4-ones as potential antimicrobial agents. Indian J. Heterocycl. Chem. 2004, 13, 197-200.
  • Patel KH, Metha AG. Synthesis and antifungal activity of azetidinones and thiazolidinones derivative of of 2,3- amino-6- (2-naphthalenyl) thiazolo [3, 2-d] thiadiazole E.J.Chem. 2006, 3, 267-273.
  • Trautman HD, Longe LM. The Synthesis Disubstituted-4-thiazolidones J. Am. Chem. Soc. 1948, 70, 3436-3439.
  • Surray AR. 4-Thiazolidones. IV. The Preparation of Some 3-Alkylaminoalkyl-2-aryl Derivatives J. Am. Chem. Soc. 1949, 71, 3354-3356.
  • Patel N, Shaikh F. Synthesis and antimicrobial activity of new 4-thiazolidinone derivatives containing 2-amino-6-methoxybenzothiazole. Saudi. Pharm. J.2010,18,129-136.
  • Doran WJ, Sholen HA. Dialkyl thiazolidinones J. Org. Chem. 1938, 3, 193-197.
  • Sayed BB. Synthesis and biological activity of some new 5-hydrothiazolo[4,3-b]- (thia) 1,3,4-oxa diazoles and 5-hydrothiazolo[3,4-b]-1,2,4-triazoles containing 1,2,3-selena(thia)diazole moiety Acta Pol Pharma (Poland), 1991, 13, 48.
  • Yadav R, Srivastav SD, Srivastav SK. synthesis, antimicrobial and anti-inflammatory activitiy of 4-oxothiazolidines and their 5-arylidines Indian J. Chem. 2005, 44B, 1262-1266.
  • Oza H, Joshi D, Parekh H. Synthesis and antitubercular activitiy of novel thiazolidinone derivatives. Indian J. Chem. 1998, 37B, 822.
  • Rawal RK, Tripathi R, Katti S, Pennacouque C, Clercq E. Design,synthesis, and evaluation of 2-aryl-3-heteroaryl-1,3-thiazolidin-4-ones as anti-HIV agents. Bioorg.Med.Chem. Lett.2007,15,1725-1731
  • Patel RB, Desai PS, Desai KR, Chikhalia KH. Synthesis of pyrimidine based thiazolidinones and azetidinones: Antimicrobial and antitubercular agens. Indian J. Chem. 2006 ,45B, 773-778.
  • Solankee AN, Patel KP, Patel RB. A facile synthesis and studies of some new 4-thiazolidinones and 5-arylidines Pelagia Research Library 2012, 3, 117-122.
  • Zangade SB, Mokle SS, Shinde AT, Vibhute YB. An atom efficient, green synthesis of 2-pyrazoline derivatives under solvent-free conditions using grinding techniqueGreen Chem. Lett. Rev. 2013,6, 123-127
  • Zangade S, Shinde A, Patil A, Vibhute Y. An efficient and facile ring closure of 2’-hydroxychalcones under irradiation of tungsten light. Eur.J.Chem. 2012, 3, 208-210.
  • Karamunge KG, Sayed M.A, Vibhute AY, Vibhute YB. Synthesis of some new chalcones, pyrazolines and acetyl pyrazolines derived from piperonal and halogenohydroxy acetophenones as antimicrobial agents J. Indian. Chem. Soc. 2011, 88, 443.
  • Zangade S, Mokle S, Chavan S, Vibhute Y. Orbital: Electronic J. Chem. 2-Methoxyethanol as an alternative reaction solvent for the synthesis of 1,5-benzodiazepines under microwave irradiation 2011, 3, 144-149.
  • Zangade SB, Shinde AT, Vibhute AY, Vibhute YB. An Improved Synthesis And Biological Evaluation Of Some New 4,5-dihydro-pyrazole-1-Carbaldehyde Derivatives Pak. J. Chem. 2012, 2, 1-6.
  • Bhusare SR, ShindeAB, Pawar RP, Vibhute YB. Synthesis and antimicrobial activity of Schiff bases, 4-thiazolidinones and 2-azetidinones. Indian J. Pharm. Sci. 2004, 66, 228-231.
  • Pawar RP, Andurkar NM, Vibhute YB. Studies on synthesis and antibacterial Schiff bases, 4-thiazolidinones and 2-azetidinones. J.Indian Chem. Soc. 1999, 76, 271-272
  • Shinde AT, Zangade SB,Chavan SB, Vibhute AY, Nalwar YS, Vibhute YB. A Practical Iodination of Aromatic Compounds by Using Iodine and Iodic Acid. Synth. Commun. 2010, 40, 3506-3513.
  • Varma S. A solvent-free organic synthesis. Using supported reagents and microwave irradiation Green Chem. 1999, 1, 43.
  • Borah R, Kalita DJ, Sarma JC. Microwave promoted selective preparations of acetals and esters from aldehydes Indian J. Chem. 2002, 41B, 1032.
  • Narl RS, Rao MN. Scavenging of free- radicals and inhibition of lipid peroxidation by 3-phenylsyndone. J.pharm. pharmacol. 1995, 47, 623
  • Kaur IP, Geetha T. Screeninig methods for antioxidants-a review. Mini Reviews in Med.Chem. 2006, 6, 305
  • Chavan SB, Zangade SB, Mokle SS, Vibhute YB. Synthesis of new bis-schiff bases via environmentally benign grindstone technique. Der Pharma Chemica, 2010, 2,139-143
  • Shinde A, Zangade S, Chavan S, Vibhute Y. Microwave induced synthesis of bis-schiff bases from propane-1,3-diamine as promising antimicrobial analogs. Org.Commun, 2014, 7,60-67

Yeni bis-2-azetidinon ve bis-4-tiyazolidinon türevlerinin sentezi ve antioksidan aktivitesi

Year 2015, Volume: 2 Issue: 4, 22 - 31, 24.04.2015
https://doi.org/10.18596/jotcsa.24082

Abstract

Bu çalışmada, pek çok bis-2-azetidinon bileşikleri (2a-g) ve bis-4-tiyazolidinonlar (3a-g) etilendiaminbis-Schiff bazlarından geleneksel yöntemlerle ve mikrodalga teknikleri ile sentezlenmiştir. Yeni sentezlenmiş bileşikler spektroskopik teknikler temelinde incelenmiştir. Bunun ötesinde, bütün bileşikler antioksidan aktivitesi bakımından görüntülenmiştir; bileşiklerin pek çoğu oldukça yüksek aktivite göstermektedir.

References

  • Dave TK, Purohit DH, Akbari JD, Joshi SH. Synthesis and pharmacological study of thiazolidinones and mannich bases of 4-amino-3-mercapto-5-pyridin-3'-yl-[1,2,4]triazole. Indian J. Chem. 2007, 46B, 352-356.
  • Patel RB, Chikhalia, KH. Synthesis and biological activity of some 2,4,6-trisubstituted- 1,3,5-s-triazines J. Indian Chem. Soc. 2003, 80, 138.
  • Kumar VM, Nagraja TS, Shameer H, Jayachandran E, Sreenivasa GM. N – Substituted–3 –chloro– V, Nagaraja 2-azetidinones: Synthesis and characterization of new novel anti-inflammatory agents. J. Pharm. Sci. Res. 2009,1, 83-92.
  • Udupi RH, Kasinath NM, Bhat AR. Synthesis and biological activity of some 2-(6-methoxy Napthyl) propionamido azetidine-2-ones. Indian J. Heterocycl. Chem. 1998, 17, 221-224.
  • Samadhiya P, Sharma R, SrivastavaSK, Srivastava SD. Synthesis and biological evaluation of 4-thiazolidinone derivatives as antitubercular and antimicrobial agents. Arebian J. chem.2014,7,657-665
  • Chavan AA, Pai NR. Synthesis and Biological Activity of N-Substituted-3-chloro-2-azetidinones Molecules 2007, 12, 2467-2477.
  • Havaldar FH, Mishra SJ. Azetidin-2-ones and thiazolidin-4-ones as potential antimicrobial agents. Indian J. Heterocycl. Chem. 2004, 13, 197-200.
  • Patel KH, Metha AG. Synthesis and antifungal activity of azetidinones and thiazolidinones derivative of of 2,3- amino-6- (2-naphthalenyl) thiazolo [3, 2-d] thiadiazole E.J.Chem. 2006, 3, 267-273.
  • Trautman HD, Longe LM. The Synthesis Disubstituted-4-thiazolidones J. Am. Chem. Soc. 1948, 70, 3436-3439.
  • Surray AR. 4-Thiazolidones. IV. The Preparation of Some 3-Alkylaminoalkyl-2-aryl Derivatives J. Am. Chem. Soc. 1949, 71, 3354-3356.
  • Patel N, Shaikh F. Synthesis and antimicrobial activity of new 4-thiazolidinone derivatives containing 2-amino-6-methoxybenzothiazole. Saudi. Pharm. J.2010,18,129-136.
  • Doran WJ, Sholen HA. Dialkyl thiazolidinones J. Org. Chem. 1938, 3, 193-197.
  • Sayed BB. Synthesis and biological activity of some new 5-hydrothiazolo[4,3-b]- (thia) 1,3,4-oxa diazoles and 5-hydrothiazolo[3,4-b]-1,2,4-triazoles containing 1,2,3-selena(thia)diazole moiety Acta Pol Pharma (Poland), 1991, 13, 48.
  • Yadav R, Srivastav SD, Srivastav SK. synthesis, antimicrobial and anti-inflammatory activitiy of 4-oxothiazolidines and their 5-arylidines Indian J. Chem. 2005, 44B, 1262-1266.
  • Oza H, Joshi D, Parekh H. Synthesis and antitubercular activitiy of novel thiazolidinone derivatives. Indian J. Chem. 1998, 37B, 822.
  • Rawal RK, Tripathi R, Katti S, Pennacouque C, Clercq E. Design,synthesis, and evaluation of 2-aryl-3-heteroaryl-1,3-thiazolidin-4-ones as anti-HIV agents. Bioorg.Med.Chem. Lett.2007,15,1725-1731
  • Patel RB, Desai PS, Desai KR, Chikhalia KH. Synthesis of pyrimidine based thiazolidinones and azetidinones: Antimicrobial and antitubercular agens. Indian J. Chem. 2006 ,45B, 773-778.
  • Solankee AN, Patel KP, Patel RB. A facile synthesis and studies of some new 4-thiazolidinones and 5-arylidines Pelagia Research Library 2012, 3, 117-122.
  • Zangade SB, Mokle SS, Shinde AT, Vibhute YB. An atom efficient, green synthesis of 2-pyrazoline derivatives under solvent-free conditions using grinding techniqueGreen Chem. Lett. Rev. 2013,6, 123-127
  • Zangade S, Shinde A, Patil A, Vibhute Y. An efficient and facile ring closure of 2’-hydroxychalcones under irradiation of tungsten light. Eur.J.Chem. 2012, 3, 208-210.
  • Karamunge KG, Sayed M.A, Vibhute AY, Vibhute YB. Synthesis of some new chalcones, pyrazolines and acetyl pyrazolines derived from piperonal and halogenohydroxy acetophenones as antimicrobial agents J. Indian. Chem. Soc. 2011, 88, 443.
  • Zangade S, Mokle S, Chavan S, Vibhute Y. Orbital: Electronic J. Chem. 2-Methoxyethanol as an alternative reaction solvent for the synthesis of 1,5-benzodiazepines under microwave irradiation 2011, 3, 144-149.
  • Zangade SB, Shinde AT, Vibhute AY, Vibhute YB. An Improved Synthesis And Biological Evaluation Of Some New 4,5-dihydro-pyrazole-1-Carbaldehyde Derivatives Pak. J. Chem. 2012, 2, 1-6.
  • Bhusare SR, ShindeAB, Pawar RP, Vibhute YB. Synthesis and antimicrobial activity of Schiff bases, 4-thiazolidinones and 2-azetidinones. Indian J. Pharm. Sci. 2004, 66, 228-231.
  • Pawar RP, Andurkar NM, Vibhute YB. Studies on synthesis and antibacterial Schiff bases, 4-thiazolidinones and 2-azetidinones. J.Indian Chem. Soc. 1999, 76, 271-272
  • Shinde AT, Zangade SB,Chavan SB, Vibhute AY, Nalwar YS, Vibhute YB. A Practical Iodination of Aromatic Compounds by Using Iodine and Iodic Acid. Synth. Commun. 2010, 40, 3506-3513.
  • Varma S. A solvent-free organic synthesis. Using supported reagents and microwave irradiation Green Chem. 1999, 1, 43.
  • Borah R, Kalita DJ, Sarma JC. Microwave promoted selective preparations of acetals and esters from aldehydes Indian J. Chem. 2002, 41B, 1032.
  • Narl RS, Rao MN. Scavenging of free- radicals and inhibition of lipid peroxidation by 3-phenylsyndone. J.pharm. pharmacol. 1995, 47, 623
  • Kaur IP, Geetha T. Screeninig methods for antioxidants-a review. Mini Reviews in Med.Chem. 2006, 6, 305
  • Chavan SB, Zangade SB, Mokle SS, Vibhute YB. Synthesis of new bis-schiff bases via environmentally benign grindstone technique. Der Pharma Chemica, 2010, 2,139-143
  • Shinde A, Zangade S, Chavan S, Vibhute Y. Microwave induced synthesis of bis-schiff bases from propane-1,3-diamine as promising antimicrobial analogs. Org.Commun, 2014, 7,60-67
There are 32 citations in total.

Details

Primary Language Turkish
Journal Section Articles
Authors

Avinash Shinde

Sainath Zangade This is me

Shivaji Chavan This is me

Sachin Tiwde This is me

Publication Date April 24, 2015
Submission Date February 10, 2015
Published in Issue Year 2015 Volume: 2 Issue: 4

Cite

Vancouver Shinde A, Zangade S, Chavan S, Tiwde S. Yeni bis-2-azetidinon ve bis-4-tiyazolidinon türevlerinin sentezi ve antioksidan aktivitesi. JOTCSA. 2015;2(4):22-31.