SYNTHESIS AND BIOLOGICAL ACTIVITY OF 2-(THIAZOLIDIN-4-ONE) PHENYL]-1H-PHENYLBENZIMIDAZOLES AND 2-[4-(AZETIDIN-2-ONE)-3-CHLORO-4- PHENYL] -1H-PHENYL BENZIMIDAZOLES
Abstract
A new series of 2-[4-(azetidin-2-one)-3-Chloro-4-phenyl]-1H-Phenylbenzimidazoles and 2-(thiazolidin-4-one)-Phenyl]-1H-Phenylbenzimidazoles were synthesized by the reaction of schiff base [2-(4-aminophenyl)-Benzimidazole and substituted Benzaldehyde] with chloroacetyl chloride and mercaptoacetic acid respectively. The chemical structures of the synthesized compounds were confirmed by IR, 1H-NMR, mass spectral and C, H, N analysis. The synthesized compounds were screened for antibacterial (Bacillus cereus, Escherichia coli, Micrococcus luteus, Klebssiela pneumoniae, Staphylococcus aureus and Salmonella epidermidis), antifungal (Aspergillus niger and Candida albicans), analgesic activity by writhing reflex method and anti-inflammatory activity by carrageenan induced paw edema method. The synthesized compound showed significant activity of antibacterial, antifungal, analgesic and anti-inflammatory activity comparable to that of standard.
Keywords:
Azetidinone, Thiazolidinone, Benzimidazole, Analgesic, Anti-inflammatory, Antibacterial, AntifungalDOI
https://doi.org/10.25004/IJPSDR.2010.020206References
1. Singh GS, Mmolotsi BJ. Synthesis of 2-azetidinones from 2-diazo-1, 2-diaryl ethanones and N-(2-thienylidene) imines as possible antimicrobial agents. Il Farmaco. 2005; 60(9): 727-730.
2. Rahman VPM, Mukhtar S, Ansari WH, Lemiere G. Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide. Eur J Med Chem. 2005; 40: 173-184.
3. Kucukguzel SG, Oruc EE, Rollas S, 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.
4. Rawal RK, Prabhakar YS, Katti SB, De Clercq E. 2-(Aryl)-3-furan-2-yl-methyl-thiazolidin-4-ones as selective HIV-RT inhibitors. Bioorg Med Chem 2005; 13: 6771-6776.
5. Vigorita MG, Ottana R, Monforte F, Maccari R, Trovato A, Monforte MT, Taviano MF. Synthesis and anti-inflammatory, analgesic activity of 3, 3’-(1-2-Ethanediyl)-bis [2-aryl-4-thiazolidinone] chiral compounds part 10. Bioorg Med Chem Lett. 2001; 11: 2791-2794.
6. Goel B, Ram T, Tyagi R, Bansal E, Kumar A, Mukherjee D, Sinha JN. 2-Substituted-3-(4-bromo-2-carboxyphenyl)-5-methyl-4-thiazolidinones as potential anti-inflammatory agents. Eur J Med Chem. 1999; 34: 265-269.
7. Guven OO, Erdogan T, Goker H, Yildiz S. Synthesis and antimicrobial activity of some novel phenyl and benzimidazole substituted benzyl ethers. Bioorg Med Chem Lett. 2007; 17(8): 2233-6.
8. Mohamed BG, Abdel-Alim AA, Hussein MA. Synthesis of 1-acyl-2-alkylthio-1, 2, 4-triazolobenzimidazoles with antifungal, anti-inflammatory and analgesic effects. Acta Pharm. 2006; 56(1): 31-48.
9. Starcevic K, Kralj M, Ester K, Sabol I, Grce M, Pavelic K, Karminski-Zamola G. Synthesis, antiviral and antitumor activity of 2-substituted-5-amidino-benzimidazoles. Bioorg Med chem. 2007; 15(13): 4419-26.
10. Ayhan-Kilcigil G, Kus C, Ozdamar ED, Can-Eke B, Iscan M. Synthesis and antioxidant capacities of some new benzimidazole derivatives. Arch Pharm. 2007; 340(11): 607-611.
11. Mavrova ATs, Anichina KK, Vuchev DI, Tsenov JA, Denkova PS, Kondeva MS, Micheva MK. Antihelminthic activity of some newly synthesized 5(6) - un)substituted –1H-benzimidazol-2-ylthioacetylpiperazine derivatives. Eur J Med Chem. 2006; 41(12): 1412-20.
12. Chua MS, Shi DF, Wrigley S, Bradshaw TD, Hutchinson I, Shaw PN, Barrett DA, Stanley LA, Stevens MFG. Antitumor benzothiazoles 7: Synthesis of 2(4-acylaminophenyl)benzothiazoles and investigations into the role of acetylation in the antitumor activities of the parent amines. J Med Chem. 1999; 42(3): 381-392.
13. Conli M, Gulielmetli R, Metzger J. Synthesis, Physicochemical properties of schiff base in the benzothiazole series. Bull Soc Chim Fr. 1967; 8: 2834-2841.
14. Maurya MR, Kumar A, Ebel M, Rehder D, Synthesis, characterization, reactivity and catalytic potential of model vanadium (IV, V) complexes with benzimidazole-derived ONN donor ligands. Inorg Chem. 2006; 45(15): 5924-37.
15. Fahmy HH, El-Eraky W. Synthesis and evaluation of the analgesic and anti-inflammatory activities of o-substituted salicylamides. Arch Pharm Res. 2001; 24(3): 171-179.
16. More SV, Dongarkhadekar DV, Chavan RN, Jadhav WN, Bhusare SR, Pawar RP. Synthesis and antibacterial activity of new schiff bases, 4-thiazolidinones and 2-azetidinones. J Indian Chem soc. 2002; 79: 768-769.
17. Gillespie SH. “Medical Microbiology–Illustrated”, Butterworth Heinemann Ltd., United Kingdom, 1994, pp. 234-247.
18. Hawkey PM, Lewis DA. “Medical Bacteriology–A practical approach”, Oxford University Press, United Kingdom. 1994, pp. 181-194.
19. Turner RA. Peter Hebborn (Edt): “Screening Methods in Pharmacology”, Vol. II, Academic Press, New York, 1971.
2. Rahman VPM, Mukhtar S, Ansari WH, Lemiere G. Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide. Eur J Med Chem. 2005; 40: 173-184.
3. Kucukguzel SG, Oruc EE, Rollas S, 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.
4. Rawal RK, Prabhakar YS, Katti SB, De Clercq E. 2-(Aryl)-3-furan-2-yl-methyl-thiazolidin-4-ones as selective HIV-RT inhibitors. Bioorg Med Chem 2005; 13: 6771-6776.
5. Vigorita MG, Ottana R, Monforte F, Maccari R, Trovato A, Monforte MT, Taviano MF. Synthesis and anti-inflammatory, analgesic activity of 3, 3’-(1-2-Ethanediyl)-bis [2-aryl-4-thiazolidinone] chiral compounds part 10. Bioorg Med Chem Lett. 2001; 11: 2791-2794.
6. Goel B, Ram T, Tyagi R, Bansal E, Kumar A, Mukherjee D, Sinha JN. 2-Substituted-3-(4-bromo-2-carboxyphenyl)-5-methyl-4-thiazolidinones as potential anti-inflammatory agents. Eur J Med Chem. 1999; 34: 265-269.
7. Guven OO, Erdogan T, Goker H, Yildiz S. Synthesis and antimicrobial activity of some novel phenyl and benzimidazole substituted benzyl ethers. Bioorg Med Chem Lett. 2007; 17(8): 2233-6.
8. Mohamed BG, Abdel-Alim AA, Hussein MA. Synthesis of 1-acyl-2-alkylthio-1, 2, 4-triazolobenzimidazoles with antifungal, anti-inflammatory and analgesic effects. Acta Pharm. 2006; 56(1): 31-48.
9. Starcevic K, Kralj M, Ester K, Sabol I, Grce M, Pavelic K, Karminski-Zamola G. Synthesis, antiviral and antitumor activity of 2-substituted-5-amidino-benzimidazoles. Bioorg Med chem. 2007; 15(13): 4419-26.
10. Ayhan-Kilcigil G, Kus C, Ozdamar ED, Can-Eke B, Iscan M. Synthesis and antioxidant capacities of some new benzimidazole derivatives. Arch Pharm. 2007; 340(11): 607-611.
11. Mavrova ATs, Anichina KK, Vuchev DI, Tsenov JA, Denkova PS, Kondeva MS, Micheva MK. Antihelminthic activity of some newly synthesized 5(6) - un)substituted –1H-benzimidazol-2-ylthioacetylpiperazine derivatives. Eur J Med Chem. 2006; 41(12): 1412-20.
12. Chua MS, Shi DF, Wrigley S, Bradshaw TD, Hutchinson I, Shaw PN, Barrett DA, Stanley LA, Stevens MFG. Antitumor benzothiazoles 7: Synthesis of 2(4-acylaminophenyl)benzothiazoles and investigations into the role of acetylation in the antitumor activities of the parent amines. J Med Chem. 1999; 42(3): 381-392.
13. Conli M, Gulielmetli R, Metzger J. Synthesis, Physicochemical properties of schiff base in the benzothiazole series. Bull Soc Chim Fr. 1967; 8: 2834-2841.
14. Maurya MR, Kumar A, Ebel M, Rehder D, Synthesis, characterization, reactivity and catalytic potential of model vanadium (IV, V) complexes with benzimidazole-derived ONN donor ligands. Inorg Chem. 2006; 45(15): 5924-37.
15. Fahmy HH, El-Eraky W. Synthesis and evaluation of the analgesic and anti-inflammatory activities of o-substituted salicylamides. Arch Pharm Res. 2001; 24(3): 171-179.
16. More SV, Dongarkhadekar DV, Chavan RN, Jadhav WN, Bhusare SR, Pawar RP. Synthesis and antibacterial activity of new schiff bases, 4-thiazolidinones and 2-azetidinones. J Indian Chem soc. 2002; 79: 768-769.
17. Gillespie SH. “Medical Microbiology–Illustrated”, Butterworth Heinemann Ltd., United Kingdom, 1994, pp. 234-247.
18. Hawkey PM, Lewis DA. “Medical Bacteriology–A practical approach”, Oxford University Press, United Kingdom. 1994, pp. 181-194.
19. Turner RA. Peter Hebborn (Edt): “Screening Methods in Pharmacology”, Vol. II, Academic Press, New York, 1971.
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01-04-2010
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“SYNTHESIS AND BIOLOGICAL ACTIVITY OF 2-(THIAZOLIDIN-4-ONE) PHENYL]-1H-PHENYLBENZIMIDAZOLES AND 2-[4-(AZETIDIN-2-ONE)-3-CHLORO-4- PHENYL] -1H-PHENYL BENZIMIDAZOLES”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 2, no. 2, Apr. 2010, pp. 115-9, https://doi.org/10.25004/IJPSDR.2010.020206.
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Copyright (c) 2010 P. Shanmugapandiyan, K. S. Denshing, R. Ilavarasan, N. Anbalagan, R. Nirmala
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How to Cite
“SYNTHESIS AND BIOLOGICAL ACTIVITY OF 2-(THIAZOLIDIN-4-ONE) PHENYL]-1H-PHENYLBENZIMIDAZOLES AND 2-[4-(AZETIDIN-2-ONE)-3-CHLORO-4- PHENYL] -1H-PHENYL BENZIMIDAZOLES”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 2, no. 2, Apr. 2010, pp. 115-9, https://doi.org/10.25004/IJPSDR.2010.020206.
