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SYNTHESIS OF NOVEL FLUOROQUINOLONE-TRIAZOLE HYBRID COMPOUNDS AS ANTIMICROBIAL AGENTS

Year 2016, Volume: 3 Issue: 3, 515 - 534, 08.01.2017
https://doi.org/10.18596/jotcsa.55734

Abstract

Abstract: The hydrazide compound (2) was synthesized starting from 1-(2-fluorophenyl)piperazine via two stage. The reaction of compound (2) with different alkyl(aryl)isothiocyanates afforded the corresponding compounds (3a-c). 1,3-Thiazolidine derivatives (4a-c) were synthesized from the treatment of (3a-c) with ethyl bromoacetate. Mannich bases (6a-d) were yielded the treayment of (5a-c) with various suitable amines in the exictence of formaldehyde. Compound (3) derivatives were converted to 1,2,4-triazole as the starting material of fluoroquinolone analogues (11a-c). Finally synthesized compounds were examined their biological properties and some of these showed potent activity.

References

  • References
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  • Mentese MY, Bayrak H, Uygun Y, Mermer A, Ulker S, Karaoglu SA, Demirbas N. Microwave assisted synthesis of some hybrid molecules derived from norfloxacin and investigation of their biological activities, European Journal of Medicinal Chemistry. 2013; (67): 230-242.
  • Bayrak H, Demirbas A, Karaoglu SA, Demirbas N. Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities. Eur. J. Med. Chem. 2009; (44): 1057-1066.
  • Ulusoy-Guzeldemirci N, Kuçukbasmacı O. Synthesis and antimicrobial activity evaluation of new 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b]thiazole moiety. Eur. J. Med. Chem. 2010; (45): 63-68.
  • Bayrak H, Demirbas A, Demirbas N, Karaoglu SA. Synthesis of some new 1,2,4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activitie. Eur. J. Med. Chem. 2009; (44): 4362-4366.
  • Tozkoparan B, Küpeli E, Yesilada E, Ertan M. Preparation of 5-aryl-3-alkylthio-l,2,4-triazoles and corresponding sulfones with antiinflammatoryel analgesic activity. Bioorg. Med. Chem. 2007; (15): 1808-1814.
  • Stefanska J, Szulczyk D, Koziol AE, Miroslawc B, Kedziersk E, Fidecka S, Busonera B, Sanna G, Giliberti G, Colla PL, Struga M, Disubstituted thiourea derivatives and their activity on CNS: synthesis and biological evaluation. Eur.J. Med. Chem. 2012; (55): 205-213.
  • Kumar GVS, Rajendraprasad Y, Mallikarjuna BP, Chandrashekar SM, Kistayya C, Synthesis of some novel 2-substituted-5-[isopropylthiazole]clubbed 1,2,4-triazole and 1,3,4-oxadiazoles as potential antimicrobial and antitubercular agents. Eur. J. Med. Chem. 2010; (45): 2063-2074.
  • Küçükgüzel I, Tatar E, Küçükgüzel SG, Rollas S, Clercq ED. Synthesis of some novel thiourea derivatives obtained from 5-[(4-aminophenoxy)methyl]-4-alkyl/aryl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and evaluation as antiviral/anti-HIV and anti-tuberculosis agents. Eur. J. Med. Chem. 2008; (43): 381-392.
  • Rashid M, Husain A, Siddiqui AA, Mishra R. Benzimidazole clubbed with triazolo-thiadiazoles and triazolo-thiadiazines: new anticancer agents. Eur. J.Med. Chem. 2013; (62): 785-798.
  • Johnsona E, Espinel-Ingroff A, Szekelya A, Hockeyc H, Troked P. Activity of voriconazole, itraconazole, fluconazole and amphotericin B in vitro against 1763 yeasts from 472 patients in the voriconazole phase III clinical studies. Int. J. Antimicrob. Agents 2008; (32): 511-514.
  • Guo Q, Feng LS, Liu ML, Zhang YB, Chai Y, Lv K, Guo HY, Han LY. Synthesis and in vitro antibacterial activity of fluoroquinolone derivatives containing 3-(N0-alkoxycarbamimidoyl)-4-(alkoxyimino) pyrrolidines. European Journal of Medicinal Chemistry. 2010; (45): 5498-5506.
  • Cui SF, Ren Y, Zhang SL, Peng XM, Damu GLV, Geng RX, Zhou CE. Synthesis and biological evaluation of a class of quinolone triazoles as potential antimicrobial agents and their interactions with calfthymus DNA. Bioorganic & Medicinal Chemistry Letters. 2013; (23): 3267–3272.
  • Kaur K, Kumar V, Gupta GK. Trifluoromethylpyrazoles as anti-inflammatory and antibacterial agents. Journal of Fluorine Chemistry. 2015; (178): 306–326.
  • Rahim F, Zaman K, Ullah H, Taha M, Wadood A, Javed MT, Rehman W, Ashraf M, Uddin R, Uddin I, Asghar H, Khan AA, Khan KM. Synthesis of 4-thiazolidinone analogs as potent in vitro anti-urease agents. Bioorganic Chemistry. 2015; (63): 123–131.
  • Bala S, Sharma N, Kajal A, Kamboj S and Saini V. Mannich Bases: An Important Pharmacophore in Present Scenario. International Journal of Medicinal Chemistry. 2014; http://dx.doi.org/10.1155/2014/191072.
  • Oloyede GK, Willie IE, Adeeko OO. Synthesis of Mannich bases: 2-(3- Phenylaminopropionyloxy)-benzoic acid and 3-Phenylamino-1-(2,4,6-trimethoxy-phenyl)-propan-1-one, their toxicity, ionization constant, antimicrobial and antioxidant activities. Food Chemistry. 2014; (165): 515–521.
  • Abuo-Rahma G.A.A, Sarhan H.A, Gad G.F.M. Design, synthesis, antibacterial activity and hysicochemical parameters of novel N-4-piperazinyl derivatives of norfloxacin. Bioorg. Med. Chem. 2009; (17): 3879-3886.
  • Dixit S. K, Yadev N, Kumar S, Good L, Awasthi K, Synthesis and antibacterial activity of novel fluoroquinolone analogs, Medicinal Chem Research 2014; (23): 5237-5249.
  • Basoglu S, Yolal M, Demirbas A, Bektas H, Abbasoglu R, Demirbas N. Synthesis of linezolid-like molecules and evaluation of their antimicrobial activities. Turk. J. Chem. 2012; (36): 37–53.
  • Demirci S, Demirbas A, Ulker S, Alpay-Karaoglu S, and Demirbas N. Synthesis of Some Heterofunctionalized Penicillanic Acid Derivatives and Investigation of Their Biological Activities. Arch. Pharm. Chem. Life Sci. 2014; (347): 200–220.
  • Willanova, P. A.; National Committee for Clinical Laboratory Standard, NCCLS Document M7-A3, 1993; 13.
Year 2016, Volume: 3 Issue: 3, 515 - 534, 08.01.2017
https://doi.org/10.18596/jotcsa.55734

Abstract

References

  • References
  • Panda Siva S, Liaqat S, Girgis SA, Samir A, Hall D,Katritzky AR. Novel antibacterial active quinolone–fluoroquinolone conjugates and 2D-QSAR studies. Bioorganic & Medicinal Chemistry Letters. 2015; (25): 3816–3821.
  • Mentese MY, Bayrak H, Uygun Y, Mermer A, Ulker S, Karaoglu SA, Demirbas N. Microwave assisted synthesis of some hybrid molecules derived from norfloxacin and investigation of their biological activities, European Journal of Medicinal Chemistry. 2013; (67): 230-242.
  • Bayrak H, Demirbas A, Karaoglu SA, Demirbas N. Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities. Eur. J. Med. Chem. 2009; (44): 1057-1066.
  • Ulusoy-Guzeldemirci N, Kuçukbasmacı O. Synthesis and antimicrobial activity evaluation of new 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b]thiazole moiety. Eur. J. Med. Chem. 2010; (45): 63-68.
  • Bayrak H, Demirbas A, Demirbas N, Karaoglu SA. Synthesis of some new 1,2,4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activitie. Eur. J. Med. Chem. 2009; (44): 4362-4366.
  • Tozkoparan B, Küpeli E, Yesilada E, Ertan M. Preparation of 5-aryl-3-alkylthio-l,2,4-triazoles and corresponding sulfones with antiinflammatoryel analgesic activity. Bioorg. Med. Chem. 2007; (15): 1808-1814.
  • Stefanska J, Szulczyk D, Koziol AE, Miroslawc B, Kedziersk E, Fidecka S, Busonera B, Sanna G, Giliberti G, Colla PL, Struga M, Disubstituted thiourea derivatives and their activity on CNS: synthesis and biological evaluation. Eur.J. Med. Chem. 2012; (55): 205-213.
  • Kumar GVS, Rajendraprasad Y, Mallikarjuna BP, Chandrashekar SM, Kistayya C, Synthesis of some novel 2-substituted-5-[isopropylthiazole]clubbed 1,2,4-triazole and 1,3,4-oxadiazoles as potential antimicrobial and antitubercular agents. Eur. J. Med. Chem. 2010; (45): 2063-2074.
  • Küçükgüzel I, Tatar E, Küçükgüzel SG, Rollas S, Clercq ED. Synthesis of some novel thiourea derivatives obtained from 5-[(4-aminophenoxy)methyl]-4-alkyl/aryl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and evaluation as antiviral/anti-HIV and anti-tuberculosis agents. Eur. J. Med. Chem. 2008; (43): 381-392.
  • Rashid M, Husain A, Siddiqui AA, Mishra R. Benzimidazole clubbed with triazolo-thiadiazoles and triazolo-thiadiazines: new anticancer agents. Eur. J.Med. Chem. 2013; (62): 785-798.
  • Johnsona E, Espinel-Ingroff A, Szekelya A, Hockeyc H, Troked P. Activity of voriconazole, itraconazole, fluconazole and amphotericin B in vitro against 1763 yeasts from 472 patients in the voriconazole phase III clinical studies. Int. J. Antimicrob. Agents 2008; (32): 511-514.
  • Guo Q, Feng LS, Liu ML, Zhang YB, Chai Y, Lv K, Guo HY, Han LY. Synthesis and in vitro antibacterial activity of fluoroquinolone derivatives containing 3-(N0-alkoxycarbamimidoyl)-4-(alkoxyimino) pyrrolidines. European Journal of Medicinal Chemistry. 2010; (45): 5498-5506.
  • Cui SF, Ren Y, Zhang SL, Peng XM, Damu GLV, Geng RX, Zhou CE. Synthesis and biological evaluation of a class of quinolone triazoles as potential antimicrobial agents and their interactions with calfthymus DNA. Bioorganic & Medicinal Chemistry Letters. 2013; (23): 3267–3272.
  • Kaur K, Kumar V, Gupta GK. Trifluoromethylpyrazoles as anti-inflammatory and antibacterial agents. Journal of Fluorine Chemistry. 2015; (178): 306–326.
  • Rahim F, Zaman K, Ullah H, Taha M, Wadood A, Javed MT, Rehman W, Ashraf M, Uddin R, Uddin I, Asghar H, Khan AA, Khan KM. Synthesis of 4-thiazolidinone analogs as potent in vitro anti-urease agents. Bioorganic Chemistry. 2015; (63): 123–131.
  • Bala S, Sharma N, Kajal A, Kamboj S and Saini V. Mannich Bases: An Important Pharmacophore in Present Scenario. International Journal of Medicinal Chemistry. 2014; http://dx.doi.org/10.1155/2014/191072.
  • Oloyede GK, Willie IE, Adeeko OO. Synthesis of Mannich bases: 2-(3- Phenylaminopropionyloxy)-benzoic acid and 3-Phenylamino-1-(2,4,6-trimethoxy-phenyl)-propan-1-one, their toxicity, ionization constant, antimicrobial and antioxidant activities. Food Chemistry. 2014; (165): 515–521.
  • Abuo-Rahma G.A.A, Sarhan H.A, Gad G.F.M. Design, synthesis, antibacterial activity and hysicochemical parameters of novel N-4-piperazinyl derivatives of norfloxacin. Bioorg. Med. Chem. 2009; (17): 3879-3886.
  • Dixit S. K, Yadev N, Kumar S, Good L, Awasthi K, Synthesis and antibacterial activity of novel fluoroquinolone analogs, Medicinal Chem Research 2014; (23): 5237-5249.
  • Basoglu S, Yolal M, Demirbas A, Bektas H, Abbasoglu R, Demirbas N. Synthesis of linezolid-like molecules and evaluation of their antimicrobial activities. Turk. J. Chem. 2012; (36): 37–53.
  • Demirci S, Demirbas A, Ulker S, Alpay-Karaoglu S, and Demirbas N. Synthesis of Some Heterofunctionalized Penicillanic Acid Derivatives and Investigation of Their Biological Activities. Arch. Pharm. Chem. Life Sci. 2014; (347): 200–220.
  • Willanova, P. A.; National Committee for Clinical Laboratory Standard, NCCLS Document M7-A3, 1993; 13.
There are 23 citations in total.

Details

Journal Section Articles
Authors

Serap Başoğlu Özdemir This is me

Publication Date January 8, 2017
Submission Date June 23, 2016
Published in Issue Year 2016 Volume: 3 Issue: 3

Cite

Vancouver Başoğlu Özdemir S. SYNTHESIS OF NOVEL FLUOROQUINOLONE-TRIAZOLE HYBRID COMPOUNDS AS ANTIMICROBIAL AGENTS. JOTCSA. 2017;3(3):515-34.

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