Citation: Hardik H. Jardosh, Chetan B. Sangani, Manish P. Patel, Ranjan G. Patel. One step synthesis of pyrido[1,2-a]benzimidazole derivatives of aryloxypyrazole and their antimicrobial evaluation[J]. Chinese Chemical Letters, ;2013, 24(2): 123-126. shu

One step synthesis of pyrido[1,2-a]benzimidazole derivatives of aryloxypyrazole and their antimicrobial evaluation

1.
Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar-388120, Gujarat, India

Corresponding author: Manish P. Patel,
Received Date: 3 September 2012
Available Online: 31 December 2012

A new series of pyrido[1,2-a]benzimidazole derivatives bearing the aryloxypyrazole nucleus have been synthesized by base-catalyzed cyclocondensation reaction through multi-component reaction (MCR) approach. All the synthesized compounds were investigated against a representative panel of pathogenic strains using broth microdilution minimum inhibitory concentration (MIC) method for their in vitro antimicrobial activity. Reviewing the data, majority of the compounds were found to be active against employed pathogens. SAR study explores that antimicrobial activity is strongly depends on the nature of the substituents at the ether linked aryl ring attached to the pyrazole unit, together with the substituent present on the C₅ of the benzimidazole unit.
- Aryloxypyrazole,
- Pyrido[1,2-a]benzimidazole,
- Multicomponent reaction,
- Antimicrobial activity
1. [1]
  [1] V. Aloush, S. Navon-Venezia, Y. Seigman-Igra, S. Cabili, Y. Carmeli, Multidrugresistant pseudomonas aeruginosa: risk factors and clinical impact, Antimicrob. Agents Chemother. 50 (2006) 43-48.
2. [2]
  [2] H.G. Kathrotiya, N.A. Patel, R.G. Patel, M.P. Patel, An efficient synthesis of 3'-quinolinyl substituted imidazole-5-one derivatives catalyzed by zeolite and their antimicrobial activity, Chin. Chem. Lett. 23 (2012) 273-276.
3. [3]
  [3] J.A. Makawana, M.P. Patel, R.G. Patel, Synthesis and in vitro antimicrobial activity of N-arylquinoline derivatives bearing 2-morpholinoquinoline moiety, Chin. Chem. Lett. 23 (2012) 427-430.
4. [4]
  [4] H.H. Jardosh, M.P. Patel, Microwave-assisted CAN-catalyzed solventfree synthesis of N-allyl quinolone-based pyrano[4,3-b]chromene and benzopyrano[3,2-c]chromene derivatives and their antimicrobial activity, Med. Chem. Res. (2012), http://dx.doi.org/10.1007/s00044-012-0085-z.
5. [5]
  [5] H.H. Jardosh, M.P. Patel, Lanthanum triflate-triggered synthesis of tetrahydroquinazolinone derivatives of N-allylquinolone and their biological assessment, J. Serb. Chem. Soc. 77 (2011) 1561-1570.
6. [6]
  [6] H.H. Jardosh, M.P. Patel, Microwave-induced CAN promoted atom-economic synthesis of 1H-benzo[b]xanthene and 4H-benzo[g]chromene derivatives of Nallyl quinolone and their antimicrobial activity, Med. Chem. Res. (2012), http://dx.doi.org/10.1007/s00044-012-0301-x.
7. [7]
  [7] N.K. Ladani, D.C. Mungra, M.P. Patel, R.G. Patel, Microwave assisted synthesis of novel Hantzsch 1 4-dihydropyridines, acridine-1,8-diones and polyhydroquinolines bearing the tetrazolo[1,5-a]quinoline moiety and their antimicrobial activity assess, Chin. Chem. Lett. 22 (2011) 1407-1410.
8. [8]
  [8] C.B. Sangani, D.C. Mungra, M.P. Patel, R.G. Patel, Synthesis and antimicrobial screening of pyrano[32-c]chromene derivatives of 1H-pyrazoles, Cent. Eur. J. Chem. 9 (2011) 635-647.
9. [9]
  [9] C.B. Sangani, D.C. Mungra, M.P. Patel, R.G. Patel, Synthesis and in vitro antimicrobial screening of new pyrano[43-b]pyrane derivatives of 1H-pyrazole, Chin. Chem. Lett. 23 (2012) 57-60.
10. [10]
  [10] C.B. Sangani, N.M. Shah, M.P. Patel, R.G. Patel, Microwave assisted synthesis of novel 4H-chromene derivatives bearing phenoxypyrazole and their antimicrobial activity assess, J. Serb. Chem. Soc. 77 (2012) 1165-1174.
11. [11]
  [11] L.S. Bai, Y. Wang, X.H. Liu, H.L. Zhu, B.A. Song, Novel dihydropyrazole derivatives linked with multi(hetero)aromatic ring: synthesis and antibacterial activity, Chin. Chem. Lett. 20 (2009) 427-430.
12. [12]
  [12] M.M.M. Ramiz, I.S.A. Hafiz, M.A.M.A. Reheim, H.M. Gaber, Pyrazolones as building blocks in heterocyclic synthesis: synthesis of new pyrazolopyran, pyrazolopyridazine and pyrazole derivatives of expected antifungicidal activity, J. Chin. Chem. Soc. 59 (2012) 72-80.
13. [13]
  [13] H.A. Abdel-Aziz, K.A. Al-Rashood, K.E.H. ElTahir, H.S. Ibrahim, Microwave-assisted synthesis of novel 34-bis-chalcone-N-arylpyrazoles and their anti-inflammatory activity, J. Chin. Chem. Soc. 58 (2011) 863-868.
14. [14]
  [14] A.R. Trivedi, V.R. Bhuva, B.H. Dholariya, et al., Novel dihydropyrimidines as a potential new class of antitubercular agents, Bioorg. Med. Chem. Lett. 20 (2010) 6100-6102.
15. [15]
  [15] M.D. Joksovic, V. Markovic, Z.D. Juranic, et al., Synthesis, characterization and antitumor activity of novel N-substituted a-amino acids containing ferrocenyl pyrazole-moiety, J. Organomet. Chem. 694 (2009) 3935-3942.
16. [16]
  [16] D.M. Lyons, K.M. Huttunen, K.A. Browne, et al., Inhibition of the cellular function of perforin by 1-amino-24-dicyanopyrido[1,2-a]benzimidazoles, Bioorg. Med. Chem. 19 (2011) 4091-4100.
17. [17]
  [17] A.J. Ndakala, R.K. Gessner, P.W. Gitari, et al., Antimalarial pyrido[12-a]benzimidazoles, J. Med. Chem. 54 (2011) 4581-4589.
18. [18]
  [18] S.M. Rida, S.A.M. EI-Hawash, H.T.Y. Fahmy, A.A. Hazzaa, M.M. El-Meligy, Synthesis of novel benzofuran and related benzimidazole derivatives for evaluation of in vitro anti-HIV-1, anticancer and antimicrobial activities, Arch. Pharm. Res. 29 (2006) 826-833.
19. [19]
  [19] National Committee for Clinical Laboratory Standards (NCCLS), 940, West Valley Road, Suite 1400, Wayne, Pennsylvania 19087-1898, USA. Performance standards for antimicrobial susceptibility testing; Twelfth Informational Supplement (ISBN 1-56238-454-6), M100-S12 M7 (2002).
20. [20]
  [20] H.Q. Xiao, G.P. Ouyang, X.D. Sun, et al., Synthesis of pyrazole oxime esters, Chin. J. Synth. Chem. 13 (2005) 600-602.
21. [21]
  [21] M.S. Park, H.J. Park, K.H. Park, K.I. Lee, Introduction of N-containing heterocycles into pyrazole by nucleophilic aromatic substitution, Synth. Commun. 34 (2004) 1541-1550.
22. [22]
  [22] H. Dai, L. Shi, H.J. Zhang, et al., Synthesis and bioactivities of novel 1-phenyl-3-methyl-5-aryloxy-1H-pyrazole-4-carbaldehyde-O-((2-chloropyridin-5-yl)methyl) oximes, Chin. J. Org. Chem. 32 (2012) 1060-1066.
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1.
沈阳化工大学材料科学与工程学院沈阳 110142