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.
1. [1]
  Meihui Cai , Yi Huang , Xingxing Ma , Qiuling Song . Exploring the Mysteries of the Petasis-Boronic Acid-Mannich Reaction. University Chemistry, 2025, 40(11): 184-190. doi: 10.12461/PKU.DXHX202412054
2. [2]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
3. [3]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
4. [4]
  Jun Huang , Jiangping Qin , Caijin Ban , Jingmei Yuan , Jing Yang , Guoping Yang . Visible-light induced cascade sulfonation/cyclization reaction in water towards sulfonated dihydroisoquinolino[1,2-b]quinazolinones. Chinese Chemical Letters, 2026, 37(2): 111379-. doi: 10.1016/j.cclet.2025.111379
5. [5]
  Jiao Chen , Zihan Zhang , Guojin Sun , Yudi Cheng , Aihua Wu , Zefan Wang , Wenwen Jiang , Fulin Chen , Xiuying Xie , Jianli Li . Benzo[4,5]imidazo[1,2-a]pyrimidine-based structure-inherent targeting fluorescent sensor for imaging lysosomal viscosity and diagnosis of lysosomal storage disorders. Chinese Chemical Letters, 2024, 35(11): 110050-. doi: 10.1016/j.cclet.2024.110050
6. [6]
  Huiru Sheng , Rui Qi , Chao Shen , Hao Xu , Jiabin Shen , Pengfei Zhang . Green synthesis of pyrrolo[1,2-a]quinoxaline derivatives as antineoplastic agents: a comprehensive chemistry laboratory teaching exploration. University Chemistry, 2026, 41(7): 266-273. doi: 10.12461/PKU.DXHX202505015
7. [7]
  Wei-Tao Dou , Qing-Wen Zeng , Yan Kang , Haidong Jia , Yulian Niu , Jinglong Wang , Lin Xu . Construction and application of multicomponent fluorescent droplets. Chinese Chemical Letters, 2025, 36(1): 109995-. doi: 10.1016/j.cclet.2024.109995
8. [8]
  Haifeng ZHENG , Xingzhe GUO , Yunwei WEI , Xinfang WANG , Huimin QI , Yuting YAN , Jie ZHANG , Bingwen LI . Post-synthetic modification strategy to construct Co-MOF composites for boosting oxygen evolution reaction activity. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 193-202. doi: 10.11862/CJIC.20250029
9. [9]
  Zixu Xie , Pengfei Zhang , Ziyao Zhang , Chen Chen , Xing Wang . The choice of antimicrobial polymers: Hydrophilic or hydrophobic?. Chinese Chemical Letters, 2024, 35(9): 109768-. doi: 10.1016/j.cclet.2024.109768
10. [10]
  Gaowa Xing , Yuxuan Li , Hongren Yao , Qiang Zhang , Zengnan Wu , Caihou Lin , Jin-Ming Lin . Tryptophan accumulation and inflammation of glioblastoma cells in a multicomponent microchip for gut-brain-axis simulation. Chinese Chemical Letters, 2025, 36(12): 111035-. doi: 10.1016/j.cclet.2025.111035
11. [11]
  Fuyun Chi , Man Zhang , Yiman Han , Fukui Shen , Shijie Peng , Bo Su , Yuanyuan Hou , Gang Bai . Covalent modulation of mPGES1 activity via α,β-unsaturated aldehyde group: Implications for downregulating PGE2 expression and antipyretic response. Chinese Chemical Letters, 2025, 36(4): 109913-. doi: 10.1016/j.cclet.2024.109913
12. [12]
  Bofei JIA , Zhihao LIU , Zongyuan GAO , Shuai ZHOU , Mengxiang WU , Qian ZHANG , Xiamei ZHANG , Shuzhong CHEN , Xiaohan YANG , Yahong LI . Cu(Ⅱ) and Cu(Ⅰ) complexes based on derivatives of imidazo[1,5-a]pyridine: Synthesis, structures, in situ metal-ligand reactions, and catalytic activity. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 1020-1036. doi: 10.11862/CJIC.20240317
13. [13]
  Yang Liu , Jing Liang , Mengzhu Zheng , Haoze Song , Lixia Chen , Hua Li . PD-L1/SHP2 dual PROTACs inhibit melanoma by enhancing T-cell killing activity. Chinese Chemical Letters, 2025, 36(6): 110317-. doi: 10.1016/j.cclet.2024.110317
14. [14]
  Gen Zhang , Ying Gu , Lin Li , Fuli Ma , Dan Yue , Xiaoguang Zhou , Chungui Tian . Anion-modulated HER and OER activity of 1D Co-Mo based interstitial compound heterojunctions for the effective overall water splitting. Chinese Chemical Letters, 2025, 36(7): 110110-. doi: 10.1016/j.cclet.2024.110110
15. [15]
  Zhilei Chen , Zhaoxia Li , Yunjiang Yu , Mingdeng Xiang , Cheng Ding , Entian Cui , Jizhou Jiang . Unveiling the enhanced activity origin of BiO_1-xCl/C₃N₅ photocatalyst in CO₂-to-CO directional conversion. Chinese Chemical Letters, 2026, 37(9): 112313-. doi: 10.1016/j.cclet.2025.112313
16. [16]
  Juntao Cai , Qian Wang , Xu Shen , Lifeng Zhu , Shiqing Jiang , Jian Yin , Chunhong Dong . Chemical strategies for the stereoselective construction of 1,2-cis-galacturonic and aminogalacturonic acid glycosides. Chinese Chemical Letters, 2026, 37(5): 112235-. doi: 10.1016/j.cclet.2025.112235
17. [17]
  Na Li , Zhihui Shang , Enyan Guo , Qifang Lu , Mingzhi Wei , Xue-Yang Ji , Xinghui Liu . Identifying dynamic active sites in Ni_xCo_1-_xMoO₄ nanotubes for enhanced electrocatalytic hydrogen evolution reaction. Chinese Chemical Letters, 2026, 37(8): 111908-. doi: 10.1016/j.cclet.2025.111908
18. [18]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
19. [19]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
20. [20]
  Yunli Xu , Xuwen Da , Lei Wang , Yatong Peng , Wanpeng Zhou , Xiulian Liu , Yao Wu , Wentao Wang , Xuesong Wang , Qianxiong Zhou . Ru(Ⅱ)-based aggregation-induced emission (AIE) agents with efficient ¹O₂ generation, photo-catalytic NADH oxidation and anticancer activity. Chinese Chemical Letters, 2025, 36(5): 110168-. doi: 10.1016/j.cclet.2024.110168

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(2008)
HTML views(49)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142