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.
-
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.
-
-
[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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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]
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
-
[2]
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
-
[3]
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
-
[4]
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
-
[5]
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
-
[6]
Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351
-
[7]
Yaxian Liang , Qingyi Li , Liwei Hu , Ruohan Zhai , Fan Liu , Lin Tan , Xiaofei Wang , Huixu Xie . Environmentally friendly polylysine gauze dressing for an innovative antimicrobial approach to infected wound management. Chinese Chemical Letters, 2024, 35(10): 109459-. doi: 10.1016/j.cclet.2023.109459
-
[8]
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
-
[9]
Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
-
[10]
You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
-
[11]
Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
-
[12]
Fangping Yang , Jin Shi , Yuansong Wei , Qing Gao , Jingrui Shen , Lichen Yin , Haoyu Tang . Mixed-charge glycopolypeptides as antibacterial coatings with long-term activity. Chinese Chemical Letters, 2025, 36(2): 109746-. doi: 10.1016/j.cclet.2024.109746
-
[13]
Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
-
[14]
Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228
-
[15]
Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Yongfeng Wang . Recent progress on surface chemistry Ⅰ: Assembly and reaction. Chinese Chemical Letters, 2024, 35(12): 110055-. doi: 10.1016/j.cclet.2024.110055
-
[16]
Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
-
[17]
Xinyi Hu , Riguang Zhang , Zhao Jiang . Depositing the PtNi nanoparticles on niobium oxide to enhance the activity and CO-tolerance for alkaline methanol electrooxidation. Chinese Journal of Structural Chemistry, 2023, 42(11): 100157-100157. doi: 10.1016/j.cjsc.2023.100157
-
[18]
Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
-
[19]
Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co2P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
-
[20]
Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(686)
- HTML views(10)