Synthesis, Characterization and Biological Activities of N-Acyl-3-(3-pyridyl)-5-aryl-pyrazoles

doi:10.1007/s40242-013-2469-0

Abstract

Abstract:

Ten novel N-acyl-3-(3-pyridyl)-5-aryl-pyrazoles were synthesized by Claisen condensation of the aryl methyl ketones with ethyl nicotinate, the cyclization with hydrazine hydrate and the N-acylation with acyl chloride in turn. The structures of all the compounds synthesized were confirmed by means of Fourier transform infrared(FTIR), ¹H NMR, mass spectroscopy and elemental analysis. The biological activities of the title compounds were examined by disc diffusion method against Escherichia coli, Staphylococcus aureus, Pyricularia oryzae and Rhizoctnia solani. All the N-acyl-3-(3-pyridyl)-5-aryl-pyrazoles exhibited a certain degree of antibacterial and antifungal activities. Comparatively, compounds 3c and 3d exhibited much significant antibacterial and antifungal activities than the other pyrazole derivatives.

Key words: N-Acyl-3-(3-pyridyl)-5-aryl-pyrazole, b-Diketone, 1H-Pyrazole, Biological activity

KANG Yan-fang, WANG Dun-jia, XU Ben-po, WEI Xian-hong, ZHENG Jing. Synthesis, Characterization and Biological Activities ofN-Acyl-3-(3-pyridyl)-5-aryl-pyrazoles[J]. Chemical Research in Chinese Universities, 2013, 29(2): 227-230.

References

[1] Mamolo M. G., Zampieri D., Falagiani V., Vio L., Banfi E., Il Farmaco, 2001,56, 593

[2] Rahimizadeh M., Pordel M., Bakavoli M., Rezaeian S., Sadeghian A., World J. Microbiol. Biotechnol., 2010, 26, 317

[3] Reddy C. S., Devi M. V., Sunitha M., Nagaraj A., Chem. Pharm. Bull., 2010, 58, 1622

[4] López S. N., Castelli M. V., Zacchino S. A., Domínguez J. N., Lobo G., Charris-Charris J., Cortés J. C. G., Ribas J. C., Devia C., Rodríguez A. M., Enriz R. D., Bioorg. Med. Chem., 2001, 9, 1999

[5] Gadakh A. V., Pandit C., Rindhe S. S., Karale B. K., Bioorg. Med. Chem. Lett.,2010, 20, 5572

[6] Lahm G. P., Selby T. P., Freudenberger J. H., Stevenson T. M., Myers B. J., Seburyamo G., Smith B. K., Flexner L., Clark C. E., Cordova D., Bioorg. Med. Chem. Lett.,2005, 15, 4898

[7] Bekhit A. A., Hymete A., Asfaw H., Bekhit A. E. A., Arch. Pharm. Life Sci., 2012, 345, 147

[8] Xu H., Hu X. H., Zou X. M., Zhu Y. Q., Liu B., Hu F. Z., Yang H. Z., Chem. Res. Chinese Universities, 2012, 28(5), 824

[9] Xu J. Y., Dong W. L., Xiong L. X., Li Z. M., Chem. J. Chinese Universities, 2012, 33(2), 298

[10] Gautam V., Chawla V., Sonar P. K., Saraf S. K., E-Journal of Chemistry,2010, 7, 1190

[11] Abdel-Wahab B. F., Abdel-Aziz H. A., Ahmed E. M., Arch. Pharm. Life Sci., 2008, 341, 734

[12] Wang D. J., Zheng C. Y., Fan L., J. Mol. Struct., 2009, 938, 311

[13] Wang D. J., Fan L., Zheng C. Y., Fang Z. D., J. Fluorine Chem., 2010, 131, 584

[14] Wang D. J., Kang Y. F., Xu B. P., Zheng J., Wei X. H., Spectrochimica Acta Part A,2013, 104, 419

[15] Kirkpatrick W. R., Turner T. M., Fothergill A. W., McCarthy D. I., Redding S. W., Rinaldi M. G., Patterson T. F., J. Clin. Microbiol., 1998, 36, 3429

[16] Hegazy W. H., Monatsh. Chem., 2001, 132, 639

[17] Bunting J. W., Kanter J. P., Nelander R., Wu Z., Can. J. Chem., 1995, 73, 1305

[18] Gautam V., Chawla V., Sonar P. K., Saraf S. K., J. Saudi Chem. Soc., 2013, 17(in press, doi:10.1016/j.jscs.2011.12.006)

[19] Manna F., Chimenti F., Fioravanti R., Bolasco A., Secci D., Chimenti P., Ferlini C., Scambia G., Bioorg. Med. Chem. Lett., 2005, 15, 4632

[20] Yang J. F., Cao H., Liu H., Li B. Q., Ma Y. M., J. Chin. Chem. Soc., 2011, 58, 369

Synthesis, Characterization and Biological Activities ofN-Acyl-3-(3-pyridyl)-5-aryl-pyrazoles

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	LIU Fei, LI Ren, YE Jing, REN Yujie, TANG Zhipeng, LI Rongchen, ZHANG Cuihua, LI Qunlin. Study of Aldo-keto Reductase 1C3 Inhibitor with Novel Framework for Treating Leukaemia Based on Virtual Screening and In vitro Biological Activity Testing [J]. Chemical Research in Chinese Universities, 2021, 37(3): 778-786.
[2]	HUA Xuewen, WEI Wei, ZHU Liangliang, ZHOU Yunyun. Synthesis and Bioactivity Evaluation of Novel N-Pyridylpyrazolemethanamine Derivatives [J]. Chemical Research in Chinese Universities, 2018, 34(5): 744-750.
[3]	CHENG Dandan, WEI Wei, LI Yuxin, HUA Xuewen, ZHOU Yunyun, LIU Jingbo, LI Yonghong, YU Shujing, XIONG Lixia, LI Zhengming. Design, Synthesis and Biological Activities of Novel 4,5-Disubstituted-3-S-(β-D-acetylglycosyl)-1,2,4-triazole Derivatives [J]. Chemical Research in Chinese Universities, 2017, 33(5): 758-764.
[4]	LIU Jingbo, LI Yuxin, CHEN Youwei, WU Changchun, WAN Yingying, WEI Wei, XIONG Lixia, ZHANG Xiao, YU Shujing, LI Zhengming. Design, Synthesis and Biological Activities of Novel Anthranilic Diamides Containing Dihydroisoxazoline and Isoxazole [J]. Chemical Research in Chinese Universities, 2016, 32(1): 41-48.
[5]	SHI Fangyuan, FANG Hao, XU Wenfang. Design, Synthesis and Biological Activity of Novel Chalcone Derivatives as Anti-influenza Agents [J]. Chemical Research in Chinese Universities, 2016, 32(1): 28-34.
[6]	TANG Xiaobin, LI Zhenghui, LI Yonghong, LIU Wei, YU Peng, LI Lixin, GUO Yu, YANG Cheng. Synthesis and Biological Evaluation of Novel Saccharin Derivatives Containing 1,2,3-Triazole Moiety [J]. Chemical Research in Chinese Universities, 2015, 31(1): 71-77.
[7]	SUN Xiao-xiao, SUN Tao, WANG Tai-yi, ZHANG Yan, LIU Hui-juan, WANG Quan, NIU Guo-jun, LIU Wei, ZHOU Hong-gang, YANG Cheng. Synthesis and Characterization of Pyrazoleanthrone Derivatives as Aurora A Kinase Inhibitors [J]. Chemical Research in Chinese Universities, 2013, 29(6): 1098-1103.
[8]	SUN Jing-bo, LIU Rong-wang, XUAN Li-li, LENG Wei-chun, WU Jin-chang. Synthesis and Anti-HIV Activity of Triazolo-fused 3',4'-Cyclic and 4'-Spiro Nucleoside Analogues [J]. Chemical Research in Chinese Universities, 2013, 29(3): 473-476.
[9]	LIANG Di, YANG Xiao-hong, SUN Wei, WANG Wen-na, YANG Jin-zhu, LIU Yin-yan, WANG Guang-shu. Synthesis, Crystal Structure and Biological Activities of Naproxen-eugenol Ester Prodrug [J]. Chemical Research in Chinese Universities, 2013, 29(2): 245-248.
[10]	CHEN Xiao-dong, WANG Chao, HU Ai-xi, YE Jiao, ZHANG Cui-yang. Synthesis, Crystal Structure and Biological Activites of Rotenone O-Alkyl Oximes [J]. Chemical Research in Chinese Universities, 2012, 28(5): 837-842 .
[11]	YAN Tao, YU Guan-ping, LIU Peng-fei, XIONG Li-xia, YU Shu-jing, LI Zheng-ming. Synthesis, Crystal Structure and Biological Activities of Novel Anthranilic(Isophthalic) Acid Esters [J]. Chemical Research in Chinese Universities, 2012, 28(1): 53-56.
[12]	WANG Shi-hui, WANG Yan, ZHU Yu-ying, LIU Si-jie, HAN Jian, ZHOU Yi-fan, LI. Design, Synthesis and Biological Evaluation of 2-Aroyl-3-aryl-6,7-dihydro-5H-furo[3,2-g]chromen Derivatives as a Novel Series of Estrogen Receptor Modulators [J]. Chemical Research in Chinese Universities, 2011, 27(1): 54-59.
[13]	ZHI Hui, CHEN Lan-mei, ZHANG Lin-lin, LIU Si-jie, David Chi Cheong WAN....... Design, Synthesis, and Biological Evaluation of 5H-Thiazolo[3,2-a]pyrimidine-6-carboxylic Acid Ethyl Ester Derivatives as a Novel Series of Acetylcholinesterase Inhibitors [J]. Chemical Research in Chinese Universities, 2009, 25(3): 332-337.
[14]	WANG Hao-an, LI Yu-xin, LI Zheng-ming , CHENG Hai-ying, WANG Su-hua , LIU Bin. Synthesis and Biological Activity of Novel 2,3-Dihydro-2-phenylsulfonylhydrazono-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)thiazoles [J]. Chemical Research in Chinese Universities, 2009, 25(1): 52-55.
[15]	XU Liang-zhong , XU Zhong-jie, ZHANG Gong-sheng, ZHOU Kai , ZHAI Zhi-wei . Synthesis, Characterization and Biological Activities of Novel Acrylamide Compounds [J]. Chemical Research in Chinese Universities, 2008, 24(5): 575-578.