Abstract
An ultrasonic-assisted synthesis of bis-isoxazole derivatives was developed. Eight 3-(6-chloropyridin-3-yl)-5-{[(3-arylisoxazol-5-yl)methoxy]methyl}isoxazoles were synthesized by 1,3-dipolar cycloaddition reaction between substituted isoxazolyl alkyne compounds and 6-chloro-N-hydroxynicotinimidoyl chloride. The structures of the synthesized compounds were confirmed by HRMS, FTIR, 1H and 13C NMR spectroscopy. Wherein, the antifungal and antibacterial activities of target compounds were tested. The synthesized compounds 6a and 6h exhibited better antifungal activity in comparison with the standard drug itraconazole. The minimum inhibitory concentrations(MICs) of both compound 6a and compound 6h were both 4 µg/mL against Candida albicans ATCC 10231.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Zhu J., Mo J., Lin H. Z., Chen Y., Sun H. P., Bioorgan. Med. Chem., 2018, 26, 3065
Brown G. D., Denning D. W., Gow N. A., Levitz S. M., Netea M. G., White T. C., Sci. Transl. Med., 2012, 4, 165
Lee Y., Puumala E., Robbins N., Cowen L. E., Chem. Rev., 2020, DOI: https://doi.org/10.1021/acs.chemrev.0c00199
Haque F., Alfatah M., Ganesan K., Bhattacharyya M. S., Sci. Rep-UK, 2016, 6, 23575
Li S., Shi H., Chang W., Li Y., Zhang M., Qiao Y., Lou H., Bioorgan. Med. Chem., 2017, 25, 5764
Rajendran R., Borghi E., Falleni M., Perdoni F., Tosi D., Lappin D. F., Nile C., Eukaryot. Cell, 2015, 14, 834
Pairas G. N., Perperopoulou F., Tsoungas P. G., Varvounis G., ChemMedChem, 2017, 12, 408
Dravyakar B. R., Kawade D. P., Khedekar P. B., Bhusari K. P., Cheminform, 2009, 40, 1559
Lopes E. F., Penteado F., Thurow S., Pinz M., Reis A. S., Wilhelm E. A., Luchese C., Barcellos T., Dalberto B., Alves D., Silva M. S., Lenardão E. J., J. Org. Chem., 2019, 84(19), 12452
Jadhav S. B., Shastri R. A., Gaikwad K. V., Gaikwad S. V., Journal of Chemistry, 2009, 6, S183
Barbachyn M. R., Cleek G. J., Dolak L. A., Garmon S. A., Morris J., Seest E. P., Thomas R. C., Toops D. S., Watt W., Wishka D. G., Ford C. W., Zurenko G. E., Hamel J. C., Schaadt R. D., Stapert D., Yagi B. H., Adams W. J., Friis J. M., Slatter J. G., Sams J. P., Oien N. L., Zaya M. J., Wienkers L. C., Wynalda M. A, J. Med. Chem., 2003, 46(2), 284
Kumar A., Maurya R. A., Sharma S., Ahmad P., Singh A. B., Tamrakar A. K., Srivastava A. K., Bioorgan. Med. Chem., 2009, 17, 5285
Karabasanagouda A., Adhikari A. V., Girisha M., Cheminform, 2009, 40, 430
Li Z., Liu N., Tu J., Ji C. J., Han G. Y., Sheng C. Q., ACS Infect. Dis., 2019, 5, 1376
Hua X. W., Liu C., Zhou S., Chen M. G., Xiong L. X., Li Y. Q., Li Z. M., Chem. Res. Chinese Universities, 2017, 33(6), 882
Yang H. L., Xu G. X., Pei Y. Z., Chem. Res. Chinese Universities, 2017, 33(1), 61
Zhang D. W., Lin F., Li B. C., Liu H. W., Zhao T. Q., Zhang Y. M., Gu Q., Chem. Pap., 2015, 69, 1500
Quilico A., d’Alcontres G. S., Grünanger P., Nature, 1950, 166, 226
Minakata S., Okumura S., Nagamachi T., Takeda Y., Org. Lett., 2011, 13, 2966
Yoshimura A., Middleton K. R., Todora A. D., Kastern B. J., Kosk S. R., Maskaev A. V., Zhdankin V. V., Org. Lett., 2013, 15, 4010
Stevens R. V., Tetrahedron, 1976, 32, 1599
Katritzky A. R., Button M. A., Denisenko S. N., J. Heterocycl. Chem., 2000, 37, 1505
Souza F. B., Pimenta D. C., Stefani H. A., Tetrahedron Lett., 2016, 57, 1592
Driowya M., Puissant A., Robert G., Auberger P., Benhida R., Bougrin K., Ultrason. Sonochem., 2012, 19, 1132
Shi Y. P., Jiang K., Zheng R., Fu J. X., Yan L. Q., Gu Q., Zhang Y. M., Lin F., Chem. Biodivers., 2019, 16, e1800510
Desai N. C., Pandya D. D., Kotadiya G. M., Desai P., Med. Chem. Res., 2014, 23, 1474
Chhajed S. S., Upasani C. D., Jagdale S. B., J. Pharm. Res., 2010, 3, 1250
Li J., Liu H. W., Meng F. W., Yan L. Q., Shi Y. P., Zhang Y. M., Gu Q., Chem. Res. Chinese Universities, 2018, 34(2), 197
Clinical and Laboratory Standards Institute, NCCLS Reference Method for Broth Dilution Antifungal Susceptibility Testing of Filamentous Fungi, Proposed Standard, NCCLS Document M38-A, Philadelphia, USA, 1998, 18, 1
Yan L. Q., Fu J. X., Li S., Zhang J. L., Wang S., Gu Q., Zhang Y. M., Lin F., Chem. Res. Chinese Universities, 2021, DOI: https://doi.org/10.1007/s40242-020-0274-0
Gagneux A. R., Häfliger F., Meier R., Eugster C. H., Tetrahedron Lett., 1965, 6, 2081
Lunn M. L., Hogner A., Stensbøl T. B., Gouaux E., Egebjerg J., Kastrup J. S., J. Med. Chem., 2003, 46, 872
Murugesan N., Gu Z., Stein P. D., Spergel S., Mathur A., Leith L., Marino A., J. Med. Chem., 2000, 43, 3111
Murugesan N., Gu Z., Fadnis L., Tellew J. E., Baska R. A. F., Yang Y., Humphreys W. G., J. Med. Chem., 2005, 48, 171
Pirrung M. C., Tumey L. N., Raetz C. R., Jackman J. E., Snehalatha K., McClerren A. L., Rusche K. M., J. Med. Chem., 2002, 45, 4359
Renard J. F., Arslan D., Garbacki N., Pirotte B., de Leval X., J. Med. Chem., 2009, 52, 5864
Liu M. C., Lin T. S., Cory J. G., Cory A. H., Sartorelli A. C., J. Med. Chem., 2016, 39, 2586
Li G., Qian X., Cui J., Huang Q., Zhang R., Guan H., J. Agr. Food Chem., 2006, 54, 125
Acknowledgements
We are grateful to Dr. WANG Chunyu(College of Chemistry, Jilin University, China) for NMR spectra and Dr. WEI Zhonglin(College of Chemistry, Jilin University, China) for MS spectra.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflicts of interest.
Rights and permissions
About this article
Cite this article
Feng, F., Li, J., Zhang, Z. et al. Design, Ultrasonic-assisted Synthesis and Evaluation In vitro Antimicrobial Activity of Bis-isoxazole Derivatives Bearing Chloro-pyridinyl Group. Chem. Res. Chin. Univ. 37, 668–673 (2021). https://doi.org/10.1007/s40242-021-0009-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s40242-021-0009-x