Synthesis, antimycobacterial and antifungal evaluation of new 4-(furan-2-ylmethyl)-6-methylpyridazin-3(2H)-ones

Article Sidebar

PDF (764 kB) Supplementary Mat. PDF (3.78 MB)
Published: Apr 1, 2024
DOI: https://doi.org/10.2298/JSC230424040K
Keywords:
pyridazinone furan biological activity

Main Article Content

Burcu Karayavuz
Department of Pharmaceutical Chemistry, Faculty of Farmacy, Hacettepe University, Ankara, Turkey
Siva Krishna Vagolu
Unit for Genome Dynamics, Department of Microbiology, University of Oslo, Oslo, Norway
Didem Kart
Department of Pharmaceutical Microbiology, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey
Tone Tønjum
Unit for Genome Dynamics, Department of Microbiology, University of Oslo, Oslo, Norway
https://orcid.org/0000-0002-1709-6921
Oya Unsal-Tan
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Hacettepe University, 06100, Ankara, Turkey
https://orcid.org/0000-0002-4152-069X

Abstract

This study reports the synthesis and evaluation of a series of new pyridazin-3-ones with furan moieties 5a-j and 6a-f, to test for their antimycobacterial and antifungal activities. The structures of the target compounds were confirmed by elemental analysis and spectroscopic techniques (IR, mass, 1H- and 13C- NMR). Amongst the compounds tested, 5e, 5g, 5i and 6e exhibited highest activity against Mycobacterium tuberculosis, while 5h, 6d and 6f showed moderate in vitro antifungal activities against C. albicans and C. parapsilosis.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

Article Details

How to Cite
[1]
B. . Karayavuz, S. K. Vagolu, D. Kart, T. Tønjum, and O. Unsal-Tan, “Synthesis, antimycobacterial and antifungal evaluation of new 4-(furan-2-ylmethyl)-6-methylpyridazin-3(2H)-ones”, J. Serb. Chem. Soc., Apr. 2024.
Issue
Accepted Manuscripts
Section
Biochemistry & Biotechnology
Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Creative Commons лиценца
Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution license 4.0 that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.

Read more....

Crossref
Scopus
Google Scholar
Europe PMC

Funding data

References

World Health Organization. Global Tuberculosis Report 2022

M. M. Sirim, V. S. Krishna, D. Sriram, O. Unsal Tan, Eur. J. Med. Chem. 188 (2020) 112010 (https://doi.org/10.1016/j.ejmech.2019.112010)

D. Falzon, H. J. Schünemann, E. Harausz, L. González-Angulo, C. Lienhardt, E. Jaramillo, K. Weyer, Eur. Respir. J. 49 (2017); 1

(http://dx.doi.org/10.1183/13993003.02308-2016)

A. Koch, H. Cox, V. Mizrahi, Curr. Opin. Pharmacol. 42 (2018) 7 (https://doi.org/10.1016/j.coph.2018.05.013)

V. Dartois, Nat. Rev. Microbiol. 12 (2014) 159 (https://doi.org/10.1038/nrmicro3200)

H. Getahun, A. Matteelli, R. E. Chaisson, M. Raviglione, N. Engl. J. Med. 372 (2015) 2127 (https://doi.org/10.1056/NEJMRA1405427)

G. Grüber, Prog. Biophys. Mol. Biol. 152 (2020) 2 (https://doi.org/10.1016/J.PBIOMOLBIO.2020.02.003)

O. U. Tan, K. Ozadali, P. Yogeeswari, D. Sriram, A. Balkan, Med. Chem. Res. 21 (2012) 2388 (http://dx.doi.org/10.1007/s00044-011-9770-6)

D. Mantu, M. C. Luca, C. Moldoveanu, G, Zbancioc, I. I. Mangalagiu, Eur. J. Med. Chem. 45 (2010) 5164 (http://dx.doi.org/10.1016/J.EJMECH.2010.08.029)

H. B. V. Sowmya, T. S. Kumara, G. Nagendrappa et al., J. Mol. Struct. 1054 (2013) 179 (http://dx.doi.org/10.1016/J.MOLSTRUC.2013.09.046)

G. Zhou, P. C. Ting, R. Aslanian, J. Cao, D. W. Kim, R. Kuang, J. F. Lee, J. Schwerdt, H. Wu, R. J. Herr, A. J. Zych, J. Yang, S. Lam, S. Wainhaus, T. A. Black, P. M. McNicholas, Y. Xu, S. S. Walker, Bioorg. Med. Chem. Lett. 21 (2011); 2890 (http://dx.doi.org/10.1016/J.BMCL.2011.03.083)

D. Li, P. Zhan, H. Liu, C. Pannecouque, J. Balzarini, E. De Clercq, X. Liu, Bioorg. Med. Chem. 21 (2013); 2134 (http://dx.doi.org/10.1016/J.BMC.2012.12.049)

J. Singh, D. Sharma, R. Bansal, Future Med. Chem. 9 (2016) 95 (http://dx.doi.org/10.4155/FMC-2016-0194)

X. Zhang, J. Luo, Q, Li, Q. Xin, L. Ye, Q. Zhu, Z. Shi, F. Zhan, B. Chu, Z. Liu, Y. Jiang, Eur. J. Med. Chem. 226 (2021) 113812 (http://dx.doi.org/10.1016/J.EJMECH.2021.113812)

A. A. Siddiqui, S. Partap, S. Khisal, M. Shahar Yar, R. Mishra, Bioorg. Chem. 99 (2020) 103584 (http://dx.doi.org/10.1016/J.BIOORG.2020.103584)

S. Utku, M. Gökçe, G. Aslan, G. Bayram, Turkish J. Chem. 35 (2011); 331 (http://dx.doi.org/10.3906/kim-1009-63)

M. Asif, M. Imran, Anal. Chem. Lett. 10 (2020) 414 (http://dx.doi.org/10.1080/22297928.2020.1776633)

M. Asif, A. Singh, S. A. Khan, A. Husain, Brazilian J. Pharm. Sci. 54 (2018); 1 (http://dx.doi.org/10.1590/S2175-97902018000300040)

M. Asif, A. Imran, M. Imran., IJPSR. 11 (2020); 826 (http://dx.doi.org/ 10.13040/IJPSR.0975-8232.11(2).826-31)

L. R. Chiarelli, M. Mori, G. Beretta, A. Gelain, E. Pini, J. C. Sammartino, G, Stelitano, D, Barlocco, L. Costantino, M. Lapillo, G, Poli, I. Caligiuri, F, Rizzolio, M. Bellinzoni, T. Tuccinardi, S. Villa, F. Meneghetti, J. Enzyme Inhib. Med. Chem. 34 (2019) 823 (http://dx.doi.org/10.1080/14756366.2019.1589462)

L. R. Chiarelli, M. Mori, D. Barlocco, G. Beretta, A. Gelain, E. Pini, M. Porcino, G. Mori, G. Stelitano, L. Costantino, M. Lapillo, D. Bonanni, G. Poli, T. Tuccinardi, S. Villa, F. Meneghett, Eur. J. Med. Chem. 155 (2018) 754 (http://dx.doi.org/10.1016/j.ejmech.2018.06.033)

R. P. Tangallapally, R. Yendapally, R. E. Lee, K. Hevener. V. C. Jones, A. J. M. Lenaerts, M. R. McNeil, Y. Wang, S. Franzblau, R. E. Lee, J. Med. Chem. 47 (2004) 5276 (http://dx.doi.org/10.1021/jm049972y)

Y. L. Fan, J. B. Wu, X. Ke, Z. P. Huang, Bioorg. Med. Chem. Lett. 28 (2018) 3064 (https://doi.org/10.1016/j.bmcl.2018.07.046)

R. P. Tangallapally, D. Sun, N. Budha, R. E. Lee, A. J. M. Lenaerts, N. Budha, R. E. Lee, Bioorg. Med. Chem. Lett. 17 (2007) 6638 (http://dx.doi.org/10.1016/j.bmcl.2007.09.048)

N. R. Tawari, R. Bairwa, M. K. Ray, M. G. R. Rajan, M. S. Degani, Bioorg. Med. Chem. Lett., 20 (2010); 6175 (http://dx.doi.org/10.1016/j.bmcl.2010.08.127)

N. H. Zuma, J. Aucamp, D. D. N’Da, Eur. J. Pharm. Sci. 140 (2019) 105092 (https://doi.org/10.1016/j.ejps.2019.105092)

N. H. Zuma, F. J. Smit, R. Seldon, J. Aucamp, A. Jordaan, D. F. Warner, D. D. N'Da, Bioorg. Chem. 96 (2020) 103587 (https://doi.org/10.1016/j.bioorg.2020.103587)

Z. Yang, Y. Sun, Q. Liu, A. Li, W. Wang, W. Gu, J. Agric. Food Chem. 69 (2021) 13373 (https://doi.org/10.1021/acs.jafc.1c03857)

A. Evidente, G. Cristinzio, B. Punzo, A. Andolfi, A. Testa, D. Melck, Chem. Biodivers. 6 (2009) 328 (http://dx.doi.org/10.1002/CBDV.200800292)

O. S. Trefzger, N. V. Barbosa, R. L. Scapolatempo, A. R. das Neves, M. L. F. S. Ortale, D. B. Carvalho, A. M. Honorato, M. R. Fragoso, C. Y. K. Shuiguemoto, R. T. Perdomo, M. F. C. Matos, M. R. Chang, C. C. P. Arruda, A. C. M. Baroni, Arch. Pharm.353 (2020) 1900241 (http://dx.doi.org/10.1002/ARDP.201900241)

G. B. Wang, L. F. Wang, C. Z. Li, J. Sun, G. M. Zhou, D. C. Yang, Res. Chem. Intermed. 38 (2012). (https://doi.org/10.1007/s11164-011-0327-6)

Clinical and Laboratory Standards Institute (CLSI), Ref. Method Broth Dilution Antifung. Susceptibility Test. Yeasts. Approv. Stand. 3th Ed. 28 (2008) 0–13. https://clsi.org/media/1461/m27a3_sample.pdf.