Login Register Cart 0
Generic placeholder image

Current Catalysis

Editor-in-Chief

ISSN (Print): 2211-5447
ISSN (Online): 2211-5455

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Validation of Inhibitory Activity of Thiazolidine-4-carboxylic Acid Derivatives against Novel Influenza Neuraminidase Enzyme

Author(s): Namrata Jain, Anita K. and Aakanksha Yadav*

Volume 12, Issue 1, 2023

Published on: 09 June, 2023

Page: [18 - 25] Pages: 8

DOI: 10.2174/2211544712666230406123325

Price: $65

Abstract

Background: Neuraminidase enzymes are a large family found in a range of organisms. The best-known neuraminidase is viral neuraminidase, a drug target for the prevention of the spread of influenza infection. The viral neuraminidases are frequently used as antigenic determinants found on the surface of the influenza virus.

Objective: Thiazolidine derivatives have been synthesized and explored previously, and further compounds have been designed on the basis of leading compounds. This research aimed to validate those previously synthesized compounds and a new series of compounds.

Methods: A series of 28 compounds of thiazolidine-4-carboxylic acid derivatives were studied and evaluated for their ability to inhibit the neuraminidase (NA) of the influenza A virus. Twenty-eight compounds were differentiated into a training set of 21 compounds and a test set of 07 compounds.

Results: The validated compounds demonstrated moderate inhibitory activity against influenza A neuraminidase. The most potent compound was acetaminophen mercapturate (C13H16N2O5S) (MW: 312.34). S-(5-acetamido-2-hydroxyphenyl)-N-acetyl-L-cysteine is an S-substituted N-acetyl-Lcysteine in which the S-substituent is specified as 5-acetamido-2-hydroxyphenyl. It acts as a drug metabolite, a human urinary metabolite, and a rat metabolite. It is a member of acetamides, an organic sulphide, a member of phenols and an S-substituted N-acetyl-L-cysteine. It derives from “paracetamol”.

Conclusion: Validation of inhibitory activity of thiazolidine-4-carboxylic acid derivatives as novel influenza NA shows drug discovery of a more potent and reliable drug for the influenza virus.

« Previous Next »
[1]
von Itzstein, M.; Wu, W.Y.; Kok, G.B.; Pegg, M.S.; Dyason, J.C.; Jin, B.; Van Phan, T.; Smythe, M.L.; White, H.F.; Oliver, S.W.; Colman, P.M.; Varghese, J.N.; Ryan, D.M.; Woods, J.M.; Bethell, R.C.; Hotham, V.J.; Cameron, J.M.; Penn, C.R. Rational design of potent sialidase-based inhibitors of influenza virus replication. Nature, 1993, 363(6428), 418-423.
[http://dx.doi.org/10.1038/363418a0] [PMID: 8502295]
[2]
Kim, C.U.; Lew, W.; Williams, M.A.; Liu, H.; Zhang, L.; Swaminathan, S.; Bischofberger, N.; Chen, M.S.; Mendel, D.B.; Tai, C.Y.; Laver, W.G.; Stevens, R.C. Influenza neuraminidase inhibitors possessing a novel hydrophobic interaction in the enzyme active site: design, synthesis, and structural analysis of carbocyclic sialic acid analogues with potent antiinfluenza activity. J. Am. Chem. Soc., 1997, 119(4), 681-690.
[http://dx.doi.org/10.1021/ja963036t] [PMID: 16526129]
[3]
Hatakeyama, S.; Sugaya, N.; Ito, M.; Yamazaki, M.; Ichikawa, M.; Kimura, K.; Kiso, M.; Shimizu, H.; Kawakami, C.; Koike, K.; Mitamura, K.; Kawaoka, Y. Emergence of influenza B viruses with reduced sensitivity to neuraminidase inhibitors. JAMA, 2007, 297(13), 1435-1442.
[http://dx.doi.org/10.1001/jama.297.13.1435] [PMID: 17405969]
[4]
Kiso, M.; Mitamura, K.; Sakai-Tagawa, Y.; Shiraishi, K.; Kawakami, C.; Kimura, K.; Hayden, F.G.; Sugaya, N.; Kawaoka, Y. Resistant influenza A viruses in children treated with oseltamivir: Descriptive study. Lancet, 2004, 364(9436), 759-765.
[http://dx.doi.org/10.1016/S0140-6736(04)16934-1] [PMID: 15337401]
[5]
Hayden, F.G. Antiviral resistance in influenza viruses-implications for management and pandemic response. N. Engl. J. Med., 2006, 354(8), 785-788.
[http://dx.doi.org/10.1056/NEJMp068030]
[6]
Ward, P.; Small, I.; Smith, J.; Suter, P.; Dutkowski, R. Oseltamivir (Tamiflu®) and its potential for use in the event of an influenza pandemic. J. Antimicrob. Chemother., 2005, 55(Suppl. 1), i5-i21.
[http://dx.doi.org/10.1093/jac/dki018]
[7]
Le, Q.M.; Kiso, M.; Someya, K.; Sakai, Y.T.; Nguyen, T.H.; Nguyen, K.H.L.; Pham, N.D.; Ngyen, H.H.; Yamada, S.; Muramoto, Y.; Horimoto, T.; Takada, A.; Goto, H.; Suzuki, T.; Suzuki, Y.; Kawaoka, Y. Isolation of drug-resistant H5N1 virus. Nature, 2005, 437(7062), 1108.
[http://dx.doi.org/10.1038/4371108a] [PMID: 16228009]
[8]
de Jong, M.D.; Thanh, T.T.; Khanh, T.H.; Hien, V.M.; Smith, G.J.D.; Chau, N.V.; Cam, B.V.; Qui, P.T.; Ha, D.Q.; Guan, Y.; Peiris, J.S.M.; Hien, T.T.; Farrar, J. Oseltamivir Resistance during Treatment of Influenza A (H5N1) Infection. N. Engl. J. Med., 2005, 353(25), 2667-2672.
[http://dx.doi.org/10.1056/NEJMoa054512]
[9]
Bantia, S.; Arnold, C.S.; Parker, C.D.; Upshaw, R.; Chand, P. Anti-influenza virus activity of peramivir in mice with single intramuscular injection. Antiviral Res., 2006, 69(1), 39-45.
[http://dx.doi.org/10.1016/j.antiviral.2005.10.002] [PMID: 16325932]
[10]
Chand, P.; Bantia, S.; Kotian, P.L.; El-Kattan, Y.; Lin, T.H.; Babu, Y.S. Comparison of the anti-influenza virus activity of cyclopentane derivatives with oseltamivir and zanamivir in vivo. Bioorg. Med. Chem., 2005, 13(12), 4071-4077.
[http://dx.doi.org/10.1016/j.bmc.2005.03.048] [PMID: 15911320]
[11]
Nicholson, K.G. Impact of influenza and respiratory syncytial virus on mortality in England and Wales from January 1975 to December 1990. Epidemiol. Infect., 1996, 116(1), 51-63.
[http://dx.doi.org/10.1017/S0950268800058957] [PMID: 8626004]
[12]
Wang, G.T.; Chen, Y.; Wang, S.; Gentles, R.; Sowin, T.; Kati, W.; Muchmore, S.; Giranda, V.; Stewart, K.; Sham, H.; Kempf, D.; Laver, W.G. Design, synthesis, and structural analysis of influenza neuraminidase inhibitors containing pyrrolidine cores. J. Med. Chem., 2001, 44(8), 1192-1201.
[http://dx.doi.org/10.1021/jm000468c] [PMID: 11312919]
[13]
Ryu, Y.B.; Curtis-Long, M.J.; Lee, J.W.; Ryu, H.W.; Kim, J.Y.; Lee, W.S.; Park, K.H. Structural characteristics of flavanones and flavones from Cudrania tricuspidata for neuraminidase inhibition. Bioorg. Med. Chem. Lett., 2009, 19(17), 4912-4915.
[http://dx.doi.org/10.1016/j.bmcl.2009.07.098] [PMID: 19660948]
[14]
Ryu, Y.B.; Curtis-Long, M.J.; Kim, J.H.; Jeong, S.H.; Yang, M.S.; Lee, K.W.; Lee, W.S.; Park, K.H. Pterocarpans and flavanones from Sophora flavescens displaying potent neuraminidase inhibition. Bioorg. Med. Chem. Lett., 2008, 18(23), 6046-6049.
[http://dx.doi.org/10.1016/j.bmcl.2008.10.033] [PMID: 18938076]
[15]
Liu, A.L.; Wang, H.D.; Lee, S.M.; Wang, Y.T.; Du, G.H. Structure–activity relationship of flavonoids as influenza virus neuraminidase inhibitors and their in vitro anti-viral activities. Bioorg. Med. Chem., 2008, 16(15), 7141-7147.
[http://dx.doi.org/10.1016/j.bmc.2008.06.049] [PMID: 18640042]
[16]
Seo, E.J.; Curtis-Long, M.J.; Lee, B.W.; Kim, H.Y.; Ryu, Y.B.; Jeong, T.S.; Lee, W.S.; Park, K.H. Xanthones from cudrania tricuspidata displaying potent α-glucosidase inhibition. Bioorg. Med. Chem. Lett., 2007, 17(23), 6421-6424.
[http://dx.doi.org/10.1016/j.bmcl.2007.10.007] [PMID: 17950599]
[17]
Ryu, Y.B.; Curtis-Long, M.J.; Lee, J.W.; Kim, J.H.; Kim, J.Y.; Kang, K.Y.; Lee, W.S.; Park, K.H. Characteristic of neuraminidase inhibitory xanthones from Cudrania tricuspidata. Bioorg. Med. Chem., 2009, 17(7), 2744-2750.
[http://dx.doi.org/10.1016/j.bmc.2009.02.042] [PMID: 19285413]
[18]
García-Sosa, A.T.; Sild, S.; Maran, U. Design of multi-binding-site inhibitors, ligand efficiency, and consensus screening of avian influenza H5N1 wild-type neuraminidase and of the oseltamivirresistant H274Y variant. J. Chem. Inf. Model., 2008, 48(10), 2074-2080.
[http://dx.doi.org/10.1021/ci800242z] [PMID: 18847186]
[19]
Dao, T.T.; Tung, B.T.; Nguyen, P.H.; Thuong, P.T.; Yoo, S.S.; Kim, E.H.; Kim, S.K.; Oh, W.K. C-Methylated flavonoids from Cleistocalyx operculatus and their inhibitory effects on novel influenza A (H1N1) neuraminidase. J. Nat. Prod., 2010, 73(10), 1636-1642.
[http://dx.doi.org/10.1021/np1002753] [PMID: 20886838]
[20]
Hunga, H. C.; Tsenga, C. P.; Yangb, J. M.; Jua, Y. W.; Tsengc, S. N.; Chenb, Y. F.; Chaod, Y. S.; Hsiehd, H. P.; Hsud, T.A. Antiviral Res., 2008.
[http://dx.doi.org/10.1016/j.antiviral.2008.10.006]
[21]
Liu, Y.; Jing, F.; Xu, Y.; Xie, Y.; Shi, F.; Fang, H.; Li, M.; Xu, W. Design, synthesis and biological activity of thiazolidine-4-carboxylic acid derivatives as novel influenza neuraminidase inhibitors. Bioorg. Med. Chem., 2011, 19(7), 2342-2348.
[http://dx.doi.org/10.1016/j.bmc.2011.02.019] [PMID: 21382719]
[22]
Neelu, S.; Basheerulla, S.; Neeraj, K.; Anita, K.; Agrawal, V.P.; Gupta, S. QSAR and molecular modeling studies on a series of indole-based pyridone analogues as HCV NS5B polymerase inhibitors. Lett. Drug Design Discov., 2016, 13(8), 757-770.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy