Synthesis of Highly Potent Anti-Inflammatory Compounds (ROS Inhibitors) from Isonicotinic Acid
Abstract
:1. Introduction
2. Results and Discussion
3. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
- Chen, L.Z.; Wu, J.; Li, K.; Wu, Q.Q.; Chen, R.; Liu, X.H.; Ruan, B.F. Novel phthalide derivatives: Synthesis and anti-inflammatory activity in vitro and in vivo. Eur. J. Med. Chem. 2020, 206. [Google Scholar] [CrossRef]
- Chelombitko, M.A. Role of Reactive Oxygen Species in Inflammation: A Minireview. Moscow Univ. Biol. Sci. Bull. 2018, 73, 199–202. [Google Scholar] [CrossRef] [Green Version]
- Mittal, M.; Siddiqui, M.R.; Tran, K.; Reddy, S.P.; Malik, A.B. Reactive oxygen species in inflammation and tissue injury. Antioxidants Redox Signal. 2014, 20, 1126–1167. [Google Scholar] [CrossRef] [Green Version]
- Shrestha, A.; Jin Oh, H.; Kim, M.J.; Pun, N.T.; Magar, T.B.T.; Bist, G.; Choi, H.; Park, P.H.; Lee, E.S. Design, synthesis, and structure-activity relationship study of halogen containing 2-benzylidene-1-indanone derivatives for inhibition of LPS-stimulated ROS production in RAW 264.7 macrophages. Eur. J. Med. Chem. 2017, 133, 121–138. [Google Scholar] [CrossRef]
- Perillo, B.; Di Donato, M.; Pezone, A.; Di Zazzo, E.; Giovannelli, P.; Galasso, G.; Castoria, G.; Migliaccio, A. ROS in cancer therapy: The bright side of the moon. Exp. Mol. Med. 2020, 52, 192–203. [Google Scholar] [CrossRef] [PubMed]
- Santos, D.C.; Henriques, R.R.; de Abreu Lopes Junior, M.A.; Farias, A.B.; do Couto Nogueira, T.L.; Quimas, J.V.F.; Romeiro, N.C.; da Silva, L.L.; de Souza, A.L.F. Acylhydrazones as isoniazid derivatives with multi-target profiles for the treatment of Alzheimer’s disease: Radical scavenging, myeloperoxidase/acetylcholinesterase inhibition and biometal chelation. Bioorg. Med. Chem. 2020, 28, 115470. [Google Scholar] [CrossRef]
- Lu, X.; Zhang, H.; Li, X.; Chen, G.; Li, Q.-S.; Luo, Y.; Ruan, B.-F.; Chen, X.-W.; Zhu, H.-L. Design, synthesis and biological evaluation of pyridine acyl sulfonamide derivatives as novel COX-2 inhibitors. Bioorg. Med. Chem. 2011, 19, 6827–6832. [Google Scholar] [CrossRef]
- Desogus, A.; Schenone, S.; Brullo, C.; Tintori, C.; Musumeci, F. Bcr-Abl tyrosine kinase inhibitors: A patent review. Expert Opin. Ther. Pat. 2015, 25, 397–412. [Google Scholar] [CrossRef]
- Ghiano, D.G.; Recio-Balsells, A.; Bortolotti, A.; Defelipe, L.A.; Turjanski, A.; Morbidoni, H.R.; Labadie, G.R. New one-pot synthesis of anti-tuberculosis compounds inspired on isoniazid. Eur. J. Med. Chem. 2020, 208, 112699. [Google Scholar] [CrossRef]
- Fu, Y.-D.; Huang, M.-J.; Guo, J.-W.; You, Y.-Z.; Liu, H.-M.; Huang, L.-H.; Yu, B. Targeting histone demethylase KDM5B for cancer treatment. Eur. J. Med. Chem. 2020, 208, 112760. [Google Scholar] [CrossRef]
- Judge, V.; Narasimhan, B.; Ahuja, M.; Sriram, D.; Yogeeswari, P.; De Clercq, E.; Pannecouque, C.; Balzarini, J. Isonicotinic acid hydrazide derivatives: Synthesis, antimicrobial activity, and QSAR studies. Med. Chem. Res. 2012, 21, 1451–1470. [Google Scholar] [CrossRef]
- Scott, F.; Fala, A.M.; Pennicott, L.E.; Reuillon, T.D.; Massirer, K.B.; Elkins, J.M.; Ward, S.E. Development of 2-(4-pyridyl)-benzimidazoles as PKN2 chemical tools to probe cancer. Bioorg. Med. Chem. Lett. 2020, 30, 127040. [Google Scholar] [CrossRef]
- Koltun, D.O.; Parkhill, E.Q.; Kalla, R.; Perry, T.D.; Elzein, E.; Li, X.; Simonovich, S.P.; Ziebenhaus, C.; Hansen, T.R.; Marchand, B.; et al. Discovery of potent and selective inhibitors of calmodulin-dependent kinase II (CaMKII). Bioorg. Med. Chem. Lett. 2018, 28, 541–546. [Google Scholar] [CrossRef]
- Luo, Z.; Yue, X.; Yang, H.; Liu, H.; Klein, R.S.; Tu, Z. Design and synthesis of pyrazolopyridine derivatives as sphingosine 1-phosphate receptor 2 ligands. Bioorg. Med. Chem. Lett. 2018, 28, 488–496. [Google Scholar] [CrossRef]
- Bayrak, H.; Demirbas, A.; Demirbas, N.; Karaoglu, S.A. Synthesis of some new 1,2,4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities. Eur. J. Med. Chem. 2009, 44, 4362–4366. [Google Scholar] [CrossRef]
- Fiorino, F.; Ciano, A.; Magli, E.; Severino, B.; Corvino, A.; Perissutti, E.; Frecentese, F.; Di Vaio, P.; Izzo, A.A.; Capasso, R.; et al. Synthesis, in vitro and in vivo pharmacological evaluation of serotoninergic ligands containing an isonicotinic nucleus. Eur. J. Med. Chem. 2016, 110, 133–150. [Google Scholar] [CrossRef]
- Yue, X.; Dhavale, D.D.; Li, J.; Luo, Z.; Liu, J.; Yang, H.; Mach, R.H.; Kotzbauer, P.T.; Tu, Z. Design, synthesis, and in vitro evaluation of quinolinyl analogues for α-synuclein aggregation. Bioorg. Med. Chem. Lett. 2018, 28, 1011–1019. [Google Scholar] [CrossRef] [PubMed]
- Hayat, F.; Azam, A.; Shin, D. Recent progress on the discovery of antiamoebic agents. Bioorg. Med. Chem. Lett. 2016, 26, 5149–5159. [Google Scholar] [CrossRef] [PubMed]
- Gilani, S.J.; Khan, S.A.; Alam, O.; Singh, V.; Arora, A. Thiazolidin-4-one, azetidin-2-one and 1,3,4-oxadiazole derivatives of isonicotinic acid hydrazide: Synthesis and their biological evaluation. J. Serbian Chem. Soc. 2011, 76, 1057–1067. [Google Scholar] [CrossRef]
- Al-Omar, M.A.; Amr, A.E.G.E.; Al-Salahi, R.A. Anti-inflammatory, analgesic, anticonvulsant and antiparkinsonian activities of some pyridine derivatives using 2,6-disubstituted isonicotinic acid hydrazides. Arch. Pharm. (Weinheim) 2010, 343, 648–656. [Google Scholar] [CrossRef]
- Helfand, S.L.; Werkmeister, J.; Roder, J.C. Chemiluminescence response of human natural killer cells: I. the relationship between target cell binding, chemiluminescence, and cytolysis. J. Exp. Med. 1982, 156, 492–505. [Google Scholar] [CrossRef] [PubMed]
Compounds | Anti-Inflammatory Activity | |
---|---|---|
% Inhibition * | IC50 (µg/mL) ** | |
5 | 95.9 | 1.42 ± 0.1 |
6 | 67.3 | 8.6 ± 0.5 |
7a | 29.3 | na |
7b | 25..8 | na |
7c | 15.7 | na |
7d | 21.6 | na |
7e | 13.2 | na |
8a | 66.6 | 19.6 ± 3.4 |
8b | 85.4 | 3.7 ± 1.7 |
8c | 44.6 | na |
8d | -7.7 | na |
8e | 5.8 | na |
Ibuprofen | 73.2 | 11.2 ± 1.9 |
Compound | Binding Energy (Kcal/mol) | Hydrogen Bonding | Hydrophobic Interaction | ||
---|---|---|---|---|---|
Ligand | Residue | Distance (Å) | |||
Ibuprofen | −7.61 | Lig:CO2−Salt bridge | Tyr356:OH Arg121 | 1.97 3.55 | Val350, Leu353, Tyr356, Leu360, Tyr386, Trp388, Val524, Ala528 |
5 | −6.66 | Lig:N(1) | Arg121:NH2+ | 3.05 | Val350, Leu353, Tyr386, Val524, Ala528 |
Lig:N(1) | Tyr356:OH | 2.32 | |||
Lig:N(3) | Met523:CO | 2.45 | |||
6 | −6.56 | Lig:N(1) | Arg121:NH2+ | 3.00 | Val350, Leu353, Tyr386, Val524, Ala528 |
Lig:N(1) | Tyr356:OH | 2.33 | |||
8a | −6.86 | Lig:N(3) Lig:O(3) Lig:N(3) | Arg121:NH2+ Arg121:NH2+ Tyr356:OH | 2.87 2.19 2.82 | Val117, Val350, Leu353, Tyr356, Phe519, Val524, Ala528, Trp388 |
8b | −7.26 | Lig:N(1) Lig:N(3) | Arg121:NH Ser531:OH | 3.03 2.39 | Phe206, Phe210, Val345, Val350, Leu353, Phe382, Tyr386, Val524, Ala528 |
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Yaqoob, S.; Nasim, N.; Khanam, R.; Wang, Y.; Jabeen, A.; Qureshi, U.; Ul-Haq, Z.; El-Seedi, H.R.; Jiang, Z.-H.; Khan, F.-A. Synthesis of Highly Potent Anti-Inflammatory Compounds (ROS Inhibitors) from Isonicotinic Acid. Molecules 2021, 26, 1272. https://doi.org/10.3390/molecules26051272
Yaqoob S, Nasim N, Khanam R, Wang Y, Jabeen A, Qureshi U, Ul-Haq Z, El-Seedi HR, Jiang Z-H, Khan F-A. Synthesis of Highly Potent Anti-Inflammatory Compounds (ROS Inhibitors) from Isonicotinic Acid. Molecules. 2021; 26(5):1272. https://doi.org/10.3390/molecules26051272
Chicago/Turabian StyleYaqoob, Sana, Nourina Nasim, Rahila Khanam, Yan Wang, Almas Jabeen, Urooj Qureshi, Zaheer Ul-Haq, Hesham R. El-Seedi, Zi-Hua Jiang, and Farooq-Ahmad Khan. 2021. "Synthesis of Highly Potent Anti-Inflammatory Compounds (ROS Inhibitors) from Isonicotinic Acid" Molecules 26, no. 5: 1272. https://doi.org/10.3390/molecules26051272