Abstract
A series of ethyl 2-(2-(arylidene)hydrazinyl)thiazole-4-carboxylates (2a–r) was synthesized in two steps from thiosemicarbazones (1a–r), which were cyclized with ethyl bromopyruvate to ethyl 2-(2-(arylidene)hydrazinyl)thiazole-4-carboxylates (2a–r). The structures of compounds (2a–r) were established by FT-IR, 1H- and 13C-NMR. The structure of compound 2a was confirmed by HRMS. The compounds (2a–r) were then evaluated for their antimicrobial and antioxidant assays. The antioxidant studies revealed, ethyl 2-(2-(4-hydroxy-3-methoxybenzylidene)hydrazinyl)thiazole-4-carboxylate (2g) and ethyl 2-(2-(1-phenylethylidene)hydrazinyl)thiazole-4-carboxylate (2h) as promising antioxidant agents with %FRSA: 84.46 ± 0.13 and 74.50 ± 0.37, TAC: 269.08 ± 0.92 and 269.11 ± 0.61 and TRP: 272.34 ± 0.87 and 231.11 ± 0.67 μg AAE/mg dry weight of compound. Beside bioactivities, density functional theory (DFT) methods were used to study the electronic structure and properties of synthesized compounds (2a–m). The potential of synthesized compounds for possible antiviral targets is also predicted through molecular docking methods. The compounds 2e and 2h showed good binding affinities and inhibition constants to be considered as therapeutic target for Mpro protein of SARS-CoV-2 (COVID-19). The present in-depth analysis of synthesized compounds will put them under the spot light for practical applications as antioxidants and the modification in structural motif may open the way for COVID-19 drug.
Funding source: University of Bisha
Award Identifier / Grant number: UB-COVID-12-1441
Funding source: King Khalid University
Award Identifier / Grant number: RGP.1/168/42
Acknowledgements
The author from University of Bisha Saudi Arabia extend his appreciation to the Deanship of Scientific Research at University of Bisha for funding this work through COVID-19 Initiative Project under Grant Number (UB-COVID-12-1441). The author Muhammad Haroon is thankful to HEC, Pakistan for six months IRSIP fellowship and Prof. Alan S. Goldman, Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, USA, for providing NMR facility. The author from King Khalid University of Saudi Arabia extends his appreciation to the Deanship of Scientific Research at King Khalid University for funding the work through Project (RGP.1/168/42). For computer time, this research used the resources of the Supercomputing Laboratory at King Abdullah University of Science & Technology (KAUST) in Thuwal, Saudi Arabia.
-
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
-
Research funding: The author from University of Bisha Saudi Arabia extend his appreciation to the Deanship of Scientific Research at University of Bisha for funding this work through COVID-19 Initiative Project under Grant Number (UB-COVID-12-1441). The author from King Khalid University of Saudi Arabia extends his appreciation to the Deanship of Scientific Research at King Khalid University for funding the work through Project (RGP.1/168/42).
-
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Sadek, B, Al-Tabakha, MM, Fahelelbom, KMS. Antimicrobial prospect of newly synthesized 1, 3-thiazole derivatives. Molecules 2011;16:9386–96. https://doi.org/10.3390/molecules16119386.Search in Google Scholar
2. Borcea, A-M, Ionuț, I, Crișan, O, Oniga, O. An overview of the synthesis and antimicrobial, antiprotozoal, and antitumor activity of thiazole and bisthiazole derivatives. Molecules 2021;26:624. https://doi.org/10.3390/molecules26030624.Search in Google Scholar
3. Hameed, S, Akhtar, T, Al-Masoudi, NA, Al-Masoudi, WA, Jones, PG, Pannecouque, C. Synthesis, crystal structure, anti-HIV, and antiproliferative activity of new oxadiazole and thiazole analogs. Med Chem Res 2016;25:2399–409.10.1007/s00044-016-1669-9Search in Google Scholar
4. Hamade, E, Habib, A, Hachem, A, Hussein, AH, Abbas, M, Hirz, T, et al.. Biological and anti-inflammatory evaluation of two thiazole compounds in RAW cell line: potential cyclooxygenase-2 specific inhibitors. Med Chem 2012;8:401–8. https://doi.org/10.2174/1573406411208030401.Search in Google Scholar
5. Venkatachalam, T, Qazi, S, Samuel, P, Uckun, F. Substituted heterocyclic thiourea compounds as a new class of anti-allergic agents inhibiting IgE/FcεRI receptor mediated mast cell leukotriene release. Bioorg Med Chem 2003;11:1095–105. https://doi.org/10.1016/s0968-0896(02)00531-x.Search in Google Scholar
6. Dawood, KM, Eldebss, TM, El-Zahabi, HS, Yousef, MH. Synthesis and antiviral activity of some new bis-1,3-thiazole derivatives. Eur J Med Chem 2015;102:266–76. https://doi.org/10.1016/j.ejmech.2015.08.005.Search in Google Scholar PubMed
7. de Souza, MVN, de Almeida, MV. Drogas anti-VIH: passado, presente e perspectivas futuras. Quim Nova 2003;26:366–72. https://doi.org/10.1590/s0100-40422003000300014.Search in Google Scholar
8. Borisenko, V, Koll, A, Kolmakov, E, Rjasnyi, A. Hydrogen bonds of 2-aminothiazoles in intermolecular complexes (1:1 and 1:2) with proton acceptors in solutions. J Mol Struct 2006;783:101–15. https://doi.org/10.1016/j.molstruc.2005.08.006.Search in Google Scholar
9. Milne, G. In: Ashgate, G, editor. Handbook of antineoplastic agents. London, UK; 2000.Search in Google Scholar
10. Maj, J, Rogóż, Z, Skuza, G, Kołodziejczyk, K. Antidepressant effects of pramipexole, a novel dopamine receptor agonist. J Neural Transm 1997;104:525–33. https://doi.org/10.1007/bf01277669.Search in Google Scholar PubMed
11. Poff, CD, Balazy, M. Drugs that target lipoxygenases and leukotrienes as emerging therapies for asthma and cancer. Curr Drug Targets Inflamm Allergy 2004;3:19–33. https://doi.org/10.2174/1568010043483917.Search in Google Scholar PubMed
12. Knadler, M, Bergstrom, RF, Callaghan, JT, Rubin, A. Nizatidine, an H2-blocker. Its metabolism and disposition in man. Drug Metabol Dispos 1986;14:175–82.Search in Google Scholar
13. Breslow, R. On the mechanism of thiamine action. IV. 1 Evidence from studies on model systems. J Am Chem Soc 1958;80:3719–26. https://doi.org/10.1021/ja01547a064.Search in Google Scholar
14. Duncia, JV, Chiu, AT, Carini, DJ, Gregory, GB, Johnson, AL, Price, WA, et al.. The discovery of potent nonpeptide angiotensin II receptor antagonists: a new class of potent antihypertensives. J Med Chem 1990;33:1312–29. https://doi.org/10.1021/jm00167a007.Search in Google Scholar PubMed
15. Siddiqui, HL, Zia-Ur-Rehman, M, Ahmad, N, Weaver, GW, Lucas, PD. Synthesis and antibacterial activity of bis [2-amino-4-phenyl-5-thiazolyl] disulfides. Chem Pharmaceut Bull 2007;55:1014–7. https://doi.org/10.1248/cpb.55.1014.Search in Google Scholar PubMed
16. Nayab, RS, Maddila, S, Krishna, MP, Titinchi, SJ, Thaslim, BS, Chintha, V, et al.. In silico molecular docking and in vitro antioxidant activity studies of novel α-aminophosphonates bearing 6-amino-1,3-dimethyl uracil. J Recept Sig Transduct 2020;40:166–72. https://doi.org/10.1080/10799893.2020.1722166.Search in Google Scholar PubMed
17. Karalı, N, Güzel, Ö, Özsoy, N, Özbey, S, Salman, A. Synthesis of new spiroindolinones incorporating a benzothiazole moiety as antioxidant agents. Eur J Med Chem 2010;45:1068–77.10.1016/j.ejmech.2009.12.001Search in Google Scholar PubMed
18. Patil, VP, Markad, VL, Kodam, KM, Waghmode, SB. Facile preparation of tetrahydro-5H-pyrido [1, 2, 3-de]-1,4-benzoxazines via reductive cyclization of 2-(8-quinolinyloxy) ethanones and their antioxidant activity. Bioorg Med Chem Lett 2013;23:6259–63. https://doi.org/10.1016/j.bmcl.2013.09.088.Search in Google Scholar PubMed
19. Abdel-Wahab, BF, Abdel-Gawad, H, Awad, GE, Badria, FA. Synthesis, antimicrobial, antioxidant, anti-inflammatory, and analgesic activities of some new 3-(2′-thienyl) pyrazole-based heterocycles. Med Chem Res 2012;21:1418–26. https://doi.org/10.1007/s00044-011-9661-x.Search in Google Scholar
20. Usol’tseva, S, Andronnikova, G, Shevyrin, V. Bromination of 2-thiazolylhydrazones. Chem Heterocycl Compd 1993;29:226–30. https://doi.org/10.1007/bf00531672.Search in Google Scholar
21. Metwally, MA, Bondock, S, El-Azap, H, Kandeel, E-EM. Thiosemicarbazides: synthesis and reactions. J Sulfur Chem 2011;32:489–519. https://doi.org/10.1080/17415993.2011.601869.Search in Google Scholar
22. Haroon, M, Khalid, M, Akhtar, T, Tahir, MN, Khan, MU, Muhammad, S, et al.. Synthesis, crystal structure, spectroscopic, electronic and nonlinear optical properties of potent thiazole based derivatives: joint experimental and computational insight. J Mol Struct 2020;1202:127354. https://doi.org/10.1016/j.molstruc.2019.127354.Search in Google Scholar
23. Haroon, M, Khalid, M, Akhtar, T, Tahir, MN, Khan, MU, Saleem, M, et al.. Synthesis, spectroscopic, SC-XRD characterizations and DFT based studies of ethyl2-(substituted-(2-benzylidenehydrazinyl)) thiazole-4-carboxylate derivatives. J Mol Struct 2019;1187:164–71. https://doi.org/10.1016/j.molstruc.2019.03.075.Search in Google Scholar
24. Haroon, M, Akhtar, T, Yousuf, M, Baig, MW, Tahir, MN, Rasheed, L. Synthesis, spectroscopic characterization and crystallographic behavior of ethyl 2-(4-methyl-(2-benzylidenehydrazinyl)) thiazole-4-carboxylate: experimental and theoretical (DFT) studies. J Mol Struct 2018;1167:154–60. https://doi.org/10.1016/j.molstruc.2018.04.083.Search in Google Scholar
25. Haroon, M, de Barros Dias, MCH, da Silva Santos, AC, Pereira, VRA, Freitas, LAB, Balbinot, RB, et al.. The design, synthesis, and in vitro trypanocidal and leishmanicidal activities of 1,3-thiazole and 4-thiazolidinone ester derivatives. RSC Adv 2021;11:2487–500. https://doi.org/10.1039/d0ra06994a.Search in Google Scholar PubMed PubMed Central
26. Wang, P, Hu, M, Wang, H, Chen, Z, Feng, Y, Wang, J, et al.. The evolution of flexible electronics: from nature, beyond nature, and to nature. Adv Sci 2020;7:2001116. https://doi.org/10.1002/advs.202001116.Search in Google Scholar PubMed PubMed Central
27. Kazmi, STB, Majid, M, Maryam, S, Rahat, A, Ahmed, M, Khan, MR, et al.. Quercus dilatata Lindl. ex Royle ameliorates BPA induced hepatotoxicity in Sprague–Dawley rats. Biomed Pharmacother 2018;102:728–38. https://doi.org/10.1016/j.biopha.2018.03.097.Search in Google Scholar PubMed
28. Kato, T, Ozaki, T, Tamura, K, Suzuki, Y, Akima, M, Ohi, N. Novel calcium antagonists with both calcium overload inhibition and antioxidant activity. 2. Structure–activity relationships of thiazolidinone derivatives. J Med Chem 1999;42:3134–46. https://doi.org/10.1021/jm9900927.Search in Google Scholar PubMed
29. Gouda, MA, Abu‐Hashem, AA. Synthesis, characterization, antioxidant and antitumor evaluation of some new thiazolidine and thiazolidinone derivatives. Arch Pharmazie 2011;344:170–7. https://doi.org/10.1002/ardp.201000165.Search in Google Scholar PubMed
30. Shih, M-H, Ke, F-Y. Syntheses and evaluation of antioxidant activity of sydnonyl substituted thiazolidinone and thiazoline derivatives. Bioorg Med Chem 2004;12:4633–43. https://doi.org/10.1016/j.bmc.2004.06.033.Search in Google Scholar PubMed
31. Djukic, M, Fesatidou, M, Xenikakis, I, Geronikaki, A, Angelova, VT, Savic, V, et al.. In vitro antioxidant activity of thiazolidinone derivatives of 1,3-thiazole and 1,3,4-thiadiazole. Chem Biol Interact 2018;286:119–31. https://doi.org/10.1016/j.cbi.2018.03.013.Search in Google Scholar PubMed
32. Gjorgieva Ackova, D, Kotur-Stevuljevic, J, Bhushan Mishra, C, Mehta Luthra, P, Saso, L. Antioxidant properties of synthesized bicyclic thiazolopyrimidine derivatives as possible therapeutic agents. Appl Sci 2019;9:113.10.3390/app9010113Search in Google Scholar
33. Omar, K, Geronikaki, A, Zoumpoulakis, P, Camoutsis, C, Soković, M, Ćirić, A, et al.. Novel 4-thiazolidinone derivatives as potential antifungal and antibacterial drugs. Bioorg Med Chem 2010;18:426–32. https://doi.org/10.1016/j.bmc.2009.10.041.Search in Google Scholar PubMed
34. Shrivastava, B, Sharma, O, Sharma, P, Singh, J. Synthesis, characterization and antimicrobial evaluation of novel azole based (Benzoic Acid) derivatives. Asian J Pharm Pharmacol 2019;5:368–72. https://doi.org/10.31024/ajpp.2019.5.2.21.Search in Google Scholar
35. Jain, AK, Vaidya, A, Ravichandran, V, Kashaw, SK, Agrawal, RK. Recent developments and biological activities of thiazolidinone derivatives: a review. Bioorg Med Chem 2012;20:3378–95. https://doi.org/10.1016/j.bmc.2012.03.069.Search in Google Scholar PubMed
36. Šarkanj, B, Molnar, M, Čačić, M, Gille, L. 4-Methyl-7-hydroxycoumarin antifungal and antioxidant activity enhancement by substitution with thiosemicarbazide and thiazolidinone moieties. Food Chem 2013;139:488–95.10.1016/j.foodchem.2013.01.027Search in Google Scholar PubMed
37. Caricato, M, Trucks, GW, Frisch, MJ, Wiberg, KB. Electronic transition energies: a study of the performance of a large range of single reference density functional and wave function methods on valence and Rydberg states compared to experiment. J Chem Theor Comput 2010;6:370–83. https://doi.org/10.1021/ct9005129.Search in Google Scholar PubMed
38. Wang, Y-J, Zhao, Y-F, Li, W-L, Jian, T, Chen, Q, You, X-R, et al.. Observation and characterization of the smallest borospherene, B28− and B28. J Chem Phys 2016;144:064307. https://doi.org/10.1063/1.4941380.Search in Google Scholar PubMed
39. Hanwell, MD, Curtis, DE, Lonie, DC, Vandermeersch, T, Zurek, E, Hutchison, GR. Avogadro: an advanced semantic chemical editor, visualization, and analysis platform. J Cheminf 2012;4:1–17. https://doi.org/10.1186/1758-2946-4-17.Search in Google Scholar PubMed PubMed Central
40. Andrienko, GA. Chemcraft. Graphical software for visualization of quantum chemistry computations. 2010.Search in Google Scholar
41. Khan, MU, Iqbal, J, Khalid, M, Hussain, R, Braga, AAC, Hussain, M, et al.. Designing triazatruxene-based donor materials with promising photovoltaic parameters for organic solar cells. RSC Adv 2019;9:26402–18. https://doi.org/10.1039/c9ra03856f.Search in Google Scholar PubMed PubMed Central
42. Rafiq, M, Khalid, M, Tahir, MN, Ahmad, MU, Khan, MU, Naseer, MM, et al.. Synthesis, XRD, spectral (IR, UV–Vis, NMR) characterization and quantum chemical exploration of benzoimidazole‐based hydrazones: a synergistic experimental–computational analysis. Appl Organomet Chem 2019;33:e5182. https://doi.org/10.1002/aoc.5182.Search in Google Scholar
43. Khan, B, Khalid, M, Shah, MR, Tahir, MN, Khan, MU, Ali, A, et al.. Efficient synthesis by mono‐carboxy methylation of 4,4′‐biphenol, X‐ray diffraction, spectroscopic characterization and computational study of the crystal packing of ethyl 2‐((4′‐hydroxy‐[1,1′‐biphenyl]‐4‐yl) oxy) acetate. ChemistrySelect 2019;4:9274–84. https://doi.org/10.1002/slct.201901422.Search in Google Scholar
44. Hussain, A, Khan, MU, Ibrahim, M, Khalid, M, Ali, A, Hussain, S, et al.. Structural parameters, electronic, linear and nonlinear optical exploration of thiopyrimidine derivatives: a comparison between DFT/TDDFT and experimental study. J Mol Struct 2020;1201:127183. https://doi.org/10.1016/j.molstruc.2019.127183.Search in Google Scholar
45. Tariq, S, Raza, AR, Khalid, M, Rubab, SL, Khan, MU, Ali, A, et al.. Synthesis and structural analysis of novel indole derivatives by XRD, spectroscopic and DFT studies. J Mol Struct 2020;1203:127438. https://doi.org/10.1016/j.molstruc.2019.127438.Search in Google Scholar
46. Raza, AR, Nisar, B, Khalid, M, Gondal, HY, Khan, MU, de Alcântara Morais, SF, et al.. A facile microwave assisted synthesis and structure elucidation of (3R)-3-alkyl-4,1-benzoxazepine-2,5-diones by crystallographic, spectroscopic and DFT studies. Spectrochim Acta Mol Biomol Spectrosc 2020;230:117995. https://doi.org/10.1016/j.saa.2019.117995.Search in Google Scholar PubMed
47. Khalid, M, Ali, A, Adeel, M, Din, ZU, Tahir, MN, Rodrigues-Filho, E, et al.. Facile preparation, characterization, SC-XRD and DFT/DTDFT study of diversely functionalized unsymmetrical bis-aryl-α, β-unsaturated ketone derivatives. J Mol Struct 2020;1206:127755. https://doi.org/10.1016/j.molstruc.2020.127755.Search in Google Scholar
48. Tariq, S, Khalid, M, Raza, AR, Rubab, SL, de Alcântara Morais, SF, Khan, MU, et al.. Experimental and computational investigations of new indole derivatives: a combined spectroscopic, SC-XRD, DFT/TD-DFT and QTAIM analysis. J Mol Struct 2020;1207:127803. https://doi.org/10.1016/j.molstruc.2020.127803.Search in Google Scholar
49. Ali, A, Khalid, M, Marrugo, KP, Kamal, GM, Saleem, M, Khan, MU, et al.. Spectroscopic and DFT/TDDFT insights of the novel phosphonate imine compounds. J Mol Struct 2020;1207:127838. https://doi.org/10.1016/j.molstruc.2020.127838.Search in Google Scholar
50. Parr, RG, Lv, S, Liu, S. Electrophilicity index. J Am Chem Soc 1999;121:1922–4. https://doi.org/10.1021/ja983494x.Search in Google Scholar
51. Parr, RG, Donnelly, RA, Levy, M, Palke, WE. Electronegativity: the density functional viewpoint. J Chem Phys 1978;68:3801–7. https://doi.org/10.1063/1.436185.Search in Google Scholar
52. Chattaraj, PK, Roy, DR. Update 1 of: electrophilicity index. Chem Rev 2007;107:PR46–74. https://doi.org/10.1021/cr078014b.Search in Google Scholar
53. Khalid, M, Ali, A, Jawaria, R, Asghar, MA, Asim, S, Khan, MU, et al.. First principles study of electronic and nonlinear optical properties of A–D–π–A and D–A–D–π–A configured compounds containing novel quinoline–carbazole derivatives. RSC Adv 2020;10:22273–83. https://doi.org/10.1039/d0ra02857f.Search in Google Scholar PubMed PubMed Central
54. Srnec, M, Solomon, EI. Frontier molecular orbital contributions to chlorination versus hydroxylation selectivity in the non-heme iron halogenase SyrB2. J Am Chem Soc 2017;139:2396–407. https://doi.org/10.1021/jacs.6b11995.Search in Google Scholar PubMed PubMed Central
55. Guo, L, Zhu, S, Zhang, S, He, Q, Li, W. Theoretical studies of three triazole derivatives as corrosion inhibitors for mild steel in acidic medium. Corrosion Sci 2014;87:366–75. https://doi.org/10.1016/j.corsci.2014.06.040.Search in Google Scholar
56. Wang, T, Yuan, X-S, Wu, M-B, Lin, J-P, Yang, L-R. The advancement of multidimensional QSAR for novel drug discovery-where are we headed? Expet Opin Drug Discov 2017;12:769–84. https://doi.org/10.1080/17460441.2017.1336157.Search in Google Scholar PubMed
57. Trott, O, Olson, AJ. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 2010;31:455–61. https://doi.org/10.1002/jcc.21334.Search in Google Scholar PubMed PubMed Central
58. Morris, G, Huey, R, Lindstrom, W, Sanner, M., Belew, R., Goodsell, D, et al.. AutoDock4, AutoDockTo, ols4: automated docking with selective receptor flexibility. J Comput Chem 2009;30:2785–91. https://doi.org/10.1002/jcc.21256.Search in Google Scholar PubMed PubMed Central
59. Systèmes, D. Biovia, discovery studio modeling environment. San Diego, CA, USA: Dassault Systèmes Biovia; 2016.Search in Google Scholar
60. Bolarin, JA, Oluwatoyosi, MA, Orege, JI, Ayeni, EA, Ibrahim, YA, Adeyemi, SB, et al.. Therapeutic drugs for SARS-CoV-2 treatment: current state and perspective. Int Immunopharm 2021;90:107228. https://doi.org/10.1016/j.intimp.2020.107228.Search in Google Scholar PubMed PubMed Central
61. Yang, Y, Zhu, Z, Wang, X, Zhang, X, Mu, K, Shi, Y, et al.. Ligand-based approach for predicting drug targets and for virtual screening against COVID-19. Briefings Bioinf 2021;22:1053–64. https://doi.org/10.1093/bib/bbaa422.Search in Google Scholar PubMed PubMed Central
62. Hayden, FG, Turner, RB, Gwaltney, JM, Chi-Burris, K, Gersten, M, Hsyu, P, et al.. Phase II, randomized, double-blind, placebo-controlled studies of ruprintrivir nasal spray 2-percent suspension for prevention and treatment of experimentally induced rhinovirus colds in healthy volunteers. Antimicrob Agents Chemother 2003;47:3907–16. https://doi.org/10.1128/aac.47.12.3907-3916.2003.Search in Google Scholar PubMed PubMed Central
63. Yang, H, Xie, W, Xue, X, Yang, K, Ma, J, Liang, W, et al.. Design of wide-spectrum inhibitors targeting coronavirus main proteases. PLoS Biol 2005;3:e324. https://doi.org/10.1371/journal.pbio.0030324.Search in Google Scholar PubMed PubMed Central
64. Shi, L, Bucknall, MP, Young, TL, Zhang, M, Hu, L, Bing, J, et al.. Gas chromatography–mass spectrometry analyses of encapsulated stable perovskite solar cells. Science 2020;368. https://doi.org/10.1126/science.aba2412.Search in Google Scholar PubMed
65. Zhang, L, Lin, D, Sun, X, Curth, U, Drosten, C, Sauerhering, L, et al.. Crystal structure of SARS-CoV-2 main protease provides a basis for design of improved α-ketoamide inhibitors. Science 2020;368:409–12. https://doi.org/10.1126/science.abb3405.Search in Google Scholar PubMed PubMed Central
66. Muhammad, S, Hassan, SH, Al-Sehemi, AG, Shakir, HA, Khan, M, Irfan, M, et al.. Exploring the new potential antiviral constituents of Moringa oliefera for SARS-COV-2 pathogenesis: an in silico molecular docking and dynamic studies. Chem Phys Lett 2021;767:138379. https://doi.org/10.1016/j.cplett.2021.138379.Search in Google Scholar PubMed PubMed Central
67. Mohan, B, Muhammad, S, Al‐Sehemi, AG, Bharti, S, Kumar, S, Choudhary, M. Synthesis of copper (II) coordination complex, its molecular docking and computational exploration for novel functional properties: a dual approach. ChemistrySelect 2021;6:738–45. https://doi.org/10.1002/slct.202003738.Search in Google Scholar
Supplementary material
The online version of this article offers supplementary material (https://doi.org/10.1515/znc-2021-0042).
© 2021 Walter de Gruyter GmbH, Berlin/Boston
