How to cite this paper
Ouzebla, D., Ourhriss, N., Eşme, A., idrissi, M & Zeroual, A. (2024). Synthesis of some ribonucleosides derivatives and molecular docking analysis against variant corona virus omicrone.Current Chemistry Letters, 13(2), 445-450.
Refrences
1. Andreeva OV., Garifullin BF., Zarubaev V.V., Slita AV., Yesaulkova IL., Saifina LF., Shulaeva MM., Belenok MG., Semenov VE., Kataev VE. (2021) Synthesis of 1,2,3‑triazolyl nucleoside analogues and their antiviral Activity. Molecular Diversity, 25, 473–490. DOI:10.1007/s11030-020-10141-y.
2. Blanco JL., Ambrosioni J., Garcia F., Martinez E., Soriano A., Mallolas J., et al. (2020) Investigators, COVID-19 in Patients With HIV: Clinical Case Series. Lancet HIV, 7:e314–6. DOI: 10.1016/S2352-3018(20)30111-9.
3. Del Amo J., Polo R., Moreno S., Díaz A., Martínez E., Arribas JR., et al. (2020) Antiretrovirals and Risk of COVID-19 Diagnosis and Hospitalization in HIV-Positive Persons. Epidemiology, 31:e49–51. DOI:10.1097/ EDE.0000000000001235.
4. Dallocchio RN., Dessi A., De Vito A., Delogu G., Serra PA., Madeddu G. (2021) Early Combination Treatment With Existing HIV Antivirals: An Effective Treatment for COVID-19. Eur Rev Med Pharmacol Sci, 25:2435–48. DOI: 10.21203/rs.3.rs-35791/v1.
5. Saxena RK., Samad AA., Khan UR., Vinay V., Wankhede SV., et al. (2021) Assessment Prevalence of SARS-CoV-2 Infection in Patients on Anti-HBV (Lamivudine) Treatment: A Questionnaire Based Survey. IP Int J Med Microbiol Trop Dis, 7:7. DOI: 10.18231/j.ijmmtd.2021.005.
6. Yamauchi N., Maruyama D., Choi I., Atsuta Y., Sakai R., Miyashita K., et al. (2021) Prophylactic Antiviral Therapy for Hepatitis B Virus Surface Antigen-Positive Patients With Diffuse Large B-Cell Lymphoma Treated With Rituximab- Containing Chemotherapy. Cancer Sci, 112:1943–54. DOI: 10.1111/cas.14846.
7. Zhang S., Li N., Sheng Y., Chen W., Ma Q., Yu X., et al. (2021) Hepatitis B Virus Induces Sorafenib Resistance in Liver Cancer via Upregulation of cIAP2 Expression. Infect Agent Cancer, 16:20. DOI: 10.1186/s13027-021-00359-2.
8. Hui VW., Chan SL., Wong VW., Liang LY., Yip TC., Lai JC., et al. (2020) Increasing Antiviral Treatment Uptake Improves Survival in Patients With HBV-Related HCC. JHEP Rep, 2:100152. DOI: 10.1016/j.jhepr.2020.100152.
9. Wang X., Liu X., Dang Z., Yu L., Jiang Y., Wang X., et al. (2020) Nucleos(t)ide Analogues for Reducing Hepatocellular Carcinoma in Chronic Hepatitis B Patients: A Systematic Review and Meta-Analysis. Gut Liver, 14:16. DOI: 10.5009/gnl18546.
10. Madeddu G., Fiore V., Melis M., Ortu S., Mannu F., Muredda AA., et al. (2020) Mitochondrial Toxicity and Body Shape Changes During Nucleos(T)Ide Analogues Administration in Patients With Chronic Hepatitis B. Sci Rep, 10:2014. DOI: 10.1038/s41598-020-58837-3.
11. Arun KG., Sharanya CS., Abhithaj J., Francis D., Sadasivan C. (2020) Drug Repurposing Against SARS-CoV-2 Using E-Pharmacophore Based Virtual Screening, Molecular Docking and Molecular Dynamics With Main Protease as the Target. J Biomol Struct Dyn, 1–12. DOI: 10.1080/07391102. 2020.1779819.
12. Prajapat M., Shekhar N., Sarma P., Avti P., Singh S., Kaur H., et al. (2020) Virtual Screening and Molecular Dynamics Study of Approved Drugs as Inhibitors of Spike Protein S1 Domain and ACE2 Interaction in SARS-CoV-2. J Mol Graph Model, 101:107716. DOI: 10.1016/j.jmgm.2020.107716.
13. Fadaka AO., Aruleba RT., Sibuyi NRS., Klein A., Madiehe AM., Meyer M. (2020) Inhibitory Potential of Repurposed Drugs Against the SARS-CoV-2 Main Protease: A Computational-Aided Approach. J Biomol Struct Dyn, 1–13. DOI: 10.1080/07391102.2020.1847197.
14. Jacome R., Campillo-Balderas JA., Ponce de Leon S., Becerra A., Lazcano A. (2020) Sofosbuvir as a Potential Alternative to Treat the SARS-CoV-2 Epidemic. Sci Rep, 10:9294. DOI: 10.1038/s41598-020-66440-9.
15. Chien M., Anderson TK., Jockusch S., Tao C., Li X., Kumar S., et al. (2022) Nucleotide Analogues as Inhibitors of SARS-CoV-2 Polymerase, a Key Drug Target for COVID-19. J Proteome Res, 19:4690–7.
16. El idrissi M., El ghozlani M., Eşme A., Ríos-Gutiérrez M., Ouled Aitouna A., Salah M., El Alaoui El Abdallaoui H., Zeroual A., Mazoir N., Domingo L.R. (2021) Mpro-SARS-CoV-2 Inhibitors and Various Chemical Reactivity of 1-Bromo- and 1-Chloro-4-vinylbenzene in [3 + 2] Cycloaddition Reactions. Organics, 2 1-16. DOI: 10.3390/org2010001.
17. Raji H., Ouled Aitouna A., Barhoumi A., Chekroun A., Zeroual A., Syed A., Elgorban A. M., Verma M., Benharref A., Varma R. S. (2023) Antiviral docking analysis, semisynthesis and mechanistic studies on the origin of stereo- and chemoselectivity in epoxidation reaction of α′-trans-Himachalene, Journal of Molecular Liquids, 385: 122204, https://doi.org/10.1016/j.
18. Del Amo J., Polo R., Moreno S., Díaz A., Martínez E., Arribas JR., et al. (2020) Antiretrovirals and Risk of COVID-19 Diagnosis and Hospitalization in HIV-Positive Persons. Epidemiology 31:e49–51. DOI: 10.1097/EDE.0000000000001235.
19. Grein J., Ohmagari N., Shin D., Diaz G., Asperges E., Castagna A., et al. (2020) Compassionate Use of Remdesivir for Patients With Severe COVID-19. N Engl J Med, 382:2327–36. DOI: 10.1056/NEJMoa2007016.
20. Chien M., Anderson TK., Jockusch S., Tao C., Kumar S., Li X., et al. (2020) Nucleotide Analogues as Inhibitors of SARS-CoV-2 Polymerase, a Key Drug Target forCOVID-19. J Proteome Res, 19:4690–7. DOI: 10.1021/acs.jproteome.0c00392.
21. Ju J., Li X., Kumar S., Jockusch S., Chien M., Tao C., et al. (2020) Nucleotide Analogues as Inhibitors of SARS-CoV Polymerase. Pharmacol Res Perspect, 8:e00674. DOI: 10.1002/prp2.674.
22. Koulgi S., Jani V., NMU V., Sonavane U., Joshi R. (2021) Structural Insight Into theBinding Interactions of NTPs and Nucleotide Analogues to RNA Dependent RNA Polymerase of SARS-CoV-2. J Biomol Struct Dyn, 1–15. DOI: 10.1080/07391102.2021.1894985.
23. Khan S., Attar F., Bloukh SH., Sharifi M., Nabi F., Bai Q., et al. (2021) A Review on the nInteraction of Nucleoside Analogues With SARS-CoV-2 RNA Dependent RNA Polymerase. Int J Biol Macromol, 181:605–11. DOI: 10.1016/ j.ijbiomac.2021.03.112.
24. Abou-Elkhair R.A.I., Wasfy A.A., Mao S., Du J., Eladl S., Metwally K., Sheng, J. (2020) 2-Hydroxyimino-6-aza-pyrimidine nucleosides: Synthesis, DFT calculations, and antiviral evaluations. New Journal of Chemistry, 44, 19650-19662. DOI: 10.1039/DONJ04154H.
25. Umesh P., Aher ORCID Logo., Dhananjai Srivastava., Girij P., Singh and Jayashree B.S. (2021) Synthetic strategies toward 1,3-oxathiolane nucleoside analogues. J. Org. Chem, 17, 2680–2715. DOI: 10.3762/bjoc.17.182.
26. Gregory L.B., Michael S.B., Benjamin M.C., Junying F., Jonathan M., Chris Sfouggataki. (2019) Follow the Silyl Cation: Insights into the Vorbrüggen Reaction, Org. Process Res. Dev, 23, 9, 2050–2056. DOI:10.1021/acs.oprd.9b00304.
27. Lenka T., Jakub S. (2021) Study of the N7 Regioselective Glycosylation of 6-Chloropurine and 2,6-Dichloropurine with Tin and Titanium Tetrachloride,. J. Org. Chem, 86, 19, 13265–13275. DOI: 10.1021/acs.joc.1c01186.
28. Miller J.M., Goodchild M., Lakshmi L. J., Wails D., Hartman, J. S. (2000) Friedel–Crafts catalysis using supported reagents. Synthesis, characterization, and catalytic application of ZnCl2 supported on sol–gel-derived alumina. Mat. Lett, 44, 164-169. DOI:10.1016/j.apcata.2014.04.016.
29. Pillai, S. K., Abidli, A., Belkacemi, K. (2014) Triacylglycerol self-metathesis over highly chemoselective methyltrioxorhenium supported on ZnCl2-promoted mesoporous alumina. Appl. Catal. A, 479, 121-133. DOI:10.1016/j.apcata.2014.04.016.
30. Jacob R.G., Radatz C.S., Rodrigues M.B., Alves D., Perin G., Lenardão E.J., Savegnago L. (2011) Synthesis of 1-H-1,5-benzodiazepines derivatives using SiO2/ZnCl2. Heteroatom Chem, 22, 180-185. DOI:10.1002/hc.20674.
31. Baddi L., Ouzebla D., El Mansouri A., Smietana M., Vasseur J-J., Lazrek H.B. (2020) Efficient one-pot, three-component procedure to prepare new α-aminophosphonate and phosphonic acid acyclic nucleosides, Nucleosides, Nucleotides & Nucleic Acids, 40:1, 43-67. DOI: 10.1080/15257770.2020.1826516.
32. Collie, S., Champion, J., Moultrie, H., Bekker, L.G., and Gray, G. (2021) Effectiveness of BNT162b2 Vaccine against Omicron Variant in South Africa. The New England Journal of Medicine, 3:386(5):494-496. DOI: 10.1056/NEJMc2119270.
33. Salah M., El Alaoui El Abdallaoui O., Zeroual A., Acharjee N., El idrissi M. (2023) Insight into a new discovery of SARS-CoV-2 inhibitor activated through Chloroquine derivatives. Current Chemistry Letters, 12, 477–488. DOI:10.5267/j.ccl.2023.8.010.
34. Salah M., Belghiti M.E., Aitouna A.O., Zeroual A., Jorio S., El Alaoui Abdellaoui H., El Hadki H., Marakchi K., Komiha N. (2021) MEDT Study of the 1,3-DC Reaction of Diazomethane with Psilostachyin and investigation about the interactions of some pyrazoline derivatives with Protease (Mpro) of nCoV-2, Journal of Molecular Graphics and Modelling, 102, 107763. DOI: 10.1016/j.jmgm.2020.107763.
35. Schooley RT,. Carlin AF,. Beadle JR. (2021) Rethinking remdesivir: synthesis, antiviral activity and pharmacokinetics of oral lipid prodrugs. Antimicrobial Agents and Chemotherapy DOI: 10.1101/2020.08.26.269159.
36. Sanner M.F. (1999) Python: a programming language for software integration and development, J. Mol. Graphics Mod. 17, 57-61.
37. https://www.rcsb.org/
38. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., Olson A.J.. (1998) Automated docking using a lamarckian genetic algorithm and empirical binding free energy function, J. Comput. Chem. 19, 1639-1662.
39. The PyMOL Molecular Graphics System, Version 1.5.0.4 Schrodinger LLC. (2010).
2. Blanco JL., Ambrosioni J., Garcia F., Martinez E., Soriano A., Mallolas J., et al. (2020) Investigators, COVID-19 in Patients With HIV: Clinical Case Series. Lancet HIV, 7:e314–6. DOI: 10.1016/S2352-3018(20)30111-9.
3. Del Amo J., Polo R., Moreno S., Díaz A., Martínez E., Arribas JR., et al. (2020) Antiretrovirals and Risk of COVID-19 Diagnosis and Hospitalization in HIV-Positive Persons. Epidemiology, 31:e49–51. DOI:10.1097/ EDE.0000000000001235.
4. Dallocchio RN., Dessi A., De Vito A., Delogu G., Serra PA., Madeddu G. (2021) Early Combination Treatment With Existing HIV Antivirals: An Effective Treatment for COVID-19. Eur Rev Med Pharmacol Sci, 25:2435–48. DOI: 10.21203/rs.3.rs-35791/v1.
5. Saxena RK., Samad AA., Khan UR., Vinay V., Wankhede SV., et al. (2021) Assessment Prevalence of SARS-CoV-2 Infection in Patients on Anti-HBV (Lamivudine) Treatment: A Questionnaire Based Survey. IP Int J Med Microbiol Trop Dis, 7:7. DOI: 10.18231/j.ijmmtd.2021.005.
6. Yamauchi N., Maruyama D., Choi I., Atsuta Y., Sakai R., Miyashita K., et al. (2021) Prophylactic Antiviral Therapy for Hepatitis B Virus Surface Antigen-Positive Patients With Diffuse Large B-Cell Lymphoma Treated With Rituximab- Containing Chemotherapy. Cancer Sci, 112:1943–54. DOI: 10.1111/cas.14846.
7. Zhang S., Li N., Sheng Y., Chen W., Ma Q., Yu X., et al. (2021) Hepatitis B Virus Induces Sorafenib Resistance in Liver Cancer via Upregulation of cIAP2 Expression. Infect Agent Cancer, 16:20. DOI: 10.1186/s13027-021-00359-2.
8. Hui VW., Chan SL., Wong VW., Liang LY., Yip TC., Lai JC., et al. (2020) Increasing Antiviral Treatment Uptake Improves Survival in Patients With HBV-Related HCC. JHEP Rep, 2:100152. DOI: 10.1016/j.jhepr.2020.100152.
9. Wang X., Liu X., Dang Z., Yu L., Jiang Y., Wang X., et al. (2020) Nucleos(t)ide Analogues for Reducing Hepatocellular Carcinoma in Chronic Hepatitis B Patients: A Systematic Review and Meta-Analysis. Gut Liver, 14:16. DOI: 10.5009/gnl18546.
10. Madeddu G., Fiore V., Melis M., Ortu S., Mannu F., Muredda AA., et al. (2020) Mitochondrial Toxicity and Body Shape Changes During Nucleos(T)Ide Analogues Administration in Patients With Chronic Hepatitis B. Sci Rep, 10:2014. DOI: 10.1038/s41598-020-58837-3.
11. Arun KG., Sharanya CS., Abhithaj J., Francis D., Sadasivan C. (2020) Drug Repurposing Against SARS-CoV-2 Using E-Pharmacophore Based Virtual Screening, Molecular Docking and Molecular Dynamics With Main Protease as the Target. J Biomol Struct Dyn, 1–12. DOI: 10.1080/07391102. 2020.1779819.
12. Prajapat M., Shekhar N., Sarma P., Avti P., Singh S., Kaur H., et al. (2020) Virtual Screening and Molecular Dynamics Study of Approved Drugs as Inhibitors of Spike Protein S1 Domain and ACE2 Interaction in SARS-CoV-2. J Mol Graph Model, 101:107716. DOI: 10.1016/j.jmgm.2020.107716.
13. Fadaka AO., Aruleba RT., Sibuyi NRS., Klein A., Madiehe AM., Meyer M. (2020) Inhibitory Potential of Repurposed Drugs Against the SARS-CoV-2 Main Protease: A Computational-Aided Approach. J Biomol Struct Dyn, 1–13. DOI: 10.1080/07391102.2020.1847197.
14. Jacome R., Campillo-Balderas JA., Ponce de Leon S., Becerra A., Lazcano A. (2020) Sofosbuvir as a Potential Alternative to Treat the SARS-CoV-2 Epidemic. Sci Rep, 10:9294. DOI: 10.1038/s41598-020-66440-9.
15. Chien M., Anderson TK., Jockusch S., Tao C., Li X., Kumar S., et al. (2022) Nucleotide Analogues as Inhibitors of SARS-CoV-2 Polymerase, a Key Drug Target for COVID-19. J Proteome Res, 19:4690–7.
16. El idrissi M., El ghozlani M., Eşme A., Ríos-Gutiérrez M., Ouled Aitouna A., Salah M., El Alaoui El Abdallaoui H., Zeroual A., Mazoir N., Domingo L.R. (2021) Mpro-SARS-CoV-2 Inhibitors and Various Chemical Reactivity of 1-Bromo- and 1-Chloro-4-vinylbenzene in [3 + 2] Cycloaddition Reactions. Organics, 2 1-16. DOI: 10.3390/org2010001.
17. Raji H., Ouled Aitouna A., Barhoumi A., Chekroun A., Zeroual A., Syed A., Elgorban A. M., Verma M., Benharref A., Varma R. S. (2023) Antiviral docking analysis, semisynthesis and mechanistic studies on the origin of stereo- and chemoselectivity in epoxidation reaction of α′-trans-Himachalene, Journal of Molecular Liquids, 385: 122204, https://doi.org/10.1016/j.
18. Del Amo J., Polo R., Moreno S., Díaz A., Martínez E., Arribas JR., et al. (2020) Antiretrovirals and Risk of COVID-19 Diagnosis and Hospitalization in HIV-Positive Persons. Epidemiology 31:e49–51. DOI: 10.1097/EDE.0000000000001235.
19. Grein J., Ohmagari N., Shin D., Diaz G., Asperges E., Castagna A., et al. (2020) Compassionate Use of Remdesivir for Patients With Severe COVID-19. N Engl J Med, 382:2327–36. DOI: 10.1056/NEJMoa2007016.
20. Chien M., Anderson TK., Jockusch S., Tao C., Kumar S., Li X., et al. (2020) Nucleotide Analogues as Inhibitors of SARS-CoV-2 Polymerase, a Key Drug Target forCOVID-19. J Proteome Res, 19:4690–7. DOI: 10.1021/acs.jproteome.0c00392.
21. Ju J., Li X., Kumar S., Jockusch S., Chien M., Tao C., et al. (2020) Nucleotide Analogues as Inhibitors of SARS-CoV Polymerase. Pharmacol Res Perspect, 8:e00674. DOI: 10.1002/prp2.674.
22. Koulgi S., Jani V., NMU V., Sonavane U., Joshi R. (2021) Structural Insight Into theBinding Interactions of NTPs and Nucleotide Analogues to RNA Dependent RNA Polymerase of SARS-CoV-2. J Biomol Struct Dyn, 1–15. DOI: 10.1080/07391102.2021.1894985.
23. Khan S., Attar F., Bloukh SH., Sharifi M., Nabi F., Bai Q., et al. (2021) A Review on the nInteraction of Nucleoside Analogues With SARS-CoV-2 RNA Dependent RNA Polymerase. Int J Biol Macromol, 181:605–11. DOI: 10.1016/ j.ijbiomac.2021.03.112.
24. Abou-Elkhair R.A.I., Wasfy A.A., Mao S., Du J., Eladl S., Metwally K., Sheng, J. (2020) 2-Hydroxyimino-6-aza-pyrimidine nucleosides: Synthesis, DFT calculations, and antiviral evaluations. New Journal of Chemistry, 44, 19650-19662. DOI: 10.1039/DONJ04154H.
25. Umesh P., Aher ORCID Logo., Dhananjai Srivastava., Girij P., Singh and Jayashree B.S. (2021) Synthetic strategies toward 1,3-oxathiolane nucleoside analogues. J. Org. Chem, 17, 2680–2715. DOI: 10.3762/bjoc.17.182.
26. Gregory L.B., Michael S.B., Benjamin M.C., Junying F., Jonathan M., Chris Sfouggataki. (2019) Follow the Silyl Cation: Insights into the Vorbrüggen Reaction, Org. Process Res. Dev, 23, 9, 2050–2056. DOI:10.1021/acs.oprd.9b00304.
27. Lenka T., Jakub S. (2021) Study of the N7 Regioselective Glycosylation of 6-Chloropurine and 2,6-Dichloropurine with Tin and Titanium Tetrachloride,. J. Org. Chem, 86, 19, 13265–13275. DOI: 10.1021/acs.joc.1c01186.
28. Miller J.M., Goodchild M., Lakshmi L. J., Wails D., Hartman, J. S. (2000) Friedel–Crafts catalysis using supported reagents. Synthesis, characterization, and catalytic application of ZnCl2 supported on sol–gel-derived alumina. Mat. Lett, 44, 164-169. DOI:10.1016/j.apcata.2014.04.016.
29. Pillai, S. K., Abidli, A., Belkacemi, K. (2014) Triacylglycerol self-metathesis over highly chemoselective methyltrioxorhenium supported on ZnCl2-promoted mesoporous alumina. Appl. Catal. A, 479, 121-133. DOI:10.1016/j.apcata.2014.04.016.
30. Jacob R.G., Radatz C.S., Rodrigues M.B., Alves D., Perin G., Lenardão E.J., Savegnago L. (2011) Synthesis of 1-H-1,5-benzodiazepines derivatives using SiO2/ZnCl2. Heteroatom Chem, 22, 180-185. DOI:10.1002/hc.20674.
31. Baddi L., Ouzebla D., El Mansouri A., Smietana M., Vasseur J-J., Lazrek H.B. (2020) Efficient one-pot, three-component procedure to prepare new α-aminophosphonate and phosphonic acid acyclic nucleosides, Nucleosides, Nucleotides & Nucleic Acids, 40:1, 43-67. DOI: 10.1080/15257770.2020.1826516.
32. Collie, S., Champion, J., Moultrie, H., Bekker, L.G., and Gray, G. (2021) Effectiveness of BNT162b2 Vaccine against Omicron Variant in South Africa. The New England Journal of Medicine, 3:386(5):494-496. DOI: 10.1056/NEJMc2119270.
33. Salah M., El Alaoui El Abdallaoui O., Zeroual A., Acharjee N., El idrissi M. (2023) Insight into a new discovery of SARS-CoV-2 inhibitor activated through Chloroquine derivatives. Current Chemistry Letters, 12, 477–488. DOI:10.5267/j.ccl.2023.8.010.
34. Salah M., Belghiti M.E., Aitouna A.O., Zeroual A., Jorio S., El Alaoui Abdellaoui H., El Hadki H., Marakchi K., Komiha N. (2021) MEDT Study of the 1,3-DC Reaction of Diazomethane with Psilostachyin and investigation about the interactions of some pyrazoline derivatives with Protease (Mpro) of nCoV-2, Journal of Molecular Graphics and Modelling, 102, 107763. DOI: 10.1016/j.jmgm.2020.107763.
35. Schooley RT,. Carlin AF,. Beadle JR. (2021) Rethinking remdesivir: synthesis, antiviral activity and pharmacokinetics of oral lipid prodrugs. Antimicrobial Agents and Chemotherapy DOI: 10.1101/2020.08.26.269159.
36. Sanner M.F. (1999) Python: a programming language for software integration and development, J. Mol. Graphics Mod. 17, 57-61.
37. https://www.rcsb.org/
38. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., Olson A.J.. (1998) Automated docking using a lamarckian genetic algorithm and empirical binding free energy function, J. Comput. Chem. 19, 1639-1662.
39. The PyMOL Molecular Graphics System, Version 1.5.0.4 Schrodinger LLC. (2010).