利巴韦林的结构修饰及应用研究进展

doi:10.6023/cjoc202601025

摘要/Abstract

对核苷类似物进行结构修饰是研发新型药物的重要策略。利巴韦林作为代表性核苷类似物之一,是一种广谱抗病毒药物。然而,长期或过量使用可能导致白细胞减少、抑制红细胞生成等副作用。因此,大量研究致力于开发高效低毒的利巴韦林衍生物。本文系统总结了利巴韦林的结构修饰及应用,主要包括：1)糖基修饰;2)碱基修饰。同时,也探讨了新的合成方法及其在药物开发中的潜在应用,以期为新型抗病毒药物的研发提供参考。

关键词: 利巴韦林, 结构修饰, 应用, 糖基修饰, 碱基修饰

Structural modification of nucleoside analogues is an important strategy for developing novel drugs. Ribavirin, as one of the representative nucleoside analogues, is a broad-spectrum antiviral nucleoside drug. However, its prolonged or excessive use can lead to side effects, such as reduction in white blood cell count and inhibition of red blood cell production. Therefore, extensive research has focused on developing ribavirin derivatives with improved efficacy and reduced toxicity. This minireview systematically summarizes the structural modifications and applications of ribavirin, primarily including: 1) glycosyl modifications and 2) base modifications. Additionally, novel synthetic methods and potential applications in drug development are discussed, providing insights for the development of novel antiviral drugs.

Key words: Ribavirin, Structural Modification, Application, Glycosyl Modification, Base Modification

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吕洁, 李停停. 利巴韦林的结构修饰及应用研究进展[J]. 有机化学, doi: 10.6023/cjoc202601025.

Lv Jie, Li Tingting. Recent Advances in the Structural Modifications and Applications of Ribavirin[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202601025.

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参考文献

[1] Saenger W.Angew. Chem. Int. Ed. 1973, 12, 591-601.
[2] Leonard N. J.; Tolman G. L.Ann. N. Y. Acad. Sci. 1975, 255, 43-58.
[3] Banoub J. H.; Newton R. P.; Esmans E.; Ewing D. F.; Mackenzie G.Chem. Rev. 2005, 105, 1869-1916.
[4] Peters G. M.; Davis J. T.Chem. Soc. Rev. 2016, 45, 3188-3206.
[5] Roy B.; Depaix A.; Perigaud C.; Peyrottes S.Chem. Rev. 2016, 116, 7854-7897.
[6] Dimakos V.; Taylor M. S.Chem. Rev. 2018, 118, 11457-11517.
[7] Pu F.; Ren J.; Qu X.Chem. Soc. Rev. 2018, 47, 1285-1306.
[8] Fialho D. M.; Roche T. P.; Hud N. V.Chem. Rev. 2020, 120, 4806-4830.
[9] Shet H.; Sahu R.; Sanghvi Y. S.; Kapdi A. R.Chem. Rec. 2022, 22, e202200066.
[10] Seley-Radtke, K. L.; Yates, M. K.Antiviral Res. 2018, 154, 66-86.
[11] Yates M. K.;Seley-Radtke, K. L.Antiviral Res. 2019, 162, 5-21.
[12] Hu H.;Mady Traore, M. D.; Li, R.; Yuan, H.; He, M.; Wen, B.; Gao, W.; Jonsson, C. B.; Fitzpatrick, E. A.; Sun, D.J. Med. Chem. 2022, 65, 12044-12054.
[13] Thomson P. J.; Illing P. T.; Farrell J.; Alhaidari M.; Bell C. C.; Berry N.; O’Neill, P. M.; Purcell, A. W.; Park, K. B.; Naisbitt, D. J.Allergy 2020, 75, 636-647.
[14] Lin X.; Liang C.; Zou L.; Yin Y.; Wang J.; Chen D.; Lan W.Eur. J. Med. Chem. 2021, 214, 113233.
[15] Knight V.; Wilson S.; Quarles J.; Greggs S.; McClung, H.; Waters, B.; Cameron, R.; Zerwas, J.; Couch, R.The Lancet 1981, 318, 945-949.
[16] Reichard O.; Andersson J.; Schvarcz R.; Weiland O.The Lancet 1991, 337, 1058-1061.
[17] Wiley J. S.; Jones S. P.; Sawyer W. H.; Paterson A. R.J. Clin. Invest. 1982, 69, 479-489.
[18] Bonkovsky H. L.; Stefancyk D.;McNeal, K.; Banner, B. F.; Liu, Q.; Zucker, G. M.; Israel, J.; Stagias, J.; Colker, J. Digest. Dis. Sci. 2001, 46, 2051-2059.
[19] Santagostino E.; Rumi M. G.; Rivi M.; Colombo M.; Mannucci P. M.Blood 2002, 99, 1089-1091.
[20] Hunsucker S. A.; Mitchell B. S.; Spychala J.Pharmacol Ther. 2005, 107, 1-30.
[21] Smal C.; Vertommen D.; Bertrand L.; Ntamashimikiro S.; Rider M. H.; Van Den Neste, E.; Bontemps, F.J. Biol. Chem. 2006, 281, 4887-4893.
[22] Li F.; Maag H.; Alfredson T.J. Pharm. Sci. 2008, 97, 1109-1134.
[23] Saiki Y.; Yoshino Y.; Fujimura H.; Manabe T.; Kudo Y.; Shimada M.; Mano N.; Nakano T.; Lee Y.; Shimizu S.; Oba S.; Fujiwara S.; Shimizu H.; Chen N.; Nezhad Z. K.; Jin G.; Fukushige S.; Sunamura M.; Ishida M.; Motoi F.; Egawa S.; Unno M.; Horii A.Biochem. Biophys. Res. Commun. 2012, 421, 98-104.
[24] Thornton P. J.; Kadri H.; Miccoli A.; Mehellou Y.J. Med. Chem. 2016, 59, 10400-10410.
[25] Pawlotsky J. M.; Dahari H.; Neumann A. U.; Hezode C.; Germanidis G.; Lonjon I.; Castera L.; Dhumeaux D.Gastroenterology 2004, 126, 703-714.
[26] Swenson C. S.; Velusamy A.; Argueta-Gonzalez H. S.; Heemstra, J. M. J. Am. Chem. Soc.2019, 141, 19038-19047.
[27] Muralidharan A.; Boukany P. E.Trends Biotechnol. 2023, 42, 780-798.
[28] Mehellou Y.; Rattan H. S.; Balzarini J.J. Med. Chem. 2018, 61, 2211-2226.
[29] Sun Y.; Kang D.; Gao, S. Chinese J. Med. Chem.2021, 31, 55-75 (in Chinese).
孙彦莹, 康东伟, 高升华.中国药物化学杂志, 2021, 31, 55-75.
[30] Hanna N. B.; Robins R. K.; Revankar G. R.Carbohydr. Res. 1987, 165, 267-274.
[31] Tamarez M.; Morgan B.; Wong G. S.K.; Tong, W.; Bennett, F.; Lovey, R.; McCormick, J. L.; Zaks, A.Org. Process Res. Dev. 2002, 7, 951-953.
[32] Li Q.; Chen S.; Jiang, N. Chin. J. Org. Chem.2004, 24, 1432-1435 (in Chinese).
李清寒, 陈淑华, 蒋宁. 有机化学, 2004, 24, 1432-1435.
[33] Li Z.; Chen S.; Jiang N.; Cui G.Nucleos. Nucleot. Nucl. 2003, 22, 419-435.
[34] Liu B. K.; Wang N.; Wu Q.; Xie C. Y.; Lin X. F.Biotechnol. Lett. 2005, 27, 717-720.
[35] Liu B. K.; Wang N.; Chen Z. C.; Wu Q.; Lin, X. F. Bioorg. Med. Chem. Lett.2006, 16, 3769-3771.
[36] Liu B. K.; Wu Q.; Xu J. M.; Lin X. F.Chem. Commun. 2007, 295-297.
[37] Brookes S.; Biessels P.; Ng N. F.L.; Woods, C.; Bell, D. N.; Adamson, G.Bioconjugate Chem. 2006, 17, 530-537.
[38] Li X.; Wu Q.; Lu M.; Zhang F.; Lin X.J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 2734-2744.
[39] Liu B.; Qian X.; Wu Q.; Lin X.Enzyme Microb. Technol. 2008, 43, 375-380.
[40] Li X.; Wu Q.; Chen Z.; Gong X.; Lin X.Polymer 2008, 49, 4769-4775.
[41] Leisvuori A.; Aiba Y.; Lonnberg T.;Poijarvi-Virta, P.; Blatt, L.; Beigelman, L.; Lonnberg, H. Org. Biomol. Chem. 2010, 8, 2131-2141.
[42] Oleynikova I. A.; Kulak T. I.; Bolibrukh D. A.; Kalinichenko E. N.Helv. Chim. Acta 2013, 96, 463-472.
[43] Ni Z.; Lin X.J. Mol. Model. 2013, 19, 349-358.
[44] Xu F.; Zhang M.; Wu Q.; Lin X.J. Mol. Catal. B: Enzym. 2014, 105, 49-57.
[45] Kryger M. B.L.; Wohl, B.M.; Smith, A. A. A.; Zelikin, A. N. Chem. Commun. 2013, 49, 2643-2645.
[46] Dong Z.; Li Q.; Guo D.; Shu Y.; Polli J. E.J. Pharm. Sci. 2015, 104, 2864-2876.
[47] Riber C. F.; Hinton T. M.; Gajda P.; Zuwala K.; Tolstrup M.; Stewart C.; Zelikin A. N.Mol. Pharm. 2017, 14, 234-241.
[48] Lv J.; Zou J.; Nong Y.; Song J.; Shen T.; Cai H.; Mou C.; Lyu W.; Jin Z.; Chi Y. R.ACS Catal. 2023, 13, 9567-9576.
[49] Ramasamy K. S.; Tam R. C.; Bard J.; Averett D. R.J. Med. Chem. 2000, 43, 1019-1028.
[50] Vivet-Boudou, V.; Paillart, J. C.; Burger, A.; Marquet, R.Nucleos. Nucleot. Nucl. 2007, 26, 743-746.
[51] Xu R. G.; Liu F.; Liu Y. J.; Chen B. Q.; Liu F. W.Chin. J. Chem . 2013, 31, 855-860.
[52] Qureshi A.; Bano S.Med. Chem. Res. 2024, 33, 1554-1567.
[53] Wang Q.; Hu W.; Wang S.; Pan Z.; Tao L.; Guo X.; Qian K.; Chen C.-H.; Lee K.-H.; Chang J.Eur. J. Med. Chem. 2011, 46, 4178-4183.
[54] Kini G. D.; Robins R. K.; Avery T. L.J. Med. Chem. 2002, 32, 1447-1449.
[55] Wu Q.; Qu F.; Wan J.; Zhu X.; Xia Y.; Peng L.Helv. Chim. Acta 2004, 87, 811-819.
[56] Wan J. Q.; Zhu R. Z.; Xia Y.; Qu F. Q.; Wu Q. Y.; Yang G. F.; Neyts J.; Peng L.Tetrahedron Lett. 2006, 47, 6727-6731.
[57] Chung D. H.; Kumarapperuma S. C.; Sun Y.; Li Q.; Chu Y. K.; Arterburn J. B.; Parker W. B.; Smith J.; Spik K.; Ramanathan H. N.; Schmaljohn C. S.; Jonsson C. B.Antiviral Res. 2008, 79, 19-27.
[58] Zhang, Y.; Wang, L.; Peng, Y.; Lin, D. Chin. J. Synth. Chem. 2010, 18, 712-714 (in Chinese).
张逸伟, 王琳, 彭云铁, 林东恩. 合成化学, 2010, 18, 712-714.