Synthesis and Anti-HIV Activity of Triazolo-fused 3',4'-Cyclic and 4'-Spiro Nucleoside Analogues

doi:10.1007/s40242-013-2375-5

高等学校化学研究 ›› 2013, Vol. 29 ›› Issue (3): 473-476.doi: 10.1007/s40242-013-2375-5

Synthesis and Anti-HIV Activity of Triazolo-fused 3',4'-Cyclic and 4'-Spiro Nucleoside Analogues

SUN Jing-bo¹, LIU Rong-wang¹, XUAN Li-li², LENG Wei-chun², WU Jin-chang¹

1. College of Chemistry, Jilin University, Changchun 130012, P. R. China;
2. China-Japan Union Hospital of Jilin University, Changchun 130033, P. R. China

收稿日期:2012-09-28 修回日期:2012-11-04 出版日期:2013-06-01 发布日期:2013-05-15
通讯作者: WU Jin-chang, E-mail: jcwu@jlu.edu.cn E-mail:jcwu@jlu.edu.cn

Synthesis and Anti-HIV Activity of Triazolo-fused 3',4'-Cyclic and 4'-Spiro Nucleoside Analogues

SUN Jing-bo¹, LIU Rong-wang¹, XUAN Li-li², LENG Wei-chun², WU Jin-chang¹

1. College of Chemistry, Jilin University, Changchun 130012, P. R. China;
2. China-Japan Union Hospital of Jilin University, Changchun 130033, P. R. China

Received:2012-09-28 Revised:2012-11-04 Online:2013-06-01 Published:2013-05-15

摘要/Abstract

摘要：

Triazolo-fused 3',4'-cyclic nucleoside 4'-spiro nucleoside analogues were synthesized by an intramolecular 1,3-dipolar cycloaddition of 4'-azido nucleoside derived azido-alkynes in a regio- and stereo-specific manner. The thymine nucleoside base in these target compounds was transformed into the corresponding 5-methyl cytosine component. The synthesized compounds were examined in an MAGI(multinuclear-activation galactosidase indicator) assay for exploring the anti-HIV activity and in a H9 T(human T lymphocytes H9) assay for measuring the cell toxicity.

关键词: 4'-Spiro nucleoside, 3',4'-fused nucleoside, Biological activity, 1,3-Dipolar cycloaddition

Abstract:

Key words: 4'-Spiro nucleoside, 3',4'-fused nucleoside, Biological activity, 1,3-Dipolar cycloaddition

SUN Jing-bo, LIU Rong-wang, XUAN Li-li, LENG Wei-chun, WU Jin-chang. Synthesis and Anti-HIV Activity of Triazolo-fused 3',4'-Cyclic and 4'-Spiro Nucleoside Analogues[J]. 高等学校化学研究, 2013, 29(3): 473-476.

SUN Jing-bo, LIU Rong-wang, XUAN Li-li, LENG Wei-chun, WU Jin-chang. Synthesis and Anti-HIV Activity of Triazolo-fused 3',4'-Cyclic and 4'-Spiro Nucleoside Analogues[J]. Chemical Research in Chinese Universities, 2013, 29(3): 473-476.

参考文献

[1] de Clercq E., J. Clin. Vir., 2004, 30, 115

[2] de Clercq E., Biochem. Pharm., 2007, 73, 911

[3] de Clercq E., Biochim. Biophys. Acta, 2002, 1587, 258

[4] de Clercq E., Biochem. Pharm., 2004, 68, 2301

[5] Brady R. C., Bernstein D. I., Antivir Res., 2004, 61, 73

[6] Papatheodoridis G. V., Dimou E., Papadimitropoulos V., Am. J. Gastroenterology, 2002, 97, 1618

[7] Blagosklonny M. V., Cell Cycle, 2004, 3, 1035

[8] Robak T., Korycka A., Kasznicki M., Wrzesien-Kus A., Smolewski P., Curr. Cancer Drug Targets, 2005, 5, 421

[9] Balzarini J., Pharm. World Sci., 1994, 16, 113

[10] Stein D. S., Moore K. H., Pharmacotherapy, 2001, 21, 11

[11] de Clercq E., International Journal of Antimicrobial Agents, 2009, 33, 307

[12] de Clercq E., Antivir Res., 2005, 67, 56

[13] Len C., Mackenzie G., Tetraheron, 2006, 62, 9085

[14] de Clercq E., Biochim. Biophys. Acta, 2002, 1587, 258

[15] Barchi J., Karki R. G., Nicklaus M. C., Siddiqui M. A., George C., Mikhailopulo I. A., Marquez V. E., J. Am. Chem. Soc., 2008, 130, 9048

[16] Shaikh I. K., Kumar S., Lundhus L., Bond A. D., Sharma P. K., Nielsen P., J. Org. Chem., 2009, 74, 1557

[17] Zhou C., Chattopadhyaya J., Curr. Opin. Drug. Discov. Devel., 2009, 12, 876

[18] Ewing D. F., Fahmi N. E., Len C., Mackenzie G., Pranzo A., J. Chem. Soc., Perkin Trans. 1, 2000, 3561

[19] Kolb H. C., Finn M. G., Sharpless K. B., Angew. Chem. Int. Ed. Engl., 2001, 40, 2004

[20] Bock V. D., Hiemstra H., Maarseveen J. H., Eur. J. Org. Chem., 2006, 51

[21] Binder W. H., Sachsenhofer R., Macromol. Rapid Commun., 2007, 28, 15

[22] Binder W. H., Sachsenhofer R., Macromol. Rapid Commun., 2008, 29, 952

[23] Alvarez R., Velazquez S., San-Felix A., Aquaro S., de Clercq E., Perno C. F., Karlsson A., Balzarini J., Camarasa M. J., J. Med. Chem., 1994, 37, 4185

[24] Genin M. J., Allwine D. A., Anderson D. J., Barbachyn M. R., Emmert D. E., Garmon S. A., Graber D. R., Grega K. C., Hester J. B., Hutchinson D. K., Morris J., Reischer R. J., Ford C. W., Zurenko G. E., Hamel J. C., Schaadt R. D., Stper D., Yagi B. H., J. Med. Chem., 2000, 43, 953

[25] Lewis W. G., Green L. G., Grynszpan F., Radic Z., Carlier P. R., Taylor P., Finn M. G., Sharpless K. B., Angew. Chem., Int. Ed., 2002, 41, 1053

[26] KolbH. C., Sharpless K. B., Drug Discovery Today, 2003, 8, 1128

[27] Tron G. C., Pirali T., Billington R. A., Canonico P. L., Sorba G., Genazzani A. A., Med. Res. Rev., 2008, 28, 278

[28] Lutz J. F., Zarafshani Z., Adv. Drug. Delivery Rev., 2008, 60, 958

[29] Moorhouse A. D., Moses J. E., Chem. Med. Chem., 2008, 3, 715

[30] de Clercq E., Nature Review Drug Discovery, 2002, 1, 13

[31] Sun J. B., Liu X. Y., Li H. M., Duan R. H., Wu J. C., Hel. Chim. Acta, 2012, 95, 772

[32] Maag H., Rydzewski R. M., McRoberta M. J., Crawford-Ruth D., Verheyden J. P. H., Prisbe E. J., J. Med. Chem., 1992, 35, 1440

[33] Smith D. B., Kalayanov G., Sund C., Winqvist A., Pinho P. O., Maltseva T., Morisson V., Leveque V., Rajyaguru S., Le Pogam S., Najera I., Benkestock K., Zhou X. X., Maag H., Cammack N., Martin J. A., Swallow S., Johansson N. G., Klumpp K., Smith M., J. Med. Chem., 2009, 52, 219

[34] Teste K., Colombeau L., Hadj-Bouazza A., Lucas R., Zerrouki R., Krausza P., Champavier Y., Carbohydrate Research, 2008, 343, 1490

[35] Matsuda A., Yasuoka J., Ueda T., Chem. Pharm. Bull., 1989, 37, 1659

[36] Yu X., Yu Y., Liu B., Luo K., Kong W., Mao P., Yu X. F., Science, 2003, 302, 1056

[37] Kimpton J., Emerman M., J. Virol., 1992, 66, 2232

[38] Tian C., Yu X., Zhang W., Wang T., Xu R., Yu X. F., J. Virol., 2006, 80, 3112

Synthesis and Anti-HIV Activity of Triazolo-fused 3',4'-Cyclic and 4'-Spiro Nucleoside Analogues

Synthesis and Anti-HIV Activity of Triazolo-fused 3',4'-Cyclic and 4'-Spiro Nucleoside Analogues

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