通过不对称氢转移/动态动力学拆分合成碳环N3-嘌呤核苷

doi:10.6023/cjoc201907053

有机化学 ›› 2020, Vol. 40 ›› Issue (2): 376-383.DOI: 10.6023/cjoc201907053 上一篇下一篇

研究论文

通过不对称氢转移/动态动力学拆分合成碳环N³-嘌呤核苷

张齐英, 张一铭, 郝二军, 白娟, 渠桂荣, 郭海明

河南师范大学化学化工学院绿色化学介质与反应教育部重点实验室精细化学品绿色制造河南省协同创新中心河南省有机功能分子与药物创新重点实验室河南新乡 453007

收稿日期:2019-07-30 修回日期:2019-09-30 发布日期:2019-10-25
通讯作者: 郭海明 E-mail:ghm@htu.edu.cn
基金资助:
国家自然科学基金（Nos.21602045，U1604283）和高等学校学科创新引智计划（111计划，No.D17007）资助项目.

Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution for the Construction of Carbocyclic N³-Purine Nucleosides

Zhang Qiying, Zhang Yiming, Hao Erjun, Bai Juan, Qu Guirong, Guo Haiming

Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007

Received:2019-07-30 Revised:2019-09-30 Published:2019-10-25
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21602045, U1604283), and the Overseas Expertise Introduction Project for Discipline Innovation (111 Project, No. D17007).

文章分享

1. 200376S.pdf.pdf(11049KB)

摘要/Abstract

N³-嘌呤核苷由于可能同时被嘌呤和嘧啶代谢酶识别，因而有望作为双靶点药物应用于抗病毒治疗.报道了一种以α-（N³-嘌呤）取代的环烷酮为原料，通过不对称氢转移反应实现动态动力学拆分，高收率高立体选择性地合成系列碳环N³-嘌呤核苷化合物.该催化体系也适用于α-嘧啶取代的环烷酮底物，且产物通过进一步衍生，合成了2'-F-，AcS-，N₃-修饰的碳环嘧啶核苷.

关键词: 碳环核苷, 双靶点抑制剂, 动态动力学拆分, 不对称氢转移反应

N³-Purine nucleoside can be employed as a potent dual inhibitor to inhibit viruses more effectively because it could be possibly recognized by both purine-and pyrimidine-metabolizing enzymes. Herein, an asymmetric transfer hydrogenation via dynamic kinetic resolution of rac-α-(purin-3-yl)cyclopentones has been developed to produce a wide range of carbocyclic N³-purine nucleosides in high yields and excellent stereoselectivities. Moreover, the catalytic system was suitable for rac-α-pyrimidinyl cyclopentones. With additional transformations, several 2'-F-, AcS-, N₃-modified carbocyclic nucleosides could be obtained with good to excellent yields and excellent enantioselectivities.

Key words: carbocyclic nucleosides, dual inhibitors, dynamic kinetic resolution, asymmetric transfer hydrogenation

引用此文

张齐英, 张一铭, 郝二军, 白娟, 渠桂荣, 郭海明. 通过不对称氢转移/动态动力学拆分合成碳环N³-嘌呤核苷[J]. 有机化学, 2020, 40(2): 376-383.

Zhang Qiying, Zhang Yiming, Hao Erjun, Bai Juan, Qu Guirong, Guo Haiming. Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution for the Construction of Carbocyclic N³-Purine Nucleosides[J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 376-383.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] (a) Zhou, H.; Zeng, X.; Ding, L.; Xie, Y.; Zhong, G. Org. Lett. 2015, 17, 2385.
(b) Trost, B. M.; Madsen, R.; Guile, S. D.; Brown, B. J. Am. Chem. Soc. 2000, 122, 5947.
(c) Kakuda, T. N. Clin. Ther. 2000, 22, 685.
(d) Boutureira, O.; Matheu, M. I.; Díaz, Y.; Castillón, S. Chem. Soc. Rev. 2013, 42, 5056.
(e) Forsman, J. J.; Leino, R. Chem. Rev. 2011, 111, 3334.
(f) Lebreton, J.; Escudier, J.-M.; Arzel, Len, C. Chem. Rev. 2010, 110, 3371.
(g) Amblard, F.; Cho, J. H.; Schinazi, R. F. Chem. Rev. 2009, 109, 4207.
(h) Liu, Y.; Guo, X.; Bai, P. Chin. J. Org. Chem. 2014, 34, 2202(in Chinese). (刘亚君, 郭翔海, 白鹏, 有机化学, 2014, 34, 2202.)
(i) Fan, X.-S; Zhang, X.-Y.; Wang, X.; Qu, G.-R. Chin. J. Org. Chem. 2008, 28, 1888(in Chinese). (范学森, 张新迎, 王霞, 渠桂荣, 有机化学, 2008, 28, 1888.)
[2] (a) Barral, K.; Courcambeck, J.; Pèpe, G.; Balzarini, J.; Neyts, J.; Clercq, E. D.; Camplo, M. J. Med. Chem. 2005, 48, 450.
(b) Keane, S. J.; Ford, A.; Mullins, N. D.; Maguire, N. M.; Legigan, T.; Balzarini, J.; Maguire, A. R. J. Org. Chem. 2015, 80, 2479.
(c) Gai, X.; Song, W.; Heng, S.; Yang, W. Chin. J. Integr. Tradit. West. Med. Liver Dis. 2005, 15, 50(in Chinese). (盖欣, 宋万玲, 桓树学, 杨文东, 中西医结合肝病杂志, 2005, 15, 50.)
[3] (a) Hu, L.; Ren, Y.; Ramström, O. J. Org. Chem. 2015, 80, 8478.
(b) Singh, U. S.; Mishra, R. C.; Shankar, R.; Chu, C. K. J. Org. Chem. 2014, 79, 3917.
(c) Caso, M. F.; D'Alonzo, D.; D'Errico, S.; Palumbo, G.; Guaragna, A. Org. Lett. 201517, 2626.
[4] (a) Silverman, R. B. The Organic Chemistry of Drug Design and Drug Action, Elsevier, Evanston, 2004.
(b) Kompis, I. M.; Islam, K.; Then, R. L. Chem. Rev. 2005, 105, 583.
(c) Lyon, M. A.; Ducruet, A. P.; Wipf, P.; Lazo, J. S. Nat. Rev. Drug Disc. 2002, 1, 961.
(d) Gangjee, A.; Li, W.; Yang, J.; Kisliuk, R. L. J. Med. Chem. 2008, 51, 68.
[5] (a) Jeong, L. S.; Lee, J. A. Antiviral Chem. Chemother. 2004, 15, 235.
(b) Liu, Y.; Guo, X.; Bai, P. Chin. J. Org. Chem. 2014, 34, 2202.
(c) Boutureira, O.; Matheu, M. I.; Díaz, Y.; Castillón, S. Chem. Soc. Rev. 2013, 42, 5056.
[6] (a) Xie, M.-S.; Wang, Y.; Li, J.-P.; Du, C.; Zhang, Y.-Y.; Hao, E.-J.; Zhang, Y.-M.; Qu, G.-R.; Guo, H.-M. Chem. Commun. 2015, 51, 12451.
(b) Huang, K.-X.; Xie, M.-S.; Zhang, Q.-Y.; Niu, H.-Y.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2018, 20, 5398.
(c) Wang, J.; Zhang, Q.-Y.; Xie, M.-S.; Wang, D.-C.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2018, 20, 6578.
(d) Gao, Y.-W.; Niu, H.; Zhang, Q.-Y.; Xie, M.; Qu, G.; Guo, H. Adv. Synth. Catal. 2018, 360, 2813.
[7] (a) Bhat, B.; Neelima, N. J.; Leonard, H.; Robinson, A.; Wang, H.-J. J. Am. Chem. Soc. 1996, 118, 3065.
(b) Leonard, N. J.; Laursenf, R. A. Biosci., Biotechnol., Biochem. 1965, 4, 354.
[8] (a) Sadler, J. M.; Mosley, S. L.; Dorgan, K. M.; Zhou, Z. S.; Seley-Radtke, K. L. Bioorg. Med. Chem. 2009, 17, 5520.
(b) Jiang, M. X.-W.; Warshakoon, N. C.; Miller, M. J. J. Org. Chem. 2005, 70, 2824.
[9] (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
(b) Liu, S.; Xie, J.-H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem. 2007, 119, 7650; Angew. Chem., Int. Ed. 2007, 46, 7506.
(c) Liu, S.; Xie, J.-H.; Li, W.; Kong, W.-L.; Wang, L.-X.; Zhou, Q.-L. Org. Lett. 2009, 11, 4994.
(d) Zhou, Q.; Xie, J.; Zhu, S.; Wang, L. Tianjin Sci. Technol. 2014, 41, 11(in Chinese). (周其林, 谢建华, 朱守非, 王立新, 天津科技, 2014, 41, 11.)
[10] (a) Zhang, Q.; Ma, B.-W.; Wang, Q.-.Q.; Wang, X.-X.; Hu, X.; Xie, M.-S.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2014, 16, 2014.
(b) Vyas, V. K.; Bhanage, B. M. Org. Lett. 2016, 18, 6436.
(c) Matsunami, A.; Ikeda, M.; Nakamura, H.; Yoshida, M.; Kuwata, S.; Kayaki, Y. Org. Lett. 2018, 20, 5213.
(d) Vyas, V. K.; Bhanage, B. M. Asian J. Org. Chem. 2018, 7, 346.
(e) Liu, Q.; Wang, C.; Zhou, H.; Wang, O.; Lv, J.; Cao, Lu; Fu, Y. Org. Lett. 2018, 20, 971.
[11] (a) Zhang, Y.-M.; Zhang, Q.-Y.; Wang, D.-C.; Xie, M.-S.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2019, 21, 2998.
(b) Sun, H.-L.; Chen, F.; Xie, M.-S.; Guo, H.-M.; Qu, G.-R.; He, Y.-M.; Fan, Q.-H. Org. Lett. 2016, 18, 2260.
[12] (a) Chan, A. S. C.; Pluth, J. J.; Halpern, J. J. Am. Chem. Soc. 1980, 102, 5952.
(b) Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.

通过不对称氢转移/动态动力学拆分合成碳环N³-嘌呤核苷

Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution for the Construction of Carbocyclic N³-Purine Nucleosides

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 9

编辑推荐

相关统计

本文评价

[1]	李晖, 殷亮. P-手性化合物的不对称催化合成研究进展[J]. 有机化学, 2022, 42(10): 3183-3200.
[2]	顾依钰, 吕晓庆, 马晓东, 张浩健, 嵇媛媛, 丁婉婧, 沈立. 新型吡啶苯磺酰胺联喹啉基异羟肟酸类PI3K/HDAC双靶点抑制剂的设计、合成和生物活性研究[J]. 有机化学, 2020, 40(1): 95-107.
[3]	倪国伟, 汤佳伟, 邹杰, 陈少欣, 鞠佃文, 张福利. 羰基还原酶在动态动力学拆分中的应用进展[J]. 有机化学, 2019, 39(2): 339-349.
[4]	刘亚君, 郭翔海, 白鹏. 近年碳环核苷类似物的合成研究进展[J]. 有机化学, 2014, 34(11): 2202-2216.
[5]	廖本仁, 安国成, 竹俊如, 杨帆, 汤杰. 苯甘氨酰胺结晶诱导的动态动力学拆分[J]. 有机化学, 2011, 31(9): 1495-1498.
[6]	程咏梅, 徐刚, 吴坚平, 杨立荣. 脂肪酶-酸性树脂耦合催化1-苯乙醇的动态动力学拆分[J]. 有机化学, 2010, 30(11): 1695-1699.
[7]	范学森* 张新迎王霞渠桂荣. 碳环核苷的合成研究进展[J]. 有机化学, 2008, 28(11): 1888-1898.
[8]	张占辉,刘庆彬. 酶-过渡金属配合物催化的动态动力学拆分研究进展[J]. 有机化学, 2005, 25(07): 780-787.
[9]	刘培念, 陈应春, 邓金根, 涂永强. 树状催化剂在不对称氢转移反应中的回收循环使用研究[J]. 有机化学, 2005, 25(05): 598-600.