Chinese Journal of Organic Chemistry >
One-Step Synthesis of 1,2,4-Triazolo[3,4-i]purine Derivatives
Received date: 2021-10-08
Revised date: 2022-01-26
Online published: 2022-02-10
Supported by
National Natural Science Foundation of China(U1604283); National Science and Technology Major Project(2014ZX09J14101-01A); Medical and Health Project of Luoyang Science and Technology Plan(1720001A-8)
1,2,4-Triazolo[3,4-i]purine derivatives are potential xanthine oxidase (XO) inhibitors and expected to be used in the treatment of gout. A new one-step method for the preparation of 1,2,4-triazolo[3,4-i]purine derivatives has been reported. Seventeen novel 1,2,4-triazolo[3,4-i]purine derivatives were synthesized with 6-hydrazinyl-N9-substituted purine and aliphatic monocarboxylic acid as starting materials and anhydrous magnesium sulfate as dehydrating agent. The method is easy to operate without using other catalysts and oxidants, and the yield is good. Meanwhile, the factors affecting the reaction were discussed, which laid a foundation for the study of 1,2,4-triazolo[3,4-i]purine compounds
Zhiliang Chu , Huijuan Chen , Shuai Shan , Xiaona Wang , Chunfang Gao , Guirong Qu , Zhongyu Liu , Haiming Guo . One-Step Synthesis of 1,2,4-Triazolo[3,4-i]purine Derivatives[J]. Chinese Journal of Organic Chemistry, 2022 , 42(5) : 1551 -1556 . DOI: 10.6023/cjoc202110007
| [1] | Freeman, S.; Gardiner, J. M. Mol. Biotechnol. 1996, 5, 125. |
| [2] | Zhu, M.; Dong, B.; Zhang, G.-N.; Wang, J.-X.; Cen, S.; Wang, Y.-C. Bioorg. Med. Chem. Lett. 2019, 29, 1541. |
| [3] | Kohgo, S.; Imoto, S.; Tokuda, R.; Takamatsu, Y.; Higashi-Kuwata, N.; Aoki, M.; Amano, M.; Kansui, H.; Onitsuka, K.; Maeda, K.; Mitsuya, H. ChemistrySelect 2018, 3, 3313. |
| [4] | Kuo, T.-C.; Li, L.-W.; Pan, S.-H.; Fang, J.-M.; Liu, J.-H.; Cheng, T.-J.; Wang, C.-J.; Hung, P.-F.; Chen, H.-Y.; Hong, T.-M.; Hsu, Y.-L.; Wong, C.-H.; Yang, P.-C. J. Med. Chem. 2016, 59, 8521. |
| [5] | He, H.; Zatorska, D.; Kim, J.; Aguirre, J.; Llauger, L.; She, Y.; Wu, N.; Immormino, R. M.; Gewirth, D. T.; Chiosis, G. J. Med. Chem. 2006, 49, 381. |
| [6] | Fernández-Sáez, N.; Rubio-Ruiz, B.; Campos, J. M.; Unciti-Broceta, A.; Carrión, M. D.; Camacho, M. E. Feture Med. Chem. 2019, 11, 83. |
| [7] | Zhao, T.-Q.; Zhao, Y.-D.; Liu, X.-Y.; Li, Z.-H.; Wang, B.; Zhang, X.-H.; Cao, Y.-Q.; Ma, L.-Y.; Liu, H.-M. Eur. J. Med. Chem. 2019, 161, 493. |
| [8] | Hao, E.-J.; Li, G.-X.; Liang, Y.-R.; Xie, M.-S.; Wang, D.-C.; Jiang, X.-H.; Cheng, J.-Y.; Shi, Z.-X.; Wang, Y.; Guo, H.-M. J. Med. Chem. 2021, 64, 2077. |
| [9] | Jiang, Z.-H.; Cheng, Y.-N.; Shen, G.-F.; Zhang, M.-M.; Su, Z.-Y.; Sun, L.-S.; Li, H.-L. Chin. J. Org. Chem. 2020, 40, 2575. (in Chinese) |
| [9] | (蒋振华, 程绎南, 申国富, 张蒙萌, 苏子洋, 孙连省, 李洪连, 有机化学, 2020, 40, 2575.) |
| [10] | Yu, W.; Wang, H.; Min, L.-J.; Hua, X.-W.; Liu, X.-H. Chin. J. Org. Chem. 2021, 41, 826. (in Chinese) |
| [10] | (余玮, 王翰, 闵莉静, 华学文, 刘幸海, 有机化学, 2021, 41, 826.) |
| [11] | Nagamatsu, T.; Yamasaki, H.; Fujita, T.; Endo, K.; Machida, H. J. Chem. Soc., Perkin Trans. 1 1999, 3117. |
| [12] | Kochetkov, N. K.; Shibaev, V. N.; Kost, A. A. Tetrahedron Lett. 1971, 12, 1993. |
| [13] | Barrio, J. R.; Secrist III, J. A.; Leonard, N. J. Biochem. Biophys. Res. Commun. 1972, 46, 597. |
| [14] | Sattsangi, P. D.; Leonard, N. J.; Frihart, C. R. J. Org. Chem. 1977, 42, 3292. |
| [15] | Kost, A. A.; Ivanov, M. V. Chem. Heterocycl. Compd. 1980, 16, 209. |
| [16] | Kusmierek, J. T.; Jensen, D. E.; Spengler, S. J.; Stolarski, R.; Singer, B. J. Org. Chem. 1987, 52, 2374. |
| [17] | Xie, M.-S.; Chu, Z.-L.; Niu, H.-Y.; Qu, G.-R.; Guo, H.-M. J. Org. Chem. 2014, 79, 1093. |
| [18] | Li, R.-L.; Liang, L.; Xie, M.-S.; Qu, G.-R.; Niu, H.-Y.; Guo, H.-M. J. Org. Chem. 2014, 79, 3665. |
| [19] | Nagamatsu, T.; Yamasaki, H.; Akiyama, T.; Hara, S.; Mori, K.; Kusakabe, H. Synthesis 1999, 655. |
| [20] | Chen, H.-J.; Shang, Z.-H.; Chang, J.-B. Synth. Commun. 2006, 36, 445. |
| [21] | Ou, J.-J.; Liu, K.-C.; Wang, Y.; Zhang, H.; Liu, R.-Q.; Li, Q.-B.; Wang, Q.-M.; Li, Y.-Q.; Rui, C.-H.; Liu, S.-Z. Chin. J. Org. Chem. 2014, 34, 526. (in Chinese) |
| [21] | (欧俊军, 刘克昌, 王毅, 张浩, 刘瑞全, 李奇博, 王清民, 李永强, 芮昌辉, 刘尚钟, 有机化学, 2014, 34, 526.) |
| [22] | Montgomery, J. A.; Jr, C. T. J. Am. Chem. Soc. 1961, 83, 630. |
| [23] | Zhang, Y. M.S. Thesis, Henan Normal University, Xinxiang, 2011. (in Chinese) |
| [23] | (张禹, 硕士论文,河南师范大学,新乡, 2011.) |
/
| 〈 |
|
〉 |