Synthesis of Nucleoside Derivatives Containing Benzophenoxazinone Moiety
Synthesis of Nucleoside Derivatives Containing Benzophenoxazinone Moiety
摘要
Two new nucleoside derivatives containing benzophenoxazinone moiety were synthesized. Their luminescence spectra show that they have strong near infrared fluorescence. Our study provides a new method for direct introduction of near infrared fluorescent probe to bioactive molecules.
Two new nucleoside derivatives containing benzophenoxazinone moiety were synthesized. Their luminescence spectra show that they have strong near infrared fluorescence. Our study provides a new method for direct introduction of near infrared fluorescent probe to bioactive molecules.
参考文献14
-
1[1]G. Patonay, M. D. Antoine, Anal. Chem., 1991, 63, 321A.
-
2[2]J. L. Seifert, R. E. Connor, S. A. Kushon, et al., J. Am. Chem. Soc., 1999, 121, 2987.
-
3[3]M. S. J. Briggs, I. Bruce, J. N. Miller, et al., J. Chem. Soc. Perkin Trans. 1, 1997, 1051.
-
4[4]D. B. Shealy, M. Lipowska, J. Lipowski, et al., Anal. Chem., 1995, 67, 247.
-
5[5]G. M. Rehberg, J. L. Rutherford, J. Heterocyclic Chem., 1996, 32, 1643.
-
6[6]J. F. Deye, T. A. Berger, A. G. Anderson, Anal. Chem., 1990, 62, 615.
-
7[7]1H-NMR (200 MHz) data for 6a (DMSO-d6, δ ppm): 1.30-1.52 (m, 9 H, -CH2CH3, -C(CH3)2), 2.61-2.73 (m, 2 H, -NCH2CH2-), 3.05 (s, 3 H, -NCH3), 3.83-3.95 (m, 2 H, -NCH2CH2-), 4.15-4.42 (m, 5 H, -OCH2CH3, 2×H-5′, H-4′), 4.73-4.82 (m, 1 H, H-3′), 5.04-5.14 (m, 1 H, H-2′), 5.62 (d, 1 H, J =7.6 Hz, base H-5), 5.70 (s, 1 H, base H-3), 5.75 (d, 1 H, J =2.3 Hz, H-1′), 6.68 (d, 1 H, J =2.0 Hz, H-8), 6.98 (dd, 1 H, J =9.7, 2.2 Hz, H-10), 7.66-7.82 (m, 4 H, H-2, H-3, H-11,base H-6), 8.14 (d, 1 H, J =7.5 Hz, H-4), 8.60 (d, 1 H, J =7.3 Hz, H-1); MS (FAB) data for 6a (m/z): 687.3 (M+1).
-
8[8]1H-NMR (200 MHz) data for 6b (DMSO-d6, δ ppm): 1.33-1.51 (m, 9 H, -CH2CH3, -C(CH3)2), 2.58-2.72 (m, 2 H, -NCH2CH2-), 3.02 (s, 3 H, -NCH3), 3.78-3.86 (m, 2 H, -NCH2CH2-), 4.06-4.38 (m, 5 H, -OCH2CH3, 2×H-5′, H-4′), 4.98-5.04 (m, 1 H, H-3′), 5.40-5.47 (m, 1 H, H-2′), 6.17 (d, 1 H, J =1.9 Hz, H-1′), 6.62 (d, 1 H, J =2.2 Hz, H-8), 6.94 (dd, 1 H, J =9.5, 2.1 Hz, H-10), 7.29 (s, 2 H, base -NH2), 7.64-7.83 (m, 3 H, H-2, H-3, H-11), 8.11-8.14 (m, 2 H, H-4, base H-2), 8.28 (s, 1 H, base H-8), 8.57 (d, 1 H, J =7.3 Hz, H-1); MS (FAB) data for 6b (m/z): 710.3 (M+1).
-
9[9]J. F. Thrope, J. Chem. Soc., 1907, 91, 324.
-
10[10]J. Long, Y. Wang, T. Matsuura, J. Meng, J. Heterocyclic Chem., 1999, 36, 895.
-
1赵宝娟,于文全,常俊标,李二通,丁群山,李凤娟,陈光英,王娜.3'-氟-2'-O,3'-C-乙烯基键联并环尿苷的合成与表征[J].高等学校化学学报,2014,35(1):58-62.
-
2杜杨,许雯,姚其正,刘祖亮.5(4H)-吡啶酮并氧化呋咱及其核苷衍生物的合成及结构表征[J].有机化学,2010,30(6):928-932. 被引量:2
-
3GUOHui ZOUWu-xin JIQi MAYu-xin MENGJi-ben.Syntheses of Nucleoside Derivatives Containing Fmocor Trityl-protected Amino Acids[J].Chemical Research in Chinese Universities,2005,21(4):447-451.
-
4Jian-Jun Li,Xing-Xing Gui.L-ProT catalyzed highly regioselective N-alkoxyalkylation of purine rings with vinyl ethers[J].Chinese Chemical Letters,2014,25(10):1341-1345. 被引量:1
-
5Zhang, YS,Wang, LX,Zhang, LH.O-(1-BENZOTRIAZOLYL)-SULFATE AS ALEAVING GROUP IN SUBSTITUTION OF NUCLEOSIDE[J].Chinese Chemical Letters,1995,6(7):549-552.
-
6有机化学[J].中国学术期刊文摘,2007,13(3):70-71.
-
7李在国,孙会凯,曹焕岩,黄润秋,邵瑞链.新型含三唑杂环的α-氨基膦酸(酯)的合成及生物活性[J].厦门大学学报(自然科学版),1999,38(S1):459-459.
-
8尚志强,陈茹玉,黄有.尿苷5′-O-α-(苄氧羰基氨基)芳甲基膦酸酯的合成及其生物活性研究[J].合成化学,2004,12(2):142-146. 被引量:2
-
9沙耀武,王欣,蔡孟深.吡唑并(5,4-e)-1,2,4-三嗪核苷衍生物合成研究[J].化学通报,1996(11):35-38. 被引量:8
-
10苗志伟,付华,冯玉萍,韩波,涂光忠,赵玉芬.Studies on Synthesis and Intramolecular Catalyzed Hydrolysis of Thiophosphoramidate Derivatives of Nucleoside[J].Chinese Journal of Chemistry,2002,20(11):1434-1438.