Synthesis of new 1H-1,2,4-triazolylcoumarins and their antitumor and anti-HIV activities

被引:0
作者
Al-Soud Y.A. [1 ]
Al-Masoudi I.A. [2 ]
Saeed B. [3 ]
Beifuß U. [4 ]
Al-Masoudi N.A. [5 ]
机构
[1] Department of Chemistry, College of Science, University of Al Al-Bayt, Al-Mafraq
[2] College of Veterinary, University of Basrah, Basrah
[3] Department of Chemistry, College of Education, University of Basrah, Basrah
[4] Fakultät für Chemie, Universität Hohenheim
关键词
1,2,4-triazoles; Antitumor activity; Antiviral activity; Coumarin; Cycloaddition;
D O I
10.1007/s10593-006-0130-2
中图分类号
学科分类号
摘要
A variety of 7-[(1,5-dialkyl-1H-1,2,4-triazolyl)methoxy(and methyl)]coumarins were synthesized from cycloaddition of 2-(2H-benzopyran-7- yloxy)acetonitrile and 2-(5-methoxy-4-methyl-2H-benzopyran-7-yloxy)acetonitrile, respectively, with various reactive cumulene >C=N+=N- intermediates via spontaneous rearrangements. The anticancer (breast, lung, CNS cancers) and antiviral (HIV-1, HIV-2) properties of some compounds were investigated in vitro. 5-Methoxy-4-methyl-7-[(6,7,8,9-tetrahydro-5H-[1,2,4] triazolo[1,5-a]azepin-2-yl)methyl]coumarin showed some inhibition of HIV-1. ©2006 Springer Science+Business Media, Inc.
引用
收藏
页码:583 / 590
页数:7
相关论文
共 42 条
  • [1] Ito C., Chiliro M., Katsuno S., Omura M., Tokuda H., Nishino H., Furukawa H., J. Nat. Prod., 63, (2000)
  • [2] Abyshev A.Z., D'Yachuk G.I., Semenov E.V., Pukhov M.P., Pharm. Chem. J., 27, (1993)
  • [3] Kontogiorgis C.A., Hadjipavlou D.J., Bioorg. Med. Chem. Lett., 14, (2004)
  • [4] Abyshev A.Z., Alekseev A.T., Platonov V.G., Byrkin I.A., Pharm. Chem. J., 30, (1996)
  • [5] Teran C., Santana L., Uriarte E., Fall Y., Lena L., Tolf B.-R., Bioorg. Med. Chem. Lett., 8, (1998)
  • [6] Wang T.-C., Chen Y.-L., Cherng C.-C., Liou S.-S., Chang Y.-L., Teng C.-M., Helv. Chim. Acta, 79, (1996)
  • [7] El-Syed A.M., Ghattas A.-B.A.G., El-Wassimy M.T., Abd Allah O.A., Farmaco, 54, (1999)
  • [8] Kuehne M.E., Chem. Abstr., 61, (1964)
  • [9] Pochet L., Frederic R., Masereel B., Curr. Pharm. Design, 10, (2004)
  • [10] Padmawinata K., Acta Pharm., 4, (1973)