Synthesis and anti-influenza activity of aminoalkyl rupestonates

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 6, 2012, Pages 2321-2325

  Zhao, Jiangyu ^a,b   Aisa, Haji Akber ^a  

^a XINJIANG TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Anti influenza activity; Rupestonic acid; Synthesis

Indexed keywords

ANTIVIRUS AGENT; OSELTAMIVIR; RIBAVIRIN; RUPESTONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ANTIVIRAL ACTIVITY; ARTICLE; BIOASSAY; CONTROLLED STUDY; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; INFLUENZA VIRUS A H1N1; INFLUENZA VIRUS A H3N2; INFLUENZA VIRUS B; NONHUMAN;

AMINATION; ANIMALS; ANTIVIRAL AGENTS; AZULENES; CELL LINE; DOGS; HALOGENATION; HUMANS; INFLUENZA A VIRUS, H1N1 SUBTYPE; INFLUENZA A VIRUS, H3N2 SUBTYPE; INFLUENZA B VIRUS; INFLUENZA, HUMAN; SESQUITERPENES; STRUCTURE-ACTIVITY RELATIONSHIP;

CERCOPITHECINE HERPESVIRUS 1; ORTHOMYXOVIRIDAE;

EID: 84862823629     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.01.056     Document Type: Article

References (19)

1. C.U. Kim, W. Lew, M.A. Williams, H. Wu, L. Zhang, X. Chen, P.A. Escarpe, D.B. Mendel, W.G. Laver, and R.C. Stevens J. Med. Chem. 41 1998 2451
2. A.C. Schmidt Drugs 64 2004 2031
3. A. Moscona N. Engl. J. Med. 353 2005 1363
4. R.J. Russell, L.F. Haire, D.J. Stevens, P.J. Collins, Y.P. Lin, G.M. Blackburn, A.J. Hay, S.J. Gamblin, and J.J. Skehel Nature 443 2006 45
5. Q.M. Le, M. Kiso, K. Someya, Y.T. Sakai, T.H. Nguyen, K.H.L. Nguyen, N.D. Pham, H.H. Ngyn, S. Yamada, Y. Muramoto, T. Horimoto, A. Takada, H. Goto, T. Suzuki, Y. Suzuki, and Y. Kawaoka Nature 437 2005 1108
6. J.J. Treanor, F.G. Hayden, P.S. Vrooman, R. Barbarash, R. Bettis, D. Riff, S. Singh, N. Kinnersley, P. Ward, and R.G. Mills J. Am. Med. Assoc. 283 2000 1016
7. M. Miski, D.H. de Luengo, and T.J. Mabry Phytochemistry 26 1987 199
8. J.P. Yong, and H.A. Aisa Chem. Nat. Compd. 44 2008 311
9. Aisa, H. A.; Zhao, J. Y., Cao, L. H. [P] C. N. CN101857613A.
10. The MDDR is a database covering the patent literature, journals, meetings and congresses that is produced by Symyx and Prous Science (http://www.prous. com/index.html). The MDDR contains over 180,000 biologically relevant compounds and well-defined derivatives, with approximately 10,000 added to the database every year.
11. J.W. Nilsson, F. Thorstensson, I. Kvarnstrom, T. Oprea, B. Samuelsson, and I. Nilsson J. Comb. Chem. 3 2001 546
12. W. Kuipers, C.G. Kruse, I. van Wijngaarden, P.J. Standaar, M.T.M. Tulp, N. Veldman, A.L. Spek, and A.P. Ijzerman J. Med. Chem. 40 1997 300
13. M. Perez, C. Fourrier, I. Sigogneau, P.J. Pauwels, C. Palmier, G.W. John, J.P. Valentin, and S. 189 Halazy J. Med. Chem. 38 1995 3602
14. S.H. Zhao, A.K. Miller, J. Berger, and L.A. Flippin Tetrahedron Lett. 37 1996 4463
15. X.Z. Li, and Z.X. Si Agrochemicals 1 2003 4
16. +, 30).
17. Y.M. Ma, H.A. Aisa, L.X. Liao, E.B. Srapil, T.Y. Zhang, and Y. Ito J. Chromatogr., A 1076 2005 198
18. 3): δ 208.1, 174.0, 166.6, 146.0, 138.0, 124.1, 71.2, 46.1, 41.6, 38.5, 38.2, 36.8, 35.6, 31.9, 27.2, 12.2, 8.2; ESI-MS (m/z, %): 355 ([M+1], 98), 357 ([M+3], 100), 377 ([M+Na], 25).
19. 3): δ 208.2, 174.4, 167.2, 151.3, 146.8, 138.1, 129.3, 123.0, 120.0, 116.4, 65.1, 58.4, 50.0, 46.1, 46.0, 41.7, 38.5, 38.3, 37.1, 35.5, 31.9, 30.0, 29.1, 28.6, 26.4, 25.9, 12.3, 8.0; ESI-MS (m/z, %): 521 ([M+1], 100), 522 ([M+2], 50).