Synthesis and antiviral activities of synthetic glutarimide derivatives

Chemical and Pharmaceutical Bulletin

Volumn 58, Issue 11, 2010, Pages 1436-1441

  Ji, Xing Yue ^a   Zhong, Zhao Jin ^a   Xue, Si Tu ^a   Meng, Shuai ^a   He, Wei Ying ^a   Gao, Rong Mei ^a   Li, Yu Huan ^a   Li, Zhuo Rong ^a  

^a INSTITUTE OF MEDICINAL BIOTECHNOLOGY   (China)

Author keywords

Antiviral activity; Glutarimide derivative; Structure activity relationship; Synthesis

Indexed keywords

(2,6 DIOXOPIPERIDIN 4 YL)ACETALDEHYDE; 2,4 DIMETHYLPHENYL (2,6 DIOXOPIPERIDIN 4 YL)ACETATE; 4 (2 HYDROXY 4 OXO 5,2 TOLYLHEXYL)PIPERIDIN 2,6 DIONE; 4 (2 HYDROXY 4 OXO 5,2 TOLYLPENTYL)PIPERIDIN 2,6 DIONE; 4 (2 HYDROXY 5 METHYL 4 OXOHEXYL)PIPERIDIN 2,6 DIONE; 4 (4 OXO 5,2 TOLYLHEX 2 ENYL)PIPERIDIN 2,6 DIONE; 4 (4 OXO 5,2 TOLYLPENT 2 ENYL)PIPERIDIN 2,6 DIONE; 4 (5 METHYL 4 OXOHEX 2 ENYL)PIPERIDIN 2,6 DIONE; 4 [2 (2 OXOCYCLOHEXYLIDENE)ETHYL]PIPERIDIN 2,6 DIONE; 4 [2 (2 OXOCYCLOPENTYLIDENE)ETHYL]PIPERIDIN 2,6 DIONE; 4 [2 (5 METHYL 2 OXOCYCLOHEXYLIDENE)ETHYL]PIPERIDIN 2,6 DIONE; 4 [2 HYDROXY 2 (2 HYDROXY 3,5 DIMETHYLPHENYL)ETHYL]PIPERIDIN 2,6 DIONE; 4 [2 HYDROXY 2 (2 OXOCYCLOHEXYL)ETHYL]PIPERIDIN 2,6 DIONE; 4 [2 HYDROXY 2 (2 OXOCYCLOPENTYL)ETHYL]PIPERIDIN 2,6 DIONE; 4 [2 HYDROXY 2 (5 METHYL 2 OXOCYCLOHEXYL)ETHYL]PIPERIDIN 2,6 DIONE; ACTIPHENOL; GLUTARIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CONFORMATIONAL TRANSITION; COXSACKIE VIRUS B3; CYTOPATHOGENIC EFFECT; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 2; IC 50; INFLUENZA VIRUS A; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIVIRAL AGENTS; CELL LINE; CELL SURVIVAL; CERCOPITHECUS AETHIOPS; COXSACKIEVIRUS INFECTIONS; ENTEROVIRUS B, HUMAN; HERPES SIMPLEX; HERPESVIRUS 2, HUMAN; HUMANS; INFLUENZA A VIRUS; MOLECULAR STRUCTURE; ORTHOMYXOVIRIDAE INFECTIONS; PIPERIDONES; STRUCTURE-ACTIVITY RELATIONSHIP; VERO CELLS;

EID: 78049452663     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.58.1436     Document Type: Article

References (29)

1. Allen M. S., Becker A. M., Rickards R. W., Aust. J. Chem., 29, 673-679 (1976).
2. Whiffen A. J., Bohonas J. N., Emerson R. L., J. Bacteriol., 52, 610-611 (1946).
3. Johnson F., Starkovsky N. A., Gurowitz W. D., J. Am. Chem. Soc., 87, 3492-3500 (1965).
4. Nakae K., Yoshimoto Y., Ueda M., Sawa T., Takahashi Y., Naganawa H., Takeuchi T., Imoto M., J. Antibiot., 53, 1228-1230 (2000).
5. Shan D., Chen L., Njardarson J. T., Gaul C., Ma X., Danishefsky S. J., Huang X. Y., Proc. Natl. Acad. Sci. U.S.A., 102, 3772-3776 (2005).
6. Struck R. F., Schaeffer H. J., Krauth C. A., Kemp R. T., Shealy Y. F., Montgomery J. A., J. Med. Chem., 7, 646-650 (1964).
7. Phillips D. D., Acitelli M. A., Meinwald J., J. Am. Chem. Soc., 79, 3517-3519 (1957).
8. Kondo H., Oritani T., Kiyota H., Eur. J. Org. Chem., 20, 3459-3462 (2000).
9. Oritani T., Kudo S., Yamashita K., Agric. Biol. Chem., 46, 757-760 (1982).
10. Mark G. E., Taylor J. M., Broni B., Krug R. M., J. Virol., 29, 744-752 (1979).
11. Watanabe Y., Kudo H., Graham A. F., J. Virol., 1, 36-44 (1967).
12. Friedman R. M., Grimley P. M., J. Virol., 4 292-299 (1969).
13. Kim B. S., Moon S. S., Hwang B. K., J. Agric. Food Chem., 47, 3372-3380 (1999).
14. Okuda T., Suzuki M., Egawa Y., Ashino K., Chem. Pharm. Bull., 7, 27-30 (1959).
15. Guo H. F., Li Y. H., Tao P. Z., Yi H., Wang S. Q., He W. Y., Jang J. D., Li Z. R., Acta Pharm. Sinica, 45, 268-273 (2010).
16. He J. M., Li X. M., Liu M., Li D. D., Liu Q. Y., J. Tianjin Med. Univ., 7, 151-153 (2001).
17. Ford J. H., Leach B. E., J. Am. Chem. Soc., 70, 1223-1225 (1948).
18. Flint R. W. Jr., Valentine S., Papandrea D. Jr., Neuroscience, 148, 833-844 (2007).
19. Ito K., Kiyosawa N., Kumagai K., Manabe S., Matsunuma N., Yamoto T., Toxicology, 219, 175-186 (2006).
20. Egama Y., Suzuki M., Okuda T., Chem. Pharm. Bull., 11, 589-596 (1963).
21. Gupta K. A., Saxena A. K., Jain P. C., Anand N., Indian J. Chem., Sect. B, 26, 341-343 (1987).
22. Amat M., Bassas O., Cantó M., Llor N., Santos M. M. M., Bosch J., Tetrahedron, 61, 7693-7702 (2005).
23. Frohardt R. P., Dion H. W., Jakubowski Z. L., Ryder A., French J. C., Bartz Q. R., J. Am. Chem. Soc., 81, 5500-5506 (1959).
24. Rao K. V., J. Am. Chem. Soc., 82, 1129-1132 (1960).
25. Kornfeld C. E., Jones R. J., Parke T. V., J. Am. Chem. Soc., 71, 150-159 (1949).
26. Kudo S., Oritani T., Yamashita K., Agric. Biol. Chem., 48, 2315-2319 (1984).
27. Kondo H., Oritani T., Yamashita K., Agric. Biol. Chem., 52, 129-133 (1988).
28. Johnson F., J. Org. Chem., 27, 3658-3660 (1962).
29. Lakhvich F. A., Buravskaya T. N., Akhrem A. A., Chem. Nat. Comp., 29, 526-529 (1993).