Preparation of aromatic β-selenolactams and their bioactivities as agricultural chemicals

Archives of Pharmacal Research

Volumn 30, Issue 8, 2007, Pages 938-944

  Kimura, Mitsutoshi ^a,c   Ishihara, Hideharu ^a   Kato, Shinzi ^b  

^a GIFU UNIVERSITY   (Japan)

^b CHUBU UNIVERSITY   (Japan)

^c KAO CORPORATION   (Japan)

Author keywords

Selenolactam; Acarianicide; Agricultural chemical; Antibacterial activity; Cycloaddition; Insecticide

Indexed keywords

AGRICULTURAL CHEMICAL; AROMATIC HYDROCARBON; BETA LACTAM; INSECTICIDE; ORGANOSELENIUM DERIVATIVE;

ACARI; ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; DRUG EFFECT; GROWTH, DEVELOPMENT AND AGING; INSECT; SYNTHESIS;

ACARI; AGROCHEMICALS; ANIMALS; BETA-LACTAMS; CYCLIZATION; HYDROCARBONS, AROMATIC; INSECTICIDES; INSECTS; MOLECULAR STRUCTURE; ORGANOSELENIUM COMPOUNDS;

EID: 34548760920     PISSN: 02536269     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02993960     Document Type: Article

References (22)

1. Alcaide, B., Almendros, P., Alonso, J. M., Aly, M. F., Pardo, C., Saez, E., and Torres, M. R., Efficient entry to highly functionalized beta-lactams by regio- and stereoselective 1,3-dipolar cycloaddition reaction of 2-azetidinone-tethered nitrones. Synthetic applications. J. Org. Chem., 67, 7004-7013 (2002).
2. Altamura, M., Perrotta, E., Sbraci, P., Pestellini, V., Cascio, G., Lorenzi, L., Satta, G., Morandotti, G., and Sperning, R., 2-substituted penems with amino acid-related side chains: synthesis and antibacterial activity of a new series of beta-lactam antibiotics. J. Med. Chem., 38, 4244-4256 (1995).
3. Cooper, D.G., Chemistry of β-Lactams. Ed by Michael, I.P., Chapman & Hall, New York, pp. 1-352, (1992).
4. Craig, W.A., Basic pharmacodynamics of antibacterials with clinical application to the use of beta-lactams: Glycopeptides and linezolid. Infect. Dis. Clin. North. Am., 17, 479-501 (2003).
5. Creary, X., Chen, Z., and Ziqi, J., Carbocations in the lactam and thiolactam series. J. Am. Chem. Soc, 118,12332-12338 (1996).
6. Davoli, P., Alper, H., Moretti, I., and Prati, F., Carbonylation of silylated hydroxymethyl Aziridines to beta-lactams. J. Org. Chem., 64, 518-521 (1999).
7. Di Nunno, L. and Scilimati, A., A new synthesis of beta- phenylaminothioesters and beta-lactams via base-induced ring-opening of 2-phenyl-3-aryl-5-phenylthio isoxazolidines. Tetrahedron, 49, 10965-10976 (1993).
8. Hancock, R. E. and Woodruff, W. A., Roles of porin and beta-lactamase in beta-lactam resistance of Pseudomonas aeruginosa. Infect. Dis., 10, 770-775 (2000).
9. Hanessian, S., Rozema, M. J., Bhaskar, R. G., and Braganza, J. F., Tricyclic β-lactams: Total synthesis and antibacterial activity of 5α- and 5β-methyl-tribactams. Bioorg. Med. Chem. Lett., 5, 2535-2540 (1995).
10. Hirohara, H. and Nishizawa, M., Biochemical synthesis of several chiral insecticide intermediates and mechanisms of action of relevant enzymes. Biosci. Biotechnol. Biochem., 62, 1-9 (1998).
11. Hour, T. C., Chen, L., and Lin, J. K., Comparative investigation on the mutagenicities of organophosphate, phthalimide, pyrethroid and carbamate insecticides by the Ames and lactam tests. Mutagenesis, 13, 157-166 (1998).
12. Ishihara, H., Yoshimi, M., and Kato, S., A facile synthesis of beta-selenolactams. Angew. Chem., 102, 572-573 (1990); Angew. Chem. Int. Ed. Engl., 29, 530-531 (1990).
13. Kurihara, A., Naganuma, H. ,and Hisaoka, M., Prediction of human pharmacokinetics of panipenem-betamipro, a new carbapenem from animal data. Antimicrob. Agent. Chemother, 36, 1810-1816 (1992).
14. Lopez, R., Suared, D., Sordo, T. L., and Ruiz-Lopez, M. F., Theoretical study of the (2+2) cycloaddition of thioketenes with imines to form beta-thiolactams. Chem. Eur. J., 4, 328-334 (1998).
15. Manhas, M. S. and Bose, A. K., Synthesis of Penicillin: Cephalosporin C and Analogs. Dekker, New York, pp. 1-286, (1969).
16. Manhas, M. S. and Bose, A. K., Beta-lactams: Natural and Synthetic Part 1, Wiley-lnterscience, New York, pp. 161-186, (1971).
17. Rae, I. D., Carbon-13 NMR spectra of some amides and lactams and their thio and seleno analogs. Aust. J. Chem., 32, 567-573 (1979).
18. Saravanan, V., Mukherjee, C., Das, S., and Chandrasekaran, S., Facile conversion of amides and lactams to selenoamides and selenolactams using tetraethylammonium tetraseleno-tungstate. Tetrahedron Lett., 45, 681-683 (2004).
19. Schunk, S. and Enders, D., Solid phase synthesis of beta-lactams via the enolate-imine condensation route. Org. Lett., 2., 7, 907-910 (2000).
20. Shimada, J., Hori, S., Kanemitsu. K., Shoji, Y., Nakashio, S., and Yanagawa, A., A comparative study on the convulsant activity of carbapenems and beta-lactams. Drugs Exp. Clin. Res., 18, 377-381 (1992).
21. Topliss J. G., A manual method for applying the Hansch approach to drug design. J. Med. Chem., 20, 463-469 (1977).
22. Torii, S., Okumoto, H., Sadakane, M., Hai, A., and Tanaka, H., Carbonylative (2+2) cycloaddition for construction of beta-lactam skeleton with palladium catalyst. Tetrahedron Lett., 34, 6553-6556 (1993).