A Study on the synthesis of New Aminophosphonopeptides Containing P-N Amide Bonded Cephalosporin

Ik Joong Kang

Journal of Industrial and Engineering Chemistry, Vol.5, No.3, 218-223, September, 1999

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A Study on the synthesis of New Aminophosphonopeptides Containing P-N Amide Bonded Cephalosporin

Ik Joong Kang^†

Department of Chemical Engineering, Kyungwon University, Sungnam 461-701, Korea

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A new kind of aminophosphonopeptides containing cephalosporin, diphenylmethyl 7-β-O-alkyl phthalimidoglycylbenzylserylphosphonyl -3-acetoxymethyl-3-cephem-4-carbozylates 1(a)-1(d), have been synthesized. O-alkyl phthalimidoglycylbenzylserylphosphochloridate 9(a)-9(d), aminophosphonopeprides, were produced starting from benzyl 2-(N-boc)aminoserinate (2) and benzyl 2-(N-t-Boc)amino-3-bromopropionate (4) by way of benzyl 2-amino-3-alkylphosphonopropionate 7(a)-7(d). The coupling of aminophosphonopeptides 9(a)-9(d) and diphenylmethyl 7-β-amino-3-acetoxymethyl-3-cephem-4-carboxylate yielded aminophosphonopeptides containing cephalosporin 1(a)-1(d). Antibacterial activities of these compounds were examined and relationship between structure and activities was studied. As a result, these compounds showed low antibacterial activities compared to cefotaxime used as control.

Keywords:aminophosphonopeptides;cephalosporin;P-N amide bond

[References]

Kleinrok T, Stirling R, Chem. Abstr., 104, 218953 (1986)
Shimada M, Kabuto H, Yokoi I, Res. Commun. Chem. Pathol. Pharmacol., 57, 359 (1987)
Horiguchi M, Kandatsu M, Nature, 184, 901 (1959)
Kandatsu M, Horiguchi M, Agri. Bio. Chem., 29, 781 (1965)
Shimizu H, Kakimodo Y, Nagagima T, Danaza A, Nature, 207, 1197 (1965)
Alhadelff JA, Davis GD, J. Biochem., 9, 4866 (1970)
Alhadelff JA, Davis GD, J. Biochem. Biophys. Acta, 244, 221 (1971)
Ogita K, Gungi H, Fugazawa Y, Terahara A, Kinoshita T, Nagai H, Tetrahedron Lett., 24, 2283 (1971)
Gungi H, Beppu T, Abstracts of Annual Meeting of Agric. Chem. Soc. Jpn. Tokyo, Japan, p. 130 (1979)
Ogita K, Fugazawa Y, Terahara A, Kinoshita T, Nagai H, Beppu T, Abstracts of Annual Meeting of Agric. Chem. Soc. Jpn., Sendai, Japan, p. 213 (1983)
Korn ED, Dearborn DG, Fales HM, Sokoloski EA, J. Biol. Chem., 248, 2257 (1973)
Reider PJ, Grabowski ED, Edward JJ, Tetrahedron Lett., 22, 3883 (1981)
Tanaka T, Hashimoto RG, Tetrahedron Lett., 23, 1075 (1982)
Stirling I, Clarke BP, J. Chem. Soc.-Perkin Trans. 1, 3011 (1982)
Okano K, Kyotani YJ, J. Am. Chem. Soc., 105, 7186 (1983)
Basker MJ, Boon RJ, J. Antibiot., 36, 416 (1983)
Tamura N, Natsugar H, Chem. Pharm. Bull., 35, 996 (1987)
Shimizu H, Kumagai T, Jpn. Kokai Tokkyo Koho Japan Patent, 63,170,378 (1988)
Ohta T, Sato N, Tetrahedron Lett., 29, 4305 (1988)
Pfizer Inc., Brit. Patent, 1,355,872 (1974)
Takaya T, Chiba T, Jpn. Kokai Tokyo Koho Japan Patent, 55-115, 892 (1980)
Atherton FR, Hall RJ, European Patent, 0026409A1 (1981)
Satoh H, Tsuji T, Tetrahedron Lett., 25, 1733 (1984)
Satoh H, Tsuji T, Tetrahedron Lett., 25, 1737 (1984)
Jacobson NE, Bartlett PA, J. Am. Chem. Soc., 103, 654 (1981)
Elliott RL, Marks N, Berg MJ, J. Med. Chem., 28, 1208 (1985)
Allen JS, Atherton FR, Nature, 272, 56 (1978)
Niida T, Tsuruoka T, Ger. Offen., 22, 559 (1973)
Bayer E, Gugel KH, Helv. Chim. Acta, 55, 224 (1972)
Bocchi V, Jackson BG, Mueller RA, Synthesis, 957 (1972)
Baraidi PG, Winrtz M, Lavagrino ER, Synthesis, 653 (1982)
Micetich RG, Singh R, Synthesis, 693 (1985)

[Related Articles]

[1] Kleinrok T, Stirling R, Chem. Abstr., 104, 218953 (1986)

[2] Shimada M, Kabuto H, Yokoi I, Res. Commun. Chem. Pathol. Pharmacol., 57, 359 (1987)

[3] Horiguchi M, Kandatsu M, Nature, 184, 901 (1959)

[4] Kandatsu M, Horiguchi M, Agri. Bio. Chem., 29, 781 (1965)

[5] Shimizu H, Kakimodo Y, Nagagima T, Danaza A, Nature, 207, 1197 (1965)

[6] Alhadelff JA, Davis GD, J. Biochem., 9, 4866 (1970)

[7] Alhadelff JA, Davis GD, J. Biochem. Biophys. Acta, 244, 221 (1971)

[8] Ogita K, Gungi H, Fugazawa Y, Terahara A, Kinoshita T, Nagai H, Tetrahedron Lett., 24, 2283 (1971)

[9] Gungi H, Beppu T, Abstracts of Annual Meeting of Agric. Chem. Soc. Jpn. Tokyo, Japan, p. 130 (1979)

[10] Ogita K, Fugazawa Y, Terahara A, Kinoshita T, Nagai H, Beppu T, Abstracts of Annual Meeting of Agric. Chem. Soc. Jpn., Sendai, Japan, p. 213 (1983)

[11] Korn ED, Dearborn DG, Fales HM, Sokoloski EA, J. Biol. Chem., 248, 2257 (1973)

[12] Reider PJ, Grabowski ED, Edward JJ, Tetrahedron Lett., 22, 3883 (1981)

[13] Tanaka T, Hashimoto RG, Tetrahedron Lett., 23, 1075 (1982)

[14] Stirling I, Clarke BP, J. Chem. Soc.-Perkin Trans. 1, 3011 (1982)

[15] Okano K, Kyotani YJ, J. Am. Chem. Soc., 105, 7186 (1983)

[16] Basker MJ, Boon RJ, J. Antibiot., 36, 416 (1983)

[17] Tamura N, Natsugar H, Chem. Pharm. Bull., 35, 996 (1987)

[18] Shimizu H, Kumagai T, Jpn. Kokai Tokkyo Koho Japan Patent, 63,170,378 (1988)

[19] Ohta T, Sato N, Tetrahedron Lett., 29, 4305 (1988)

[20] Pfizer Inc., Brit. Patent, 1,355,872 (1974)

[21] Takaya T, Chiba T, Jpn. Kokai Tokyo Koho Japan Patent, 55-115, 892 (1980)

[22] Atherton FR, Hall RJ, European Patent, 0026409A1 (1981)

[23] Satoh H, Tsuji T, Tetrahedron Lett., 25, 1733 (1984)

[24] Satoh H, Tsuji T, Tetrahedron Lett., 25, 1737 (1984)

[25] Jacobson NE, Bartlett PA, J. Am. Chem. Soc., 103, 654 (1981)

[26] Elliott RL, Marks N, Berg MJ, J. Med. Chem., 28, 1208 (1985)

[27] Allen JS, Atherton FR, Nature, 272, 56 (1978)

[28] Niida T, Tsuruoka T, Ger. Offen., 22, 559 (1973)

[29] Bayer E, Gugel KH, Helv. Chim. Acta, 55, 224 (1972)

[30] Bocchi V, Jackson BG, Mueller RA, Synthesis, 957 (1972)

[31] Baraidi PG, Winrtz M, Lavagrino ER, Synthesis, 653 (1982)

[32] Micetich RG, Singh R, Synthesis, 693 (1985)