Synthesis and biological activity of dehydrophos derivatives

被引:0
作者
Jiménez-Andreu M.M. [1 ]
Lucía Quintana A. [2 ,3 ]
Aínsa J.A. [2 ,3 ]
Sayago F.J. [1 ]
Cativiela C. [1 ]
机构
[1] Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea ISQCH, CSIC-Universidad de Zaragoza, Zaragoza
[2] Departamento de Microbiología, Medicina Preventiva y Salud Pública, Facultad de Medicina, BIFI, Universidad de Zaragoza, Zaragoza
[3] CIBER Enfermedades Respiratorias, Instituto de Salud Carlos III, Madrid
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D O I
10.1039/c8ob03079k
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学科分类号
摘要
The synthesis of dehydrophos derivatives featuring modified peptide chains, characterized by the presence of substituents in the vinyl moiety, or possessing a phosphonic acid monoalkyl ester other than the monomethyl ester one, has been accomplished by a versatile procedure based on Horner-Wadsworth-Emmons olefination with suitable aldehydes and on the selective hydrolysis of the dialkyl phosphonate group. Such derivatives have been tested against a series of bacterial strains, using the naturally occurring peptide, dehydrophos, for comparison. Thus, the effects of the aforementioned structural variations on antimicrobial activity have been studied. ©2019 The Royal Society of Chemistry.
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页码:1097 / 1112
页数:15
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共 54 条
  • [11] Shao Z., Blodgett J.A.V., Circello B.T., Eliot A.C., Woodyer R., Li G., Van Der Donk W.A., Metcalf W.W., Zhao H., J. Biol. Chem., 283, pp. 23161-23168, (2008)
  • [12] Kuemin M., Van Der Donk W.A., Chem. Commun., 46, pp. 7694-7696, (2010)
  • [13] Horsman G.P., Zechel D.L., Chem. Rev., 117, pp. 5704-5783, (2017)
  • [14] Grzywa R., Sienczyk M., Curr. Pharm. Des., 19, pp. 1154-1178, (2013)
  • [15] Mucha A., Kafarski P., Berlicki L., J. Med. Chem., 54, pp. 5955-5980, (2011)
  • [16] Ntai I., Bachmann B.O., Bioorg. Med. Chem. Lett., 18, pp. 3068-3071, (2008)
  • [17] Seto H., Kuzuyama T., Seto H., Kuzuyama T., Nat. Prod. Rep., 16, pp. 589-596, (1999)
  • [18] Yamato M., Koguchi T., Okachi R.Y.O., Yamada K., Nakayama K., Kase H., Karasawa A., Shuto K., J. Antibiot., 39, pp. 44-52, (1986)
  • [19] Masuyer G., Cozier G.E., Kramer G.J., Bachmann B.O., Acharya K.R., FEBS J., 283, pp. 4357-4369, (2016)
  • [20] Akif M., Ntai I., Sturrock E.D., Isaac R.E., Bachmann B.O., Acharya K.R., Biochem. Biophys. Res. Commun., 398, pp. 532-536, (2010)