Synthesis and total 1H- and 13C-NMR assignment of cephem derivatives for use in ADEPT approaches.
We report the synthesis and total NMR characterization of 5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid-3-[[[(4''-nitrophenoxy)carbonyl]oxy]-methyl]-8-oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethyl ester-5-dioxide (5), a new cephalosporin derivative. This compound can be used as the carrier of a wide range of drugs containing an amino group. The preparation of the intermediate product, 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid-3-[methyl 4-(6-methoxyquinolin-8-ylamino)pentylcarbamate]-8-oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethyl ester-5-dioxide (6), as well as the synthesis of the antimalarial primaquine prodrug 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid-3-[methyl 4-(6-methoxyquinolin-8-ylamino)pentylcarbamate]-8-oxo-7-[(2-thienyloxoacetyl)amino]- 5-dioxide (7) are also described, together with their total (1)H- and (13)C-NMR assignments.
Blau
Lorena
L
Departamento de Fármacos e Medicamentos, Faculdade de Ciências Farmacêuticas, Universidade Estadual Paulista, CP 502 - 14801-902, Araraquara, SP, Brazil. lorenblau@universiabrasil.net
Menegon
Renato Farina
RF
Ferreira
Elizabeth Igne
EI
Ferreira
Antonio Gilberto
AG
Boffo
Elisangela Fabiana
EF
Tavares
Leila Aley
LA
Heleno
Vladimir Constantino Gomes
VC
Chung
Man-Chin
MC
D002511:Cephalosporins / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D011319:Primaquine / Q000138:chemical synthesis / Q000737:chemistry; D011355:Prodrugs / Q000138:chemical synthesis / Q000737:chemistry
D002511:Cephalosporins; D011355:Prodrugs; D011319:Primaquine