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C Monneret

Publications and source records attributed to C Monneret.

48 records · Page 3Linked to original sources
PubMed1989

Rationale for the synthesis and preliminary biological evaluation of highly active new antitumor nitrosoureido sugars.

Various new nitrosoureido derivatives of di- or trideoxy sugars were synthesized. The influence of the hydroxyl substitution pattern, the configuration at the anomeric center, and the absolute configuration of the sugar moiety on the antitumor activity of a series of nitrosoureido derivatives of di- and trideoxy sugars was studied. All compounds showed a very significant activity in vivo against L1210 leukemia, B16 melanocarcinoma, and Lewis lung carcinoma. Methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-2,3-dideoxy-alpha-D-arabino- hexopyranoside, 24 (NSC 609224), was found to be the most active compound. When treated with 24 (NSC 609224) at 20 mg/kg on day 1, at least 90% of the L1210 leukemia and B16 melanocarcinoma bearing mice showed a survival of over 60 days for a LD50 value for this compound of 42 mg/kg.

Amino Sugars↗
PubMed1989

[Total synthesis of oxa-9-anthracyclines].

Racemic 7-hydroxy-9-oxa-anthracyclinone (5a) has been synthetised in seven steps from quinizarin (6) and its resolution achieved after glycosylation with 3,4-di-O-acetyl-2-deoxy-L-fucose. Chiral pool syntheses of (8S)-8-hydroxymethyl-9-oxa-anthracyclinone (5b) and of (8S,10R) and (8S,10S)-8-hydroxymethyl-10-methyl-9-oxa-anthracyclinones (5c and 5d) have been achieved using (R)-2,3-O-isopropylideneglyceraldehyde (12) and leucoquinizarin (13) as starting materials. Glycosylation of aglycones 5b-5d by either 3,4-di-O-acetyl-2-deoxy-L-fucose or various 3-amino-2,3,6-trideoxy-L-hexoses yielded the corresponding anthracyclines. The synthetic glycosides do not show significant cytotoxic activity at a concentration of 1 microgram/ml against L 1210 cells.

Animals↗
PubMed1989

Synthesis and antitumor activity of new anthracyclines.

New anthracyclines including 2-deoxy-L-fucose, 2-deoxy-L-rhamnose and 2,6-dideoxy-2-iodo-alpha-L-mannose as sugar moieties, respectively 8, 11 and 14, have been obtained by glycosidation of the 4-demethoxy-9-hydroxymethyl-9-deacetyl daunorubicinone (1) with appropriate sugars under Koenigs-Knorr conditions. They were found to display high cytotoxicity on L1210 leukemia, but also an outstanding antileukemic activity in mice in the case of 8 and 14.

Animals↗
PubMed1986

Desorption chemical ionization mass spectrometry of anthracyclines and of trisaccharides related to aclacinomycin A and marcellomycin.

Desorption chemical ionization mass spectrometry with ammonia as the reagent gas was used to obtain positive ion spectra of twelve alkyl-anthraquinones, seven anthracyclinones, eleven anthracycline antibiotics and nine oligosaccharides (di- and trisaccharides). Ions corresponding to the intact molecules (M) were present in all spectra as pseudo-molecular ions [M + H]+ and/or [M + NH]+. However, the most significant results were obtained in the case of anthracyclines and oligosaccharides. With anthracyclines, in addition to the preceding ions, spectra exhibited characteristic fragment ions due to the aglycon or to the sugar moiety while ions corresponding to the sequential loss of monosaccharide units were observed with oligosaccharides. All these fragment ions can be readily explained by an initial site of protonation located at the oxygen atom of the glycosidic linkages.

Aclarubicin↗
PubMedDate not supplied

Further studies of the glucomannan from Aloe vahombe (liliaceae). II. Partial hydrolyses and NMR 13C studies.

The polysaccharide from Aloe vahombe (lilaceae) was submitted to partial hydrolyses by sulfuric, oxalic and phosphoric acid. Some oligosaccharides were isolated and investigated by chemical and 13C NMR spectroscopic methods. Their structure was determined. The results prove unambiguously that in the analyzed material the D-mannose is linked to the D-glucose by beta-1----4 linkages to form a carbohydrate heteropolymer.

Hydrolysis↗