1,5-Naphthyridines and their n-oxides III. Synthesis and biological activity of some mono- and disubstituted 1,5-naphthyridines and their n-oxides
In order to search for biologically active compounds in the 1,5-naphthyridine series, we synthesized 2-mercaptoand 2-(4'-aminobenzenesulfonamido)-l,5naphthyridines and some of their 6-substituted derivatives. 2-(4'-Aminobenzenesulfonamido)-l,5-naphthyridine (I) was obtained by reaction of 2-amino-l,5naphthyridine with 4-carbomethoxyaminobenzenesulfonyl chloride in pyridine with subsequent saponification of the carbomethoxy group in the resulting 2-(4'carbomethoxyaminobenzenesulfonamido)-l,5-naphthyridine (II).
Tautomerism of 3-alkoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline derivatives
The compound previously formulated as ethyl 1,2-dihydro-2-oxoquinoxalin-3-ylacetate has the isomeric structure 3-ethoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline in the solid state. In solution the 1-methyl derivative has been shown by nuclear magnetic resonance studies to exist as a tautomeric mixture of unsaturated and saturated esters.
Two new organic reference materials for delta13C and delta15N measurements and a new value for the delta13C of NBS 22 oil.
Analytical grade L-glutamic acid is chemically stable and has a C/N mole ratio of 5, which is close to that of many of natural biological materials, such as blood and animal tissue. Two L-glutamic acid reference materials with substantially different 13C and 15N abundances have been prepared for use as organic reference materials for C and N isotopic measurements. USGS40 is analytical grade L-glutamic acid and has a delta13C value of -26.24 per thousand relative to VPDB and a delta15N value of -4.52 per thousand relative to N2 in air. USGS41 was prepared by dissolving analytical grade L-glutamic acid with L-glutamic acid enriched in 13C and 15N. USGS41 has a delta13C value of +37.76 per thousand and a delta15N value of +47.57 per thousand. The delta13C and delta15N values of both materials were measured against the international reference materials NBS 19 calcium carbonate (delta13C=+1.95 per thousand ), L-SVEC lithium carbonate (delta13C=-46.48 per thousand ), IAEA-N-1 ammonium sulfate (delta15N=0.43 per thousand ), and USGS32 potassium nitrate (delta15N=180 per thousand ) by on-line combustion continuous-flow and off-line dual-inlet isotope-ratio mass spectrometry. Both USGS40 and USGS41 are isotopically homogeneous; reproducibility of delta13C is better than 0.13 per thousand, and that of delta15N is better than 0.13 per thousand in 100-microg amounts. These two isotopic reference materials can be used for (i) calibrating local laboratory reference materials, and (ii) quantifying drift with time, mass-dependent fractionations, and isotope-ratio-scale contraction in the isotopic analysis of various biological materials. Isotopic results presented in this paper yield a delta13C value for NBS 22 oil of -29.91 per thousand, in contrast to the commonly accepted value of -29.78 per thousand for which off-line blank corrections probably have not been quantified satisfactorily.