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Five new quinones have been isolated from a sponge tentatively classified as Stelospongia conulata. Isospongiaquinone (7) has a rearranged drimane skeleton whereas spongiaquinone (19), cyclo- spongiaquinone-1 (20), cyclospongiaquinone-2 (21) and dehydrocyclospongiaquinone-1 (22) have a normal drimane skeleton. The structures of these were derived from chemical and spectral evidence.

Aus fermentierten Kulturen von streptomyces antibioticus wurden die Titelverbindung (I) als eins der Hauptprodukte und das neue Dihydroindolon (II) als ein Nebenprodukt isoliert.

Cyclobuten-1-carbonsaureester (I) und der Cyclohexenon-carbonsaureester (II) reagieren zum Addukt (III), das thermisch zum Germacradien-carbonsaureester (IVa) fuhrt.

The 2-benzazepine 9-chloro-7-(2-chlorophenyl)-5H-pyrimido[5,4-d] [2]benzazepine (1) has been selected for development as an anxiolytic agent. In support of this program, we have confirmed by chemical synthesis the structures of three in vitro (rat liver homogenate) metabolites of 1 and confirmed the structure of the major in vivo (dog and man) metabolite of 1, compound 2. Two of the metabolites, arising from hydroxylation of the pyrimidobenzazepine ring at the 5-position (2) and N-oxide formation at the 3-position of the pyrimidobenzazepine ring (3), were found to be as active as 1 in a series of pharmacological tests. The third metabolite, formed by hydroxylation of the 7-phenyl group in the 4-position (4), was found to be inactive in the same pharmacological screens.

A series of novel 2- and 3-acylmorphinans (8-14) was synthesized in our search for a potent analgesic agent with low addiction potential. The compounds were evaluated for antinociceptive potency and receptor binding affinity. Among these compounds, the levorotatory 3-acetyl-N-(cyclopropylmethyl)morphinan (12) was found to be an orally active analgesic, comparable in potency to morphine (1), yet only weakly able to substitute for morphine (1) in morphine-dependent rats.

Synthesis of 1-beta-D-ribofuranosyltetrazole and two 5-substituted derivatives, i.e., the 5-carboxamide and 5-acetamide, is described. The stereochemical structure of the parent tetrazole ribonucleoside has been established by means of nuclear Overhauser effect and x-ray crystallography. By analogy to the parent compound, the two 5-substituted tetrazole nucleosides are also assigned the beta configuration on the basis of the NMR coupling constant of the anomeric proton and the site of N-ribosylation is determined by 13C NMR studies. Results are also presented on antiviral testing of these synthetic tetrazole nucleosides against influenza A2/Asian/J-305 virus infection in mice.

Bei fruheren Untersuchungen zum Metabolismus des als Antiarrhythmicum in klinischer Prufung befindlichen Cibenzolins (I) wurden neben dem Imidazol (II) die hydroxylierten Derivate (VII) als Metaboliten des tierischen (Hund, Ratte) Stoffwechsels isoliert und identifiziert.

Die durch HClO4-katalysierte Thermolyse des Antibioticums Bicyclomycin (I) verlauft unter Umlagerung zu den Heterospiranen (IIa) und (IIIa), die erst uber die Brombenzoate (IIb) bzw. (IIIb) getrennt werden konnen.

Aus dem Aminomethyl- benzodiazepin (II) erhalt man mit Zink/Essigsaure das Reduktionsprodukt (I), wahrend mit Orthoessigsaureester (III) das Cyclisierungsprodukt (IV) gebildet wird.