Preparation and biological properties of (-)- and (+)-6-hydroxydopa

Zusammenfassung Die optischen Isomeren von 6-Hydroxydopa wurden synthetisiert und ihr Effekt auf den Katecholaminspiegel verschiedener Organe in der Ratte bestimmt. Dem (–)-Isomeren gegenüber waren Herz und Nebennieren äusserst empfindlich und im Gehirn wurde der Norepinephrinspiegel erniedrigt.

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B.A.B. is the recipient of a Roche Institute of Molecular Biology postdoctoral fellowship.     

Quantitative differences in the pharmacological effects of (+)- and (-)-cathinone

The optically pure isomers of cathinone were prepared by separating synthetic cathinone racemate and used to study central and peripheral effects of these indirect sympathomimetics in rats and guinea pigs. The (-)-isomer was significantly more potent than the (+)-isomer in stimulating locomotor activity whereas no difference was observed with respect to their cardiac effects. In analogy to observations with (+)- and (-)-amphetamine such variable isomer discrimination may be due to different stereoselectivities of amine uptake mechanisms in the target tissues.     

Hashish VI1: Conversion of (-)-Δ 1(6)-Tetrahydrocannabinol to (-)-Δ 1(7)-Tetrahydrocannabinol. Stability of (-)-Δ 1 and (-)-Δ 1(6)-Tetrahydrocannabinols

Zusammenfassung Die Synthese von (—)-¹⁽⁷⁾-Tetrahydrocannabinol (THC) auf (—)-¹⁽⁶⁾ wird beschrieben. Das Hauptprodukt der oxidativen Zerstörung von (—)-¹-THC ist Cannabinol. Beschleunigte Versuche der Luftoxidation von (—)-¹-THC und (—)-¹⁽⁶⁾-THC haben gezeigt, dass das letztere beständiger ist. Dieser Unterschied kann mit der Reaktivität des C₃-benzylisch-allylischen Wasserstoffes in (—)-¹-THC erklärt werden.     

(S)-(+)-4,4,4-Trifluoro-3-(indole-3-)butyric acid,a novel fluorinated plant growth regulator

Racemic 4,4,4-trifluoro-3-(indole-3-)butyric acid (TFIBA) has been synthesized and shown to inhibitAvena coleoptile elongation. (S)-(+)-TFIBA (fig. 1), which was prepared by an enzymatic method and markedly promotes root growth of Chinese cabbage, lettuce and rice plants, is a novel fluorinated plant growth regulator. Activity of the (S)-(+)-enantiomer of TFIBA was 10-fold greater than that of the (R)-(–)-enantiomer in the first two plant species and 5-fold greater in rice.     

Stereospecific reduction of geraniol to (R)-(+)-citronellol bySaccharomyces cerevisiae

Summary (R)-(+)-citronellol, a useful C₁₀ chiral synthon for natural terpenoid products, can be obtained in enantiomerically pure form and satisfactory yield by yeast reduction of geraniol.     

Total synthesis of derivatives of (±)-6-oxa and aza-estrone

Zusammenfassung Es wird über die Totalsynthese von verschiedenen Derivaten des (±)-6-Oxa- und Aza-Östrons und die Umwandlung von (±)-17-Oxy-3-methoxy-6-oxa-östratrien-1, 3, 5¹⁰ zu Verbindungen der (±)-19-Nor-6-oxa-testosteron-Klasse berichtet. Die biologische Wirksamkeit der Glieder in der 6-Oxa-Reihe wird beschrieben.     

Conformations and biological properties of apomorphine and its phenanthro(10,1-b,c)azepine homologue.

11,12-Dihydroxy-7-methyl-4,5,6,7,7a,8-hexahydrophenanthro[10,1-b,c]-azepine (2), a homologue of apomorphine (1), has been found to be devoid of dopaminergic effects. The biological differences between apomorphine and this homologue are explained in terms of differences in conformation of the two molecules.     

5-(Hydroxyimino)-4-methoxy-2-(pivaloylimino)thiazolidine-3 -acetamide, a reduced nitroheterocyclic derivative with potent schistosomicidal properties

The synthesis and antischistosome properties of 5-(hydroxyimino)-4-methoxy-2-(pivaloylimino)thiazolidine-3- acetamide (1) are described. The compound was prepared by reduction of the nitrothiazoline (2) with stannous chloride in methanol, and represents the first example of a reduced nitroheterocyclic compound showing potent schistosomicidal properties. The possible relationship of compounds such as 1 to the as yet unidentified reduced active but toxic entities formed in vivo from nitroheterocyclics like metronidazole is discussed.     

5-(Hydroxyimino)-4-methoxy-2-(pivaloylimino)thiazolidine-3-acetamide,a reduced nitroheterocyclic derivative with potent schistosomicidal properties

Summary The synthesis and antischistosome properties of 5-(hydroxyimino)-4-methoxy-2-(pivaloylimino)thiazolidine-3-acetamide (1) are described. The compound was prepared by reduction of the nitrothiazoline (2) with stannous chloride in methanol, and represents the first example of a reduced nitroheterocyclic compound showing potent schistosomicidal properties. The possible relationship of compounds such as1 to the as yet unidentified reduced active but toxic entities formed in vivo from nitroheterocyclics like metronidazole is discussed.Acknowledgments. The authors are grateful to Dr A. J. Everett and his staff for the physical chemistry measurements, and to Mr G. Dickerson for the antischistosome testing.     

(+)-α-Selinene,and enantiomeric eudesmane fromChiloscyphus polyanthus (L.) corda

Zusammenfassung Nachweis des optischen Isomeren eines Sesquiterpens im LebermoosChiloscyphus polyanthus mit (+)--Selinen als Hauptanteil.

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This work has been supported, in part, by a National Institutes of Health grant No. GM-18143.