Cell cultures of THUJA OCCIDENTIALIS L. were found to biosynthesize various mono- and diterpenes when grown on B5-medium. The identification of the constituents was achieved mainly by capillary GLC-MS using fused silica columns and E.I.-mass spectrometry. Monoterpenes of the menthane type were only isolated from the culture medium whereas diterpenes were found in the cell extracts. Thujaplicin derivatives, monoterpenes of an irregular type, were detected in the medium as well as in the cells. Major differences were found between the terpene composition of the cell culture extracts and those from THUJA leaves. The cell cultures accumulated some compounds which are presently unknown as constituents of THUJA plants. On the other hand, the cultures were evidently unable to synthesize the thujone type of monoterpenes.
Die Synthese von 6-und 7-Amino-, -Methylamino-und -Dimethylaminc-1,3-dimethyllumazinen (2-4 und 12-14) wird beschrieben, wobei der nucleophile Austausch bei den 7-Halogen-1,3-dimethyllumazinen 10, 11 recht glatt verlauft. Fur die Darstellung der 6-Amino-Derivate erwies sich dagegen die Amidierung des 6-Hydroxy-l,3-dirnethyllumazins (I) mit Diamidophosphorsaure-phenylestern als vorteilhafter. Das 6-Amino-I ,3-dimethyllumazin (2) gewinnt man besser aus 6-Chlor-l,3-dimethyllumazin (7) iiber das 6-Hydrazino-Derivat 5 und nachfolgende Reduktion. Durch pK,-Wert-Bestimmung und Aufnahme der Spektren der Kationen sowie der neutralen Verbindungen la& sich zeigen, daL3 die Protonierung in beiden Reihen an N-5 erfolgt. Die physikalischen Eigenschaften werden diskutiert.Pteridines, LXXIII). -Synthesis and Properties of 6-and 7-Amino-l,3-dimethyllumazines The synthesis of 6-and 7-amino-, -methylamino-, and -dirnethylamino-l,3-dirnethyllumazines (2 -4 and 12 -14) is described. The nucleophilic displacement reaction proceeds easily with the 7-halo-I ,3-dimethyllumazines 10, 11 whereas the amidation of 6-hydroxy-I ,3-dimethyllumazine (1) with phenyl diamidophosphates is recommended for the formation of &amino derivatives. 6-Amino-l,3-dirnethyllumazine (2) is synthesized best from 6-chloro-l,3-dimethyllumazine (7) via the 6-hydrazino derivative 5 and subsequent reduction. From pK, value determinations and UV absorption spectra of the cationic and neutral forms can be seen that protonation takes place in both series at N-5. The physical properties of the newly synthcsized compounds are discussed.Anknupfend an Untersuchungen uber G2) und 7-Hydroxylumazine3) interessierten uns die entsprechenden 6-und 7-Amino-l,3-dimethyllumazine und einige ihrer physikalisch-chemischen Eigenschaften. In der Literatur ist lediglich das 7-Amino-I ,3-dimethyllumazin (12) genannt, das Blicke und God14) durch Cyanmethylierung des 5,6-Diamino-l,3-dimethyluracils zum 6-Amino-5-cyanmethylamino-1,3-dimethyluracil, dessen Cyclisierung zum 7-Amino-5,6-dihydro-1,3-dimethyllumazin (21) und anschliefiende Oxidation dargestellt haben. Da wir nach einem allgemeineren Syntheseweg -auch fur 6-und 7-substituierte Amino-l,3-dimethyllumazine -suchten, erschien die Darstellung aus 6-bzw. 7-Halogen-I ,3-dimethyllumazinen (7, 8, 10, 11) mit nachfolgender nucleophiler Substitutionsreaktion am erfolgreichsten.
Die Synthese der Aminolumazine (II) gelingt aus den Hydroxylumazinen (I) entweder direkt durch Umsetzen mit den entsprechenden Diamidophosphorsäureestern oder über die Chlorderivate (III).
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