Certain Transformations of Anabasine and Nicotine

Musina, L. A.; Astaf’eva, Z. M.; Balpanov, D. S.; Шакиров, М. М.; Шульц, Э. Э.; Krichevskii, L. A.; Кагарлицкий, А. Д.; Адекенов, С. М.

doi:10.1023/b:conc.0000033932.15694.35

Chemistry of Natural Compounds

2004

DOI: 10.1023/b:conc.0000033932.15694.35

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Certain Transformations of Anabasine and Nicotine

L. A. Musina

Z. M. Astaf’eva

D. S. Balpanov

et al.

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“…7,8 Anabasine derivatives containing bulky acyl and alkyl sub stituents at the piperidine ring nitrogen atom exert an antinicotinic action, 9 and its hydrogenated derivatives ex hibit analgesic activities. 10 Thus, targeted synthetic transformations of anabasine may produce effective analogues with other types of physi ological activities.This paper describes a study of the oxidation of ana basine (1) and its N acetyl (2), N benzoyl (3) and N methyl (4) derivatives on treatment with tert butyl hydroperoxide (TBHP) and МCРBA and some transfor mations of the N oxides thus formed. …”

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Syntheses based on anabasine. Preparation and transformations of N-oxides

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The oxidation of N acetyl and N benzoylanabasine with the tert butyl hydroperoxide (TBHP)-МoCl 5 system or МCРBA proceeds selectively at the nitrogen atom of the pyridine ring. The oxidation of N methylanabasine under similar conditions gives a mixture of stereo isomeric N oxides at the piperidine nitrogen atom, their ratio depending on the reagent used. The oxidation of anabasine by TBHP-МoCl 5 or МCРBA is accompanied by dehydrogenation and results in anabaseine N oxide. The reactions of anabasine and anabaseine pyridine N oxides with acetic anhydride were investigated. The substituted 1H 3 pyridin 2 ones were prepared. 2 pyridone, N acetylpiperidyl 2 pyridone, anabasein 3 one.Anabasine, 3 (2 piperidyl)pyridine (1), is the princi pal alkaloid of the Anabasis aphylla L. plant. 1 Anabasine hydrochloride is used as a means for giving up smoking; 2 the mechanism of its action includes binding to nicotine sensitive receptors. The anabasine base exhibits clear cut physiological activity. The action of this alkaloid is due to affection of the H cholinoreactive structures of various parts of the nervous system and violation of the mem brane permeability of cells, which results in a faulty course of redox processes in the organism. 3 Anabasine is an initial base in the synthesis of revers ible and irreversible choline esterase inhibitors, 4 in par ticular, phosphamide, 5 carbamide derivatives, 6 and a number of pharmacologically valuable compounds ob tained by reactions at the piperidine ring nitrogen atom. 7,8 Anabasine derivatives containing bulky acyl and alkyl sub stituents at the piperidine ring nitrogen atom exert an antinicotinic action, 9 and its hydrogenated derivatives ex hibit analgesic activities. 10 Thus, targeted synthetic transformations of anabasine may produce effective analogues with other types of physi ological activities.This paper describes a study of the oxidation of ana basine (1) and its N acetyl (2), N benzoyl (3) and N methyl (4) derivatives on treatment with tert butyl hydroperoxide (TBHP) and МCРBA and some transfor mations of the N oxides thus formed. Results and DiscussionPreviously, 11 we demonstrated that anabasine oxida tion with hydrogen peroxide in acetic acid is accompa nied by cleavage of the piperidine ring. No N oxidation of anabasine or its derivatives 2-4 by other reagents has yet been carried out. We found that refluxing of anabasine (1) in the presence of the TBHP-MoCl 5 system in benzene with water removal gives crystalline anabaseine N oxide (5) in 54% yield (Scheme 1). Thus, the hydroperoxide serves as a dehydrogenating agent. The oxidation of N acetyl (2) or N benzoylanabasine (3) under the ac tion of TBHP-MoCl 5 affords individual N acetyl and N benzoylanabasine pyridine N oxides 6 and 7 in 79 and 89% yields, respectively. It should be emphasized that previously, this reagent has been successfully used for N oxidation of diverse pyridine derivatives. 12-14 The use of VO(acac) 2 as the catalyst proved inefficient. The at tempted N oxidation of anabasine derivatives 2 and ...

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Syntheses based on anabasine. Preparation and transformations of N-oxides

et al. 2006

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Certain Transformations of Anabasine and Nicotine

Cited by 1 publication

References 1 publication

Syntheses based on anabasine. Preparation and transformations of N-oxides

Syntheses based on anabasine. Preparation and transformations of N-oxides

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