Synthesis, structure, and properties of pyrazolo[4,3-b]quinuclidine derivatives

Turchin, K. F.; Yanina, A. D.; Filipenko, T. Ya.; Mikhlina, E. E.; Sheinker, Yu. N.; Yakhontov, L. N.

doi:10.1007/bf00515032

Cited by 2 publications

(2 citation statements)

References 5 publications

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“…During the crystallization from MeOH, compound III readily transforms into IV, especially so in the presence of mace amounts of acid. The ketal structure of compound IV is confirmed by the strong screening of atom C-4a (as manifested by the small chemical shift 5 = 96.7 ppm compared to ~ 200 ppm for ketones I and II [19]). Treatment of Ib or III with an HC1 solution in i-PrOH or BuOH leads to the corresponding/so-propoxy and n-butoxy derivatives (X, XI), which can be readily separated by extraction with heptane from the more polar 0091 In the preliminary publication [13], we have reported that the above reaction of compound Ia leads to a mixture of Va, Via, and VIIa with the component ratio 1 : 1 : 1, from which VIIa-HCI was isolated upon crystallization from MeOH.…”

mentioning

confidence: 74%

Search for no donors. Part I. 3-Quinuclidone oximes

Koikov¹,

Алексеева²,

Grigor'ev³

et al. 1997

Pharm Chem J

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Identification of the "endothelial relaxation factor" as the endogenic NO formed from L-arginine in the vascular endothelium [1] has stimulated the search for new generation of cardiovascular drugs [2][3][4][5]. At present, it has been established that biochemical synthesis of NO proceeds by different pathways. Exogenic organic nitrates (nitroglycerin, nitrosorbid, and other classical vasodilators) are subject to reduction [6], as well as the new NO precursors such as N-nitropyrazoles [7] and furoxanes [8]. On the contrary, L-arginine -the main NO source in the organism -is oxidized by the enzyme NO-synthase (NOS) to . NOS is also capable of forming NO from [3-mercaptoethylguanidine [9,10]. Study of the weU-known vasodilator molsidomin showed that this agent generates NO by reaction with atmospheric oxygen [3]. It was found that 1,2-diazetine-l,2-dioxides form NO upon thermolysis and/or hydrolysis [I1]. Muller et al. [12] reported on the use of (+)-3-(E)-4ethyl-2[(E)-hydroxyimino]-5-nitro-3-hexenamide (FK 409) as the NO donor in solutions at pH -7.5, but failed t o establish a group (oxime, nitro, or both) acting as the source of NO [12]. Recently we have demonstrated that 3-quinuclidone oximes may serve as the source of NO and activate the soluble guanylate cyclase [13]. The purpose of this work was to extend the group of oximes and study their hypotensive activity.The NO precursors were obtained on the basis of both well-known (Va/VIa, Vb/VIb, Ve/VIe, Vi/VIi) [14], (Vc/VIc, Vd/VId, VIIb] [13], and newly synthesized (VfiVlfVh/VIh) 2-arylmethylene-3-quinuclidone oximes and their hydrogenated analogs IXb and IXe. The compact rind framework structure of quinuclidine (1-azabicyclo[2.2.2]octane) provides spatial fixation of the substituents and sufficiently high solubility of hydrochlorides, while the double bond in position 2 sometimes allows us to obtain the (Z/E) isomer

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confidence: 74%

Search for no donors. Part I. 3-Quinuclidone oximes

Koikov¹,

Алексеева²,

Grigor'ev³

et al. 1997

Pharm Chem J

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“…When subjected to platinum-or palladium-catalysed hydrogenation, methylidene-and arylmethylidenequinuclidinones were transformed into saturated ketones 173. 288,291,292,298,305 The corresponding allylic alcohols 174 were selectively obtained with the use of NaBH 4 . 288,308,324,325 Stereospecific reduction of both functional groups in the benzylidenequinuclidinone 151 (R = Ph) with lithium aluminium hydride afforded benzylquinuclidinol trans-175 (R = Ph).…”

Section: Methylidene-and Arylmethylidenequinuclidin-3-onesmentioning

confidence: 99%

Captodative aminoalkenes

Rulev¹

2002

Russ. Chem. Rev.

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Synthesis, structure, and properties of pyrazolo[4,3-b]quinuclidine derivatives

Cited by 2 publications

References 5 publications

Search for no donors. Part I. 3-Quinuclidone oximes

Search for no donors. Part I. 3-Quinuclidone oximes

Captodative aminoalkenes

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