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Recent advances in synthesis and biological activity of triterpenic acylated oximes.

Bednarczyk-Cwynar B, Zaprutko L - Phytochem Rev (2014)

Bottom Line: A reactive hydroxyimine group can undergo the action of acylating agents, such as carboxylic acids or their derivatives, also the ones with significant pharmacological activity.In many cases the pharmacological effects of the tested acyloxyiminotriterpenes were comparable to those of appropriate standard drugs.One of the newest application of acyl derivatives of triterpenic oximes is their ability to form organogels.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences, Grunwaldzka Str. No. 6, 60-780 Poznan, Poland.

ABSTRACT

During the last few decades more and more attention has been paid to triterpenes-a group of compounds with five- or four-ring skeleton and carboxyl, hydroxyl or oxo groups. Triterpenes with unsubstituted C-3 hydroxyl group can be easily transformed into appropriate ketones and then into oximes. The carbonyl group can be created not only from the hydroxyl group at C-3 position, but also at C-2, C-12 or C-28 positions. Several methods of creation of two = NOH groups within one molecule of triterpene are known. There are also known triterpenes with two carbonyl groups, e.g. at C-3 and C-11 positions, which differ in reactivity: among them only C-3 group can be transformed into oxime. A reactive hydroxyimine group can undergo the action of acylating agents, such as carboxylic acids or their derivatives, also the ones with significant pharmacological activity. Acyl derivatives of triterpenic oximes exhibit important pharmacological activity. The biological tests performed with the use of cell cultures inoculated with viruses showed inhibitory activity of some triterpenic acyloximes against type 1 HSV (H7N1), ECHO-6 and HIV-1 viruses. Another acylated oximes derived from triterpenes shown cytotoxic or antiproliferative activity against many lines of cancer cells. In many cases the pharmacological effects of the tested acyloxyiminotriterpenes were comparable to those of appropriate standard drugs. One of the newest application of acyl derivatives of triterpenic oximes is their ability to form organogels.

No MeSH data available.


Related in: MedlinePlus

The synthesis of acylated oxime 41 derived from oleanolic acid (1)
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Sch9: The synthesis of acylated oxime 41 derived from oleanolic acid (1)

Mentions: Oleanolic acid (1) or its methyl ester (2) were oxidizied with Jones reagent in acetone to the appropriate ketones 3 and 4, respectively. Next the oxoderivatives 3 and 4 were subjected to the action of n-butyl nitrite and as a result α-ketooximes 37 and 38, respectively, were obtained (Scheme 9). These compounds were next refluxed in pyridine with hydroxylamine hydrochloride and yielded α-dioximes: 39 and 40, respectively. The compound 39 reacted with acetic anhydride at room temperature in pyridine in the presence of DMAP (Table 1, route 8) to afford diacetyloxime 41 with the yield of 51 %.Scheme 9


Recent advances in synthesis and biological activity of triterpenic acylated oximes.

Bednarczyk-Cwynar B, Zaprutko L - Phytochem Rev (2014)

The synthesis of acylated oxime 41 derived from oleanolic acid (1)
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4379416&req=5

Sch9: The synthesis of acylated oxime 41 derived from oleanolic acid (1)
Mentions: Oleanolic acid (1) or its methyl ester (2) were oxidizied with Jones reagent in acetone to the appropriate ketones 3 and 4, respectively. Next the oxoderivatives 3 and 4 were subjected to the action of n-butyl nitrite and as a result α-ketooximes 37 and 38, respectively, were obtained (Scheme 9). These compounds were next refluxed in pyridine with hydroxylamine hydrochloride and yielded α-dioximes: 39 and 40, respectively. The compound 39 reacted with acetic anhydride at room temperature in pyridine in the presence of DMAP (Table 1, route 8) to afford diacetyloxime 41 with the yield of 51 %.Scheme 9

Bottom Line: A reactive hydroxyimine group can undergo the action of acylating agents, such as carboxylic acids or their derivatives, also the ones with significant pharmacological activity.In many cases the pharmacological effects of the tested acyloxyiminotriterpenes were comparable to those of appropriate standard drugs.One of the newest application of acyl derivatives of triterpenic oximes is their ability to form organogels.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences, Grunwaldzka Str. No. 6, 60-780 Poznan, Poland.

ABSTRACT

During the last few decades more and more attention has been paid to triterpenes-a group of compounds with five- or four-ring skeleton and carboxyl, hydroxyl or oxo groups. Triterpenes with unsubstituted C-3 hydroxyl group can be easily transformed into appropriate ketones and then into oximes. The carbonyl group can be created not only from the hydroxyl group at C-3 position, but also at C-2, C-12 or C-28 positions. Several methods of creation of two = NOH groups within one molecule of triterpene are known. There are also known triterpenes with two carbonyl groups, e.g. at C-3 and C-11 positions, which differ in reactivity: among them only C-3 group can be transformed into oxime. A reactive hydroxyimine group can undergo the action of acylating agents, such as carboxylic acids or their derivatives, also the ones with significant pharmacological activity. Acyl derivatives of triterpenic oximes exhibit important pharmacological activity. The biological tests performed with the use of cell cultures inoculated with viruses showed inhibitory activity of some triterpenic acyloximes against type 1 HSV (H7N1), ECHO-6 and HIV-1 viruses. Another acylated oximes derived from triterpenes shown cytotoxic or antiproliferative activity against many lines of cancer cells. In many cases the pharmacological effects of the tested acyloxyiminotriterpenes were comparable to those of appropriate standard drugs. One of the newest application of acyl derivatives of triterpenic oximes is their ability to form organogels.

No MeSH data available.


Related in: MedlinePlus