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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 oximes 23a–23c, 24a–24c, 25a–25c derived from betulin (13)
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Sch3: The synthesis of acylated oximes 23a–23c, 24a–24c, 25a–25c derived from betulin (13)

Mentions: The next information on acyloxyimino derivatives of lupane triterpenes was published in 2004 (Flekhter et al. 2004). In order to obtain such compounds, betulin (13) was transformed into betulonic acid (17), methyl betulonate (18) and 28-oxo-allobetulon (19) with the use of known methods (Scheme 3). The resulted 3-oxoderivatives 17, 18 and 19 were subjected to the reaction with hydroxylamine hydrochloride in anhydrous pyridine which led to the obtaining of appropriate oximes (20, 21 and 22) with high yields. The compounds 20, 21 and 22 acylated in anhydrous benzene with carboxylic acid anhydrides (acetic, succinic or phthalic anhydride, Table 1, route 2) gave acylated oximes 23a–23c, 24a–24c, 25a–25c with the yields from 64 % to 77 %.Scheme 3


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

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

The synthesis of acylated oximes 23a–23c, 24a–24c, 25a–25c derived from betulin (13)
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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

Sch3: The synthesis of acylated oximes 23a–23c, 24a–24c, 25a–25c derived from betulin (13)
Mentions: The next information on acyloxyimino derivatives of lupane triterpenes was published in 2004 (Flekhter et al. 2004). In order to obtain such compounds, betulin (13) was transformed into betulonic acid (17), methyl betulonate (18) and 28-oxo-allobetulon (19) with the use of known methods (Scheme 3). The resulted 3-oxoderivatives 17, 18 and 19 were subjected to the reaction with hydroxylamine hydrochloride in anhydrous pyridine which led to the obtaining of appropriate oximes (20, 21 and 22) with high yields. The compounds 20, 21 and 22 acylated in anhydrous benzene with carboxylic acid anhydrides (acetic, succinic or phthalic anhydride, Table 1, route 2) gave acylated oximes 23a–23c, 24a–24c, 25a–25c with the yields from 64 % to 77 %.Scheme 3

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