Oleanolic acid (OA) is a compound widely distributed in plant kingdom. It occurs in a form of free acid or numerous glycosides. As it is known from numerous publications, oleanolic acid and another triterpenes, mostly from ursane, oleanane and lupane group, show great variety of pharmacological actions: they have been shown in experimental and clinical studies to demonstrate promising anticancer [1], gastroprotective [2], analgesic, anti-inflammatory [3] and many other important activities.

In our researches oleanolic acid was transformed into miscellaneous derivatives within A or C ring as well as hydroxyl or carboxylic group. New compounds were obtained on the basis of multistep set of transformations with the usage of reactions such as: methylation of carboxylic group, reduction of free or esterified carboxylic group, transformation of carboxylic group into amide, acylation in pyridine or dioxane, hydrolysis, different types of oxidation (Jones oxidation, allylic oxidation, m-CPBA oxidation), transformation of ketone group into oxime function, Beckmann rearrangement, thionation of C=O group into C=S function.

The new-obtained products were tested against many tumorous MDR cell lines, as percutaneous penetration enhancers, and as analgesic, anti-inflammatory or antituberculosis agents. It is known from biological tests that the derivatives of OA that possesses double-bounded group at C-3 position (C=O, C=NOH, C=NOAcyl) belong to a class of the most active species. These compounds exhibited cytotoxic activity towards cancer lines, which were resist to many known anticancer drugs [4–6] and some of this derivatives turned to be active analgesic and anti-inflammatory agents [7]. Some derivatives of oleanolic acid have anti-inflammatory effects influencing TNFα, IL-1or IL-12 production [8]. Azaderivatives of oleanolic acid with A- or C-ring lactam system are effective transdermal penetration enhancers [9].

[1] P. Srivastava, N. Kasoju, U. Bora et al., Biotechnol. Bioprocess Eng., 2010, 15, 1038–1046. [2] M. Sánchez, C. Theoduloz, G. Schmeda–Hirschmann et al., Life Sci., 2006, 79, 1349–1356. [3] M.F. Otuki, F. Vieira-Lima, A. Malheiros et al., Eur. J. Pharmacol., 2005, 507, 253–259. [4] A. Paszel, B. Rubiś, B. Bednarczyk – Cwynar et al., Pharmacol. Rep., 2011, 63, 1500 – 1517. [5] B. Bednarczyk–Cwynar, L. Zaprutko, P. Ruszkowski et al., Org. Biomol. Chem., 2012, 10, 2201–2205. [6] D. Kaminskyy, B. Bednarczyk – Cwynar, O. Vasylenko et al., Med. Chem. Res., DOI: 10.1007/s00044-011-9893-9. [7] B. Bednarczyk–Cwynar, L. Zaprutko, J. Marciniak et al., 6th Polish-German Symposium on Pharmaceutical Sciences „Perspectives for a new decade”, Dusseldorf 20 – 21 V 2011, Book of Abstract p. P037. [8] E. Rojczyk, B. Bednarczyk–Cwynar, L. Zaprutko et al., VII Mižnarodna Naukova Konferenciâ Studentiv ta Aspirantiv "Molod' i postup biologii", Lwów, 5 – 8 IV 2011, Book of Abstract p. 307 – 308. [9] L. Zaprutko, D. Partyka, B. Bednarczyk–Cwynar, Bioorg. Med. Chem. Lett., 2004, 14, 4723 – 4726.

• Legal notice:
  

  Copyright (c) Pielaszek Research, all rights reserved.
  The above materials, including auxiliary resources, are subject to Publisher's copyright and the Author(s) intellectual rights. Without limiting Author(s) rights under respective Copyright Transfer Agreement, no part of the above documents may be reproduced without the express written permission of Pielaszek Research, the Publisher. Express permission from the Author(s) is required to use the above materials for academic purposes, such as lectures or scientific presentations.
  In every case, proper references including Author(s) name(s) and URL of this webpage: https://science24.com/paper/25460 must be provided.

1. The new azole connections as potential biologically active agents
2. SYNTHESIS OF NEW DERIVATIVES OF OLEANOLIC ACID AS POTENTIAL TRANSDERMAL PENETRATION PROMOTERS
3. SOLVENT-FREE THIONATION OF FRAGRANT HETEROKETONES UNDER MICROWAVE CONDITIONS
4. MICROWAVE-ASSISTED SYNTHESIS OF UNSATURATED HETEROCYCLIC FRAGRANT COMPOUNDS RELATED TO JASMONE
5. THE ANTITUBERCULAR ACTIVITY OF 7-NITROIMIDAZOOXAZOLES
6. NEW ADAMANTACYL DERIVATIVES OF DINITROIMIDAZOLE