4356-30-3Relevant academic research and scientific papers
Semisynthesis, cytotoxicity, antimalarial evaluation and structure-activity relationship of two series of triterpene derivatives
Cargnin, Simone Tasca,Staudt, Andressa Finkler,Medeiros, Patrícia,de Medeiros Sol Sol, Daniel,de Azevedo dos Santos, Ana Paula,Zanchi, Fernando Berton,Gosmann, Grace,Puyet, Antonio,Garcia Teles, Carolina Bioni,Gnoatto, Simone Baggio
supporting information, p. 265 - 272 (2018/02/15)
In this report, we describe the semisynthesis of two series of ursolic and betulinic acid derivatives through designed by modifications at the C-3 and C-28 positions and demonstrate their antimalarial activity against chloroquine-resistant P. falciparum (W2 strain). Structural modifications at C-3 were more advantageous to antimalarial activity than simultaneous modifications at C-3 and C-28 positions. The ester derivative, 3β-butanoyl betulinic acid (7b), was the most active compound (IC50 = 3.4 μM) and it did not exhibit cytotoxicity against VERO nor HepG2 cells (CC50 > 400 μM), showing selectivity towards parasites (selectivity index > 117.47). In combination with artemisinin, compound 7b showed an additive effect (CI = 1.14). While docking analysis showed a possible interaction of 7b with the Plasmodium protease PfSUB1, with an optimum binding affinity of ?7.02 kcal/mol, the rather low inhibition displayed on a Bacillus licheniformis subtilisin A protease activity assay (IC50 = 93 μM) and the observed accumulation of ring forms together with a delay of appearance of trophozoites in vitro suggests that the main target of 3β-butanoyl betulinic acid on Plasmodium may be related to other molecules and processes pertaining to the ring stage. Therefore, compound 7b is the most promising compound for further studies on antimalarial chemotherapy. The results obtained in this study provide suitable information about scaffolds to develop novel antimalarials from natural sources.
COMPOUNDS FOR REDUCING GLUCOCORTICOIDS, AND METHODS OF TREATMENT THEREOF
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Paragraph 0138-0140, (2014/05/24)
A method for reducing glucocorticoids in an animal in need thereof comprising the use of compounds of the formula (I), wherein the definitions for R', R1-R11 and n are as disclosed in the description. The compounds of formula (I) are for the treatment or prevention of a glucocorticoid-related disorder for maintaining bone density, maintaining and improving the immune system, treating Cushing' s syndrome, treating obesity, improving reproduction efficiency, treating metabolic disorder, treating hypertension, treating hyperglycemia, treating insulin resistance, treating type 2 diabetes, and/or aiding in cancer and immune therapies
Synthesis and anticancer activity of novel betulinic acid and betulin derivatives
Kommera, Harish,Kaluderovic, Goran N.,Kalbitz, Jutta,Paschke, Reinhard
experimental part, p. 449 - 457 (2011/04/16)
A series of novel betulinic acid derivatives 3-11 and betulin derivatives 12-17 were synthesized. The compounds were characterized by the means of 1H- and 13C-NMR spectroscopy as well as mass spectrometry. The compounds have been tested on ten tumor cell lines of different histogenic origin. The most active derivatives, containing a chloroacetyl group on C-3 in betulinic acid 9 and C-28 in betulin 15, were up to ten times more cytotoxic and many fold more selective towards tumor cells in comparison to normal cells (fibroblasts) than betulinic acid. Furthermore, compound 15 was found to possess cell growth inhibition even when treated for a short time on anaplastic thyroid cancer cells (SW1736).
Synthesis of 30-amino derivatives of lupane triterpenoids
Uzenkova,Petrenko,Shakirov,Shul ts,Tolstikov
, p. 692 - 700 (2008/02/03)
New derivatives of betulin and betulinic acid containing various amines on C-30 that are of interest as potentially biologically active agents were prepared. 2005 Springer Science+Business Media, Inc.
Synthesis of A-seco derivatives of betulinic acid with cytotoxic activity
Urban, Milan,Sarek, Jan,Klinot, Jiri,Korinkova, Gabriela,Hajduch, Marian
, p. 1100 - 1105 (2007/10/03)
In this study, the relationships between the chemical structure and cytotoxic activity of betulinic acid (1) derivatives were investigated. Eight lupane derivatives (1-8), one of them new (6), five diosphenols (9-13), four of them new (10-13), two new norderivatives (14 and 15), five seco derivatives (16-20), four of them new (16, 17, 19, and 20), and three new seco-anhydrides (21-23) were synthesized from 1, and their activities were compared with the activities of known compounds. The effects of substitution on the A-ring and esterification of the carboxyl group in position 28 on cytotoxicity were of special interest. Significant cytotoxic activity against the T-lymphoblastic leukemia cell line CEM was found in diosphenols 9 and 13 (TCS50 4 and 5 μmol/L) and seco-anhydrides 22 and 23 (TCS50 7 and 6 μmol/L). All compounds were also tested on cancer cell lines HT 29, K562, K562 Tax, and PC-3, and these confirmed activity of diosphenols 9, 10, and 11 and anhydride 22. Diosphenols, as the most promising group of derivatives, were further tested on four more lines (A 549, DU 145, MCF 7, SK-Mel2).
Triterpenoid derivatives
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, (2008/06/13)
The present invention relates to the use of a compound of formula (I), or a pharmaceutically acceptable salt, crystal form, complex, hydrate, or hydrolysable ester thereof, in the preparation of a medicament for treating a patient suffering from leukaemia, cancer or other proliferative disorder. A further embodiment relates to the use a compound of formula (I) in an assay for detecting the phosphorylation state of cellular substrates. The present invention also relates to novel compounds of formula (I), and the chemical synthesis thereof.
Action of N-Bromosuccinimide on Triterpene Acids and Esters in Dimethyl Sulphoxide
Pradhan, B. P.,Mukherjee, M. M.,Chakrabarti, D. K,Shoolery, J. N.
, p. 12 - 16 (2007/10/02)
Action of N-bromosuccinimide on acetyloleanolic acid/ methyl ester, acetaleuritolic acid/ methyl ester and acetylbetulenic acid/methyl ester in dimethyl sulphoxide has been studied and in each case a bromo γ-lactone is formed, and in the latter two compounds lactonization occurs with rearrangements.The compounds so formed have been identified as 3β-acetyl-12α-bromooleanan-28->13-olide (V), 3β-acetyl-15α-bromooleanan-28->13-olide (II) and 3β-acetyl-29,30-dibromo-18α-oleanan-28->19β-olide (IX) respectively.
