Synthesis and evaluation of biological activity of the auaternary ammonium salts of lupane-, oleanane-, and ursane-type acids

Synthesis

Volumn , Issue 22, 2010, Pages 3839-3848

  Biedermann, David ^a   Eignerova, Barbara ^b,c   Hajduch, Marian ^d   Sarek, Jan ^d  

^a INSTITUTE OF MICROBIOLOGY   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

^c INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^d PALACKÝ UNIVERSITY   (Czech Republic)

Author keywords

amines; cytotoxicity screening; esters; natural products; terpenoids

Indexed keywords

AMMONIUM SALT; ANTICANCER ACTIVITIES; ANTICANCER PROPERTIES; BIOLOGICAL ACTIVITIES; CELL LINES; CYTOTOXIC ACTIVITIES; IN-VITRO; LEUKAEMIA CELLS; LOW MOLECULAR WEIGHT; NATURAL PRODUCTS; OLEANANE; PENTACYCLIC TRITERPENOIDS; QUATERNARY AMMONIUM; QUATERNARY SALTS; QUATERNIZATION; TERPENOIDS; TERTIARY AMINE; TRIETHANOL; TRIETHANOLAMINES; TRIETHYLAMINES; TRIMETHYLAMINE;

AMINATION; AMINES; AMMONIUM COMPOUNDS; BROMINE COMPOUNDS; CELL CULTURE; CYTOTOXICITY; ESTERIFICATION; LIPIDS; PYRIDINE; SALTS; SYNTHESIS (CHEMICAL);

ESTERS;

2 (TRIETHYLAMMONIO)ETHYL 3 BETA ACETOXY 21 OXOLUP 18 EN 28 OIC ACID BROMIDE; 2 (TRIETHYLAMMONIO)ETHYL 3 BETA HYDROXY 20 OXO 29 NORLUPAN 28 OIC ACID BROMIDE; 2 (TRIETHYLAMMONIO)ETHYL 3 BETA HYDROXYLUP 20(29) EN 28 OIC ACID BROMIDE; 2 (TRIETHYLAMMONIO)ETHYL 3 BETA HYDROXYLUPAN 28 OIC ACID BROMIDE; 2 (TRIMETHYLAMMONIO)ETHYL 3 BETA ACETOXY 21 OXOLUP 18 EN 28 OIC ACID BROMIDE; 2 (TRIMETHYLAMMONIO)ETHYL 3 BETA HYDROXY 20 OXO 29 NORLUPAN 28 OIC ACID BROMIDE; 2 (TRIMETHYLAMMONIO)ETHYL 3 BETA HYDROXYLUP 20(29) EN 28 OIC ACID BROMIDE; 2 [BIS (2 HYDROXYETHYL)AMINO]ETHYL 3 BETA ACETOXY 21 OXOLUP 18 EN 28 OIC ACID BROMIDE; 2 [BIS (2 HYDROXYETHYL)AMINO]ETHYL 3 BETA HYDROXY 20 OXO 29 NORLUPAN 28 OIC ACID; 2 [BIS (2 HYDROXYETHYL)AMINO]ETHYL 3 BETA HYDROXYLUP 20(29) EN 28 OIC ACID; 2 [BIS(2 HYDROXYETHYL)AMINO]ETHYL 3 BETA HYDROXYLUPAN 28 OIC ACID; 2 BROMOETHYL 3 BETA ACETOXY 21 OXOLUP 18 EN 28 OIC ACID; 2 BROMOETHYL 3 BETA HYDROXY 20 OXO 29 NORLUPAN 28 OIC ACID; 2 BROMOETHYL 3 BETA HYDROXYLUP 20(29) EN 28 OIC ACID; 2 PYRIDINIOETHYL 3 BETA ACETOXY 21 OXOLUP 18 EN 28 OIC ACID BROMIDE; 2 PYRIDINIOETHYL 3 BETA HYDROXY 20 OXO 29 NORLUPAN 28 OIC ACID BROMIDE; 2 PYRIDINIOETHYL 3 BETA HYDROXYLUP 20(29) EN 28 OIC ACID BROMIDE; ANTINEOPLASTIC AGENT; BETULIC ACID; OLEANOLIC ACID; PENTACYCLIC TRITERPENE; PYRIDINE; QUATERNARY AMMONIUM DERIVATIVE; TERTIARY AMINE; TRIETHANOLAMINE; TRIETHYLAMINE; TRIMETHYLAMINE; TRITERPENOID; UNCLASSIFIED DRUG; UNINDEXED DRUG; URSOLIC ACID;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CYTOTOXICITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; IC 50; IN VITRO STUDY; LEUKEMIA CELL LINE; LYMPHATIC LEUKEMIA; MOLECULAR WEIGHT; REACTION TIME; STRUCTURE ACTIVITY RELATION; T LYMPHOBLAST;

EID: 78149467182     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258293     Document Type: Article

References (22)

1. Connolly J D., Hill R A., Nat. Prod. Rep. 2007 24 465
2. Dzubak P, Hajduch M, Vydra D, Hustova A, Kvasnica M, Biedermann D, Markova L, Urban M, Sarek J, Nat. Prod. Rep. 2006 23 394
3. Setzer W N., Setzer M C., Mini Rev. Med. Chem. 2003 3 540
4. Prasad S, Kalra N, Shukla Y, Mol. Nutr. Food Res. 2007 51 352
5. Bani S, Kaul A, Khan B, Ahmad S F., Suri K A., Gupta B D., Satti N K., Qazi G N., Phytother. Res. 2006 20 279
6. Cichewicz R H., Kouzi S A., Med. Res. Rev. 2004 24 90
7. Kashiwada Y, Hashimoto F, Cosentino L M., Chen C H., Garrett P E., Lee K H., J. Med. Chem. 1996 39 1016
8. Smith P F., Ogundele A, Forrest A, Wilton J, Salzwedel K, Doto J, Allaway G P., Martin D E., Antimicrob. Agents Chemother. 2007 51 3574
9. Hoet S, Pieters L, Muccioli G G., Habib-Jiwan J L., Opperdoes F R., Quetin-Leclercq J, J. Nat. Prod. 2007 70 1360
10. Triterpenoid derivatives:, Hajduch M, Sarek J, WO 0190136 2001, Hajduch M, Sarek J, WO 0190046 2001, Hajduch M, Sarek J, WO 0190096 2001
11. Method of preparation of a soluble formulation of water-insoluble pentacyclic and tetracyclic terpenoids, a soluble formulation of a pentacyclic or tetracyclic terpenoid and a pharmaceutical composition containing this soluble formul-ation:, Sarek J, Hajduch M, Svoboda M, Novakova K, Spacilova P, Kubelka T, Biedermann D, US 2009325919 2009
12. Sarek J, Kvasnica M, Urban M, Klinot J, Hajduch M, Bioorg. Med. Chem. Lett. 2005 15 4196
13. Biedermann D, arek J, Klinot J, Hajd?ch M, Dubák P, Synthesis 2005 1157
14. , arek J, Klinot J, Dubák P, Klinotová E, Nosková V, Keek V, Ko?nková G, Thomson J P., Janotáková A, Wang S D., Parsons S, Fischer P M., Zhelev N Z., Hajd?ch M, J. Med. Chem. 2003 46 5402
15. Klinotova E, Cermakova J, Rejzek M, Krecek V, Sejbal J, Olsovsky P, Klinot J, Collect. Czech. Chem. Commun. 1999 64 329
16. Urban M, Sarek J, Kvasnica M, Tislerova I, Hajduch M, J. Nat. Prod. 2007 70 526
17. Urban M, Sarek J, Klinot J, Korinkova G, Hajduch M, J. Nat. Prod. 2004 67 1100
18. Mayer R, Arch. Pharm. (Weinheim, Ger.) 1996 329 447
19. Mukherjee R, Jaggi M, Rajendran P, Siddiqui M J. A., Srivastava S K., Vardhanb A, Burmana A C., Bioorg. Med. Chem. Lett. 2004 14 2181
20. Hajduch M, Mihal V, Minarik J, Faber E, Safarova M, Weigl E, Antalek P, Cytotechnology 1996 19 243
21. Triterpenoid derivatives for cancer treatment and preparation thereof:, arek J, Biedermann D, Hajdch M, CZ 301158 2009
22. Chen J, Liu J, Zhang L, Wu G, Hua W, Wu X, Sun H, Bioorg. Med. Chem. Lett. 2006 16 2915