Citation: Aye Aye Mar, Ali Koohang, Nathan D. Majewski, Erika L. Szotek, David A. Eiznhamer, Michael T. Flavin, Ze Qi Xu. Synthesis and cytotoxicity of 28-carboxymethoxy lupanetriterpenoids.Preference of 28-O-acylation over 28-O-alkylation of betulin by ethyl bromoacetate[J]. Chinese Chemical Letters, ;2009, 20(10): 1141-1144. doi: 10.1016/j.cclet.2009.04.001 shu

Synthesis and cytotoxicity of 28-carboxymethoxy lupanetriterpenoids.Preference of 28-O-acylation over 28-O-alkylation of betulin by ethyl bromoacetate

Advanced Life Sciences, Inc., 1440 Davey Road, Woodridge, IL 60517, USA

Received Date: 18 February 2009

28-Carboxymethoxy lupane tritepenoids 3 and 4 were synthesized by alkylation of betulin with the THP protected 2-hydroxyethyl iodide followed by oxidation and reduction.Direct reaction of betulin (5) or betulone (10) with ethyl bromoacetate led to 28-O-acylation, instead of 28-O-alkylation.The targeted compounds 3 and 4 were not cytotoxic at the highest concentrationtested (75 mmol/L), suggesting that elongation of the chain length at the 28-position in both betulinic acid (1) and betulonic acid (2)was detrimental to the cytotoxicity.The acylation products 28-O-bromoacetates (8a, 8b and 11) and 28-O-methoxyacetate 13exhibited cytotoxicity against several cancer cell lines tested.
- Betulinic acid,
- Betulin,
- Betulonic acid,
- 28-O-alkylation,
- 28-O-acylation,
- Cytotoxicity
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