Synthesis of 3-O-acyl/3-benzylidene/3-hydrazone/3-hydrazine/17-carboxyacryloyl ester derivatives of betulinic acid as anti-angiogenic agents. Academic Article

abstract

• New 3-O-acyl, 3-benzylidene, 3-hydrazone, 3-hydrazine, 17-carboxyacryloyl ester derivatives of betulinic acid (2-6, 8-11, 13, 17, 18, 21, and 22) were synthesized and evaluated in vitro for anti-angiogenic activity on endothelial cell cytotoxicity, specificity, and tube-formation ability. All derivatives reported here showed IC(50)<4 microg/mL. Compounds 3, 9, 10, 17, 21, and 22 have shown better cytotoxicity (IC(50)<1.2 microg/mL) than betulinic acid (1) and improved endothelial cell specificity (ECS>10) in some cases. Compounds 10, 17, and 18 have shown 20%, 32%, and 48% reduction in TLS, respectively, and were found better than betulinic acid (1). We have shown that 20,29-dihydrobetulinic acid derivatives have better anti-angiogenic activity as compared to betulinic acid or its other derivatives.

authors

• Rajendran, Praveen

published proceedings

• Bioorg Med Chem Lett

author list (cited authors)

• Mukherjee, R., Jaggi, M., Rajendran, P., Srivastava, S. K., Siddiqui, M., Vardhan, A., & Burman, A. C.

citation count

• 29

complete list of authors

• Mukherjee, Rama||Jaggi, Manu||Rajendran, Praveen||Srivastava, Sanjay K||Siddiqui, Mohammad JA||Vardhan, Anand||Burman, Anand C

publication date

• June 2004

publisher

• Elsevier  Publisher

published in

• Bioorganic and Medicinal Chemistry Letters  Journal

keywords

• Angiogenesis Inhibitors
• Benzylidene Compounds
• Betulinic Acid
• Cell Line, Tumor
• HT29 Cells
• Humans
• Pentacyclic Triterpenes
• Triterpenes

PubMed Central ID

• 15149668

Digital Object Identifier (DOI)

• 10.1016/j.bmcl.2004.04.010

start page

• 3169

end page

• 3172

volume

• 14

issue

• 12

URL

• http://dx.doi.org/10.1016/j.bmcl.2004.04.010