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. Author manuscript; available in PMC: 2007 Dec 15.
Published in final edited form as: Bioorg Med Chem Lett. 2006 Sep 25;16(24):6306–6309. doi: 10.1016/j.bmcl.2006.09.012

Table 1.

Inhibition of NO production in RAW cells stimulated with interferon-γ by methyl ester 3 and new betulinic acid analogues 4–18.

graphic file with name nihms15522f6.jpg

Compds R1 R2 R3 Yield (%) Inhibition of NO IC50, μMc
3 CN CO2Me H Ref. 10 0.03
4 CN CO2H H a 0.2
5 CN CO2Et H a 0.02
6 CN CONH2 H 74b 0.03
7 CN CONHMe H 70b 0.05
8 CN CONHEt H 79b 0.07
9 CN CONMe2 H 77b 0.03
10 CN graphic file with name nihms15522t1.jpg H 91b 0.03
11 CN graphic file with name nihms15522t2.jpg H 62b 0.05
12 CN graphic file with name nihms15522t3.jpg H 60b 0.03
13 CO2Me CO2Me H a 0.6
14 CO2Me CO2Me OH a 1
15 CO2Me CO2Me F a 0.3
16 CO2H CO2Me H a 0.3
17 CO2H CO2Me OH a 0.9
18 CO2H CO2Me F a 0.3
BA (1) inactive
CDDO 0.02
a

Yield is shown in the text.

b

Yield from 19.

c

RAW 264.7 cells were treated with various concentrations of compounds and interferon-γ (10 ng/mL) for 24 h. Supernatants were analyzed for NO by the Griess reaction.