Table 1.

Structure-activity relationship analysis of the benzotropolone analogs in inhibition of NO production in RAW 264.7 cells.

Compound	R1	R3		R4	R5	IC50 (µM)[a]
NCI35676	OH	H		H	H	2.45± 0.25
1	H	H		H	H	3.13± 0.11
2	H	H		H	H	2.25± 0.31
3	F	H		H	H	22.7± 1.4
4	OCH3	H		H	H	4.83± 0.25
5	OCH3	CH3		H	CH3	11.7± 1.1
6	OCH3	CH3		CH3	CH3	39.9± 0.9
7	OCOCH3	H		H	H	4.83± 0.25
8	OCOCH3	COCH3		H	COCH3	1.42± 0.21
9	OCOCH3	COCH3		COCH3	COCH3	2.35± 0.41
	R1		R6
10	OCH3		COOH			21.5± 0.4
11	OCH3		COOCH3			3.11± 0.75
12	H		COOH			16.5± 0.8
13	H		COOCH3			9.01± 0.50
14	OCH3		COOCH2CH3			2.83± 0.44
15	OCH3		COOCH(CH3)2			2.47± 0.71
16	OCH3		COO(CH2)3CH3			2.83± 0.44
17	OCH3		COO(CH2)7CH3			0.72± 0.14
18	OCH3		COO(CH2)9CH3			1.01± 0.10
19	OCH3		COO(CH2)13CH3			3.24± 0.13
20	OCH3		CONH(CH2)3CH3			1.26± 0.31
21	OCH3		CONH(CH2)5CH3			1.36± 0.21
CU-CPT22	OCH3		COO(CH2)5CH3			0.58± 0.09
23	OCH3		CH2OH			4.11± 0.74
24	OCH3		CONH(o-toluene)			1.36± 0.21
25						74.6± 2.9
26						14.8± 0.5

^[a]IC₅₀ and corresponding SD values are determined from at least three independent repeats.