Table 1.

Biological activity and cytotoxicity of 5′-O-[N-(acyl)sulfamoyl]adenosine analogues 9, 13–37.

		MIC (μM)			Kiapp (μM)		Cytotox
Cmpd	R=	GASTa	7H9b	7H9/palmitatec	FACL19d	FAAL28e	IC50 (μM)f
13	CH3(CH2)2-	>100	>100	>100	>100	>100	81.4
14	CH3(CH2)4-	100	>100	>100	>100	>100	48.6
15	CH3(CH2)6-	12.5–25	100	>100	>100	>100	6.0
16	CH3(CH2)8-	1.56	100	>100	>100	88	10.1
9	CH3(CH2)10-	0.19–0.39	50	50	67.4	6.4	28.7
17	CH3(CH2)12-	0.39–0.78	50	100	10.0	1.4	0.9
18	CH3(CH2)14-	6.25	100	>100	3.2	1.0	0.3
19	CH3(CH2)16-	100	100	>100	2.4	0.5	0.1
20	CH3(CH2)18-	>100	>100	>100	ndg	nd	0.1
21	HCC(CH2)8-	1.56	50	50	>100	>100	9.7
22	H2CHC(CH2)8-	0.39–0.78	25	25	>100	>100	11.6
23	CH3(CH2)7CH2CHCH-trans-	100	>100	>100	>100	>100	10.4
24	CH3(CH2)5CHCH(CH2)3-trans-	100	>100	>100	>100	>100	16.8
25	CH3(CH2)4CHCH(CH2)3-cis-	6.25	100	100	>100	>100	14.3
26	CH3(CH2)8CH(CH2)CH-S,S-	50	>100	>100	>100	69.8	6.1
27	HO(CH2)10-	6.25	100	100	>100	92.7	42.7
28	N3(CH2)11-	0.19	12.5–25	25	>100	28.5	5.6
29	NH2(CH2)11-	3.13	50	12.5–25	93.3	>100	27.1
30	MeOOC(CH2)10-	3.13	100	>100	>100	>100	14.0
31	HOOC(CH2)10-	25–50	>100	>100	>100	>100	>100
32	C6H5O(CH2)10-	3.13	50	50	>100	0.71	2.0
33	CH3(CH2)9CH(CH3)-R-	12.5–25	>100	>100	>100	>100	39.4
34	CH3(CH2)9CH(CH3)-S-	50	>100	>100	>100	>100	14.5
35	CH3(CH2)9C(CH3)2-	12.5–25	>100	>100	54.7	>100	6.7
36	CH3(CH2)8OCH2-	0.098–0.19	25	25–50	>100	>100	8.7
37	CH3(CH2)3O(CH2)2O(CH2)2OCH2-	6.25	>100	>100	>100	>100	16.0

Microbiological and biochemical data is from 3 replicates.

^aWhole cell inhibitory activity against Mtb H37Rv in GAST medium.

^bWhole cell inhibitory activity against Mtb H37Rv in 7H9 medium.

^cWhole cell inhibitory activity against Mtb H37Rv in 7H9/palmitate medium.

^dInhibitory activity against FACL19. The standard deviation was ≤10% of the mean.

^eInhibitory activity against FAAL28. The standard deviation was ≤10% of the mean.

^fCytotoxicity against Vero monkey cells using the MTT assay.

^gnd = no data.