In vitro anti-TB activity of compounds 8a–k, 11a–g, 13a–g, 15a–d, 18a,b.

Analogue	R	R1	X	MICa (μg mL−1)	MIC (μM)	Clog Pb
8a	6-Cl	1-Adamantane	—	>32	>89.67	2.94
8b	8-Cl	1-Adamantane	—	≥32	≥89.67	2.94
8c	8-Cl	Cyclooctane	—	>32	>96.14	3.43
8d	7,8-Dichloro	1-Adamantane	—	≥32	≥81.78	3.55
8e	7,8-Dichloro	Cyclooctane	—	≥32	≥87.13	4.04
8f	6,8-Dichloro	Cyclooctane	—	≥32	≥87.13	4.16
8g	5,8-Dichloro	1-Adamantane	—	≥32	≥81.78	3.67
8h	5,7-Dichloro	1-Adamantane	—	16	40.89	3.67
8i	5-Br	1-Adamantane	—	4	9.97	3.09
8j	7-Br	1-Adamantane	—	8	19.93	3.09
8k	8-OH	1-Adamantane	—	>32	>94.56	1.60
11a	6-Cl	1-Adamantane	—	≥32	≥89.67	3.20
11b	8-Cl	1-Adamantane	—	>32	>89.67	3.20
11c	7,8-Dichloro	1-Adamantane	—	>32	>81.78	3.81
11d	6,8-Dichloro	1-Adamantane	—	≥32	≥81.78	3.93
11e	5,8-Dichloro	1-Adamantane	—	≥32	≥81.78	3.93
11f	5,7-Dichloro	1-Adamantane	—	>32	>81.78	3.93
11g	7-Br	1-Adamantane	—	≥32	≥79.74	3.09
13a	H	Cyclooctane	N	16	56.66	4.99
13b	H	1-Adamantane	N	16	52.22	4.50
13c	H	Cyclooctane	CH	2	7.11	5.18
13d	H	1-Adamantane	CH	2	6.55	4.69
13e	5-Br	1-Adamantane	CH	≥32	≥83.26	5.70
13f	6-Br	1-Adamantane	CH	≥32	≥83.26	5.70
13g	6-OCH3	1-Adamantane	CH	≥32	≥95.40	4.82
13h	H	Cycloheptane	N	—	111 (ref. 47)	4.62
15a	NH2	1-Adamantane	—	>32	>94.32	4.85
15b	NH2	Cyclooctane	—	>32	>101	5.34
15c	OH	1-Adamantane	—	32	94.05	5.46
15d	OH	Cyclooctane	—	32	101	5.95
18a	4-Cl	—	—	32	85.81	5.87
18b	2,4-Dichloro	—	—	4	9.82	6.34
Isoniazid	—	—	—	0.04	0.29	−0.66
Ethambutol	—	—	—	1	4.89	0.11

^aThe lowest concentration of drug reducing at least 90% of bacterial growth by the Microplate Alamar Blue Assay (MABA). The reported MIC values are an average of three individual measurements.

^bCalculated using ChemDraw 16.0.