Synthesis and biological evaluation of some 4-aminoquinoline derivatives as potential antitubercular agents

Alegaon, Shankar; Kashniyal, Kamlesh; Kuncolienkar, Sanket; Kavalapure, Rohini; Salve, Preeti; Palled, Mahesh; Suryawanshi, Shailendra; Jalalpure, Sunil

doi:10.1186/s43094-019-0016-7

Table 1 Physical data and antimycobacterial activities of compound (6a-i), (7a-i), (8a-i), and (9a-i) against MTB H₃₇Rv

From: Synthesis and biological evaluation of some 4-aminoquinoline derivatives as potential antitubercular agents


Comp.	R	Mol. formula	Melting point (°C)^a	MIC (μM)^b	Drug score^c
6a	4-CH₃	C₂₆H₂₂ClN₅S	196–198	12.5	0.69
6b	4-OCH₃	C₂₆H₂₂ClN₅OS	190–192	12.5	1.02
6c	3,4-OCH₃	C₂₇H₂₄ClN₅O₂S	148–150	25.0	1.09
6d	3,4,5-OCH₃	C₂₈H₂₆ClN₅O₃S	138–140	12.5	0.98
6e	4-Cl	C₂₅H₁₉Cl₂N₅S	142–143	12.5	0.78
6f	4-F	C₂₅H₁₉ClFN₅S	178–180	50.0	0.75
6 g	4-Br	C₂₅H₁₉BrClN₅S	186–188	50.0	0.58
6 h	4-NO₂	C₂₅H₁₉ClN₆O₂S	216–218	50.0	0.24
6i	4-OH	C₂₅H₂₀ClN₅OS	230–232	50.0	0.88
7a	4-CH₃	C₂₆H₂₂ClN₅O	148–150	6.25	0.87
7b	4-OCH₃	C₂₆H₂₂ClN₅O₂	238–240	25.0	1.12
7c	3,4-OCH₃	C₂₇H₂₄ClN₅O₃	214–216	1.56	1.18
7d	3,4,5-OCH₃	C₂₈H₂₆ClN₅O₄	238–240	12.5	1.07
7e	4-Cl	C₂₅H₁₉Cl₂N₅O	174–186	12.5	0.96
7f	4-F	C₂₅H₁₉ClFN₅O	230–232	25.0	0.94
7 g	4-Br	C₂₅H₁₉BrClN₅O	244–246	1.56	0.76
7 h	4-NO₂	C₂₅H₁₉ClN₆O₃	196–198	12.5	0.35
7i	4-OH	C₂₅H₂₀ClN₅O₂	240–242	6.25	1.07
8a	4-CH₃	C₂₆H₂₂ClN₅S	238–240	12.5	0.55
8b	4-OCH₃	C₂₆H₂₂ClN₅OS	210–212	25.0	0.86
8c	3,4-OCH₃	C₂₇H₂₄ClN₅O₂S	120–122	25.0	0.94
8d	3,4,5-OCH₃	C₂₈H₂₆ClN₅O₃S	240–242	25.0	0.85
8e	4-Cl	C₂₅H₁₉Cl₂N₅S	212–214	25.0	0.62
8f	4-F	C₂₅H₁₉ClFN₅S	234–236	50.0	0.60
8 g	4-Br	C₂₅H₁₉BrClN₅S	238–240	25.0	0.43
8 h	4-NO₂	C₂₅H₁₉ClN₆O₂S	218–220	25.0	0.13
8i	4-OH	C₂₅H₂₀ClN₅OS	250–252	50.0	0.71
9a	4-CH₃	C₂₆H₂₂ClN₅O	192–194	6.25	0.73
9b	4-OCH₃	C₂₆H₂₂ClN₅O₂	188–190	12.5	0.96
9c	3,4-OCH₃	C₂₇H₂₄ClN₅O₃	254–256	12.5	1.03
9d	3,4,5-OCH₃	C₂₈H₂₆ClN₅O₄	258–260	25.0	0.94
9e	4-Cl	C₂₅H₁₉Cl₂N₅O	226–228	25.0	0.80
9f	4-F	C₂₅H₁₉ClFN₅O	198–200	25.0	0.78
9 g	4-Br	C₂₅H₁₉BrClN₅O	306–308	25.0	0.61
9 h	4-NO₂	C₂₅H₁₉ClN₆O₃	246–248	25.0	0.25
9i	4-OH	C₂₅H₂₀ClN₅O₂	234–236	25.0	0.90
INH^d	–	C₆H₇N₃O	–	1.56	0.53
Pyra^e	–	C₅H₅N₃O	–	50.0	− 0.15
Cipro^f	–	C₁₇H₁₈FN₃O₃	–	12.5	0.93

^aThe melting points were determined in open capillary tubes and are uncorrected
^bMinimum inhibitory concentration against Mycobacterium tuberculosis H₃₇Rv
^cCalculated using molsoft (http://molsoft.com/mprop/)
^dIsoniazid
^ePyrazinamide
^fCiprofloxacin

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