Discovery of novel methanone derivatives acting as antimycobacterial agents

Figures & data

Table 1.  Physicochemical characteristics and antimycobacterial activity of compounds 4a–4u.

Compound	R	R1	Yield (%)	Melting point (°C)	MIC-MTB^a (μg/mL)
4a	Pyridyl-	4-Aminophenyl	84	144	>10.0
4b	2-Chlorophenyl-	4-Aminophenyl	60	162	>10.0
4c	4-Fluorophenyl-	4-Aminophenyl	67	143	>10.0
4d	3,4-Dimethoxyphenyl-	4-Aminophenyl	72	141	10.0
4e	4-Methoxyphenyl-	4-Aminophenyl	80	128	>10.0
4f	Phenyl-	4-Aminophenyl	62	103	10.0
4g	4-Cyanophenyl-	4-Aminophenyl	71	176	>10.0
4h	Pyridyl-	3,4-Dimethoxyphenyl-	66	145	>10.0
4i	2-Chlorophenyl-	3,4-Dimethoxyphenyl-	67	164	>10.0
4j	4-Fluorophenyl-	3,4-Dimethoxyphenyl-	72	184	>10.0
4k	3,4-Dimethoxyphenyl-	3,4-Dimethoxyphenyl-	80	198	>10.0
4l	4-Methoxyphenyl-	3,4-Dimethoxyphenyl-	80	168	>10.0
4m	Phenyl-	3,4-Dimethoxyphenyl-	74	144	>10.0
4n	4-Cyanophenyl-	3,4-Dimethoxyphenyl-	68	162	>10.0
4o	Pyridyl-	4-Methoxyphenyl-	89	153	>10.0
4p	2-Chlorophenyl-	4-Methoxyphenyl-	74	151	>10.0
4q	4-Fluorophenyl-	4-Methoxyphenyl-	64	128	>10.0
4r	3,4-Dimethoxyphenyl-	4-Methoxyphenyl-	78	153	>10.0
4s	4-Methoxyphenyl-	4-Methoxyphenyl-	92	166	>10.0
4t	Phenyl-	4-Methoxyphenyl-	67	165	>10.0
4u	4-Cyanophenyl-	4-Methoxyphenyl-	70	174	>10.0

^aMycobacterium tuberculosis H37Rv.

Scheme 1.  Protocol for synthesis. (a) Reagents: NaOH/EtOH and (b) R₁CONHNH₂.