5-Nitrothiazolylthiosemicarbazones: Synthesis and antimycobacterial evaluation against tubercular and non-tubercular mycobacterial species

Figures & data

Scheme 1.  Synthesis of compounds.

Table 1.  Antimycobacterial activities of 5-nitrothiazolylthiosemicarbazones.

Compound	R	R1	IC50^a (μM)	Minimum inhibitory concentration (μM)
				MTB^b	MS^c	MM^d	MV^e	MP^f	MF^g	MK^h
4a	H	Phenyl	NT^i	40.67	2.54	81.34	5.08	2.54	5.08	2.54
4b	H	2-OH-Phenyl	NT	77.31	9.68	38.66	77.32	4.82	38.66	77.32
4c	H	2-CH3-Phenyl	NT	19.44	2.43	77.79	4.85	4.85	4.85	4.85
4d	H	4-N(CH3)2-Phenyl	NT	17.83	2.23	142.68	2.23	71.34	4.45	71.34
4e	H	4-OCH3-Phenyl	NT	37.05	2.31	148.20	74.1	18.52	4.62	2.31
4f	H	2-NO2-Phenyl	< 177.38	2.21	2.21	70.95	141.9	35.47	8.88	4.43
4g	H	4-NO2-Phenyl	< 177.38	1.10	2.21	70.95	2.21	17.74	2.21	2.21
4h	H	3-Br-Phenyl	161.81	1.00	2.01	129.45	32.36	8.10	2.01	8.10
4i	H	4-F-Phenyl	> 192.10	4.79	4.79	76.84	38.42	2.39	76.84	4.79
4j	H	4-Cl-Phenyl	182.85	4.56	2.28	36.57	36.57	2.28	73.14	36.57
4k	H	2-CF3-Phenyl	> 166.51	0.52	2.08	13.32	13.32	26.64	26.64	13.32
4l	H	2,5-(Cl)2-Phenyl	NT	16.61	16.61	132.89	33.22	8.32	4.15	2.07
4m	H	4-Benzyloxy phenyl	> 151.15	0.23	1.88	30.25	30.25	3.78	15.13	3.78
4n	CH3	Phenyl	NT	19.44	2.42	77.79	77.79	9.74	77.79	77.79
4o	CH3	2-OH-Phenyl	NT	18.52	2.31	37.05	74.10	4.62	148.20	9.27
4p	CH3	4-CH3-Phenyl	NT	9.33	4.65	74.53	74.53	4.65	37.27	2.33
4q	CH3	3-NH2-Phenyl	NT	9.30	2.32	74.32	148.63	4.63	297.27	4.63
4r	CH3	4-Br-Phenyl	156.1	3.89	15.61	62.45	124.91	1.95	124.91	31.22
4s	CH3	4-NO2-Phenyl	< 170.58	2.12	2.12	68.23	68.23	2.12	68.23	34.11
Ciprofloxacin			> 188.59	4.71	2.35	2.35	4.71	4.71	4.71	9.45
Rifampicin			> 75.94	0.23	1.89	30.38	3.80	30.38	1.89	7.59
Isoniazid			> 455.73	0.66	45.57	22.82	182.3	91.15	22.82	182.3

^aCytotoxicity in mammalian Vero cell lines.

^bM. tuberculosis; ^cM. smegmatis; ^dM. microti; ^eM. vaccae; ^fM. phlei; ^gM. fortuitum; ^hM. kansasii.

ⁱNot tested.