Table 51.

Ultrasound-assisted three-component synthesis of 1,2,4-triazol-1-yl-pyrazole-based spirooxindolopyrrolizidines 157 as antitubercular agents.

Compound	R	R1	Yield 157 (%)	MIC (μg/mL)	Cytotoxicity % Inhibition at 25 μg/mL c
157a	H	H	92	>25	-- d
157b	4-Me	H	83	>25	-- d
157c	4-MeO	H	78	12.5	-- d
157d	4-Cl	H	86	6.25	16.85
157e	4-Br	H	84	1.56	27.15
157f	3-NO2	H	92	>25	-- d
157g	4-NO2	H	90	6.25	29.61
157h	H	Cl	89	0.78	19.76
157i	4-Me	Cl	80	25.0	-- d
157j	4-MeO	Cl	76	3.12	21.65
157k	4-Cl	Cl	82	1.56	17.91
157l	4-Br	Cl	81	1.56	26.43
157m	3-NO2	Cl	90	6.25	18.96
157n	4-NO2	Cl	88	1.56	24.94
157o	H	Br	85	3.12	18.62
157p	4-MeO	Br	79	25.0	-- d
157q	4-Cl	Br	85	1.56	22.36
157r	4-Br	Br	80	1.56	21.97
157s	3-NO2	Br	86	6.25	20.08
157t	4-NO2	Br	85	6.25	26.40
Ethambutol b	--	--	--	1.56	-- d

^a Reaction conditions: Pyrazole-based chalcones 156 (1.0 mmol), substituted isatins 27 (1.0 mmol), and L-proline 28 (1.0 mmol) in [Bmim]BF₄ (3.0 mL) at 60 °C for 6–16 min under ultrasound irradiation. ^b Reference compound. ^c The cytotoxicity was determined in the RAW 264.7 cell line. ^d Not determined.