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. 2022 Jul 23;27(15):4723. doi: 10.3390/molecules27154723

Table 8.

One-pot three-component synthesis of 3-alkyl-1-(4-(aryl/heteroaryl)thiazol-2- yl)indeno[1,2-c]pyrazol-4(1H)-ones 37 as antibacterial agents.

graphic file with name molecules-27-04723-i008.jpg
Compound R R1 Yield 37 (%) MIC (μmol/mL)
SA BS PA EC
37a Me Biphenyl 74 0.0297 0.0595 0.0297 0.0297
37b Et Biphenyl 78 0.0288 0.0576 0.0288 0.0288
37c iPr Biphenyl 72 0.0559 0.0559 0.0559 0.0559
37d iBu Biphenyl 80 0.0270 0.0541 0.0270 0.0270
37e Me 2-Naphthyl 72 0.0317 0.0635 0.0317 0.0317
37f Et 2-Naphthyl 75 0.0613 0.0613 0.0306 0.0613
37g iPr 2-Naphthyl 79 0.0593 0.0593 0.0593 0.0593
37h iBu 2-Naphthyl 76 0.0287 0.0574 0.0287 0.0287
37i Me 2-Benzofuranyl 63 0.0326 0.0652 0.0326 0.0326
37j Et 2-Benzofuranyl 60 0.0629 0.0629 0.0629 0.0629
37k iPr 2-Benzofuranyl 58 0.0607 0.0607 0.0607 0.0607
37l iBu 2-Benzofuranyl 53 0.0293 0.0587 0.0293 0.0293
Ciprofloxacin b -- -- -- 0.0094 0.0094 0.0094 0.0094

a Reaction conditions: 2-acyl-(1H)-indene-1,3-(2H)dione 35 (1 mmol), thiosemicarbazide 23 (1 mmol), MeOH (30 mL), reflux, 10–15 min, then α-bromoketone 36 (5 mmol), sodium acetate (5 mmol), MeOH/AcOH (2:1, v/v) (20 mL), reflux, 5–8 h. b Positive control for the study. SA (Staphylococcus aureus), BS (Bacillus subtilis), PA (Pseudomonas aeruginosa), EC (Escherichia coli).