Synthesis and cytotoxic and analgesic activities of some 1, 5-diaryl-3-ethoxycarbonylpyrrole derivatives

Figures & data

Table I.  Some characteristics of the synthesised compounds

Comp.	R	R'	m.p. (°C)	Yield (%)	Molecular formula
2a	H	SO2NH2	199–200	82	C20H20N2O4S
2b	CH3	SO2NH2	182–184	78	C21H22N2O4S
2c	OCH3	SO2NH2	163–164	71	C21H22N2O5S
2d	F	H	217–218	82	C20H18FNO2
2e	F	OCH3	215–218	88	C21H20FNO3
2f	F	SO2NH2	94–97	77	C20H19FN2O4S
2 g	Cl	SO2NH2	113–115	71	C20H19ClN2O4S
2 h	NO2	SO2NH2	212–215	78	C20H19N3O6

Figure 1 Cytotoxicity of the compounds determined by MTT assay for F2408 fibroblast cell line. Results are the mean of quadruplicate wells. (Standard deviation less than 10%).

Table II.  IC₅₀ values of the compounds

Compounds	IC50
2a	14 ± 1.5 μM
2b	6.8 ± 2.1 μM
2c	16 ± 1.5 μM
2 g	8 ± 0.6 μM
2 h	5.5 ± 0.5 μM

Table III.  Effects of the compounds on tail-clip response in mice

Compounds	Dose(mg/kg) (i.p.)	%Analgesia (Tail-clip)
Control	–	41.58 ± 6.47
Morphine	10	95.38 ± 0.62*
Acetylsalicylic acid	100	95.15 ± 0.66*
2b	100	3.16 ± 7.03
2c	100	3.02 ± 8.84
2f	100	43.1 ± 23.6
2 g	100	90.86 ± 9.14*
2 h	100	28.15 ± 9.27

%Analgesia values are expressed as mean ± S.E.M., n = 5.

*p < 0.001 significant as compared with control, student's t-test.

Table IV.  Effects of the compounds on the tail-immersion response in mice

Compounds	Dose(mg/kg) (i.p.)	%Analgesia (Tail-immersion)
Control	–	16.35 ± 6.27
Morphine	10	50.7 ± 1.84*
Acetylsalicylic acid	100	21.9 ± 1.41
2a	100	10.05 ± 6.93
2b	100	13.79 ± 7.38
2c	100	45.2 ± 16.0*
2e	100	8.03 ± 16.1
2f	100	47.0 ± 13.4*
2 g	100	26.01 ± 6.21
2 h	100	− 14.7 ± 10.4

%Analgesia values are expressed as mean ± S.E.M., n = 5.

*p < 0.001 significant as compared with control, student's t-test

Scheme 1 Synthesis compounds 1 and 2; a: Toluene/Na; b: CH₃COOH/reflux