4-(4-Morpholinophenyl)-6-arylpyrimidin-2-amines: synthesis, spectral analysis, and in vitro microbiological evaluation

Figures & data

Scheme 1.  Synthesis reaction pathway for formation of 4-(4-morpholinophenyl)-6-aryl-pyrimidin-2-amines.

Scheme 2.  Plausible reaction mechanism for formation of target molecules.

Table 1.  Physical and analytical data of compounds 11–28.

Entry	X	Y	Yield (%)	m.p. (°C)	Elemental analysis (%)			m/z (M + 1)^+, molecular formula
					C, Calc. (Found)	H, Calc. (Found)	N, Calc. (Found)
11	H	H	95	149	77.81	6.48	4.77	294
					(77.78)	(6.46)	(4.76)	C19H19NO2
12	CH3	H	92	179	78.17	6.84	4.56	308
					(78.15)	(6.81)	(4.54)	C20H21NO2
13	Cl	H	90	143	69.72	5.50	4.28	328
					(69.70)	(5.47)	(4.26)	C19H18NO2Cl
14	OCH3	H	90	111	74.30	6.50	4.33	324
					(74.29)	(6.48)	(4.31)	C20H21NO3
15	F	H	95	160	73.31	5.78	4.50	312
					(73.29)	(5.76)	(4.48)	C19H18NO2F
16	Br	H	85	145	61.30	4.87	3.76	372
					(61.27)	(4.83)	(3.74)	C19H18BrNO2
17	H	NO2	87	135	67.45	5.32	8.28	339
					(67.43)	(5.29)	(8.26)	C19H18N2O4
18	H	Cl	90	138	69.72	5.50	4.28	328
					(69.69)	(5.48)	(4.25)	C19H18NO2Cl
19	H	F	90	154	73.31	5.78	4.50	312
					(73.28)	(5.74)	(4.47)	C19H18NO2F
20	H	H	80	118	72.09	6.30	16.80	333
					(72.05)	(6.28)	(16.77)	C20H21N4O
21	CH3	H	85	73	72.64	6.62	16.12	347
					(72.61)	(6.59)	(16.10)	C21H23N4O
22	Cl	H	78	123	65.33	5.44	15.23	367
					(65.31)	(5.41)	(15.20)	C20H20N4OCl
23	OCH3	H	80	91	69.44	6.33	15.41	363
					(69.41)	(6.31)	(15.38)	C21H23N4O2
24	F	H	90	87	68.40	5.69	15.94	351
					(68.38)	(5.66)	(15.91)	C20H20N4OF
25	Br	H	90	93	58.40	4.66	13.62	411
					(58.36)	(4.64)	(13.59)	C20H19BrN4O
26	H	NO2	85	176	65.96	5.49	15.38	364
					(65.92)	(5.47)	(15.35)	C20H20N5O3
27	H	Cl	80	135	65.33	5.44	15.23	367
					(65.30)	(5.42)	(15.20)	C20H20N4OCl
28	H	F	78	96	68.40	5.69	15.94	351
					(68.37)	(5.68)	(15.92)	C20H20N4OF

Table 2.  In vitro antibacterial activity (MIC) values for compounds 20–28.

Compound	X	Y	Minimum inhibitory concentration (MIC) (μg/mL)
			S. aureus	β-Hemolytic Streptococcus	V. cholerae	S. felxneri	K. pneumoniae	P. aeruginosa
20	H	H	100	100	12.5	100	200	25
21	CH3	H	50	100	100	—^a	100	100
22	Cl	H	6.25	50	100	100	50	50
23	OCH3	H	100	—^a	6.25	100	50	50
24	F	H	100	12.5	200	100	100	6.25
25	Br	H	6.25	25	12.5	25	25	12.5
26	H	NO2	12.5	50	200	100	6.25	50
27	H	Cl	25	100	50	50	100	12.5
28	H	F	12.5	25	12.5	6.25	6.25	25
Ciprofloxacin	—	—	25	50	25	50	50	25

^aNo inhibition even at higher concentration, i.e. 200 μg/mL.

Table 3.  In vitro antifungal activity (MIC) values for compounds 20–28.

Compound	X	Y	Minimum inhibitory concentration (MIC) (μg/mL)
			A. flavus	C. albicans	Mucor	Rhizopus
20	H	H	50	100	25	200
21	CH3	H	50	200	100	25
22	Cl	H	6.25	100	200	100
23	OCH3	H	100	6.25	25	50
24	F	H	200	100	6.25	100
25	Br	H	6.25	25	12.5	12.5
26	H	NO2	100	100	100	100
27	H	Cl	—^a	—^a	12.5	6.25
28	H	F	50	100	25	12.5
Fluconazole	—	—	25	50	50	50

^aNo inhibition even at higher concentration, i.e. 200 μg/mL.