A convenient ‘one-pot’ synthesis and in vitro microbiological evaluation of novel 2,7-diaryl-[1,4]-diazepan-5-ones

Figures & data

Scheme 1 A convenient synthesis of some novel 2,7-diaryl-[1,4]-diazepan-5-ones (25–32).

Table I.  Reaction conditions and analytical data for compounds 25–32^a.

Compound^a	R1	R2	X	Reaction time (s)	Yield^b (%)	m.p. (°C)
25	H	H	H	150	90	169
26	CH3	H	H	120	95	183
27^c	C2H5	H	H	170	83	189
28^c	CH(CH3)2	H	H	300	90	187
29	CH3	CH3	H	250	95	181
30	H	H	o–Cl	180	90	210
31	CH3	H	o–Cl	150	93	202
32	CH3	CH3	o–Cl	280	89	195

^aThe microanalysis values for C, H and N were within ± 0.4% of the theoretical values

^bYields of isolated products

^cReference [32].

Figure 1 Re-use of NaHSO₄.Al₂O₃ in the synthesis of 3-methyl-2,7-diphenyl-[1,4]-diazepan-5-one (26). The reaction was carried out in a domestic microwave oven operating at 320W.

Figure 2 Numbering of 25–32.

Table II.  In vitro antibacterial activity of compounds 25–32.

	DIAMETER OF THE ZONE OF INHIBITION
	Staphylococcus aureus			β-Heamolytic streptococcus			Vibreo cholerae			Salmonella typhii			Escherichia coli			Klebsiella pneumonia			Pseudomonas
Compounds	100	200	500	100	200	500	100	200	500	100	200	500	100	200	500	100	200	500	100	200	500
	(ppm)			(ppm)			(ppm)			(ppm)			(ppm)			(ppm)			(ppm)
25	20	23	25	21	23	26	20	21	23	21	23	24	15	16	18	21	24	28	23	25	27
26	23	24	26	21	23	25	19	20	23	20	22	25	13	15	17	26	27	29	24	26	28
27	21	23	25	20	23	25	20	22	24	21	23	25	15	17	18	22	25	27	24	26	28
28	22	25	27	22	24	26	20	22	24	22	24	26	16	17	19	25	26	28	26	27	29
29	20	23	26	20	22	25	18	20	23	20	23	25	16	17	20	25	27	29	24	26	28
30	21	24	29	22	24	27	21	21	25	22	24	27	17	18	21	22	25	29	24	26	29
31	24	25	28	22	24	26	20	21	24	21	23	26	14	17	19	26	27	28	25	27	28
32	21	24	27	21	23	26	19	21	23	21	24	26	17	18	19	26	26	27	25	26	27
Ciprofloxacin	25			28			23			22			24			26			23

Table III.  In vitro antifungal activity of compounds 25–32.

	DIAMETER OF THE ZONE OF INHIBITION
	Aspergillus flavus			Aspergillus fumigatus			Mucor			Candida albicans			Rhizopus
Compounds	100	200	500	100	200	500	100	200	500	100	200	500	100	200	500
	(ppm)			(ppm)			(ppm)			(ppm)			(ppm)
25	21	23	25	20	22	24	23	25	27	18	19	21	10	12	14
26	20	24	26	20	22	24	21	23	26	18	19	22	08	10	13
27	19	21	24	20	22	25	21	23	25	17	18	20	11	13	15
28	18	20	23	20	22	25	22	24	26	17	19	21	10	12	14
29	21	23	25	20	22	24	20	23	25	18	20	22	08	10	13
30	22	25	27	22	23	26	23	26	29	18	20	24	11	15	18
31	21	24	26	20	22	25	22	23	27	19	20	21	10	12	16
32	21	24	25	21	22	25	21	24	24	18	21	21	11	13	15
Fluconazole	20 ± 0.5 zone of inhibition against all the test fungi

Baliah V, Lakshmanan Mr, Pandiarajan K. Synthesis of some 1,2-ethanediamines. Indian J Chem 1978; 16B: 72

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