Synthesis and Biological Evaluation of New N,N′-Bis(1-substituted-ethylidene)-ethane1,2-diamine and Their Acetyl and Trifluoroacetyl Derivatives as Cytotoxic and Antimicrobial Agents

Table 1

Physical and analytical data of compounds 2–5.

Compd.	R	Yield	m.p.	Mol. formula	Calc. %			Found %
		(%)	(°C)		C	H	N	C	H	N
2a	C6H5	80	95–98	C18H20N2	81.78	7.63	10.60	81.80	7.61	10.62
2b	4-BrC6H4	86	192–194	C18H18Br2N2	51.21	4.30	6.64	51.22	4.38	6.60
2c	2-HOC6H4	92	190–192	C18H20O2N2	72.95	6.80	9.45	73.04	6.88	9.48
2d	2-CH3OC6H	76	90–92	C20H24N2O2	74.04	7.46	8.64	74.12	7.50	8.62
2e	2-Thienyl	84	142-143	C14H16N2S2	60.83	5.83	10.13	60.90	5.91	10.21
2f	3-Thienyl	82	132-133	C14H16N2S2	60.83	5.83	10.13	60.88	5.87	10.19
2g	2-Furyl	74	113–115	C14H16N2O2	68.83	6.60	11.47	68.85	6.62	11.40
2h	2-Pyridyl	72	98–100	C16H18N4	72.15	6.81	21.04	72.21	6.73	21.12
2i	4-CH3C6H4	88	110–112	C20H24N2	82.15	8.27	9.58	82.06	8.32	9.61
2j	4-CH3OC6H4	86	148–150	C20H24N2O2	74.04	7.46	8.64	74.12	7.51	8.77
2k	3,4-(CH3O)2C6H4	82	108–110	C22H28N2O4	68.73	7.34	7.29	68.81	7.48	7.33
3a	C6H5	72	252–254	C22H18F6N2O2	57.90	3.98	6.14	58.03	4.02	6.19
3b	4-BrC6H4	76	180–182	C22H16Br2F6N2O2	43.02	2.63	4.56	43.11	2.64	4.60
3c	2-Thienyl	74	158-159	C18H14F6N2O2S2	46.15	3.01	5.98	46.18	3.12	5.82
3d	3-Thienyl	72	163–165	C18H14F6N2O2S2	46.15	3.01	5.98	46.14	3.04	6.01
3e	2-Furyl	69	180–182	C18H14F6N2O4	49.55	3.23	6.42	49.65	3.28	6.47
3f	2-Pyridyl	67	196–198	C20H16F6N4O2	52.41	3.52	12.22	52.52	3.61	12.18
3g	4-CH3C6H4	78	188–190	C24H22F6N2O2	59.50	4.58	5.78	59.55	4.56	5.81
3h	4-CH3OC6H4	74	196–198	C24H22F6N2O4	55.82	4.29	5.42	55.90	4.38	5.60
3i	3,4-(CH3O)2C6H4	70	205–208	C26H26F6N2O6	54.17	4.55	19.77	54.28	4.60	19.91
4a	C6H5	76	150–152	C22H24N2O2	75.83	6.94	8.04	75.94	7.10	8.13
4b	4-BrC6H4	78	169–171	C22H22Br2N2O2	52.20	4.38	5.53	52.28	4.42	5.58
4c	2-Furyl	58	184–186	C18H20N2O4	65.84	6.14	8.53	65.93	6.22	8.46
5a	2-OHC6H4	69	204–206	C10H7F3O3	51.74	3.04	—	51.82	3.12	—
5b	2-CH3OC6H4	66	105–107	C11H9F3O3	53.67	3.68	—	53.77	3.70	—