Synthesis and in vitro biological evaluation of new heterocycles based on the indole moiety

Figures & data

Scheme 1. Synthesis of the target compounds 3a–c, 5a,b and 7.

Scheme 2. Synthesis of the target compounds 8a–c, 9a–d, 10a–c and 11a–c.

Scheme 3. Synthesis of the target compounds 12a,b, 13a,b and 14a,b.

Scheme 4. Synthesis of the target compounds 15, 16, 17a,b and 18a–c.

Table 1. Inhibition zone diameter in (mm) as a criterion of antibacterial and antifungal activities of the newly synthesized compounds.

Microorganism inhibition zone diameter(mm)
	Gram +ve bacteria		Gram −ve bacteria		Fungi
Compounds	S. aureusz	S. epidermidis	E. coli	K. pneumoniae	A. fumigatu	C. albicans
3c	18	20	20	17	14	16
5a	16	16	20	16	13	15
5b	17	17	18	16	11	13
7	18	18	18	15	12	14
8a	26	27	28	26	16	16
9a	32	31	35	28	17	21
9b	31	29	33	28	15	20
12a	25	26	26	25	15	17
12b	25	27	28	26	15	17
13a	27	27	29	26	15	16
13b	25	25	27	26	14	15
14a	32	31	36	29	21	23
14b	33	30	36	31	23	23
15	26	27	29	28	16	21
16	25	24	26	23	14	16
17a	29	31	27	26	17	20
17b	29	29	28	27	16	20
Sulfamethoxazole	36	36	39	33	–	–
Fluconazole	–	–	–	–	26	28

Table 2. Minimum inhibitory concentration (MIC) in µg/ml of the newly synthesized compounds.

Microorganism minimum inhibitory concentration
	Gram +ve bacteria		Gram −ve bacteria		Fungi
Compounds	S. aureusz	S. epidermidis	E. coli	K. pneumoniae	A. flavus	C. albicans
3c	24	24	24	48	24	24
5a	48	48	24	48	48	24
5b	48	48	48	48	48	48
7	24	24	48	48	24	24
8a	6	12	6	6	12	12
9a	6	6	6	12	12	12
9b	6	12	6	6	24	12
12a	12	12	12	12	12	12
12b	6	6	6	6	6	12
13a	6	6	12	12	24	12
13b	12	12	12	24	12	12
14a	6	6	3	6	12	6
14b	6	6	3	3	6	6
15	6	12	12	12	12	12
16	12	12	6	12	24	12
17a	12	12	6	12	12	24
17b	12	12	12	12	24	24
Sulfamethoxazole	3	3	3	3	–	–
Fluconazole	–	–	–	–	3	3

Figure 1. The cytotoxicity data of the activity of compounds (3a, 10a, 11a) against colon (HCT116) tumor cell line compared to Vinblastine sulphate IC50:9.8.

Figure 2. The cytotoxicity data of the activity of compounds (3a, 10a, 11a) against breast (MCF7) tumor cell line compared to Vinblastine sulphate IC50:11.6.

Figure 3. The cytotoxicity data of the activity of compounds (3a, 10a, 11a) against cervix (HELA) tumor cell line compared to Vinblastine sulphate IC50:10.9.

Figure 4. The cytotoxicity data of the activity of compounds (7, 18a–c) against cervix (HELA) tumor cell line compared to Vinblastine sulphate IC50:10.9.

Figure 5. The cytotoxicity data of the activity of compounds (3b, 11b, 18a) against cervix (MCF7) tumor cell line compared to Doxorubicin IC50 5.75.