Synthesis and biological evaluation of novel s-triazine based aryl/heteroaryl entities: Design, rationale and comparative study

Peer review under responsibility of University of Bahrain.

Figures & data

Figure 1 Scheme. Synthetic route for novel s-triazine based aryl/heteroaryl derivatives.

Figure 2 The strategy for design of title compounds.

Table 1 In vitro antimicrobial activity of compounds 4a–j, 5a–j, 6a–g and 7a–h.

Compound	R/X	MIC (μg/mL)
		Gram +ve		Gram −ve
		S.a	B.c	E.c	P.a
		MTCC 96	MTCC 430	MTCC 739	MTCC 741
4a	H	200	50	100	25
4b	2-Cl	25	100	12.5	50
4c	3-Cl	50	6.25	50	12.5
4d	4-Cl	12.5	3.12	200	100
4e	2-CH3	100	200	25	50
4f	3-CH3	200	200	100	25
4g	4-CH3	50	25	3.12	200
4h	2-F	6.25	100	50	100
4i	3-F	25	6.25	12.5	3.12
4j	4-F	3.12	12.5	50	25
5a	H	200	50	200	100
5b	2-CH3	100	200	25	50
5c	3-CH3	100	100	50	200
5d	4-CH3	50	200	100	50
5e	2-F	12.5	25	200	3.12
5f	3-F	50	50	200	100
5g	4-F	25	12.5	50	25
5h	2-Cl	100	12.5	25	100
5i	3-Cl	25	25	12.5	50
5j	4-Cl	12.5	100	50	50
6a	H	200	50	100	200
6b	2-Cl	50	12.5	200	25
6c	3-Cl	100	3.12	200	50
6d	2-CH3	25	50	6.25	100
6e	4-NO2	200	100	100	50
6f	4-Br	6.25	200	50	3.12
6g	4-OCH3	12.5	200	12.5	25
7a	X = N–CH3	100	50	200	25
7b	N–CH2CH3	50	100	200	50
7c	N–COCH3	3.12	200	100	100
7d	N–CH(CH3)2	200	6.25	25	12.5
7e	N–C6H5	200	25	50	3.12
7f	–CH2–	12.5	100	6.25	100
7g	–O–	6.25	200	100	12.5
7h	N–C6H4–OCH3	50	200	3.12	6.25
Cip.	–	1.72	0.28	1.40	0.62
DMSO	–	–	–	–	–

MIC = Minimum inhibitory concentration, Cip. ciprofloxacin, S.a Staphylococcus aureus, B.c Bacillus cereus, E.c Escherichia coli, P.a Pseudomonas aeruginosa.

Bold values indicates superior minimum inhibition concentration against particular microbial strain.

Table 2 In vitro antifungal activity of compounds 4a–j, 5a–j, 6a–g and 7a–h.

Compound	R/X	MIC (μg/mL)
		C.a	A.n	A.c
		MTCC 183	MTCC 282	MTCC 1323
4a	H	100	200	12.5
4b	2-Cl	50	6.25	100
4c	3-Cl	3.12	100	50
4d	4-Cl	12.5	50	3.12
4e	2-CH3	25	100	200
4f	3-CH3	100	25	50
4g	4-CH3	200	50	100
4h	2-F	50	12.5	100
4i	3-F	25	3.12	12.5
4j	4-F	12.5	25	25
5a	H	200	100	25
5b	2-CH3	50	6.25	200
5c	3-CH3	100	50	100
5d	4-CH3	25	12.5	25
5e	2-F	100	100	50
5f	3-F	12.5	25	25
5g	4-F	50	200	100
5h	2-Cl	200	100	200
5i	3-Cl	12.5	50	6.25
5j	4-Cl	6.25	200	25
6a	H	200	100	50
6b	2-Cl	50	200	12.5
6c	3-Cl	6.25	25	200
6d	2-CH3	100	6.25	200
6e	4-NO2	25	50	50
6f	4-Br	200	100	3.12
6g	4-OCH3	12.5	200	25
7a	X = N–CH3	100	200	12.5
7b	N–CH2CH3	100	100	25
7c	N–COCH3	3.12	50	6.25
7d	N–CH(CH3)2	25	50	50
7e	N–C6H5	6.25	12.5	100
7f	–CH2–	200	3.12	200
7g	–O–	200	6.25	12.5
7h	N–C6H4–OCH3	50	100	6.25
Kit.	–	1.56	1.56	0.78
DMSO	–	–	–	–

Kit. ketoconazole, C.a. Candida albicans, A.n. Aspergillus niger, A.c. Aspergillus clavatus.

Bold values indicates superior minimum inhibition concentration against particular microbial strain.

Table 3 In vitro antituberculosis activity of compounds 4a–j, 5a–j, 6a–g and 7a–h.

Compound	R/X	BACTEC MGIT method ^a
		MIC μg/ml	% Inhibition
4a	H	>12.5	–
4b	2-Cl	12.5	95
4c	3-Cl	>12.5	–
4d	4-Cl	>12.5	–
4e	2-CH3	>12.5	–
4f	3-CH3	>12.5	–
4g	4-CH3	12.5	95
4h	2-F	>12.5	–
4i	3-F	12.5	95
4j	4-F	>12.5	–
5a	H	>12.5	–
5b	2-CH3	>12.5	–
5c	3-CH3	>12.5	–
5d	4-CH3	>12.5	–
5e	2-F	>12.5	–
5f	3-F	>12.5	–
5g	4-F	>12.5	–
5h	2-Cl	>12.5	–
5i	3-Cl	>12.5	–
5j	4-Cl	>12.5	–
6a	H	>12.5	90
6b	2-Cl	12.5	95
6c	3-Cl	>12.5	92
6d	2-CH3	>12.5	90
6e	4-NO2	>12.5	90
6f	4-Br	>12.5	91
6g	4-OCH3	>12.5	90
7a	X = N–CH3	>12.5	91
7b	N–CH2CH3	>12.5	92
7c	N–COCH3	>12.5	93
7d	N–CH(CH3)2	12.5	95
7e	N–C6H5	>12.5	92
7f	–CH2–	>12.5	93
7g	–O–	>12.5	94
7h	N–C6H4–OCH3	12.5	95
Isoniazid	–	0.20	99
Rifampicin	–	0.25	99
Ethambutol	–	3.12	99
Pyrazinamide	–	6.25	99

Bold values indicates superior minimum inhibition concentration against particular microbial strain.

a Each value is the mean of three independent experiments.