Synthesis, Antibacterial and Antitubercular Evaluation of Cardanol and Glycerol-Based β-Amino Alcohol Derivatives

Manda, Bhaskar R.; Prasad, Avvari N.; Thatikonda, Narendar R.; Lacerda Jr., Valdemar; Barbosa, Layla R.; Santos, Heloa; Romão, Wanderson; Pavan, Fernando R.; Ribeiro, Camila M.; Santos, Edson A. dos; Marques, Maria R.; Lima, Dênis P. de; Micheletti, Ana C.; Beatriz, Adilson

doi:10.21577/0103-5053.20170178

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Journal of the Brazilian Chemical Society

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Articles • J. Braz. Chem. Soc. 29 (3) • Mar 2018 • https://doi.org/10.21577/0103-5053.20170178 copy

Synthesis, Antibacterial and Antitubercular Evaluation of Cardanol and Glycerol-Based β-Amino Alcohol Derivatives

Authorship SCIMAGO INSTITUTIONS RANKINGS

The synthesis of novel amino alcohol derivatives based on cardanol and glycerol were achieved in good yields and characterized by ¹H and ¹³C NMR (nuclear magnetic resonance) and MS (mass spectrometry). In addition, we evaluated the in vitro antimicrobial activity against Gram-positive (Staphylococcus aureus, standard and clinical strains), Gram-negative (Escherichia coli) and M. tuberculosis bacterial strains. The bioassay results indicated that four compounds showed activity against S. aureus, including the clinical resistant strain, with MIC (minimum inhibitory concentration) ranging from 3.90 to 15.60 µg mL^-1 and M. tuberculosis, with MIC₉₀ (minimum inhibitory concentration required to inhibit the growth of 90% of organisms) ranging from 3.18 to 7.36 µg mL^-1.

Keywords:
CNSL; cardanol; amino alcohols; epoxide ring opening; antimicrobial activity

entry	Compound	Product	time / h	Yield^b b isolated yields. / %
1	2a		8	87
2	2b		8.5	83
3	2c		8.5	85
4	2d		9	64
5	2e		10	54
6	2f		8	91
7	2g		8.5	64
8	2h		8.5	76
9	2i		9	67
10	2j		8	69
11	2k		8.5	70
12	2l		8.5	78
13	2m		9.5	66
14	2n		8	73
15	2o		8	82
16	2p	-	12	-
17	2q	-	12	3

Compound	log P^a a The theoretical log P was calculated using the MolInspiration algorithm.62	S. aureus (ATCC 25923)		S. aureus (clinical)		E. coli (ATCC 25922)		M. tuberculosis H37Rv (ATCC 27294)
Compound		MIC / (µg mL^-1)	MIC₉₀ / µM	MIC / (µg mL^-1)	MIC₉₀ / µM	MIC / (µg mL^-1)	MIC₉₀ / µM	MIC / (µg mL^-1)	MIC₉₀ / µM
2a	8.48	na		125.0	279.41	na		3.18	7.12
2b	8.99	7.81	17.53	7.80	17.51	na		3.27	7.34
2c	8.78	15.63	36.23	15.60	36.16	na		7.36	17.07
2d	10.31	na		na		na		> 25	> 30.97
2e	9.20	na		na		na		16.54	39.15
2f	9.14	3.90	8.45	7.80	16.90	na		4.37	9.46
2g	9.19	na		na		na		nd
2h	9.30	na		na		na		> 25	> 53.59
2i	9.29	na		na		na		> 25	> 53.49
2j	9.40	na		na		na		> 25	> 47.06
2k	9.38	na		na		na		> 25	> 47.06
2l	9.36	na		na		na		> 25	> 51.30
2m	9.35	na		na		na		> 25	> 51.30
2n	9.17	na		na		na		> 25	> 55.14
2o	8.85	3.90	8.45	na		na		5.22	11.51
Gentamicin		1.86	3.89	> 64		3.75	7.84	-
Rifampicin		-		-		-		0.08	0.01

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[1] *e-mail: anamicheletti@gmail.com; adilson.beatriz@ufms.br

entry	Compound	Product	time / h	Yield^b b isolated yields. / %
1	2a		8	87
2	2b		8.5	83
3	2c		8.5	85
4	2d		9	64
5	2e		10	54
6	2f		8	91
7	2g		8.5	64
8	2h		8.5	76
9	2i		9	67
10	2j		8	69
11	2k		8.5	70
12	2l		8.5	78
13	2m		9.5	66
14	2n		8	73
15	2o		8	82
16	2p	-	12	-
17	2q	-	12	3

entry	Compound	Product	time / h	Yield^b b isolated yields. / %
1	2a		8	87
2	2b		8.5	83
3	2c		8.5	85
4	2d		9	64
5	2e		10	54
6	2f		8	91
7	2g		8.5	64
8	2h		8.5	76
9	2i		9	67
10	2j		8	69
11	2k		8.5	70
12	2l		8.5	78
13	2m		9.5	66
14	2n		8	73
15	2o		8	82
16	2p	-	12	-
17	2q	-	12	3

entry	Compound	Product	time / h	Yield^b b isolated yields. / %
1	2a		8	87
2	2b		8.5	83
3	2c		8.5	85
4	2d		9	64
5	2e		10	54
6	2f		8	91
7	2g		8.5	64
8	2h		8.5	76
9	2i		9	67
10	2j		8	69
11	2k		8.5	70
12	2l		8.5	78
13	2m		9.5	66
14	2n		8	73
15	2o		8	82
16	2p	-	12	-
17	2q	-	12	3