The antimicrobial and bactericidal activity of secondary amine with 2-hydroxyethyl group

doi:10.15406/mojboc.2018.02.00070

MOJ

eISSN: 2574-819X

Bioorganic & Organic Chemistry

Opinion Volume 2 Issue 3

The antimicrobial and bactericidal activity of secondary amine with 2-hydroxyethyl group

Torosyan GH,

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Hovhannisyan NR

Environmental Engineering Department, National polytechnic university of Armenia, Armenia

Correspondence: Torosyan GH, National polytechnic university of Armenia, Armenia, Yerevan Gagik Torosyan, Doctor of Chemical sciences, professor, National polytechnic university of Armenia, Tel 3741 5546 48

Received: May 22, 2018 | Published: June 7, 2018

Citation: Torosyan GH, Hovhannisyan NR. The antimicrobial and bactericidal activity of secondary amine with 2-hydroxyethyl group. MOJ Biorg Org Chem. 2018;2(3):141-142 DOI: 10.15406/mojboc.2018.02.00070

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Abstract

Recently we reported on the possibility of selective alkylation of monoethanolamine (MEA) in phase transfer catalysis (PTC) conditions.¹ The direct mono-N alkylation of MEA with alkyl bromides as electrophilic reagent was performed in PTC system. This report is devoted to the study of the antimicrobial activity of the compounds obtained.

Keywords: monoethanolamine, phase transfer catalysis, alkyl derivatives of MEA, antimicrobial activity, Staph aureus, coli 0 III B:4. the bactericidal properties

Opinion

Alkyl derivatives of MEA are used in the production of surfactants, dyes, in the manufacture of drugs as a buffer substance and for the stabilization of emulsions, in the manufacture of herbicides, cosmetics, antihistamines, are also of practical interest.¹Here are the results on the study of the antimicrobial activity of a number of alkyl derivatives of MEA (Table1).

№	Compound	B.p. O/mm			IR	NMR
1	1	102-103/25	14,637	0,8964	1630, 980, 3020 (CH=CH₂); 3200-3400 (OH, NH)	2,65т (2H, NCH₂CH₂); 3,18 (2H, CH₂C=C-); 3,5с(1H, OH); 3,62м (2H, CH₂CH₂OH); 4,95÷6,25 (3H, CH=CH₂);
2	2	140-142/10	14,465	0,8531	-	0,85 (3H, CH₃); 1,28 м (6H, (CH₂)₃CH₂); 2,56м (4H, 2NCH₂); 3,12c (1H, OH); 3,52м (2H, CH₂O);
3	3	202-203/5	14,599	0,8687	-	0,82c (3H, CH₃); 1,22c (14H, (CH₂)₇); 2,41м (4H, 2NCH₂); 3,33м (2H, CH₂O);

Table 1 Physical-chemical data of synthesized compounds

The antimicrobial properties of substances have been studied in vitro by serial dilution in a liquid nutrient medium.² Staphylococous aurous strain N=209 "P", as the most stable species from the coccus group of bacteria, and Escherichia coli 0 III B:4-24, as the most stable species from enterobacteria, were used as indicator microorganisms. Test cultures by morphological, tinctorial, and cultural and biochemical properties are typical. Bacteria were cultured on MPA and MPB (pH =7.2-7.4). In the experiments, second generations of daily agar test cultures were used.

The substances 2, 3 have activity in relation to the Staph aureus strain #209. The substance 2 surpasses the antimicrobial ethogenium (ethylene-1,2-bis/N-dimethylcarbodecoxymethylammonium dichloride) used in medical practice for anti-staphylococcal activity and can be used in the chemical and pharmaceutical industry to produce an anti-staphylococcal preparation.² The studied compounds are not active against gram-negative microorganisms (Escherichia coli).

Acute toxicity of substance 3 was studied in non-native white rats weighing 180-200g when administered orally. The LD₅₀ of substance 3 for white mice when administered orally is 145mg/kg.

The bactericidal properties of the substances were studied by disinfection of bathy test objects contaminated with a microbial suspension (containing 2ml microbial bodies in 1ml), in reference strains of Escherichia coli (1257) and Staphylococcus aureus (906), in exposures 5, 10, 15, 20, 25, 30 minutes. Each concentration is tested in at least three replicates.

Acknowledgements

None

Conclusion

From the obtained data (Table 2) it is visible that Nonylethanolamine (3) exhibits very high bactericidal activity. Simplicity of synthesis of this compound predetermines its application in practice as antimicrobial derivative.

Substance	Test culture
Substance	Staph aureus		*E. coli* 0 III B:4
	MBSC*	MBC**	MBSC	MBC
1	X***	X	X	X
2	3,9	7,8	X	X
3	0,03	0,12	X	X

Table 2 The antimicrobial activity of synthesized amine (μg/ml)
Abbreviations: MBSC, minimal bacteriostatic concentration; MBC, minimal bactericidal concentration; X, absence of activity in the initial absence of activity in the initial