2-mercaptobenzoyl hydrazones of monose, having antimicrobial and antifungal activity

FIELD: chemistry.

SUBSTANCE: invention relates to use of 2-mercaptobenzoyl hydrazones of monose of formula (where the name of monose and value of radicals are listed in the table) as antimocrobial and antifungal agents.

EFFECT: use of 2-mercaptobenzoyl hydrazones of monose of formula (I) as antimicrobial and antifungal agents.

2 tbl, 2 ex

 

The invention relates to the field of search for new compounds, namely the synthesis of compounds with antimicrobial and antifungal activity.

With the aim of obtaining compounds with broad spectrum antimicrobial and antifungal activity by interaction of 2-mercaptobenzoic acid with monogamy, were synthesized 2-mercaptobenzimidazole the mannose that in the crystalline state have the cyclic structure of the formula:

where

№ p/pName monozyR1R2
ID-mannoseCH2OHN
IIL-rhamnoseCH3N
IIIL-rhamnose (DMSO)CH3N
IVD-glucoseCH2OHN
VL-arabinose NN
VID-galactoseCH2OHN
VIID-riboseNN
VIIID-fructoseNCH2OH

Compounds were tested against bacteria and fungi by immersion in agar, namely the method of cylinders, at various dilutions.

Experimental data showed that the compounds have antimicrobial and antifungal activity, namely the zone of growth inhibition of microorganisms are:

2-Mercaptobenzothiazole D-mannose (compound I):

against Escherichia coli ATCC 8739:

- at a dilution of 1:1 - 21 mm;

- at a dilution of 1:2 - 8 mm;

- at a dilution of 1:4 - 8 mm;

- at a dilution of 1:8 - 7 mm;

against Staphylococcus aureus was ATSS 6538-p:

- at a dilution of 1:1 - 18 mm;

- at a dilution of 1:2 to 15 mm;

- at a dilution of 1:4 - 12 mm;

- at a dilution of 1:8 - 11 mm;

against Candida albicans ATCC 3179:

- at a dilution of 1:1 to 30 mm;

2-Mercaptobenzothiazole L-ramnose (compound II):

against Escherichia coli ATCC 8739:

- when diluted and 1:1 - 12 mm;

- at a dilution of 1:2 - 8 mm;

against Candida albicans ATCC 3179:

- at a dilution of 1:1 - 25 mm;

against Staphylococcus aureus ATCC 6538-p:

- at a dilution of 1:1 - 14 mm;

- at a dilution of 1:2 to 14 mm;

- at a dilution of 1:4 - 11 mm;

- at a dilution of 1:8 - 10 mm;

- at a dilution of 1:16 - 6 mm;

towards Aspergillus niger:

- at a dilution of 1:1 to 30 mm;

- at a dilution of 1:2 - 20 mm;

- at a dilution of 1:4 - 20 mm;

- at a dilution of 1:8 - 15 mm;

2-Mercaptobenzothiazole L-ramnose (DMSO, compound III):

against Staphylococcus aureus was ATSS 6538-p:

- at a dilution of 1:1 - 15 mm;

- at a dilution of 1:2 - 10 mm;

2-Mercaptobenzothiazole D-glucose (compound IV):

against Escherichia coli was ATSS 8739:

- at a dilution of 1:1 - 14 mm;

- at a dilution of 1:2 - 8 mm;

against Candida albicans was ATSS 3179:

- at a dilution of 1:1 - 22 mm;

against Staphylococcus aureus was ATSS 6538-p:

- at a dilution of 1:1 - 18 mm;

- at a dilution of 1:2 to 15 mm;

- at a dilution of 1:4 - 14 mm;

- at a dilution of 1:8 - 12 mm;

2-Mercaptobenzothiazole L-arabinose (compound V):

against Bacillus subtilis was ATSS 6633:

- at a dilution of 1:1 to 10 mm;

against Candida albicans was ATSS 3179:

- at a dilution of 1:1 to 30 mm;

- at a dilution of 1:2 to 23 mm;

against Staphylococcus aureus was ATSS 6538-p:

- at a dilution of 1:1 - 16 mm;

- at a dilution of 1:2 to 16 mm;

- when razvedenii:4 - 15 mm;

- at a dilution of 1:8 - 15 mm;

- at a dilution of 1:16 - 14 mm;

towards Aspergillus niger:

- at a dilution of 1:1 - 35 mm;

- at a dilution of 1:2 to 32 mm;

2-Mercaptobenzothiazole D-galactose (compound VI):

against Bacillus subtilis ATCC 6633:

- at a dilution of 1:1 - 15 mm;

against Candida albicans ATCC 3179:

- at a dilution of 1:1 - 25 mm;

against Staphylococcus aureus ATCC 6538-p:

- at a dilution of 1:1 - 16 mm;

- at a dilution of 1:2 to 16 mm;

- at a dilution of 1:4 - 16 mm;

- at a dilution of 1:8 - 15 mm;

- at a dilution of 1:16 - 13 mm;

2-Mercaptobenzothiazole D-ribose (compound VII):

against Escherichia coli ATCC 8739:

- at a dilution of 1:1 - 12 mm;

against Candida albicans ATCC 3179:

- at a dilution of 1:1 to 30 mm;

- at a dilution of 1:2 to 23 mm;

against Staphylococcus aureus ATCC 6538-p:

- at a dilution of 1:1 - 21 mm;

- at a dilution of 1:2 to 17 mm;

- at a dilution of 1:4 - 14 mm;

- at a dilution of 1:8 - 10 mm;

2-Mercaptobenzothiazole D-fructose (compound VIII):

against Escherichia coli ATCC 8739:

- at a dilution of 1:1 - 16 mm;

against Bacillus subtilis ATCC6633:

- at a dilution of 1:1 to 10 mm;

against Staphylococcus aureus was ATSS 6538-p:

- at a dilution of 1:1 - 21 mm;

- at a dilution of 1:2 to 15 mm;

- at a dilution of 1:4 - 15 mm;

- at a dilution of 1:8 - 13 mm;

- at a dilution of 1:16 - 8 mm

The way to obtain

Example 1. Received the e 2-mercaptobenzothiazole D-glucose

Dissolve to 0.011 mol hydrazide 2-mercaptobenzoic acid in 15 ml of methanol, add a solution of 0.01 mol of D-glucose in 10 ml of methanol and boiled for 6 hours with constant stirring. Gradually rolled white fine crystals, which separated, washed with cold methanol and dried in vacuum. The recrystallization is conducted from methanol. Tplvl.=175-176°C (lit. 178-179°C). Output 2-mercaptobenzothiazole D-glucose was 75%. A similar technique obtained derivatives of arabinose (V) and galactose (VI). The recrystallization ribose derivatives (VIII), ramnose (II, III), mannose (I) produced from a mixture of acetonitrile - methanol (10:1). Characterization of the obtained compounds are shown in table 1.

Example 2. Determination of antimicrobial and antifungal activity of 2-mercaptobenzothiazole D-glucose

Testing of antimicrobial and antifungal activity was carried out on the following objects: Escherichia coli ATCC 8739, Bacillus subtilis ATCC 6633, Candida albicans ATCC 3179, Pseudomonas aeruginosa ATCC 9027, Staphylococcus aureus ATCC 6538-p, Aspergillus niger ATCC 16404/NCPF 2273. To this end, agar Saburo was sowing pure cultures by the method of continuous lawn. The cultivation of microorganisms and fungi was carried out at pH of 5.6 and a temperature of 37°C for 5 days. The subsequent application of a 0.02% aqueous-alcoholic solutions of the tested substances was carried out by immersion in agar, namely IU is the one of the cylinders. Measuring the zone of growth inhibition of microorganisms and fungi (in mm) was carried out after 72 hours. Determination of sensitivity was performed by serial dilution method. As the standard of comparison used 0.02% furatsilina, which was only active against Staphylococcus aureus. The results of antimicrobial and antifungal activity of 2-mercaptobenzimidazole the mannose presented in table 2.

Table 1
Feature 2-mercaptobenzimidazole the mannose
№ p/pChemical nameThe structural formulaYou
move %
Tthe melt.ProtoparmeliaThe results of elemental analysis
FoundCalculated
NNNN
I 2-mercaptan-torgerson
D-mannose
60136-138°C13H18N2O6S47,275,568,5547,265,498,48
II2-mercaptan-torgerson
L-ramnose
80159-161°C13H18N2O5S49,615,72cent to 8.8549,675,778,91
III2-mercaptan-torgerson
L-ramnose (in DMSO)
50171-172°C13H18N2O5S49,745,868,8649,675,778,91
IV2-mercaptan-torgerson
D-glucose
75175-176°C13H18N2O6S47,31of 5.538,4047,265,498,48
v2-mercaptan-torgerson
L-arabinose
60177-178°C12H16N2O5S48,06of 5.299,4147,99lower than the 5.37was 9.33
VI2-mercaptan-torgerson
D-galactose
90165-166°C13H18N2O6S47,215,558,5447,26 5,498,48
VII2-mercaptan-torgerson
D-ribose
60139-140°C12H16N2O5S47,915,439,2747,99lower than the 5.37was 9.33
VIII2-mercaptan-solverson
D-fructose
75120-122°C13H18N2O6S47,175,618,2547,265,498,48

The test results for antimicrobial and antifungal activity of 2-mercaptobenzimidazole the mannose

Table 2
Dilution 1:1
Microorganisms The number of substances
IIIIIIIVVVIVIIVIII
The amount of delay of the zones of microbial growth, mm
Escherichia coli was ATSS 87392112-14--1216
Bacillus subtilis was ATSS 6633----1015-10
Candida albicans was ATSS 3179 3025-22302530-
Pseudomonas aeruginisa ADS 9027--------
Staphylococcus aureus was ATSS 6538-p1814151816162121
Aspergillus niger was ATSS 16404/NCPF 2273-30-- 35---
Dilution 1:2
MicroorganismsThe number of substances
IIIIIIIVVVIVIIVIII
The amount of delay of the zones of microbial growth, mm
Escherichia coli was ATSS 873988-8----
Bacillus subtilis was ATSS 6633-- ------
Candida albicans was ATSS 3179----23-23-
Pseudomonas aeruginisa ADS 9027--------
Staphylococcus aureus was ATSS 6538-p151410151616 1715
Aspergillus niger was ATSS 16404/NCPF 2273-20--32---

Continuation of table 2
A dilution of 1:4
MicroorganismsThe number of substances
IIIIIIIVVVIVIIVIII
The amount of delay of the zones of microbial growth, mm
Escherichia coli was ATSS 87398- ------
Bacillus subtilis was ATSS 6633--------
Candida albicans was ATSS 3179--------
Pseudomonas aeruginisa ADS 9027--------
Staphylococcus aureus was ATSS 6538-p1211-1415161415
Aspergillus niger was ATSS 16404/NCPF2273-20------
A dilution of 1:8
MicroorganismsThe number of substances
IIIIIIIVVVIVIIVIII
The amount of delay of the zones of microbial growth, mm
Escherichia coli was ATSS 87397-------
Bacillus subtilis was ATSS 6633--------
Candida albicans was ATSS 3179--------
Pseudomonas aeruginisa ADS 9027--- -----
Staphylococcus aureus was ATSS 6538-p1110-1215151013
Aspergillus niger was ATSS 16404/NCPF 2273-15------

Staphylococcus aureus was ATSS 6538-p
Continuation of table 2
A dilution of 1:16
MicroorganismsThe number of substances
IIIIII IVVVIVIIVIII
The amount of delay of the zones of microbial growth, mm
Escherichia coli was ATSS 8739--------
Bacillus subtilis was ATSS 6633--------
Candida albicans was ATSS 3179--------
Pseudomonas aeruginisa ADS 9027--------
-6--1413-8

Sources of information

1. Zelenin PHD, Alekseev V.V. and other Zhur.org.chem., 1993, 29, 278.

2. Ershov, A., Lagoda IV and other Zhur.org.chem., 2007, 43, 1742.

3. Ershov, A., Lagoda IV and other Zhur.org.chem., 2009, 45, 678.

4. Pakalnis CENTURIES, Zerov IV and other Zhur.org.chem., 2009, 45, 295.

5. Alekseev V.V., Ershov, A. and others Zhur.org.chem., 2010, 46, 865.

6. Katz L, Karger L.S., Cohen M.S. J. Org. Chem, 1953, 18, 1380.

7. Valters R.E., F. Fulop, Karbonits D., Adv. Heterocycl. Chem. Ed. A.R. Katrizky. Amsterdam: Pergamon, 1995, 64, 251.

8. Lazar L., F. Fulop, Eur. J. Org. Chem., 2003, 16, 3025.

Application 2-mercaptobenzimidazole the mannose formula

CH3
№ p/pName monozyR1R2
ID-mannoseCH2HEN
IIL-rhamnoseCH3H
IIIL-rhamnose (DMSO)H
IVD-glucoseCH2HEH
VL-arabinoseNH
VID-galactoseCH2HEH
VIID-riboseNH
VIIID-fructoseHCH2HE

as compounds with antimicrobial and antifungal activity.



 

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