CC BY
13
48
AZ9RBAYCAN KIMYA JURNALI № 3 2017
UOT 547,64:621,892
ANTIMICROBIAL ACTIVITY OF N-3-HYDROXYPROPYL-(2-HYDROXYNAPHTALIMINE) AND ITS METAL COMPLEXES
A.R.Rahimova, Z.I.Ismayilov, T.M.Ilyasly
Baku State University [email protected]. Received 14.04.2016
Shiff bases and metal complexes have been synthesized by the condensation of 2-hidroxi-naftaldehyde and 3-aminoprophanol.The structure of the synthesized compounds assigned on the basis of elemental analysis, IR spectral studies. All the products were evaluated for their in vitro antimicrobial activity against various strains of bacteria and fungi.
Keywords: synthesis, Shiff's bases, aromatic compounds, antimicrobial activity, metal complexes.
Introduction
The common structural feature of the considered compounds is the azomethine group with a general formula RHC=N-R1, where R and R1 are alkyl, aryl, cyclo alkyl or heterocyclic groups. The latter may be variously substituted due to the relative easiness of preparation, synthetic flexibility, and the special property of C=N group. Schiff bases are generally excellent chelating agents, especially when a functional group like -OH or -SH is present close to the azomethine group so as to form a five- or six-membered ring with the metal ion versatility of Schiff base ligands and biological, analytical and industrial applications of their complexes make further investigations in this area highly desirable [3].
Nowadays, the research field dealing with Schiff base coordination chemistry has expanded enormously. The importance of Schiff base complexes for bioinorganic chemistry, catalysis and material science, separation and encapsulation processes, and formation of compounds with unusual properties and structures has been recognized and reviewed [4].
Experimental part
Preparation of the ligand. The ligand was synthesized by the condensation of 2-hidroxi-naftaldehyde with 3-aminoprophanol in 1:1 molar ratio using absolute alcohol as the reaction medium. The mixture was refluxed on a water bath for 1 and a half an hour and then allowed to stand overnight at room temperature.
The product were crystallized from the same solvent, yield - 65%, Tm.p=181°C.
Calculated, %: C 72.72, H 7.35, N 6.06, O 13.85. C14H15NO2.
Found, %: C 72.68, H 7.30, N 6.11, O
13.80.
OH
+ nh2-ch2-ch2-ch2-oh-
H=N-CH 2-CH2-CH2-OH
OH
Preparation of the complexes. The
complexes of Cu(II), Ni(II) were prepared by reacting ethanolic solution of metal acetates with ethanolic solutions of the ligand in the molar ratio 1:2. The solid coloured complexes were filtered, washed with ethanol, dried in oven, yield in all cases was 60%, Tmp=1930C.
IR spectra
The IR spectra of the ligand exhibit strong and broad at 1650 cm-1 assignable to vc=n . The band is shifted to lower wave number after the complex formation proposes involvement of azomethine N in the banding with metal ions. The linkage with N atom is further supported by the appearance of a band in far IR region in 425-395 cm-1 in the complexes assignable to vm=n. This band undergoes to shift
ANTIMICROBIAL ACTIVITY OF N-3-HYDROXYPROPYL-(2-HYDROXYNAPHTAL..... 49
after complex formation proposes coordination of metal ion through carbonyl oxygen. It is further supported by the appearance of a new
far IR band at 525-505 cm-1 in the complexes which is assignable to vM-O.
HC=
N-CH2-
OH
CH
CH
OH
Cu(CH3COO)2
-CH3COOH
HC=N— CH2—CH2—CH2—OH
O^N
Cu-..
Antimicrobial activity
In literature, it is maintained that ligands and their metal complexes are considerably active against Baccilus megaterium and Candide tropicals, but the effect of metal complexes is stronger than that of ligands. It was also reported that ligands and their metal complexes are active against Fuherica Coli, Barilum sp and Pseu-domanan acurtuginan, while that Cu are more effective. Moreover, Cu complexes of ligands were reported to be inhibiting active agents against bacteria and fungus. It was also determined that ligands could produce an inhibiting effect on the development of Aspergillus niger, Penicillium rubrum and Augergillus ferreus. Furthermore, it was also established that ligands had an actibacterial effect at 100 ppm concentration and they had and antifungicide effect.
Antimcrobial activity of the compounds was tested against using Pseudomonas Aeru-ginosa, Mycobacterium lacticolium, Aspergillus niger, Cladasporium resinale, Penicillium Chro-segenum, Chastomium gloloodium Tricho-derma viride. For bacteria meat peptone agar (MPA) and fungi we have taken susla agar (SA). The sterilized (autoclaved at 1210C for 15 min) medium (40-500C) was poured into the
Petri dishes to give a depth of 3-4 mm and allowed to solidify. The suspension of the microorganism the streaked on plates. The paper discs impregnated with the test compounds was placed on the solidified medium. The plates were pre-incubated forth at room temperature and incubated at 370C for 24 hours.
Results and discussions
The method for obtaining new Schiff bases and metal complexes has been developed. Its structure was proved by the methods of IR and NMR spectroscopy.
The functional properties of the compounds were studied in M8 oil by use of the standard laboratory methods. Results of studying antimicrobial properties of the synthesized compounds are indicated in the table. As follows from the table in condition of friction regime synthesized Schiff base and its complexes at 1% concentration have high antimicrobial properties and improve lubricating properties of the oil. Studied additives are better than the well-known additive (tricresilphos-phate). Results of the study are indicated in the table given below. As follows from this table synthesized azomethine and its metal complexes have antimicrobial properties.
+
AZERBAIJAN CHEMICAL JOURNAL № 3 2017
50
A.R.RAHIMOVA et al.
Investigation of functional properties of compounds
Zone of degradation of
oi microorganisms, cm
Ligand and complexes tran Mixed Mixed
e о n bacteria Fungi
o C (MPA) (SA)
2-hidroxi-naphftylidene- 3 - 1.0 3.1-3.1 2.9-2.9
aminopropanol 0.5 2.4-2.4 2.3-2.3
0.25 1.9-1.9 1.8-1.8
L2Cu 1.0 3.4-3.4 3.3-3.3
0.5 2.6-2.6 2.6-2.8
0.25 2.5-2.5 2.0-2.0
L2Ni 1.0 3.3-3.3 3.1-3.1
0.5 2.6-2.6 2.3-2.2
0.25 2.4-2.4 2.1-2.1
Sodium pentachlorophenolate 1.0 1.3 1.4
0.5 0.7 0.7
Tricresilpho sphate 1.0
М-8 oil - ++ ++
ConcIusion
Schiff bases of 2-hidroxinaftylden-3-aminoprophanol and their metal complexes
exhibite strong antimicrobial activity. Metal complexes have been found to be more effective than their ligands as the process of complexation dominantly affects the overall biological behaviour properties.
References
1. Schiff H. Mittheilungen aus dem universitats laboratorium in Pisa, Eine neure reihe organischer basen // Justus Liebigs Ann. Chem. 1864. 131(1). P. 256-291.
2. Wenling Qin, Sha Long, Mauro Paneenzio and Stefano Biondi, Schiff bases and its compounds // Journal of Molecules. 2013. V. 18. P. 1226412289.
3. Dhar D.N, Toploo C.L, Schiff bases and their applications // J. Sci. Ind. Res. 1982. V. 41. No 8. P. 501- 516.
4. Rishu Katwal, Harpreit Kaar, Brij Kishore Kapur. Applications of copper - Schiffs base complexes // Scientific Reviews Chem. Commun. 2013. V. 3. Issue 1. P. 1-15.
N-3-HÍDROKSÍPROPÍL-(2-HÍDROKSÍNAFTALÍMÍN) VO ONUN METAL KOMPLEKSLORÍNÍN
antímíkrob aktívlíyí
A.R.Rahimova, Z.Í.Ísmayilov, T.M.ilyasli
§iff asaslari va metal komplekslari 2-hidroksinaftaldehid va 3-aminopropanolun kondensasiyasi ila sintez edilmiçdir. Sintez edilan maddalarin quruluçlari element analizi, ÍQ spektrla üsülla ila tasdiq edilmiçdir. Bütün mahsullar gobalaklar va bakteriyalarin müxtalif kulturlarinda antimikrob aktivliklari ôyranilmiçdir.
Acar cozter: sintez, §iff asaslari, aromatik birlaçmahr, antimikrob aktivlik, metal komplekslar.
АНТИМИКРОБНАЯ АКТИВНОСТЬ ^3-ГИДРОКИПРОПИЛ-(2-ГИДРОКСИНАФТАЛЬИМИНА)
И ЕГО МЕТАЛЛОКОМПЛЕКСОВ
А.Р.Рагимова, З.И.Исмаилов, Т.М.Ильяслы
Шиффовые основания и металлические комплексы синтезированы путем конденсации 2-гидроксинафталь-дегида с 3-аминопропанолом. Структуры синтезированных соединений исследованы с помощью ИК-спектрального анализа. Изучена также антимикробная активность против различных штаммов грибов и бактерий.
Ключевые слова: синтез, основания Шиффа, ароматические соединения, противомикробная активность, комплексы металлов.
