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54
AZERBAIJAN CHEMICAL JOURNAL № 2 2023
ISSN 2522-1841 (Online) ISSN 0005-2531 (Print)
UDC 54.05
ORGANOTIN COMPLEXES BASED ON THE INTERACTION OF 2-(BENZYLIDENE AMINO) ACETIC ACID WITH ORGANOTIN CHLORIDES. SYNTHESIS, STRUCTURE
AND ANTIOXIDANT ACTIVITY
Inas J. Mahdi 1, Dhekra Jawad Hashim 2, Angham G. Hadi3, Hadeer Jasem4
1,3
Chemistry department, college of science, Babylon University, Iraq
Technical Institute of Babylon, Al-Furat Al-Awsat Technical University, Babylon, Iraq 4Medical Laboratories Techniques Department, Al-Mustaqbal University College, Babylon, Iraq
sci.angam.ganem@uobabylon.edu.iq
Received 19.09.2022 Accepted 23.11.2022
In this work, 2-(benzylidene amino) acetic acid was prepared by reflexing reaction of benzaldehyde with glycine, then this prepared and characterized compound was used as ligand to prepare tri and di-organotin complexes by condensation reaction with the corresponding organotin chloride salts. The complexes were identified by different techniques, such as infrared spectra, (tin and proton) magnetic resonance and elemental analyses. The antioxidant activity of 2-(benzylidene amino) acetic acid and prepared complexes were studied by two different methods; Free radical scavenging activity (DPPH) and CUPRRAC methods. Tri and di-tin complexes gave high percentage inhibition than ligand with both methods due to tin moiety, also Triphenyltin carboxylate complex was the best compared with the others.
Keywords: ligand, reflex, triphenyl tin chloride, methanolic solution.
doi.org/10.32737/0005-2531-2023-2-54-61
Introduction
Organotin(IV) carboxylates are well-known for their diverse and important biological properties as antifungal, antiviral, anticancer, wood preservatives, antibacterial, insecticides, photo-stabilizer and gas storage [1-13]. Organ-otin(IV) carboxylates are generally soluble in ordinary organic solvents and are stable crystalline solids with acute melting points [14-27]. Various spectroscopic analyses as well as single crystal structure have been used to describe or-ganotin(IV) carboxylates and their complexes [28-30]. Organotin(IV) complexes' geometrical properties play a crucial role in their biological action. Saxena [31] speculate that antitumor active organotin carboxylates have open coordination sites around the Sn-atom, as well as generally stable ligand-Sn bonds with little hydrolytic breakdown. The five coordinated organotin(IV) carboxylates [32] have been reported to have stronger LOX and anti-proliferative inhibitory action than the hexa coordinated ones, demonstrating the obtainability of coordination sites at tin atom. The importance of the relationship between the structure of organotin(IV) carbox-
ylates and the biological features has sparked research into tin carboxylates. Because of the rapid advancement, which includes important observations in the relevant tin(IV) chemistry. The significance of the link concerning the structure of organotin(IV) carboxylates and biological characteristics has stimulated interest in tin car-boxylates research [33, 34]. Because of the quick progress, which includes significant findings in the relevant Sn(IV) chemistry. The aryl group connected to tin has little effect, while the anion-ic group has little effect.
The presence of both of these biologically active components in a single molecule may broaden the biological spectrum of organ-otin(IV) compounds. Organotin(IV) compounds' biological activity is determined by the coordination number and structure of the Sn moiety [35-37]. Antioxidant chemicals can help reduce oxidative damage caused by aging, cardiovascular disease, cancer, inflammation, skin diseases, and malaria, causing some researchers to look for metal-based antioxidant medicinal molecules, particularly organotin(IV) [38], we report here the synthesis and characterization of organotin(IV) derivatives of 2-(benzylidene
amino) acetic acid and their antioxidant activity studies.
Experimental part
Preparation of 2-(benzylidene amino) acetic acid. (10 mmol, 10.06 gm) of benzaldehyde was mixed with (10 mmol, 0.75 gm) of glycine and (10 mmol, 0.4gm) of NaOH, then 20 ml of ethanol was added to mixture and reflexed about 4 hours. The yellow precipetate was collected and recrystalized by absolute ethanol.
Preparation of Triphentl tin(IV) Complex 1. A methanolic solution of 2-(benzylidene amino) acetic acid (5mmol, 0.815gm) was stirred with (5 mmol, 0.2 gm) NaOH for 30 minute at room temperature. A (5 mmol, 1.927 gm) from triphenyl tin chloride (Ph3SnCl) was dissolved in 30 ml hot methanol then added to 2-(benzylidene amino) acetic acid mixture, left to reflux about 4 hours with continuously stirred [9-12]. The precipitate was left to evaporate under vacuum, washed with diethyl ether.
Preparation of di-organotin(IV) Complexes 2-3. 40 ml methanolic solution of 2-(ben-zylidene amino) acetic acid (4 mmol, 0.652gm) was stirred with (4mmol, 0.16gm) NaOH for 30 minute at room temperature. (2 mmol, 0.61 gm
55
or 0.439 gm) from dibutyl or dimethyltin dichlori de (Bu2SnCl2 or Me2SnCl2) was dissolved in 30 ml of hot methanol then added to 2-(benzylidene amino) acetic acid mixture, left to reflux about 4 hours with continuously stirred [10-14]. The precipitate was left to evaporate under vacuum, washed with diethyl ether.
Antioxidant Activity Tests
a) DPPH technique
Antioxidant activity was measured using the 1,1-diphenyl-2-picrylhydrazine (DPPH) technique, as described by others [39-41]. The compounds were dissolved in methanol at different concentrations of 2; 4; 8; 16, and 32 M, respectively. DPPH (0.1 mM in methanol) was added to each test solution and carefully mixed. After 30 minutes, the solution was discarded. A UV-vis spectrophotometer was used to test the mixture's absorbance at a wavelength of 517 nm. The proportion of inhibition against DPPH was used to calculate antioxidant activity. The percentage inhibition was calculated using equation (1).
b) CUPRACMethod
Antioxidant activity test by CUPRAC method was performed according to method used by others [42].
Inhibition Percentage =
Cotrol Absorbance — Sample Absorbance
Control Absorbance
x 100
(1)
Total antioxidants levais =
A test
A STD
/mmole\
x Conce. of STD (—-—) (2)
Results and Discussion
Synthesis of Organotin(IV) Complexes 1-3. The new complexes were obtained by refluxing methanolic solutions of tri and di-organotin chloride with 2-(benzylidene amino) acetic acid, respectively, with a high yield percentage
(Schem 1 and 2). The resulting compounds were identified using FTIR, NMR (1H and Sn119) spectroscopy techniques, as well as elemental analyses. Tables 1-3 summarize the findings of each study.
2-(benzylidene amino)acetic acid
Scheme 1. Synthesis of Triphenyltin complex 1.
Scheme 2. Synthesis of dibutyl and dimethyl-tin complexes 2 and 3.
Table 1. Physical Analysis Data of 2-(benzylidene amino) acetic acid and Complexes 1-3
Compound Color Yield % MP (0C) Elemental analysis % Calculated (Found)
C H N
2-(benzylidene amino)acetic acid (L) Yellow - 181-183 66.25(65.19) 5.56(6.12) 8.58(8.02)
Ph3SnL Yellowish-white 89.5 210-212 63.32(63.88) 4.53(5.11) 2.73(3.07)
Bu2SnL2 Off white 93.6 217-219 56.04(56.49) 6.15(5.85) 5.03(5.58)
Me2 SnL2 Off white 95.3 205-207 50.77(51.21) 4.69(5.89) 5.92(5.89)
Table 2. FTIR Spectral Data of Complexes 1-3
Compound C=O C-N Sn-C Sn-O
L 1597 1560 - -
Ph3SnL 1645 1640 570 449
Bu2SnL2 1647 1637 567 424
Me2 SnL2 1645 1637 572 450
Table 3. NMR Spectral data (1H and 119Sn) of 2-(benzylidene amino) acetic acid and 1-3 Complexes
Sn(IV) Complex 1H-NMR 119Sn-NMR
L 12.92(s, 1H, COOH), 8.42-8.1 (s, H, CH=N), 6.81-7.91(m, 5H, Ar), 4.7-4.01(t, 2H, CH2). --
Ph3SnL 8.96(m, 5H, Ph), 8.52-8.1 (s, H, CH=N), 6.84-7.39(m, 5H, Ar), 4.14-4.43(t, 2H, CH2). -175
Bu2SnL2 8.44-8.21 (s, H, CH=N), 6.82-7.35(m, 5H, Ar), 4.05-4.12(t, 2H, CH2), 0.7-1.76(Bu). -227
Me2SnL2 8.54-8.21 (s, H, CH=N), 6.83-7.38(m, 5H, Ar), 4.04-4.42(t, 2H, CH2), 0.33-1.68 (s, Me). -267
Figure 1 shows the FTIR spectrum of 2-(benzylidene amino) acetic acid and Complex 2. Due to complexation with organotin compounds, bands of carboxylic acid around 34002400 cm-1 vanished, and all bands were moved to higher or lower wave length. There were also new bands at 449, 424, and 450 cm-1 that were associated to Sn-O and 570, 567, and 572 cm-1 that were related to Sn-C of (1-3) complexes.
Antioxidant Activity
The three synthesized complexes were examined in varied quantities in the antioxidant activity analysis using the two procedures outlined. After obtaining the absorbance in each measurement, the percent inhibition can be computed; also the results may be displayed in the Figures 2 and 3.
In comparison to the standard material used (Figure 4), the results indicated a high oxidation efficiency.
Fig. 1. FTIR Spectra of 2-(benzylidene amino) acetic acid and Complex 2.
Fig. 2. DPPH scavenging activity of 2-(benzylidene amino) acetic acid and its complexes at 250 ^g/mL DMSO solutions at T = 60 min.
Fig. 3. CUPRAC Method activity of 2-(benzylidene amino) acetic acid and its complexes at T = 60 min.
120 100
c 80
0
1 60
^ 40 20 0
y = 1,21x + 40,7 R2 = 0,9709
10
50
20 30 40
Concentration of ascorbic acid (^g/ml) Fig. 4. Standard Inhibition Percentage (Ascorbic Acid).
60
0
With both methods utilized, the antioxidant activity of 2-(benzylidene amino) acetic acid and complexes was measured in varied amounts. When compared to the di-complexes of butyl and methyl, the prepared complexes showed higher activity than the ligand derived from it, and the tri-phenyl complex showed higher activity than the rest of the complexes. This could be due to the presence of three groups of phenyl and an increase in aromaticity.
Conclusion
Three complexes of organotin with different organic substituents were prepared by the reaction of 2-(benzylidene amino) acetic acid with tri-phenyl tin and di-(butyl or methyl) tin salts.
DPPH and CUPRAC methods were used to assess the antioxidant activity of 2-(benzylidene amino) acetic acid and its organ-otin(IV) complexes. Using two methods, the antioxidant activity of the organotin(IV) complexes was found to be greater than that of the 2-(benzylidene amino) acetic acid.
Acknowledgements
The authors would like to thank Babylon University and Al-Mustaqbal University College for kind support.
Conflict of interest
The authors have no conflicts of interest regarding this investigation.
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2-(BENZÍLÍDENAMÍNO)SÍRKO TUR§USUNUN ORQANOTÍN XLORÍDLORÍ ÍLO QAR§ILIQLI TOSÍRÍNO OSASLANAN ORQANOTÍN KOMPLEKSLORÍ. SÍNTEZÍ, QURULU§U УЭ ANTÍOKSÍDANT
foalíyyotí
Inas J. Mahdi, Dekra Jawad Haçim, Angam G. Hadi, Hadeer Jasem
Bu içda benzaldehidin qlisinla refleks reaksiyasindan 2-(benzilidenamino)sirka turçusu alinmiç, sonra alinmiç va xarak-teriza olunan birlaçmadan müvafiq orqanotin xloridla kondensasiya reaksiyasi yolu ila tri- va di-orqanotin komplekslari almaq ûçûn liqand kimi istifada edilmiçdir. Komplekslar IR spektral aqalis, (qalay-proton) maqnit rezonansi va elementar analiz kimi müxtalif üsullarla müayyan edilmiçdir. 2-(benzilidenamino)sirka turçusunun va yaranan komplekslarin antioksidant faaliyyati iki müxtalif üsulla tadqiq edilmiçdir; Sarbast radikal tamizlama faaliyyati (DPPH) va CUPRAC üsullari. Tri- va di-qalay komplekslari qalay hissasina göra har iki üsulla liqandla müqayisada daha yüksak inhiba faizi verdi va trifenilqalay karboksilat kompleksi digarlarindan daha yaxçi idi.
Açar sözlzr: liqand, refleks, trifenilqalayxlorid, metanol тэЫиЫ.
ОЛОВООРГАНИЧЕСКИЕ КОМПЛЕКСЫ НА ОСНОВЕ ВЗАИМОДЕЙСТВИЯ 2-(БЕНЗИЛИДЕНАМИНО)УКСУСНОЙ КИСЛОТЫ С ОЛОВООРГАНИЧЕСКИМИ ХЛОРИДАМИ. СИНТЕЗ, СТРУКТУРА И АНТИОКСИДАНТНАЯ АКТИВНОСТЬ
Инас Дж.Махди, Декра Джавад Хашим, Ангам Г.Хади, Хадеер Джасем
В этой работе 2-(бензилиденамино)уксусная кислота была получена рефлекторной реакцией бензальдегида с глицином, затем полученное и охарактеризованное соединение было использовано в качестве лиганда для получения три- и ди-оловоорганических комплексов реакцией конденсации с соответствующими оловоорганическими хлоридными солями. Комплексы идентифицировали различными методами, такими как ИК- спектральный анализ, (олово-протонный) магнитный резонанс и элементарный анализ. Антиоксидантную активность 2-(бензилиденамино)уксусной кислоты и полученных комплексов изучали двумя разными методами; Активность по удалению свободных радикалов (DPPH) и методы CUPRRAC. Комплексы три- и ди-олова давали более высокий процент ингибирования, чем лиганд, с обоими методами из-за фрагмента олова, а комплекс карбоксилата трифенилолова был лучшим по сравнению с другими.
Ключевые слова: лиганд, рефлекс, трифенилоловохлорид, метанольный раствор
