Комплексы Sn(IV) с изоникотиноилгидразонами ароматических альдегидов. Синтез, характеристика, влияние на рост Mycobacterium Tuberculosis
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Дата
2017
Назва журналу
Номер ISSN
Назва тому
Видавець
Одеський національний університет імені І. І. Мечникова
Анотація
Взаимодействием SnCl4
c изоникотиноилгидразонами R-бензойных альдегидов (R-HIb) в ацетонитриле синтезированы [SnCl4 (R-Ib∙Н)], где R=H (1), 4-Br (2), 4-NO2
(3), 2-OCH3 (4), 4-OCH3 (5), -ОC7
H15(6), а с гидразоном 2-OH-нафтойного альдегида (2-OH-H2 Inf) – [SnCl3
(2-OH-Inf∙Н)](9). Комплексы охарактеризованы методами массспектрометрии, кондуктометрии, термогравиметрии и ИК спектроскопии. Установлено влияние состава комплексов, природы заместителей (R) на активность в отношении Mycobacterium tuberculosis.
Взаємодією SnCl4 з ізонікотиноїлгідразонами R-бензойних альдегідів (R-HIb) в ацетонітрілі синтезовані [SnCl4 (R-Ib∙Н)], де R=H (1), 4-Br (2), 4-NO2 (3), 2-OCH3 (4), 4-OCH3 (5), -ОC7 H15(6), а з гідразоном 2-OH-нафтойного альдегіду (2-OH-H2 Inf) – [SnCl3 (2-OH-Inf∙Н)](9). Сполуки охарактеризовані методами мас-спектрометрії, кондуктометрії, термогравіметрії та ІЧ спектроскопії. Установлено вплив складу комплексів, природи замісників (R) на активність щодо Mycobacterium tuberculosis.
Сomplexes [SnCl4 (R-Ib∙Н)], where R=H (1), 4-Br (2), 4-NO2 (3), 2-OCH3 (4), 4-OCH3 (5), -ОC7 H15(6), were synthesized by interaction of SnCl4 with isonicotinoylhydrazones of R-benzoic aldehydes (R-HIb) in acetonitrile and complex [SnCl3 (2-OH-Inf∙Н)](9) – by interaction of SnCl4 with 2-OH- naphthaldehyde isonicotinoylhydrazone (2-OH-H2 Inf). In (1-6) bidentate O(C-O)–N(N=CH)-coordination of the enol form of the ligand is realized and the coordination node {SnCl4 ON}– is formed, and in (9) the enol form remains, but the composition of the node changes – {SnCl3 O2 N}– due to O(C-O)– N(N=CH)–О(Ph-O)- tridentate coordination. The compounds were characterized by the methods of elemental analysis, mass spectrometry, conductometry, thermogravimetry. Their structure was established by comparing the mass- and IR spectra (1-6) and (9) with previously obtained and X-ray structurally characterized complexes [SnCl4 (RIb∙Н)]∙CH3 CN (R=4-N(CH3 )2 (7)) and [SnCl3 (R-Ib∙Н)]∙2CH3 CN (R=2-OH(8)) with bi- (7) and tridentate coordination (8) of isonicotinoylhydrazones, respectively. It is shown that (1-6) and (9) are complex compounds of the zwitterionic type: the negative charge on the coordination nodes of tin(IV) is delocalized by the oxyazine fragment N=C–O, and the positive charge – by the protonation of the vacant pyridine nitrogen atom of hydrazide fragment. The influence of the composition of the coordination node of complexes (1-9), as well as the nature and position of the substituents (R) in their molecules on the activity against Mycobacterium tuberculosis was determined. It was found that the effect of complexes with tridentate hydrazones (8) and (9) on the growth of pathogen is lower (MIC = 12.5 and 25 μM/ml, respectively) compared with bidentate hydrazones (MIC (1-7) = 0,8 – 6,25 μM/ml), among which [SnCl4 (2-OCH3 -Ib∙Н)] (4) stand out (MIC = 0.8 μM/ml).
Взаємодією SnCl4 з ізонікотиноїлгідразонами R-бензойних альдегідів (R-HIb) в ацетонітрілі синтезовані [SnCl4 (R-Ib∙Н)], де R=H (1), 4-Br (2), 4-NO2 (3), 2-OCH3 (4), 4-OCH3 (5), -ОC7 H15(6), а з гідразоном 2-OH-нафтойного альдегіду (2-OH-H2 Inf) – [SnCl3 (2-OH-Inf∙Н)](9). Сполуки охарактеризовані методами мас-спектрометрії, кондуктометрії, термогравіметрії та ІЧ спектроскопії. Установлено вплив складу комплексів, природи замісників (R) на активність щодо Mycobacterium tuberculosis.
Сomplexes [SnCl4 (R-Ib∙Н)], where R=H (1), 4-Br (2), 4-NO2 (3), 2-OCH3 (4), 4-OCH3 (5), -ОC7 H15(6), were synthesized by interaction of SnCl4 with isonicotinoylhydrazones of R-benzoic aldehydes (R-HIb) in acetonitrile and complex [SnCl3 (2-OH-Inf∙Н)](9) – by interaction of SnCl4 with 2-OH- naphthaldehyde isonicotinoylhydrazone (2-OH-H2 Inf). In (1-6) bidentate O(C-O)–N(N=CH)-coordination of the enol form of the ligand is realized and the coordination node {SnCl4 ON}– is formed, and in (9) the enol form remains, but the composition of the node changes – {SnCl3 O2 N}– due to O(C-O)– N(N=CH)–О(Ph-O)- tridentate coordination. The compounds were characterized by the methods of elemental analysis, mass spectrometry, conductometry, thermogravimetry. Their structure was established by comparing the mass- and IR spectra (1-6) and (9) with previously obtained and X-ray structurally characterized complexes [SnCl4 (RIb∙Н)]∙CH3 CN (R=4-N(CH3 )2 (7)) and [SnCl3 (R-Ib∙Н)]∙2CH3 CN (R=2-OH(8)) with bi- (7) and tridentate coordination (8) of isonicotinoylhydrazones, respectively. It is shown that (1-6) and (9) are complex compounds of the zwitterionic type: the negative charge on the coordination nodes of tin(IV) is delocalized by the oxyazine fragment N=C–O, and the positive charge – by the protonation of the vacant pyridine nitrogen atom of hydrazide fragment. The influence of the composition of the coordination node of complexes (1-9), as well as the nature and position of the substituents (R) in their molecules on the activity against Mycobacterium tuberculosis was determined. It was found that the effect of complexes with tridentate hydrazones (8) and (9) on the growth of pathogen is lower (MIC = 12.5 and 25 μM/ml, respectively) compared with bidentate hydrazones (MIC (1-7) = 0,8 – 6,25 μM/ml), among which [SnCl4 (2-OCH3 -Ib∙Н)] (4) stand out (MIC = 0.8 μM/ml).
Опис
Ключові слова
тетрахлорид олова, SnCl4, изоникотиноилгидразоны, комплексы Sn(IV, минимальная ингибирующая концентрация, МИК, Mycobacterium tuberculosis, станум тетрахлорид, SnCl4, ізонікотиноїлгідразони, комплекси Sn(IV), мінімальна інгібуюча концентрація, МІК, Mycobacterium tuberculosis, tin tetrachloride, SnCl4, isonicotinoylhydrazones, Sn(IV) complex, minimal inhibitory concentration, MIC, Mycobacterium tuberculosis
Бібліографічний опис
Вісник Одеського національного університету = Odesa National University Herald