in Wiley Online Library (wileyonlinelibrary.com).New aromatic aldimines, isatine substituted ketimines based on (4,6-dichloro-1,3,5-triazin-2-yl)-hydrazine scaffold and polycyclic fused thiopyranothiazoles formed using hetero-Diels-Alder reactions starting from 4-thioxo-2-thiazolidinones and 5-norbornene-2,3-dicarboxylic acid triazino-derivatives synthetic approach is described. The application of condensation and cyclocondensation reactions of N-nucleophiles and carbonyl agents for synthesis a number of biologically active triazine derivatives is reported. Screening of anticancer activity in vitro yielded the most active compounds 3a, 8b, and 8f for different cell lines.Scheme 2. Synthesis of polycyclic fused thiopyranothiazoles based on (4,6-dichloro-1,3,5-triazin-2-yl)-hydrazine 2. Scheme 1. Synthesis of Schiff bases based on (4,6-dichloro-1,3,5-triazin-2-yl)-hydrazine 2. 1420
Novel heterocyclic dichloronaphthoquinone derivatives have been synthesized by chlorine atom substitution in 2,3-dichloro-1,4-naphthoquinone to pyrazole or pyrimidine fragments. The structures of these compounds have been confirmed by FT-IR, ESI-MS, 1 H-NMR, 13 C-NMR and elementary analysis. Synthesized compounds were evaluated for their anticonvulsant action in a pentylenetetrazole (PTZ)-convulsion model and antidepressant activity in the forced swimming test (FST). All naphthoquinone derivatives at a dose 100 mg/kg indicated anticonvulsant effect in PTZ-induced test at 3 h and 24 h after oral administration. In addition, these compounds possessed prolonged antidepressant properties significantly reducing the duration of immobility time when compared to the reference drug amitriptyline.
The process of aerobic cell respiration includes several consecutive redox reactions. As is known, quinones take an active part in the oxidative phosphorylation process by mediating the electron transfer via a respiratory chain between flavoprotein and cytochrome b, involving energy evolution [ 1 ]. A decrease in the myotic energy results in disruption of the myocardium functioning during ischemia [2] and hypoxia [3]. The energy production in the myocardium depends on the cell oxygen concentration. It was therefore of interest to synthesize some new compounds on the basis of 1,4-naphthoquinone and study their antihypoxic and antiischemic activity.The initial compound was 2,3-dichloro-l,4-naphthoquinone. Interaction of this compound with aspartic and glutamic amino acids at 70~ in the presence of potassium or sodium hydroxide led to compounds (I-III).The synthesized compounds are water-soluble crystalline substances of orange, red, or brown colors. The proposed structures were confirmed by the data of elemental analyses and the IR spectra containing the absorption bands typical of the quinone fragment, aromatic rings, and a secondary amino group conjugated with the quinone nucleus. The IR spectra were measured on a Specord M-40 spectrophotometer using samples prepared by pelletizing with K_Br. The reaction products were partitioned and the purity of products was checked by thin-layer chromatography. The data of elemental analyses agreed with the results of analytical calculations.N-(l,4-dioxo-3-chloro-l,4-dihydronaphth-2-yl)aspart ic acid dipotassium salt Or). To a suspension of 2.27 g (0.01 mole) of 2,3-dichloro-l,4-naphthoquinone in 60 rnl of ethanol was added with stirring at 70~ a solution of 1.34 g (0.01 mole) of Ds acid, 0.03 mole of potassium hydroxide in 5 ml ethanol, and I0 ml of water. The mixture was stirred at 70 -80~ for 1.5 h and filtered. To the filtrate was added 100 ml of water, and the solution was cooled to 0~ and carefully acidified with hydrochloric acid. The red crystals precipitated were filtered, washed with water, and dissolved in methanol. To this solution was added a potassium hydroxide solution in methanol until pH 13 was achieved, upon which compound I was obtained in the form of dark-red crystals.N-(1,4-dioxo-3-chloro-l,4-dihydronaphth-2-yl)aspart ic acid disodium salt (H). Compound II in the form of darkbrown crystals was obtained similarly to compound I, using sodium hydroxide instead of potassium hydroxide.N-(1,4-dioxo-3--ehloro-1,4-dihydronaphth-2-yl)gluta mic acid monopotassium salt (m). Compound III in the form of orange crystals was obtained similarly to compound I: R = CH2COOK, X = K; II: R = CH2COONa, X = Na; HI: R = CH2CH2COOK., X = H.
A new approach to the synthesis of new heterocyclic compounds with triazine and 4-thiazolidone fragments in one molecule is developed. The synthesis methods
Провести дослідження антимікробної та фунгіцидної активностей амінопіразольних похідних 2,3-дихлоро-1,4-нафтохінону та спрогнозувати їхню гостру токсичність. Матеріали та методи дослідження. Протимікробну активність гетероциклічних амінопохідних нафтохінону 3a-d вивчали шляхом дифузії речовини в агар на твердому поживному середовищі та методом серійних розведень. Гостру токсичність для гризунів визначали методом моделювання QSAR, реалізованим в програмному забезпеченні GUSAR. Результати. У роботі досліджено антимікробну та фунгіцидну активності нових гетероциклічних амінопохідних нафтохінону, а також проведено визначення їх in silico гострої токсичності для щурів за чотирма типами введення субстанції. Висновки. Дослідження амінопіразольних похідних нафтохінону дозволило виявити сполуки, які проявляють високу антимікробну активність по відношенню до тест-культури Candida tenuis, а саме: 2-хлоро-3-((1-метил-1Н-піразол-4-іл)аміно)нафтален-1,4-діон 3a та 2-хлоро-3-((1-метил-1Н-піразол-3іл)аміно)нафтален-1,4-діон 3b. Встановлено, що усі синтезовані сполуки проявляють вибіркову бактеріо-і фунгістатичну активності. Визначено методом QSAR нетоксичну сполуку 3с при внутрішньочеревному шляху введення, а також нетоксичну сполуку 3d при підшкірному шляху введення Ключові слова: амінопіразолопохідні 2,3-дихлоро-1,4-нафтохінону, первинний біологічний скринінг, програма GUSAR
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