Acute toxicity and hypoglycemic activity of 7-chloro-4-thiosubstituted quinoline

Bogdan, Ana; Brazhko, Serhiy; Labenskaya, Iryna; Brazhko, Oleksandr

doi:10.26661/2410-0943-2019-1-03

Cited by 3 publications

(4 citation statements)

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“…As of now, systematic studies have been conducted to purposefully search for bioactive molecules among derivatives (quinolin-4ylthio)carboxylic acids that show antiradical, antihypoxic, cyto-and radioprotective effects. [13][14][15] They are effective ROS "traps", that have a positive effect on the cells metabolitotropic properties and restore their status. 9,16 The introduction of halogens in the 6 th position of the quinoline cycle (Fig.…”

Section: Quininementioning

confidence: 99%

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Design, Synthesis and Biological Activity of the 4-Thioquinoline Derivative

Bohdan,

Romanenko,

Zavhorodnii

et al. 2023

ChChT

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One of the promising areas in the creation of bioregulators is the modeling of compounds that combine several pharmacophores. The design of new highly efficient and low-toxic cytoprotectors is largely based on the derivatives of nitrogen-containing heterocycles, and quinoline plays a significant role among these compounds. The researchers evaluated the toxicity of the tested compounds in silico, in vitro, and in vivo, which allowed determiningseveral factors that affect the level of toxic action of 4-thioquinoline derivatives and the direction of non-toxic substances in this sequence. The studied 4-thioquinolines showed a moderate antiradical action in the experiment, inferior to the reference antioxidant Acetylcysteine. The most active compounds are 7-chloro-4-thioquinoline derivatives with propanoic acid residues in the 4th position. 2-(7-chloroquinolin-4-ylthio)propanoic acid and sodium salt of 2-amino-3-((7-chloroquinolin-4-yl)thio)propanoic acid showed the most promising results and their antioxidant action was higher than Tiotriazolin (the comparator) by 27 % and 41 %, respectively. The studied compounds showed a protective effect under H2O2-induced oxidative stress against male sperm according to the main indicators of sperm fertility. It was found that the compounds withresidues of succinic acid, cysteamine, or cysteine in the molecule structure are not inferior to reference drugs. On average, 2-((7-chloroquinolin-4-yl)thio)succinic acid and 2-((quinolin-4-yl)thio)ethanaminedihydrochloride exceeded the comparison drug Acetylcysteine and were on a par with the effect of Ascorbic acid.

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Section: Quininementioning

confidence: 99%

“…The compounds were prepared according to a previously described methods. 7,15,19,[21][22][23] 2.3.2. ((Quinolin-4-yl)thio)сarboxylic acids ( 2a,b,g-I, 4b) and its salts ( 3a,d, 5a,b).…”

Section: Generalmentioning

confidence: 99%

Design, Synthesis and Biological Activity of the 4-Thioquinoline Derivative

Bohdan,

Romanenko,

Zavhorodnii

et al. 2023

ChChT

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“…Перелік обмежень щодо використання лабораторних тварин для попередньої оцінки потенційних лікувальних засобів містить етичні питання [18], але економічні та часові витрати однаково важливі, що значно збільшує вартість і тривалість дослідження. Тим часом, на сьогоднішній день, існує достатня кількість добре стандартизованих методів, зокрема із застосуванням клітинних культур різної природи, що дозволяє отримати адекватну інформацію щодо впливу препаратів на метаболізм клітин [1].…”

Section: вступunclassified

“…Усі сполуки синтезовано за відомою методикою [6] з відповідними фізико-хімічними та спектральними даними, які відповідають літературним. Сполуки одержані згідно з попередньою методикою [1,3,4,5,14].…”

Section: матеріали та методиunclassified

Cytotoxic activity of 7-R-4-substituted quinoline

Kozyr¹,

Romanenko²

2022

Rep. of Vinnytsia Nation. Med. Univ.

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Annotation. Quinoline derivatives are important compounds for chemical synthesis and the development of new drugs and pesticides. The practical application of a number of substances with a quinoline heterocycle in medical practice and agriculture is well known. Quinoline compounds exhibit a wide range of biological effects, including cytotoxic activity. Phytotoxic (cytotoxic) activity of 15 4-substituted quinoline derivatives were studied and compared with reference drugs. 7-R-4-substituted quinoline derivatives were tested by root test on Cucumis sativus L. seedlings at different concentrations. Distilled water was used as reference in the control experiment. During the experiment, all factors were taken into account to create equal conditions for all studied elements. The obtained results were processed using the program “STATISTICA® for Windows 6.0” (StatSoft Inc, No. АХХР712D833214FAN5) by methods of variational statistics using the Student’s t-test. 7-R-4-substituted quinoline derivatives turned out to be predominantly cytotoxic compounds, that corresponds to the “structure-action” dependence between the structure of investigated compounds and their biological activity. All tested compounds have a pronounced phytotoxic effect at the concentration of 500 μg/ml. The most pronounced cytotoxic effect was recorded among the (heteryl)cysteamine derivatives – β-(quinolin-4-yl)cysteamine dihydrochloride, β-(7-chloroquinolin-4-yl)cysteamine dihydrochloride, 3-((7-chloroquinolin-4-yl)thio)propanoic acid hydrochloride. Derivatives of (heterylthio)acetic acids have shown growth-promoting effects at low concentrations. Thus, 2-(quinolin-4-ylthio)- and 2-(7-chloroquinolin-4-ylthio) acetic acids have shown the most active effect (50-250% compared to control group) at concentrations of 1-20 μg ml. Sodium 3-((7-chloroquinolin-4-yl)thio)propanoate has indicators that exceed the control by 7-60%, with the most effective growth of the main root of seedlings by 30% among all studied substances at the concentration of 100 μg/ml compared to control group. Some compounds have cytotoxic activity that can be used in crop production as growth regulators of agricultural plants.

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Influence of derivatives of 2-((6-r-quinolin-4-yl)thio)acetic acid on rhizogenesis of Paulownia clones

Zavhorodnii¹,

Derevianko²,

Shkopynska

et al. 2022

Regul. Mech. Biosyst.

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In recent years, the demand for effective and low-toxic stimulators of rhizogenesis, which are used in microclonal propagation of plants, has been increasing in Ukraine. One of the promising directions in the search for effective compounds is molecular modeling based on known natural and synthetic compounds. The development of new highly effective and low-toxic biologically active compounds is largely based on derivatives of nitrogen-containing heterocycles, and quinoline occupies a significant place among them. Modern methods of chemometric analysis make it possible to find certain regularities in the "chemical structure – biological activity" and to select the most promising compounds for experimental research. The values of lipophilicity log P for neutral forms and the value of the distribution coefficient log D at pH = 7 were obtained by quantum chemical calculation. The values of log P and log D of the studied compounds are in the most favourable interval for overcoming the biological membranes of the cells of the root system, depending on the pH of the environment. According to Lipinski’s "rule of five", all studied compounds can show high biological activity. The toxicity of compounds of 2-((6-R-quinolin-4-yl)thio)acetic acid derivatives was evaluated by computer programs and experimentally. Among the derivatives of 2-((6-R-quinolin-4-yl)thio)acetic acid, the most toxic compounds were those that did not have alkoxy substituents in the 6th position of the quinoline ring. Sodium salts are more toxic than the corresponding acids. This is due to an increase in the bioavailability of ionized compounds. Derivatives of 2-((6-R-quinolin-4-yl)thio)acetic acid (sodium salt of 2-((quinolin-4-yl)thio)acetic acid (QAC-5) showed the greatest toxic effect on the model of the study of progressive sperm motility) and 2-((quinolin-4-yl)thio)acetic acid (QAC-1), which will reduce this indicator by 15–20% compared to intact. The toxicity assessment of the studied compounds made it possible to determine a number of factors of the structure of molecules which affect the level of toxic action of 2-((6-R-quinolin-4-yl)thio)acetic acid derivatives and the directions of creation of non-toxic growth stimulants in this series. The impact on rhizogenesis during microclonal reproduction in vitro in explants Paulownia clone 112 and further adaptation of microplants in vivo hybrid molecules of quinoline and acetic acid, which are analogues of known growth stimulants, was studied. A number of factors influencing the level of influence on rhizogenesis of the action of derivatives of 2-((6-R-quinolin-4- yl)thio)acetic acid and directions of creation of highly active substances in this series was defined. The studied compounds showed a high stimulating effect on rhizogenesis in vitro in Paulownia explants. It was established that the sodium salt of 2-((quinolin-4-yl)thio)acetic acid was the greatest stimulator of rhizogenesis compared to the corresponding original acid. The presence of alkoxy groups in the 6th position and methyl in the 2nd position of the quinoline ring of 2-((6-R-quinolin-4-yl)thio)acetic acid reduced the activity of the compounds. The selection of new effective, low-toxic, less expensive substances was carried out for further testing as potential stimulators of rhizogenesis for microclonal propagation of plants.

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Acute toxicity and hypoglycemic activity of 7-chloro-4-thiosubstituted quinoline

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Cited by 3 publications

References 0 publications

Design, Synthesis and Biological Activity of the 4-Thioquinoline Derivative

Design, Synthesis and Biological Activity of the 4-Thioquinoline Derivative

Cytotoxic activity of 7-R-4-substituted quinoline

Influence of derivatives of 2-((6-r-quinolin-4-yl)thio)acetic acid on rhizogenesis of Paulownia clones

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