Synthesis and Anticancer Evaluation of Benzimidazole Derivatives Having Norbornene/Dibenzobarrelene Skeletons and Different Functional Groups

Çapan, İrfan; Servi, Süleyman; Dalkılıç, Semih; Dalkılıç, Lütfiye Kadıoğlu

doi:10.1002/slct.202004034

Cited by 8 publications

(3 citation statements)

References 24 publications

(45 reference statements)

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“…[10] In our previous studies, we focused on the synthesis of new benzimidazole derivatives, [11] some physical properties determination, [12] and their biological activities investigation, especially as HSP90 inhibitors. [2,13] In the continuation of our studies on biologically active benzimidazole derivatives, the microwave-irradiation synthesis methods and theoretical re-search results of new 1,3,4-thiadiazole and 1,2,4-triazole derivatives containing unsubstituted benzimidazole were reported for the first time in this study. All reactions which require heating were performed by both conventional and microwave-assisted methods.…”

Section: Introductionmentioning

confidence: 82%

“…It is considered an important bioactive heterocyclic building block for the discovery of new pharmacological active agents in medicinal chemistry, such as antimicrobial, antiviral, antidiabetic, and anticancer activity. [2] Besides, benzimidazoles are remarkably effective compounds, extensive biochemical and pharmacological studies have confirmed that these molecules are effective against various strains of micro-organisms. [3] 1,3,4-thiadiazole and 1,2,4-triazole are important five-membered nitrogen-containing heterocyclic compounds with a wide range of applications in organic synthesis and pharmaceutical chemistry.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, DFT Study, Molecular Docking and Drug‐Likeness Analysis of the New Hydrazine‐1‐Carbothioamide, Triazole and Thiadiazole Derivatives: Potential Inhibitors of HSP90

Çapan

Servi²,

Yıldırım

et al. 2021

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In this research, the new hydrazine-1-carbothioamides (IC32 and IC34) having unsubstituted benzimidazole skeleton were converted to 1, 2, 4-triazole derivatives (IC42 and IC44) by Ncyclization reaction using the microwave-assisted synthesis method in the basic medium with high efficiency in a short time. 2-Amino-1,3,4-thiadiazole derivatives (IC52 and IC54) were obtained from the carbothioamides in the acidic medium by S-cyclization using the conventional method. The structure of all compounds was confirmed by FT-IR, 1 H NMR, and 13 C NMR spectroscopic techniques. The optimized structures, theoretical NMR shielding values in DMSO-d 6 solvent, the frontier molecular orbital, molecular electrostatic potential, and non-linear optical properties of these molecules were calculated in the Gaussian 09 W package program by using DFT method/B3LYP function and 6-311 + + G (d, p) basis set. All calculations except NMR calculations were performed in the gas phase and the obtained results were interpreted within the related sections. The discovery of new drugs is of great importance in combating health problems and improving the quality of human life.In the light of this information, molecular docking with Autodock Vina and physicochemical calculations with the SwissADME server were performed at the end of the article. Therefore, the inhibiting potential of the ligands containing different groups in their structure was investigated for the first time in this study.

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Section: Introductionmentioning

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Synthesis, DFT Study, Molecular Docking and Drug‐Likeness Analysis of the New Hydrazine‐1‐Carbothioamide, Triazole and Thiadiazole Derivatives: Potential Inhibitors of HSP90

Çapan

Servi²,

Yıldırım

et al. 2021

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“…Два разных ангидрида, содержащие фрагменты норборнена и дибензобаррелена, были синтезированы в результате реакций циклоприсоединения Д-А с использованием диенов, таких как антрацен и циклопентадиен, и диенофилов, таких как малеиновая кислота и малеиновый ангидрид [3]. Из этих ангидридов были получены новые производные бензимидазола, несущие карбоксамидные, гуанидиновые и циклические имидные функциональные группы.…”

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Biologically Active Preparations Based on Norbornene Derivatives

Гасанов¹,

Аюбов²,

Гаджиева³

et al. 2022

Вестник Тверского Государственного Университета. Серия: Химия

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Представлены результаты исследований в области изучения биологически активных свойств производных норборненового ряда. Показано, что многие из норборнен содержащих производных входят в состав лекарственных препаратов, петидов и полипептидов, коферментов, витаминов и других биологически активных соединений. Сообщается, что соединения норборенового ряда обладают антимикробными, антифунгальными, антитромбоцитными, противоопухолевыми и целым рядом других свойств. Кроме того, показаны результаты собственных исследований авторов.. Осуществлен синтез рацемических и оптически активных форм моноэфиров бицикло(2.2.1)-гепт-5-ен-2,3-дикарбоновой кислоты. Авторы отмечают, что исходными соединениями для синтеза целевых продуктов были циклопентадиен и соответствующие моноэфиры эндиковой кислоты. Для получения оптически активных форм этих соединений использована асимметрическая реакция Дильса-Альдера в присутствии хиральных катализаторов. В качестве тест-культур были использованы грамположительные (золотистый стафилококк), грамотрицательные (кишечная палочка, синегнойная палочка) бактерии, а также дрожжеподобные грибы рода Кандида. Для изучения антимикробной активности использовали метод серийных разведений. Осуществлено сравнение антимикробной и антифунгальной активности полученных соединений с контрольными препаратами, широко применяемыми в медицинской практике (риванол, фурацилин, карболовая кислота, хлорамин). Изучена взаимосвязь строения и биологической активности синтезированных соединений. Показано, что оптически активный изомер н-пропилового моноэфира норборнендикарбоновой кислоты обладает более высокой антимикробной и антифунгальной активностью по сравнению с его рацемическим аналогом. По биологичееской активности сравниваемые соединения можно расположить в следующем порядке: оптически активный н-пропиловый моноэфир норборнендикарбоновой кислоты > его рацемический аналог > контрольный препарат (этанол). The results of research in the field of studying the biologically active properties of derivatives of the norbornene series are presented. It has been shown that many of the norbornene-containing derivatives are included in drugs, peptides and polypeptides, coenzymes, vitamins, and other biologically active compounds. It is reported that compounds of the norborene series have antimicrobial, antifungal, antiplatelet, antitumor and a number of other properties. In addition, the results of the authors' own research are shown. In particular, the synthesis and study of the biological activity of monoesters of norbornene dicarboxylic acid against various pathogenic microorganisms are reported. The synthesis of racemic and optically active forms of bicyclo(2.2.1)-hept-5-ene-2,3-dicarboxylic acid monoesters has been carried out. The authors note that the starting compounds for the synthesis of the target products were cyclopentadiene and the corresponding monoesters of endic acid. To obtain optically active forms of these compounds, the asymmetric Diels-Alder reaction in the presence of chiral catalysts was used. Gram-positive ( Staphylococcus aureus ), gram-negative ( Escherichia coli, Pseudomonas aeruginosa ) bacteria, as well as yeast-like fungi of the genus Candida, were used as test cultures. To study the antimicrobial activity, the serial dilution method was used. Comparison of the antimicrobial and nattifungal activity of the obtained compounds with control drugs widely used in medical practice (rivanol, furacilin, carbolic acid, chloramine) is carried out. For a more visual comparison of the bioactivity of the compounds under study, a graphical dependence is presented in the coordinates: exposure time (min) - concentration of an aqueous solution (mg/ml). The relationship between the structure and biological activity of the synthesized compounds has been studied. It was shown that the optically active isomer of n -propyl monoester of norbornene-dicarboxylic acid has a higher antimicrobial and antifungal activity as compared to its racemic analog. According to their biological activity, the compared compounds can be arranged in the following order: optically active n-propyl monoester of norbornene dicarboxylic acid > its racemic analogue > control drug (ethanol). Based on the results obtained, the synthesized compounds - monoesters of norbornene dicarboxylic acids are recommended for use as antiseptic drugs in medical practice.

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Regularities of the heterogeneous catalytic hydrogenation of 5-vinyl-2-norbornene

et al. 2022

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Synthesis and Anticancer Evaluation of Benzimidazole Derivatives Having Norbornene/Dibenzobarrelene Skeletons and Different Functional Groups

Cited by 8 publications

References 24 publications

Synthesis, DFT Study, Molecular Docking and Drug‐Likeness Analysis of the New Hydrazine‐1‐Carbothioamide, Triazole and Thiadiazole Derivatives: Potential Inhibitors of HSP90

Synthesis, DFT Study, Molecular Docking and Drug‐Likeness Analysis of the New Hydrazine‐1‐Carbothioamide, Triazole and Thiadiazole Derivatives: Potential Inhibitors of HSP90

Biologically Active Preparations Based on Norbornene Derivatives

Regularities of the heterogeneous catalytic hydrogenation of 5-vinyl-2-norbornene

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