scholarly journals One-Pot Three Component Synthesis of 2-(1H-Benzo[d]thiazole-2-yl)- N-Arylbenzamides in Glycerol Medium

2020 ◽  
Vol 32 (6) ◽  
pp. 1343-1351
Author(s):  
Swathi Thumula ◽  
Venkatesan Srinivasadesikan ◽  
Ravi K. Kottalanka ◽  
S. Rex Jeya Rajkumar ◽  
Balajee Ramchandran
Keyword(s):  
Docking Study ◽  
Molecular Docking Study ◽  
One Pot ◽  
Docking Result ◽  
Three Component Reaction ◽  
Antibacterial Target ◽  
Short Time ◽  
A549 Lung ◽  
Glycerol Medium ◽  
Mcf 7

In this work, a series of 2-(1H-benzo[d]thiazole-2-yl)-N-arylbenzamides is synthesized by using diethyl phthalate, anilines and 2-amino-benzenethiol by one-pot three component synthesis in glycerol medium. Phosphoric acid is used as an effective reagent for this one-pot three component reaction. This reaction got completed in a short time, easy workup and gave an excellent yield in glycerol medium. The N-arylbenzamides was found to have significant cytotoxic potentials against various cancer cells viz., A549 (lung cancer), HeLa (cervical cancer) and MCF-7 (breast cancer) using MTT assay. The molecular docking study is also employed to understand the binding mechanism of N-arylbenzamides against the antibacterial target. The docking result shows the binding energy of compound 4a is -8.6 kcal/mol. The binding affinity is a major concern and it shows that Asn and Thr residues have an interaction with compound 4a.

scholarly journals 5-(4-Fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-1H-pyrazole

Molbank ◽  
10.3390/m1197 ◽  
2021 ◽  
Vol 2021 (1) ◽  
pp. M1197
Author(s):  
Jasril Jasril ◽  
Neni Frimayanti ◽  
Yuana Nurulita ◽  
Adel Zamri ◽  
Ihsan Ikhtiarudin ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
Docking Study ◽  
2D Nmr ◽  
Conventional Heating ◽  
Molecular Docking Study ◽  
One Pot ◽  
Three Component Reaction ◽  
Oxidative Aromatization ◽  
Ft Ir ◽  
Native Ligand

A new fluorinated pyrazole, 5-(4-fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-1H-pyrazole was successfully synthesized via a two-step reaction. Firstly, the synthesis of pyrazoline was performed via one-pot three-component reaction under microwave irradiation. Secondly, the synthesis of pyrazole was performed via oxidative aromatization of pyrazoline under conventional heating. The structure of the synthesized compound was confirmed by spectroscopic analysis, including FT-IR, HR-MS, 1D and 2D NMR analysis. Then, molecular docking study showed that the binding affinity of the synthesized compound to human estrogen alpha receptor (ERα) was close to 4-OHT as a native ligand.

scholarly journals Synthesis, In Silico Prediction and In Vitro Evaluation of Antitumor Activities of Novel Pyrido[2,3-d]pyrimidine, Xanthine and Lumazine Derivatives

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 5205
Author(s):  
Samar El-Kalyoubi ◽  
Fatimah Agili
Keyword(s):  
Lung Cancer ◽  
Cancer Progression ◽  
Aromatic Aldehydes ◽  
Docking Study ◽  
Molecular Docking Study ◽  
One Pot ◽  
Three Component Reaction ◽  
Elemental Analyses ◽  
Heterocyclic Derivatives

Ethyl 5-arylpyridopyrimidine-6-carboxylates 3a–d were prepared as a one pot three component reaction via the condensation of different aromatic aldehydes and ethyl acetoacetate with 6-amino-1-benzyluracil 1a under reflux condition in ethanol. Additionally, condensation of ethyl 2-(2-hydroxybenzylidene) acetoacetate with 6-amino-1-benzyluracil in DMF afforded 6-acetylpyridopyrimidine-7-one 3e; a facile, operationally, simple and efficient one-pot synthesis of 8-arylxanthines 6a–f is reported by refluxing 5,6-diaminouracil 4 with aromatic aldehydes in DMF. Moreover, 6-aryllumazines 7a–d was obtained via the reaction of 5,6-diaminouracil with the appropriate aromatic aldehydes in triethyl orthoformate under reflux condition. The synthesized compounds were characterized by spectral (1H-NMR, 13C-NMR, IR and mass spectra) and elemental analyses. The newly synthesized compounds were screened for their anticancer activity against lung cancer A549 cell line. Furthermore, a molecular-docking study was employed to determine the possible mode of action of the synthesized compounds against a group of proteins highly implicated in cancer progression, especially lung cancer. Docking results showed that compounds 3b, 6c, 6d, 6e, 7c and 7d were the best potential docked compounds against most of the tested proteins, especially CDK2, Jak2, and DHFR proteins. These results are in agreement with cytotoxicity results, which shed a light on the promising activity of these novel six heterocyclic derivatives for further investigation as potential chemotherapeutics.

Design, Synthesis, Antimicrobial Evaluation and Molecular Modeling Study of New 2-mercaptoimidazoles (Series-III)

2019 ◽  
Vol 16 (5) ◽  
pp. 512-521 ◽  
Author(s):  
Nidhi Rani ◽  
Randhir Singh
Keyword(s):  
Sulfonic Acid ◽  
Docking Study ◽  
Molecular Docking Study ◽  
One Pot ◽  
Design Synthesis ◽  
Toluene Sulfonic Acid ◽  
Antimicrobial Evaluation ◽  
Bacteria And Fungi ◽  
High Yields ◽  
Antimicrobial Potency

Background: A series of novel substituted 2-mercaptoimidazoles was synthesised efficiently and in high yields using one-pot synthesis from m-hydroxyacetophenones. Methods: The structures of the newly synthesized compounds were established, their molecular activity was investigated against some bacteria and fungi were further validated using molecular docking study. Results: Reaction of o-hydroxyphenacylbromide (2) with substituted aniline and KSCN, in the presence of catalyst p-toluene sulfonic acid afforded 4(a-r) in good yield. The structure of compounds (4a-r) was confirmed by IR, NMR and MS. Conclusion: The compounds exhibited excellent antimicrobial potency against the tested microorganism.

scholarly journals Synthesis, Characterization and Anticancer Evaluation of Nitrogen Substituted 1-(3-Aminoprop-1-ynyl)-4-Hydroxyanthraquinone Derivatives

2021 ◽  
Author(s):  
Nafisa S. Sirazhetdinova ◽  
Dmitry S Baev ◽  
Victor A. Savelyev ◽  
Tatyana S. Golubeva ◽  
Lyubov S. Klimenko ◽  
...  
Keyword(s):  
Cancer Cells ◽  
Sonogashira Reaction ◽  
Secondary Amines ◽  
One Pot ◽  
Standard Drug ◽  
Three Component Reaction ◽  
G Quadruplex ◽  
New Compounds ◽  
Substituted 1 ◽  
Mcf 7

Abstract Anthraquinones are of significant interest due to their biological activity, coloring properties and synthetic applications. Here, we describe a mild and convenient method for modification of 1-ethynyl-4-hydroxyanthraquinone that was obtained from the Sonogashira reaction of 1-hydroxy-4-iodoanthraquinone with alkynes. The copper(I) catalyzed one-pot three component reaction (A3-coupling) of the new 1-ethynyl-4-hydroxyanthraquinone with secondary amines and formaldehyde was the main approach for the synthesis of nitrogen substituted 1-[3-(amino)prop-1-ynyl]-4-hydroxyanthraquinones. The influence of different substituent in the amine on reaction rate and yield has been evaluated. The cytotoxicity of 1-ethynyl-4-hydroxyanthraquinones was evaluated using the conventional MTT assay. Among all the compounds synthesized, anthraquinone-propargylamine derivatives 28, 29, 30 and 34 possess most promising cytotoxic potential towards glioblastoma cancer cells; compounds 14 and 19 shown selectivity towards the prostate cancer cells DU-145, and 18, and 24 – towards breast cancer cells MCF-7. The grown inhibition on these cancer cells of 18 and 24 was comparable to those of standard drug Doxorubicin. Molecular modeling of new compounds in DNA G-quadruplex binding site was performed to help understand the observed SAR trends.

Facile synthesis of new N-sulfonamidyl-4-thiazolidinone derivatives and their biological evaluation

2016 ◽  
Vol 40 (4) ◽  
pp. 3047-3058 ◽  
Author(s):  
Dnyaneshwar D. Subhedar ◽  
Mubarak H. Shaikh ◽  
Firoz A. Kalam Khan ◽  
Jaiprakash N. Sangshetti ◽  
Vijay M. Khedkar ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Molecular Docking ◽  
Antioxidant Properties ◽  
Docking Study ◽  
Biological Evaluation ◽  
Facile Synthesis ◽  
Molecular Docking Study ◽  
One Pot

A one-pot three-component facile synthesis of N-sulfonamidyl-4-thiazolidinone derivatives using a [HDBU][HSO4] reusable ionic liquid was carried out, together with an investigation into their antifungal and antioxidant properties and a molecular docking study.

Virtual Combinatorial Library Design, Synthesis and In vitro Anticancer Assessment of -2-Amino-3-Cyanopyridine Derivatives

2018 ◽  
Vol 21 (2) ◽  
pp. 138-148 ◽  
Author(s):  
Sanal Dev ◽  
Sunil. R. Dhaneshwar ◽  
Bijo Mathew
Keyword(s):  
Virtual Screening ◽  
Cell Lines ◽  
Anticancer Agents ◽  
Topoisomerase Ii ◽  
Docking Study ◽  
Assay Method ◽  
Molecular Docking Study ◽  
Binding Interaction ◽  
Mcf 7

Aim and Objective: For the development of new class of anticancer agents, a series of novel 2-amino-3-cyanopyridine derivatives were designed from virtual screening with Glide program by setting Topoisomerase II as the target. Materials and Methods: The top ranked ten molecules from the virtual screening were synthesized by microwave assisted technique and investigated for their cytotoxic activity against MCF-7 and A- 549 cell lines by using sulforhodamine B assay method. Results: The most active compound 2-amino-4-(3,5-dibromo-4-hydroxyphenyl)-6-(2,4- dichlorophenyl) nicotinonitrile (CG-5) showed significant cytotoxic profile with (LC50 = 97.1, TGI = 29.9 and GI50 = <0.1 µM) in MCF-7 and (LC50= 93.0, TGI= 50.0 and GI50= <7 µM) in A-549 cell lines. A molecular docking study was performed to explore the binding interaction of CG-5with the active site of Topoisomerase II. Conclusion: It can be concluded that halogen substituent pyridine ring was benefit for cytotoxicity.

Novel 4-thiazoline-coumarin hybrid compounds containing sugar moieties: Synthesis, biological evaluation and molecular docking study as antiproliferative agents

2021 ◽  
Author(s):  
Ngoc Toan Vu ◽  
Nguyen Dinh Thanh
Keyword(s):  
Molecular Docking ◽  
Human Liver ◽  
Docking Study ◽  
Biological Evaluation ◽  
Breast Adenocarcinoma ◽  
Molecular Docking Study ◽  
Antiproliferative Agents ◽  
Hybrid Compounds ◽  
Human Liver Cancer ◽  
Mcf 7

A new series of 2,3-4-thiazoline−coumarin hybrid compounds that contained D-glucose and D-galactose moieties (4a-g) were synthesized and evaluated their cytotoxic activity against breast adenocarcinoma (MCF-7), human liver cancer (HepG2), human...

scholarly journals Phospho sulfonic acid: A novel and efficient solid acid catalyst for the one-pot preparation of 2H-indazolo[2,1-b]-phthalazine-triones

2013 ◽  
Vol 78 (4) ◽  
pp. 469-476 ◽  
Author(s):  
Reza Kiasat ◽  
Arash Mouradezadegun ◽  
Jafar Saghanezhad
Keyword(s):  
Sulfonic Acid ◽  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Catalytic Amount ◽  
One Pot ◽  
Solvent Free Conditions ◽  
Three Component Reaction ◽  
The One ◽  
Short Time

The efficient one-pot condensation of aldehyde, dimedone, and phthalhydrazide has been achieved in the presence of a catalytic amount of phospho sulfonic acid as a novel environmentally benign heterogeneous solid acid under solvent-free conditions. A diversified 2H-indazolo[1,2-b]phthalazinetrione derivatives were prepared in good to excellent yields in short time. The economical factors (time, cost, waste etc.) for this three-component reaction hold promise for the future of organic synthesis.

scholarly journals Unexpected Synthesis, Single-Crystal X-ray Structure, Anticancer Activity, and Molecular Docking Studies of Certain 2–((Imidazole/Benzimidazol–2–yl)thio)–1–arylethanones

Crystals ◽  
2020 ◽  
Vol 10 (6) ◽  
pp. 446
Author(s):  
Tarfah Al-Warhi ◽  
Mohamed Said ◽  
Mahmoud El Hassab ◽  
Nada Aljaeed ◽  
Hazem Ghabour ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Molecular Docking ◽  
Single Crystal ◽  
Cell Lines ◽  
Docking Study ◽  
Anticancer Activities ◽  
Molecular Docking Study ◽  
X Ray ◽  
Mcf 7

In connection with our research program concerning development of novel effective benzimidazole-based anticancer candidates, herein we describe a new unexpected synthetic route to obtain a series of 2–((imidazole/benzimidazol2–yl)thio)1–arylethanones endowed with promising anti-breast cancer and Cyclin-dependent kinase 2 (CDK2) inhibitory activities. Contrary to expectations, products for the reaction of 2–mercaptoimidazole/benzimidazole 2a,b with β–keto esters 6a–c were unambiguously assigned as 2–((imidazol/benzimidazol2–yl)thio)1–arylethanones 10a–f based on NMR spectroscopy and single-crystal X-ray crystallographic analyses. In vitro anticancer activities for herein reported imidazole/benzimidazoles 10a–f were assessed through a cell-based assay against human breast cancer T4–7D and MCF–7 cell lines. Benzimidazoles 10d–f exerted better anti-proliferative action towards T4–7D and MCF–7 cell lines than their corresponding imidazole counterparts 10a–c. Furthermore, a molecular docking study suggested CDK2 kinase as a potential enzymatic target for benzimidazoles 10d–f, and investigated their possible binding pattern and interactions within CDK2 active site. Thereafter, benzimidazoles 10d–f were in vitro examined for their CDK2 inhibitory action, where they exerted good activity. Finally, several key ADME and druglikeness properties were predicted by the SwissADME online tool. Interestingly, benzimidazoles 10d–f were found to have no violations in all druglikeness rules (Veber, Lipinski, Ghose, Muegge, and Egan). In addition, they had neither PAINS nor structural alerts (Brenks). In conclusion, benzimidazoles 10d–f demonstrated not only a promising anticancer activities but also an acceptable ADME and physicochemical properties especially benzimidazole 10e.

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