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.

Design, Synthesis, In vitro Cytotoxic Activity Evaluation, and Study of Apoptosis Inducing Effect of New Styrylimidazo[1,2-a]Pyridines as Potent Anti-Breast Cancer Agents

2019 ◽  
Vol 19 (2) ◽  
pp. 265-275 ◽  
Author(s):  
Faeze Khalili ◽  
Sara Akrami ◽  
Malihe Safavi ◽  
Maryam Mohammadi-Khanaposhtani ◽  
Mina Saeedi ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Cytotoxic Activity ◽  
High Yield ◽  
Breast Cancer Cell Lines ◽  
Pyridine Derivatives ◽  
One Pot ◽  
Standard Drug ◽  
Three Component Reaction ◽  
Anti Cancer

Background: This paper reports synthesis, cytotoxic activity, and apoptosis inducing effect of a novel series of styrylimidazo[1,2-a]pyridine derivatives. Objective: In this study, anti-cancer activity of novel styrylimidazo[1,2-a]pyridines was evaluated. Methods: Styrylimidazo[1,2-a]pyridine derivatives 4a-o were synthesized through a one-pot three-component reaction of 2-aminopyridines, cinnamaldehydes, and isocyanides in high yield. All synthesized compounds 4a-o were evaluated against breast cancer cell lines including MDA-MB-231, MCF-7, and T-47D using MTT assay. Apoptosis was evaluated by acridine orange/ethidium bromide staining, cell cycle analysis, and TUNEL assay as the mechanism of cell death. Results: Most of the synthesized compounds exhibited more potent cytotoxicity than standard drug, etoposide. Induction of apoptosis by the most cytotoxic compounds 4f, 4g, 4j, 4n, and 4m was confirmed through mentioned methods. Conclusion: In conclusion, these results confirmed the potency of styrylimidazo[1,2-a]pyridines for further drug discovery developments in the field of anti-cancer agents.

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.

One-pot synthesis of 3-aminofurans using a simple and efficient recyclable CuI/[bmim]PF6 system

2021 ◽  
Author(s):  
Guguloth Veeranna ◽  
Ramesh Balaboina ◽  
Narasimha Swamy Thirukovela ◽  
Ravindhar Vadde
Keyword(s):  
Secondary Amines ◽  
Terminal Alkynes ◽  
One Pot ◽  
One Pot Synthesis ◽  
System P ◽  
Three Component Reaction ◽  
The One

The one-pot three-component reaction of several 2-ketoaldehdyes, secondary amines and terminal alkynes to access 3-aminofurans was proceeded well in [bmim][PF6] using a simple and cheap CuI catalyst. The resulted 3-aminofuran...

scholarly journals Docking studies, synthesis, characterization, and cytotoxicity activity of new bis-chalcones derivatives

2021 ◽  
Vol 8 (4) ◽  
pp. 4294-4305
Author(s):  
Mohammad Murwih Alidmat ◽  
Melati Khairuddean ◽  
Salizawati Muhamad Salhimi ◽  
Mohammad Al-Amin
Keyword(s):  
Inhibitory Concentration ◽  
Data Bank ◽  
2D Nmr ◽  
Docking Studies ◽  
Standard Drug ◽  
Discovery Studio ◽  
Cytotoxicity Activity ◽  
Diphenyl Tetrazolium Bromide ◽  
New Compounds ◽  
Mcf 7

Introduction: A bis-chalcones were prepared by the reaction of terephthalaldehyde with 3-acetyl-2,5-dichlorothiophene or 3-acetyl- 5-chlorothiophene and reaction cyclo ketone derivatives with phenyl aldehyde derivatives in good yields. Methods: The molecular docking studies were conducted using the Discovery Studio (DSv4.5) and MG. Tools installed in Window 10. The cancer receptor (3ERT) was downloaded from the protein data bank (PDB). All new compounds were characterized by IR, 1H-NMR, 13C-NMR, 2D-NMR, and CHN elemental analysis. The anticancer activity of the synthesized compounds was determined using MTT (3-(4, 5- dimethylthiazol-2-yl)-2, 5-diphenyl tetrazolium bromide) reduction assay against MCF-7 cells, and then the minimum inhibitory concentration (IC50) was determined with the reference of the standard drug tamoxifen. Results: The results showed that compound 6 showed more potent activity in inhibiting growth on both types of MCF-7 compared to reference tamoxifen.    

scholarly journals G-Quadruplex Binders Induce Immunogenic Cell Death Markers in Aggressive Breast Cancer Cells

Cancers ◽  
2019 ◽  
Vol 11 (11) ◽  
pp. 1797 ◽  
Author(s):  
Sarah Di Somma ◽  
Jussara Amato ◽  
Nunzia Iaccarino ◽  
Bruno Pagano ◽  
Antonio Randazzo ◽  
...  
Keyword(s):  
T Cell ◽  
Cancer Cells ◽  
T Cell Activation ◽  
Breast Cancer Cells ◽  
Cell Activation ◽  
G1 Phase ◽  
Immunogenic Cell Death ◽  
G Quadruplex ◽  
M Phase ◽  
Mcf 7

Background: DNA G-quadruplex (G4) structures represent potential anti-cancer targets. In this study, we compared the effect of two G4-targeting compounds, C066-3108 and the gold standard BRACO-19. Methods: In breast and prostate cancer cells, cytotoxicity induced by both molecules was measured by a sulforhodamine B assay. In breast cancer cells, cycle, apoptosis, the formation of G4 structures, calreticulin and high mobility group box 1 (HMGB1), as well as T cell activation, were analyzed by flow cytometry and adenosine triphosphate (ATP) by luminescence. Results: Both ligands inhibited cell survival and induced DNA damage. In MCF-7 cells, G4 ligands increased the subG0/G1 phase of the cell cycle inducing apoptosis and reduced intracellular ATP. In untreated MCF-7 cells, we observed a slight presence of G4 structures associated with the G2/M phase. In MDA-MB231 cells, G4 ligands decreased the G1 and enhanced the G2/M phase. We observed a decrease of intracellular ATP, calreticulin cell surface exposure and an increase of HMGB1, accompanied by T cell activation. Both compounds induced G4 structure formation in the subG0/G1 phase. Conclusions: Our data report similar effects for both compounds and the first evidence that G4 ligands induce the release of danger signals associated with immunogenic cell death and induction of T cell activation.

The Discovery of Ultrasound Irradiation as a Useful Tool for Accelerating Petasis Three-component Reaction: Synthesis of α-Arylglycines

2018 ◽  
Vol 15 (2) ◽  
pp. 256-266 ◽  
Author(s):  
Fan Yun ◽  
Chunhui Cheng ◽  
Jingxuan Li ◽  
Pingwah Tang ◽  
Qipeng Yuan
Keyword(s):  
Reaction Time ◽  
Glyoxylic Acid ◽  
Reaction Times ◽  
Ultrasound Irradiation ◽  
Secondary Amines ◽  
One Pot ◽  
Petasis Reaction ◽  
Three Component Reaction ◽  
Wide Range ◽  
High Yields

Aim and Objective: α-Arylglycines belong to an important class of non-proteinogenic amino acids. Petasis 3-component, one-pot reaction lends itself to be suitable for the synthesis of α-Arylglycines. Because of the low reactivity, Petasis reaction requires long reaction time. Our objective is to use ultrasound irradiation to accelerate this versatile Petasis' synthesis of α-Arylglycines. Materials and Methods: Ultrasound irradiation as a physical tool to accelerate the Petasis 3-component reaction without any auxiliary catalyst can significantly shorten the reaction time. The operation is simple. It can be applied to a wide range of substrates. In order to highlight the remarkable utility of the ultrasound in Petasis reaction, we have compared side-by-side the reactivity between the reaction with ultrasound and the one without ultrasound. Results: Using ultrasound, the reaction times of Petasis reactions with various amine substrates including primary and secondary amines, heterocyclic amines, with a wide variety of boronic acids having different substituents (activating and deactivating groups) in the phenyl rings, and with glyoxylic acid and salicylic aldehyde were shortened from 5 to more than 20-fold. Conclusion: We have discovered the first examples of an efficient ultrasound-promoted approach for Petasis reaction to prepare a series of α-arylglycines in high yields and in excellent purities. The low reactivity of the reactions in this study were significantly enhanced by the ultrasound irradiation. By virtue of the acceleration and the operational simplicity, the present ultrasound assisted Petasis reaction can find applications in the synthetic areas of the already widely used Petasis three-component reaction.

Assembly of N,N-disubstituted-N′-arylureas via a copper-catalyzed one-pot three-component reaction of aryl bromides, potassium cyanate, and secondary amines

Tetrahedron ◽  
2013 ◽  
Vol 69 (26) ◽  
pp. 5326-5330 ◽  
Author(s):  
Hongfei Yin ◽  
Bing Chen ◽  
Xiaojing Zhang ◽  
Xinye Yang ◽  
Yihua Zhang ◽  
...  
Keyword(s):  
Secondary Amines ◽  
One Pot ◽  
Aryl Bromides ◽  
Three Component Reaction

Selective synthesis and biological activity of triazine-porphyrins as potential anti-cancer agents

2010 ◽  
Vol 14 (02) ◽  
pp. 123-127 ◽  
Author(s):  
Shen-Chu Xiao ◽  
Chao-Zhou Liu ◽  
Wu-Kun Liu ◽  
Wen-Zhong Xie ◽  
Wei-Ying Lin ◽  
...  
Keyword(s):  
Hydroxyl Group ◽  
Selective Synthesis ◽  
One Pot ◽  
Similar Activity ◽  
H Nmr ◽  
Porphyrin Derivatives ◽  
Anti Cancer ◽  
New Compounds ◽  
Mcf 7

Ten new triazine-porphyrin derivatives were synthesized using a simple one-pot procedure from the reaction of tetraphenylporphyrin bearing a hydroxyl group with 2,4,6-trichloro-1,3,5-triazine, and then with amines or alcohols. The structures of the products were characterized by 1H NMR, LC/MS, UV-vis and elemental analysis. The cytotoxic activity of the triazine-porphyrin derivatives was evaluated in vitro against MCF-7 cell. All new compounds showed similar activity against MCF-7 cells in the absence of light when compared to 5-fluorouracil and hematoporphyrin.

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