☆ 4.5 Article

Click synthesis of new 7-chloroquinoline derivatives by using ultrasound irradiation and evaluation of their biological activity

GREEN CHEMISTRY LETTERS AND REVIEWS (2018)

Journal

GREEN CHEMISTRY LETTERS AND REVIEWS

Volume 11, Issue 3, Pages 254-263

Publisher

TAYLOR & FRANCIS LTD

DOI: 10.1080/17518253.2018.1473505

Keywords

Ultrasonic radiation; 7-chloroquinoline; click chemistry; antimalarial activity; and cytotoxicity

Categories

Chemistry, Multidisciplinary Green & Sustainable Science & Technology

Ask authors/readers for more resources

Protocol

Community support

Reagent

Community support

Abstract

This study describes the click synthesis of new 7-chloroquinoline derivatives by using ultrasound irradiation and evaluation of their activity as antimicrobial, antimalarial and the anticancer. All the compounds show moderate antimalarial activity with IC50<100M, six of them showed high antimalarial activity (2, 3, 4, 6, 8 and 9) with IC50<50M. The most active 7-chloroquinoline derivative is a compound (9). Also, the newly synthesized compounds were screened for their antitumor activity towards three lines of cancer cells, MCF-7 (human breast cancer), HCT-116 (colon carcinoma) and Hela (Cervical carcinoma) cell lines. Compounds (3) and (9) exerted the highest activity on all cell lines and showed special selectivity toward MCF-7 cells and the antibacterial screening data showed moderate to good inhibition zone (12.5 +/- 0.63-23.8 +/- 1.5) towards all the tested compounds. Elucidation of the structures of these new pure compounds was based on, IR, H-1 NMR, C-13 NMR, MS and their elemental analysis. [GRAPHICS] .

Authors

I am an author on this paper

Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.5

Not enough ratings

Secondary Ratings

Novelty

-

Significance

-

Scientific rigor

-

Rate this paper

Recommended

Article Chemistry, Medicinal

Synthesis and antimalarial activity of 7-chloroquinoline-tethered sulfonamides and their [1,2,3]-triazole hybrids

Neha Batra, Drishti Agarwal, Ishan Wadi, Chandra Sekhar Tekuri, Rinkoo D. Gupta, Mahendra Nath

Summary: In this study, two series of 7-chloroquinoline-sulfonamide hybrids were synthesized and evaluated for their antimalarial activity. The compounds demonstrated multiple modes of action and significant activity against Plasmodium falciparum. The most promising hybrids could be potential candidates for next-generation antimalarials.

FUTURE MEDICINAL CHEMISTRY (2022)

Add to Collection

Article Chemistry, Organic

Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents

Valter E. Murie, Paula Nicolino, Thiago dos Santos, Guido Gambacorta, Rodolfo H. Nishimura, Icaro S. Perovani, Luciana C. Furtado, Leticia Costa-Lotufo, Anderson Moraes de Oliveira, Ricardo Vessecchi, Ian R. Baxendale, Giuliano C. Clososki

Summary: A library of functionalized quinolines has been prepared through magnesiation of 7-chloroquinolines under mild conditions. The synthesized 4-carbinol quinolines showed interesting antiproliferative properties, with their hydroxyl group serving as a suitable amino group bioisostere. The study also reported a two-step approach for optically active derivatives.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Organic

Antitubercular, Antimalarial Activity and Molecular Docking Study of New Synthesized 7-Chloroquinoline Derivatives

Ankit J. Patel, Manish P. Patel, Amitkumar B. Dholakia, Vishant C. Patel, Darshan S. Patel

Summary: A new series of 7-chloroquinoline derivatives were synthesized by a one-step chloro-amine coupling reaction and showed promising activity against both Plasmodium falciparum and Mycobacterium tuberculosis. These compounds have the potential to be developed as a new broad-spectrum antitubercular and antimalarial agents.

POLYCYCLIC AROMATIC COMPOUNDS (2022)

Add to Collection

Article Pharmacology & Pharmacy

Quinolinotriazole antiplasmodials via click chemistry: synthesis and in vitro studies of 7-Chloroquinoline-based compounds

Guilherme Rocha Pereira, Andreza Cristina Gomes Ferreira, Pedro Henrique de Almeida Simoes Neves, Erick Bruman Souza Gomes, Maria Fernanda Alves do Nascimento, Jordano Augusto Carvalho Sousa, Juliana de Oliveira Santos, Geraldo Celio Brandao, Alaide Braga de Oliveira

Summary: In this study, 38 molecules were synthesized via click chemistry and evaluated for their activity against chloroquine-resistant malaria parasite. Some quinoline derivatives showed high antimalarial activity, low cytotoxicity, and promising potential for the development of new antimalarial drugs.

BRAZILIAN JOURNAL OF PHARMACEUTICAL SCIENCES (2021)

Add to Collection

Article Chemistry, Physical

An in silico-in vitro antimalarial and antimicrobial investigation of newer 7-chloroquinoline based Schiff-bases

Manesh S. Tople, Navin B. Patel, Parth P. Patel, Amit C. Purohit, Iqrar Ahmad, Harun Patel

Summary: Fifteen new 7-chloroquinolines were synthesized using microwave irradiation and conventional methods. These compounds showed good anti-malarial activity, with M1b and M1g exhibiting the most promising results.

JOURNAL OF MOLECULAR STRUCTURE (2023)

Add to Collection

Article Biochemistry & Molecular Biology

Synthesis, antimicrobial activity and cytotoxicity of triphenylphosphonium (TPP) conjugates of 1,2,3-triazolyl nucleoside analogues

Irina Yu Strobykina, Alexandra D. Voloshina, Olga Andreeva, Anastasiia S. Sapunova, Anna P. Lyubina, Syumbelya K. Amerhanova, Mayya G. Belenok, Liliya F. Saifina, Vyacheslav E. Semenov, Vladimir E. Kataev

Summary: Four new TPP conjugates of 1,2,3-triazolyl nucleoside analogues were synthesized and evaluated for their antibacterial, antifungal, and cytotoxic activities. Two lead compounds showed high antibacterial activity against MRSA strains resistant to Ciprofloxacin and Amoxicillin, as well as high cytotoxicity against human cancer cell lines. The bactericidal effect of the lead compounds was not caused by a violation of the integrity of the cytoplasmic membrane of bacteria and their cytotoxic activity is likely associated with apoptosis induction and cell cycle arrest.

BIOORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Physical

Synthesis and cytotoxic activity of 1,2,3-triazoles derived from 2,3-seco-dihydrobetulin via a click chemistry approach

Kinga Kuczynska, Bartlomiej Bonczak, Lucie Rarova, Marie Kvasnicova, Miroslav Strnad, Zbigniew Pakulski, Piotr Cmoch, Marcin Fialkowski

Summary: New cytotoxic derivatives based on the lupane scaffold were synthesized and tested for their activity against cancer cell lines and normal fibroblasts. Some derivatives showed cytotoxic activity against cancer cells but were also toxic to normal cells. One compound exhibited selectivity towards tumor cells without affecting the growth of normal cells.

JOURNAL OF MOLECULAR STRUCTURE (2022)

Add to Collection

Article Biochemistry & Molecular Biology

Favorable Preclinical Pharmacological Profile of a Novel Antimalarial Pyrrolizidinylmethyl Derivative of 4-amino-7-chloroquinoline with Potent In Vitro and In Vivo Activities

Nicoletta Basilico, Silvia Parapini, Sarah D'Alessandro, Paola Misiano, Sergio Romeo, Giulio Dondio, Vanessa Yardley, Livia Vivas, Shereen Nasser, Laurent Renia, Bruce M. Russell, Rossarin Suwanarusk, Francois Nosten, Anna Sparatore, Donatella Taramelli

Summary: The novel pyrrolizidinylmethyl derivative MG3 showed excellent antimalarial activity against drug-resistant parasites, both in vitro and in vivo. The compound exhibited comparable or better efficacy than chloroquine and other quinolines in rodent models of malaria, and its pharmacological profile met the requirements for further development.

BIOMOLECULES (2023)

Add to Collection

Article Chemistry, Multidisciplinary

Supramolecular Click Chemistry for Surface Modification of Quantum Dots Mediated by Cucurbit[7]uril

Katie McGuire, Suhang He, Jennifer Gracie, Charlotte Bryson, Dazhong Zheng, Alasdair W. Clark, Jesko Koehnke, David J. France, Werner M. Nau, Tung-Chun Lee, William J. Peveler

Summary: This study demonstrates that aggregation of fluorescent quantum dot (QD) linked with cucurbiturils (CBs) can be broken-up by including guest molecules, while retaining CBs adsorbed on the surface. At the same time, the QD surface can be modified by the functional tail of the guest, enabling a non-covalent, click-like modification of nanoparticles in aqueous solution. This approach provides divergent routes for nano-architectures with rich functionalities for theranostics and photonics in aqueous systems.

ACS NANO (2023)

Add to Collection

Article Biochemistry & Molecular Biology

Synthesis and Preliminary Evaluation of the Cytotoxicity of Potential Metabolites of Quinoline Glycoconjugates

Monika Dominska, Gabriela Pastuch-Gawolek, Adrian Dominski, Piotr Kurcok, Karol Erfurt

Summary: The design of prodrugs is an important strategy for selective anti-cancer therapies. Glycoconjugates, which consist of three basic building blocks, are frequently used for targeting tumor-specific markers. Research shows that the presence of all three building blocks is necessary for the full activity of glycoconjugates. Additionally, targeted drug delivery using polymer nanocarriers improves the selectivity and effectiveness of the tested compounds.

MOLECULES (2022)

Add to Collection

Article Chemistry, Medicinal

Aggregation, Cytotoxicity and DNA Binding in a Series of Calix[4]arene Amphiphile Containing Aminotriazole Groups

Diana Mironova, Egor Makarov, Islamiya Bilyukova, Kevser Akyol, Elsa Sultanova, Vladimir Evtugyn, Damir Davletshin, Elvina Gilyazova, Emil Bulatov, Vladimir Burilov, Svetlana Solovieva, Igor Antipin

Summary: The study focuses on investigating the aggregation and complexing properties of calixarenes as potential DNA condensation agents for gene delivery. Triazole derivatives of calix[4]arenes 7 and 8 containing monoammonium fragments were synthesized and characterized. The interactions between these compounds and calf thymus DNA were studied, and the cytotoxic properties against cancerous cells were evaluated. Compound 4 showed the highest toxic effect on MCF7 breast adenocarcinoma.

PHARMACEUTICALS (2023)

Add to Collection

Article Chemistry, Multidisciplinary

Containerless Bioorganic Reactions in a Floating Droplet by Levitation Technique Using an Ultrasonic Wave

Teruhiko Matsubara, Kenjiro Takemura

Summary: By using alternative process designs without plastics for chemical and biological reactions, researchers can achieve a more sustainable and risk-free reaction process, benefiting future generations.

ADVANCED SCIENCE (2021)

Add to Collection

Article Biochemistry & Molecular Biology

Synthesis and antioxidant activity of the inulin derivative bearing 1,2,3-triazole and diphenyl phosphate

Lijie Wei, Haishan Sui, Jingjing Zhang, Zhanyong Guo

Summary: A novel inulin derivative (3) bearing 1,2,3-triazole and diphenyl phosphate was successfully synthesized using CuAAC Click chemistry, showing significantly enhanced antioxidant activity compared with inulin. In vitro evaluation revealed strong radical scavenging abilities of the derivative, particularly against hydroxyl radicals and superoxide radicals. The synthetic strategy may offer an effective approach for preparing new inulin antioxidant biomaterials.

INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES (2021)

Add to Collection

Article Biochemistry & Molecular Biology

1,2,3-Triazole derivatives: synthesis, docking, cytotoxicity analysis and in vivo antimalarial activity

Fernanda Valerio Lopes, Pedro Henrique Fazza Stroppa, Juliane Aparecida Marinho, Roberta Reis Soares, Lara de Azevedo Alves, Priscila Vanessa Zabala Capriles Goliatt, Clarice Abramo, Adilson David da Silva

Summary: This study evaluated the antimalarial activity of triazole derivatives, with compound 5 showing promising potential for further development in antimalarial chemotherapy. In vitro and in vivo studies showed that compound 5 had significant parasitemia suppression and minimal cytotoxicity, making it a leading candidate for future research in antimalarial drug development.

CHEMICO-BIOLOGICAL INTERACTIONS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Synthesis, antimalarial and antioxidant activity of coumarin appended 1,4-disubstituted 1,2,3-triazoles

C. P. Kaushik, Manisha Chahal

Summary: A series of biologically interesting coumarin-triazole hybrids were synthesized using click chemistry approach, showing moderate to good antimalarial activity and potent antioxidant activity compared to standard drugs.

MONATSHEFTE FUR CHEMIE (2021)

Add to Collection

Article Biochemistry & Molecular Biology

Ball Milling Assisted Solvent and Catalyst Free Synthesis of Benzimidazoles and Their Derivatives

Taghreed H. EL-Sayed, Asmaa Aboelnaga, Mohamed Hagar

MOLECULES (2016)

Add to Collection

Review Biochemistry & Molecular Biology

Ball Milling Promoted N-Heterocycles Synthesis

Taghreed H. El-Sayed, Asmaa Aboelnaga, Mohamed A. El-Atawy, Mohamed Hagar

MOLECULES (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Schiff base/ester liquid crystals with different lateral substituents: mesophase behaviour and DFT calculations

H. A. Ahmed, M. Hagar, T. H. El-Sayed, R. B. Alnoman

LIQUID CRYSTALS (2019)

Add to Collection

Article Chemistry, Physical

Mesophase behavior and DFT conformational analysis of new symmetrical diester chalcone liquid crystals

M. Hagar, H. A. Ahmed, T. H. El-Sayed, R. Alnoman

JOURNAL OF MOLECULAR LIQUIDS (2019)

Add to Collection

Article Chemistry, Multidisciplinary

Synthesis, Characterization, and Biological Applications of New Series of Azo Triazole Organometallic Derivatives and Their Silver Nanoparticle Forms

Taghreed H. EL-Sayed, Asmaa Aboelnaga

EGYPTIAN JOURNAL OF CHEMISTRY (2020)

Add to Collection

Article Chemistry, Multidisciplinary

A New Type of Synthesis of 1,2,3-Thiadiazole and 1,2,3-Diazaphosphole Derivatives Via-Hurd-Mori Cyclization

Mona A. Hosny, Taghreed H. El-Sayed, Emtithal A. El-Sawi

E-JOURNAL OF CHEMISTRY (2012)

Add to Collection

No Data Available

© Peeref 2019-2024. All rights reserved.