Discovery of Di(het)arylmethane and Dibenzoxanthene Derivatives as Potential Anticancer Agents-Reference-Cited by-同舟云学术

Discovery of Di(het)arylmethane and Dibenzoxanthene Derivatives as Potential Anticancer Agents

Published:2024-06-18 Issue:12 Volume:25 Page:6724
ISSN:1422-0067
Container-title:International Journal of Molecular Sciences
language:en
Short-container-title:IJMS

Author:

Smolobochkin Andrey¹^ORCID,Niyazova Dinara²,Gazizov Almir¹^ORCID,Syzdykbayev Marat²³,Voloshina Alexandra¹^ORCID,Amerhanova Syumbelya¹,Lyubina Anna¹^ORCID,Neganova Margarita¹⁴^ORCID,Aleksandrova Yulia¹⁴^ORCID,Babaeva Olga¹,Voronina Julia⁵^ORCID,Appazov Nurbol²⁶,Sinyashin Oleg¹,Alabugin Igor¹⁷^ORCID,Burilov Alexander¹,Pudovik Michail¹

Affiliation:

1. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str., 8, Kazan 420088, Russia

2. Laboratory of Engineering Profile, Department of Engineering Technology, Korkyt Ata Kyzylorda University, Ayteke bi Str., 29A, Kyzylorda 120014, Kazakhstan

3. Nazarbayev Intellectual School Chemical-Biological Direction in Kyzylorda, Sultan Beybars Str., 6, Kyzylorda 120014, Kazakhstan

4. Institute of Physiologically Active Compounds at Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, Severnij pr., 1, Chernogolovka 142432, Russia

5. N.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii pr., 31, Moscow 119071, Russia

6. Limited Liability Partnership «DPS-Kyzylorda», Amangeldi Str., 112A, Kyzylorda 120014, Kazakhstan

7. Department of Chemistry and Biochemistry, Florida State University, Chieftan Way Str., 95, Tallahassee, FL 32306-3290, USA

Abstract

A family of bifunctional dihetarylmethanes and dibenzoxanthenes is assembled via a reaction of acetals containing a 2-chloroacetamide moiety with phenols and related oxygen-containing heterocycles. These compounds demonstrated selective antitumor activity associated with the induction of cell apoptosis and inhibition of the process of glycolysis. In particular, bis(heteroaryl)methane containing two 4-hydroxy-6-methyl-2H-pyran-2-one moieties combine excellent in vitro antitumor efficacy with an IC50 of 1.7 µM in HuTu-80 human duodenal adenocarcinoma models with a high selectivity index of 73. Overall, this work highlights the therapeutic potential of dimeric compounds assembled from functionalized acetals and builds a starting point for the development of a new family of anticancer agents.

Funder

Ministry of Science and Higher Education of the Russian Federation at the FRC Kazan Scientific Center

non-profit joint-stock company “Korkyt Ata Kyzylorda University”

Publisher

MDPI AG

Link

https://www.mdpi.com/1422-0067/25/12/6724/pdf

Reference40 articles.

1. Global Cancer Statistics 2020: GLOBOCAN Estimates of Incidence and Mortality Worldwide for 36 Cancers in 185 Countries;Sung;CA Cancer J. Clin.,2021

2. Review of cancer from perspective of molecular;Hassanpour;J. Cancer Res. Pract.,2017

3. Natural Products as Sources of New Drugs over the 30 Years from 1981 to 2010;Newman;J. Nat. Prod.,2012

4. Anti-Inflammatory and Anticancer Drugs from Nature;Orlikova;Adv. Nutr. Cancer,2014

5. Natural dimers of coumarin, chalcones, and resveratrol and the link between structure and pharmacology;Menezes;Eur. J. Med. Chem.,2019