Toward “E‐Ring‐Free” Lamellarin Analogues: Synthesis and Preliminary Biological Evaluation

Toward “E‐Ring‐Free” Lamellarin Analogues: Synthesis and Preliminary Biological Evaluation Full article

Journal

ChemBioChem
ISSN: 1439-7633 , E-ISSN: 1439-4227

Output data

Year: 2023, Volume: 24, Number: 11, Article number : e202300161, Pages count : DOI: 10.1002/cbic.202300161

Authors

Rusanov Daniil A ^1,2 , Mutasim Alfadul Samah ¹ , Portnyagina Ekaterina Yu ¹ , Silyanova Eugenia A ² , Kuznetsov Nikita A ^2,3 , Podpovetny Kirill E ^2,3 , Samet Alexander V ² , Semenov Victor V ² , Babak Maria ¹

Affiliations

1	Drug Discovery Lab, Department of Chemistry, City University of Hong Kong, 83 Tat Chee Avenue, Hong Kong, 999077 Hong Kong SAR
2	Laboratory of Medicinal Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Avenue 47, 119991 Moscow, Russian Federation
3	D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya sq., 125047 Moscow, Russian Federation

Since the discovery of anticancer properties of a naturally occurring hexacyclic marine alkaloid Lamellarin D, the attempts have been made to prepare its synthetic analogues and elucidate the effects of each structural component on their activity profile. While F-ring-free, A-ring-free and B-ring-open lamellarins are known, E-ring-free analogues have never been investigated. In this work, we developed a facile and straightforward synthetic method toward E-ring-free lamellarin analogues based on the [3+2]-cycloaddition. For the first time, we prepared several pentacyclic lamellarin analogues without E-ring in their structure and assessed their cytotoxicity in a panel of cancer cell lines in comparison with several hexacyclic lamellarins. E-ring-free lamellarins were devoid of cytotoxicity due to their poor solubility in cellular environment.

Rusanov D.A. , Mutasim Alfadul S. , Portnyagina E.Y. , Silyanova E.A. , Kuznetsov N.A. , Podpovetny K.E. , Samet A.V. , Semenov V.V. , Babak M.
Toward “E‐Ring‐Free” Lamellarin Analogues: Synthesis and Preliminary Biological Evaluation
ChemBioChem. 2023. V.24. N11. e202300161 . DOI: 10.1002/cbic.202300161 WOS Scopus OpenAlex

Web of science:	WOS:000979519200001
Scopus:	2-s2.0-85154605272
OpenAlex:	W4365136002

DB	Citing
OpenAlex	11
Scopus	10
Web of science	11