Cannabidiol (CBD) is a nonpsychoactive cannabinoid derived from and its potential therapeutic effects extend beyond its well-known antiepileptic properties. Exploring CBD and its analogues as anticancer agents has gained significant attention in recent years. In this study, a series of novel ring-annulated analogues of CBD with oxazinyl moiety were synthesized and evaluated for their antiproliferative effect. The analogues and demonstrate promising activity against breast and colorectal cancer. Furthermore, mechanistic insights revealed that the identified candidates arrest the G1 phase of the cell cycle and induce apoptosis via the mitochondrial pathway in breast cancer cell lines. Notably, CBD ring-annulated analogues or exhibit enhanced solubility, better metabolic stability, and lowered cytochrome P450 (CYP) inhibition liability compared to CBD. These multifaceted attributes highlight the potential of cannabinoid-based candidates for further preclinical development.
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http://dx.doi.org/10.1021/acsmedchemlett.4c00233 | DOI Listing |
ACS Med Chem Lett
November 2024
Natural Product & Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine (CSIR-IIIM), Canal Road, Jammu 180001, India.
Cannabidiol (CBD) is a nonpsychoactive cannabinoid derived from and its potential therapeutic effects extend beyond its well-known antiepileptic properties. Exploring CBD and its analogues as anticancer agents has gained significant attention in recent years. In this study, a series of novel ring-annulated analogues of CBD with oxazinyl moiety were synthesized and evaluated for their antiproliferative effect.
View Article and Find Full Text PDFEur J Med Chem
June 2015
Department of Organic Chemistry, Faculty of Chemistry, Jagiellonian University, Ingardena 3 St, 30-060 Kraków, Poland.
This review article is an effort to summarize recent developments in researches providing uracil derivatives with promising biological potential. This article also aims to discuss potential future directions on the development of more potent and specific uracil analogues for various biological targets. Uracils are considered as privileged structures in drug discovery with a wide array of biological activities and synthetic accessibility.
View Article and Find Full Text PDFSteroids
September 2014
Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland. Electronic address:
A simple method for the synthesis of yet unknown 5E-vitamin D3 analogs with an additional six-membered ring connecting C-6 and C-19 was developed. Ring-closing metathesis (RCM) was used for efficient formation thereof from the corresponding 5E-isomers of 6-alkenyl vitamin D3 compounds which in turn were prepared from the 6-oxo-3,5-cyclovitamin D3. Reinvestigation of the Grignard reactions of this latter compound as well as the following acid-catalyzed cycloreversions showed discrepancies with the literature data describing the course of such processes.
View Article and Find Full Text PDFChemistry
May 2003
Department of Organic Chemistry, Indian Institute Science Bangalore 560012 India.
A new family of ring-annulated inositols with "locked" conformations has been designed to deliver a range of these biologically important entities in "unnatural conformations" while retaining their "natural configurations". The simple "tool" of trans ring fusion has been used to "lock" the conformation of the annulated inositols. Short, simple syntheses of a range of these novel cyclitols have been achieved from readily available aromatic precursors such as tetralin and indane.
View Article and Find Full Text PDFArch Pharm (Weinheim)
February 1995
Institut für Pharmazeutische Chemie, Technischen Universität Braunschweig.
A-ring annulated heterocycles, the isoxazole 6, the pyrazoles 8 and the pyrimidines 9 are prepared starting from 2-hydroxymethylene canrenone 1. Binding studies were carried out with the compounds 1 and 6-8 using estrogen, progesterone, androgen, gluco- and mineralocorticoid receptors as well as the serum proteins SHBG and CBG: the substances were inactive on the receptor level. 1, 7 and 8a show weak binding affinity to CBG.
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