Facile, Single‐Step Synthesis of a Series of D‐Ring Ethisterones Substituted with 1,4‐1,2,3‐Triazoles: Preliminary Evaluation of Cytotoxic Activities
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Published:2023-03-22
Issue:8
Volume:18
Page:
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ISSN:1860-7179
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Container-title:ChemMedChem
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language:en
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Short-container-title:ChemMedChem
Author:
Canseco‐González Daniel1,
Rodríguez‐Victoria Isaac1,
Apan‐Ramírez Teresa2,
Viviano‐Posadas Alejandro O.2,
Serrano‐García Juan S.2,
Arenaza‐Corona Antonino2,
Orjuela Adrian L.3,
Alí‐Torres Jorge3,
Dorazco‐González Alejandro2ORCID,
Morales‐Morales David2ORCID
Affiliation:
1. CONACYT-Laboratorio Nacional de Investigación y Servicio Agroalimentario y Forestal Universidad Autónoma Chapingo Texcoco de Mora CP 56230 México
2. Instituto de Química Universidad Nacional Autónoma de México Circuito Exterior Ciudad Universitaria México D. F. CP 04510 México
3. Departamento de Química Universidad Nacional de Colombia- Sede Bogotá Bogotá 111321 Colombia
Abstract
AbstractA series of new D‐ring ethisterones substituted with 1,4‐1,2,3‐triazoles were obtained in a facile manner via click chemistry reactions. The new compounds were characterized by multinuclear NMR spectroscopy, mass spectrometry, IR and unequivocally by single crystal X‐ray diffraction studies for compound 1. The cytotoxic activity of these derivatives was tested against a series of human cancer cell lines including human glioblastoma (U‐251), human prostatic adenocarcinoma (PC‐3), human colorectal adenocarcinoma (HCT‐15), human mammary adenocarcinoma (MCF‐7), human chronic myelogenous leukemia (K562), and human lung adenocarcinoma (SKLU‐1). Derivatives (3, X=Cl) and (5, X=I) showed promising cytotoxicity activities for leukemia adenocarcinoma (K562) and lung adenocarcinoma (SKLU). CI50% of K562: 11.72±0.9 μM (3) and 24.50±1.0 μM (5). CI50% of SKLU: 14.9±0.8 μM (3) and 46.0±2.8 μM (5). In addition, DNA docking simulations showed that all compounds interact with DNA through crosslink instrastrand p‐alkyl‐like interactions.
Subject
Organic Chemistry,General Pharmacology, Toxicology and Pharmaceutics,Molecular Medicine,Drug Discovery,Biochemistry,Pharmacology
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