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Synthesis, Characterization and In-vitro Evaluation of Novel Naphthoquinone Derivatives and Related Imines: Identification of New Anticancer Leads

Quinones such as 1,4-naphthoquinones are abundant in nature and naphthoquinone based natural products are known to possess anticancer activity. This pharmacophore is known to convey anticancer activity to some drugs such as streptonigrin, mitomycin A, etc. We synthesized and characterized different...

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Autores principales: Golmakaniyoon, Sima, Askari, Vahid Reza, Abnous, Khalil, Zarghi, Afshin, Ghodsi, Razieh
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Shaheed Beheshti University of Medical Sciences 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6487425/
https://www.ncbi.nlm.nih.gov/pubmed/31089340
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author Golmakaniyoon, Sima
Askari, Vahid Reza
Abnous, Khalil
Zarghi, Afshin
Ghodsi, Razieh
author_facet Golmakaniyoon, Sima
Askari, Vahid Reza
Abnous, Khalil
Zarghi, Afshin
Ghodsi, Razieh
author_sort Golmakaniyoon, Sima
collection PubMed
description Quinones such as 1,4-naphthoquinones are abundant in nature and naphthoquinone based natural products are known to possess anticancer activity. This pharmacophore is known to convey anticancer activity to some drugs such as streptonigrin, mitomycin A, etc. We synthesized and characterized different classes of naphthoquinone derivatives including bis naphthoquinone, 2-arylaminonaphthoquinone, benzoxantene-6,11-dione and benzoacridine-5,6-dione derivatives instead of the expected 2-hydroxy-3-(substituted phenyl(aryl amino)methyl)naphthalene-1,4-dione derivatives from the reaction of 2-hydroxy1,4-naphthoquinone (lawson) with different benzaldehydes and aryl amines. Benzoacridine-5,6-dione derivatives and related imines showed potent anti-breast cancer activity in MCF-7 cancer cells. The in-vitro results revealed that five compounds benzoacridinedione derivatives (6b and 7b) and imines (13, 14 and 15) by the IC(50) range of 5.4-47.99 μM are the most potent anti-breast cancer structures.
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spelling pubmed-64874252019-05-14 Synthesis, Characterization and In-vitro Evaluation of Novel Naphthoquinone Derivatives and Related Imines: Identification of New Anticancer Leads Golmakaniyoon, Sima Askari, Vahid Reza Abnous, Khalil Zarghi, Afshin Ghodsi, Razieh Iran J Pharm Res Original Article Quinones such as 1,4-naphthoquinones are abundant in nature and naphthoquinone based natural products are known to possess anticancer activity. This pharmacophore is known to convey anticancer activity to some drugs such as streptonigrin, mitomycin A, etc. We synthesized and characterized different classes of naphthoquinone derivatives including bis naphthoquinone, 2-arylaminonaphthoquinone, benzoxantene-6,11-dione and benzoacridine-5,6-dione derivatives instead of the expected 2-hydroxy-3-(substituted phenyl(aryl amino)methyl)naphthalene-1,4-dione derivatives from the reaction of 2-hydroxy1,4-naphthoquinone (lawson) with different benzaldehydes and aryl amines. Benzoacridine-5,6-dione derivatives and related imines showed potent anti-breast cancer activity in MCF-7 cancer cells. The in-vitro results revealed that five compounds benzoacridinedione derivatives (6b and 7b) and imines (13, 14 and 15) by the IC(50) range of 5.4-47.99 μM are the most potent anti-breast cancer structures. Shaheed Beheshti University of Medical Sciences 2019 /pmc/articles/PMC6487425/ /pubmed/31089340 Text en This is an Open Access article distributed under the terms of the Creative Commons Attribution License, (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Original Article
Golmakaniyoon, Sima
Askari, Vahid Reza
Abnous, Khalil
Zarghi, Afshin
Ghodsi, Razieh
Synthesis, Characterization and In-vitro Evaluation of Novel Naphthoquinone Derivatives and Related Imines: Identification of New Anticancer Leads
title Synthesis, Characterization and In-vitro Evaluation of Novel Naphthoquinone Derivatives and Related Imines: Identification of New Anticancer Leads
title_full Synthesis, Characterization and In-vitro Evaluation of Novel Naphthoquinone Derivatives and Related Imines: Identification of New Anticancer Leads
title_fullStr Synthesis, Characterization and In-vitro Evaluation of Novel Naphthoquinone Derivatives and Related Imines: Identification of New Anticancer Leads
title_full_unstemmed Synthesis, Characterization and In-vitro Evaluation of Novel Naphthoquinone Derivatives and Related Imines: Identification of New Anticancer Leads
title_short Synthesis, Characterization and In-vitro Evaluation of Novel Naphthoquinone Derivatives and Related Imines: Identification of New Anticancer Leads
title_sort synthesis, characterization and in-vitro evaluation of novel naphthoquinone derivatives and related imines: identification of new anticancer leads
topic Original Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6487425/
https://www.ncbi.nlm.nih.gov/pubmed/31089340
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