Novel 1-(2-aryl-2-adamantyl)piperazine derivatives with antiproliferative activity

Christos  Fytas; Grigoris Zoidis; Andrew Tsotinis; George Fytas; Khondaker Rahman; David Thurston

doi:10.1016/j.ejmech.2015.02.021

Novel 1-(2-aryl-2-adamantyl)piperazine derivatives with antiproliferative activity

Christos Fytas, Grigoris Zoidis, Andrew Tsotinis, George Fytas, Khondaker Rahman, David Thurston

Institute of Pharmaceutical Science

National and Kapodistrian University of Athens

Research output: Contribution to journal › Article › peer-review

28 Citations (Scopus)

Abstract

Novel 1-(2-aryl-2-adamantyl)piperazine derivatives have been synthesized and evaluated in vitro for their antitumor properties against HeLa cervical carcinoma, MDA MB 231 breast cancer, MIA PaCa2 pancreatic cancer, and NCI H1975 non-small cell lung cancer. The parent piperazine 6 was found to exhibit a reasonable activity toward the HeLa and MDA MB 231 tumor cell lines (IC50= 9.2 and 8.4 μΜ, respectively). Concurrent benzene ring C4-fluorination and piperidine acetylation of the piperazino NH of compound 6 resulted in the most active compound 13 of the series in both of the above cell lines (IC50=8.4 and 6.8 μΜ, respectively). Noticeably, compounds 6 and 13 exhibited a significantly low cytotoxicity level over the normal human cells HUVEC (Human Umbilical Vein Endothelial Cells) and NHDF (Normal Human Dermal Fibroblasts).

Original language	English
Pages (from-to)	281-290
Number of pages	10
Journal	EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume	93
DOIs	https://doi.org/10.1016/j.ejmech.2015.02.021
Publication status	Published - 26 Mar 2015

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10.1016/j.ejmech.2015.02.021

http://www.sciencedirect.com/science/article/pii/S0223523415001178

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title = "Novel 1-(2-aryl-2-adamantyl)piperazine derivatives with antiproliferative activity",

abstract = "Novel 1-(2-aryl-2-adamantyl)piperazine derivatives have been synthesized and evaluated in vitro for their antitumor properties against HeLa cervical carcinoma, MDA MB 231 breast cancer, MIA PaCa2 pancreatic cancer, and NCI H1975 non-small cell lung cancer. The parent piperazine 6 was found to exhibit a reasonable activity toward the HeLa and MDA MB 231 tumor cell lines (IC50= 9.2 and 8.4 μΜ, respectively). Concurrent benzene ring C4-fluorination and piperidine acetylation of the piperazino NH of compound 6 resulted in the most active compound 13 of the series in both of the above cell lines (IC50=8.4 and 6.8 μΜ, respectively). Noticeably, compounds 6 and 13 exhibited a significantly low cytotoxicity level over the normal human cells HUVEC (Human Umbilical Vein Endothelial Cells) and NHDF (Normal Human Dermal Fibroblasts).",

author = "Christos Fytas and Grigoris Zoidis and Andrew Tsotinis and George Fytas and Khondaker Rahman and David Thurston",

year = "2015",

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doi = "10.1016/j.ejmech.2015.02.021",

language = "English",

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T1 - Novel 1-(2-aryl-2-adamantyl)piperazine derivatives with antiproliferative activity

AU - Fytas, Christos

AU - Zoidis, Grigoris

AU - Tsotinis, Andrew

AU - Fytas, George

AU - Rahman, Khondaker

AU - Thurston, David

PY - 2015/3/26

Y1 - 2015/3/26

N2 - Novel 1-(2-aryl-2-adamantyl)piperazine derivatives have been synthesized and evaluated in vitro for their antitumor properties against HeLa cervical carcinoma, MDA MB 231 breast cancer, MIA PaCa2 pancreatic cancer, and NCI H1975 non-small cell lung cancer. The parent piperazine 6 was found to exhibit a reasonable activity toward the HeLa and MDA MB 231 tumor cell lines (IC50= 9.2 and 8.4 μΜ, respectively). Concurrent benzene ring C4-fluorination and piperidine acetylation of the piperazino NH of compound 6 resulted in the most active compound 13 of the series in both of the above cell lines (IC50=8.4 and 6.8 μΜ, respectively). Noticeably, compounds 6 and 13 exhibited a significantly low cytotoxicity level over the normal human cells HUVEC (Human Umbilical Vein Endothelial Cells) and NHDF (Normal Human Dermal Fibroblasts).

AB - Novel 1-(2-aryl-2-adamantyl)piperazine derivatives have been synthesized and evaluated in vitro for their antitumor properties against HeLa cervical carcinoma, MDA MB 231 breast cancer, MIA PaCa2 pancreatic cancer, and NCI H1975 non-small cell lung cancer. The parent piperazine 6 was found to exhibit a reasonable activity toward the HeLa and MDA MB 231 tumor cell lines (IC50= 9.2 and 8.4 μΜ, respectively). Concurrent benzene ring C4-fluorination and piperidine acetylation of the piperazino NH of compound 6 resulted in the most active compound 13 of the series in both of the above cell lines (IC50=8.4 and 6.8 μΜ, respectively). Noticeably, compounds 6 and 13 exhibited a significantly low cytotoxicity level over the normal human cells HUVEC (Human Umbilical Vein Endothelial Cells) and NHDF (Normal Human Dermal Fibroblasts).

U2 - 10.1016/j.ejmech.2015.02.021

DO - 10.1016/j.ejmech.2015.02.021

M3 - Article

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JO - EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY

JF - EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY

ER -

Novel 1-(2-aryl-2-adamantyl)piperazine derivatives with antiproliferative activity

Abstract

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