Design, synthesis and cytotoxic evaluation of o-carboxamido stilbene analogues

Mohamad Nurul Azmi; Mohd Fadzli Md Din; Chin Hui Kee; Munirah Suhaimi; Ang Kheng Ping; Kartini Ahmad; Mohd Azlan Nafiah; Noel F. Thomas; Khalit Mohamad; Leong Kok Hoong; Khalijah Awang

doi:10.3390/ijms141223369

Design, synthesis and cytotoxic evaluation of o-carboxamido stilbene analogues

Mohamad Nurul Azmi, Mohd Fadzli Md Din, Chin Hui Kee, Munirah Suhaimi, Ang Kheng Ping, Kartini Ahmad, Mohd Azlan Nafiah, Noel F. Thomas, Khalit Mohamad, Leong Kok Hoong, Khalijah Awang

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

14 Citations (Scopus)

Abstract

Resveratrol, a natural stilbene found in grapes and wines exhibits a wide range of pharmacological properties. Resveratrol is also known as a good chemopreventive agent for inhibiting carcinogenesis processes that target kinases, cyclooxygenases, ribonucleotide reductase and DNA polymerases. A total of 19 analogues with an amide moiety were synthesized and the cytotoxic effects of the analogues on a series of human cancer cell lines are reported. Three compounds 6d, 6i and 6n showed potent cytotoxicity against prostate cancer DU-145 (IC₅₀ = 16.68 μM), colon cancer HT-29 (IC₅₀ = 7.51 μ M) and breast cancer MCF-7 (IC₅₀ = 21.24 μM), respectively, which are comparable with vinblastine. The resveratrol analogues were synthesized using the Heck method.

Original language	English
Pages (from-to)	23369-23389
Number of pages	21
Journal	International journal of molecular sciences
Volume	14
Issue number	12
DOIs	https://doi.org/10.3390/ijms141223369
Publication status	Published - Nov 27 2013
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Molecular Biology
Spectroscopy
Computer Science Applications
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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title = "Design, synthesis and cytotoxic evaluation of o-carboxamido stilbene analogues",

abstract = "Resveratrol, a natural stilbene found in grapes and wines exhibits a wide range of pharmacological properties. Resveratrol is also known as a good chemopreventive agent for inhibiting carcinogenesis processes that target kinases, cyclooxygenases, ribonucleotide reductase and DNA polymerases. A total of 19 analogues with an amide moiety were synthesized and the cytotoxic effects of the analogues on a series of human cancer cell lines are reported. Three compounds 6d, 6i and 6n showed potent cytotoxicity against prostate cancer DU-145 (IC50 = 16.68 μM), colon cancer HT-29 (IC50 = 7.51 μ M) and breast cancer MCF-7 (IC50 = 21.24 μM), respectively, which are comparable with vinblastine. The resveratrol analogues were synthesized using the Heck method.",

author = "Azmi, {Mohamad Nurul} and {Md Din}, {Mohd Fadzli} and Kee, {Chin Hui} and Munirah Suhaimi and Ping, {Ang Kheng} and Kartini Ahmad and Nafiah, {Mohd Azlan} and Thomas, {Noel F.} and Khalit Mohamad and Hoong, {Leong Kok} and Khalijah Awang",

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doi = "10.3390/ijms141223369",

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T1 - Design, synthesis and cytotoxic evaluation of o-carboxamido stilbene analogues

AU - Azmi, Mohamad Nurul

AU - Md Din, Mohd Fadzli

AU - Kee, Chin Hui

AU - Suhaimi, Munirah

AU - Ping, Ang Kheng

AU - Ahmad, Kartini

AU - Nafiah, Mohd Azlan

AU - Thomas, Noel F.

AU - Mohamad, Khalit

AU - Hoong, Leong Kok

AU - Awang, Khalijah

PY - 2013/11/27

Y1 - 2013/11/27

N2 - Resveratrol, a natural stilbene found in grapes and wines exhibits a wide range of pharmacological properties. Resveratrol is also known as a good chemopreventive agent for inhibiting carcinogenesis processes that target kinases, cyclooxygenases, ribonucleotide reductase and DNA polymerases. A total of 19 analogues with an amide moiety were synthesized and the cytotoxic effects of the analogues on a series of human cancer cell lines are reported. Three compounds 6d, 6i and 6n showed potent cytotoxicity against prostate cancer DU-145 (IC50 = 16.68 μM), colon cancer HT-29 (IC50 = 7.51 μ M) and breast cancer MCF-7 (IC50 = 21.24 μM), respectively, which are comparable with vinblastine. The resveratrol analogues were synthesized using the Heck method.

AB - Resveratrol, a natural stilbene found in grapes and wines exhibits a wide range of pharmacological properties. Resveratrol is also known as a good chemopreventive agent for inhibiting carcinogenesis processes that target kinases, cyclooxygenases, ribonucleotide reductase and DNA polymerases. A total of 19 analogues with an amide moiety were synthesized and the cytotoxic effects of the analogues on a series of human cancer cell lines are reported. Three compounds 6d, 6i and 6n showed potent cytotoxicity against prostate cancer DU-145 (IC50 = 16.68 μM), colon cancer HT-29 (IC50 = 7.51 μ M) and breast cancer MCF-7 (IC50 = 21.24 μM), respectively, which are comparable with vinblastine. The resveratrol analogues were synthesized using the Heck method.

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Design, synthesis and cytotoxic evaluation of o-carboxamido stilbene analogues

Abstract

All Science Journal Classification (ASJC) codes

UN SDGs

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