6, N-2-Diaryl-1,3,5-triazine-2,4-diamines: synthesis, antiproliferative activity and 3D-QSAR modeling

Ahmad Junaid; Felicia Phei Lin Lim; Lay Hong Chuah; Anton V. Dolzhenko

doi:10.1039/d0ra00643b

6, N-2-Diaryl-1,3,5-triazine-2,4-diamines: synthesis, antiproliferative activity and 3D-QSAR modeling

Ahmad Junaid, Felicia Phei Lin Lim, Lay Hong Chuah, Anton V. Dolzhenko

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

4 Citations (Scopus)

Abstract

A library of 126 compounds with a 6,N²-diaryl-1,3,5-triazine-2,4-diamine scaffold was prepared using a one-pot, microwave-assisted method from readily available cyanoguanidine, aromatic aldehydes and arylamines. The three-component condensation of these reagents in the presence of hydrochloric acid was followed by the treatment with a base, which promoted a rearrangement of the dihydrotriazine ring and its dehydrogenative aromatization. The antiproliferative properties of the prepared compounds were evaluated using three breast cancer cell lines. The most promising results were obtained in the growth inhibition of the triple negative MDA-MB231 breast cancer cells. The active compounds were also selective against cancer cells and did not affect growth of the non-cancerous MCF-10A breast cell line. Analyzing the structure-activity relationship within the series, we built a 3D-QSAR model for the further design of more potent anticancer compounds.

Original language	English
Pages (from-to)	12135-12144
Number of pages	10
Journal	RSC Advances
Volume	10
Issue number	21
DOIs	https://doi.org/10.1039/d0ra00643b
Publication status	Published - 25 Mar 2020

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10.1039/d0ra00643bLicence: CC BY

341060886-oaFinal published version, 2.61 MBLicence: CC BY

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New Strategy for the Efficient and Safe Preparation of Carbendazim and its Analogues as Agents for Crop Protection with a Potential for Repurposing as Anticancer Therapeutics
Chuah, A., Chow, S. C., Dolzhenko, A. V., Ting, A. & Ju Yen, F.
1/01/19 → 30/09/22
Project: Research

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title = "6, N-2-Diaryl-1,3,5-triazine-2,4-diamines: synthesis, antiproliferative activity and 3D-QSAR modeling",

abstract = "A library of 126 compounds with a 6,N2-diaryl-1,3,5-triazine-2,4-diamine scaffold was prepared using a one-pot, microwave-assisted method from readily available cyanoguanidine, aromatic aldehydes and arylamines. The three-component condensation of these reagents in the presence of hydrochloric acid was followed by the treatment with a base, which promoted a rearrangement of the dihydrotriazine ring and its dehydrogenative aromatization. The antiproliferative properties of the prepared compounds were evaluated using three breast cancer cell lines. The most promising results were obtained in the growth inhibition of the triple negative MDA-MB231 breast cancer cells. The active compounds were also selective against cancer cells and did not affect growth of the non-cancerous MCF-10A breast cell line. Analyzing the structure-activity relationship within the series, we built a 3D-QSAR model for the further design of more potent anticancer compounds.",

author = "Ahmad Junaid and Lim, {Felicia Phei Lin} and Chuah, {Lay Hong} and Dolzhenko, {Anton V.}",

note = "Funding Information: This work is supported by the Ministry of Higher Education, Malaysia under the Fundamental Research Grant Scheme, grant number FRGS/1/2018/STG01/MUSM/02/2. The work is also partially supported by the Bridging Grant from the School of Pharmacy, Monash University Malaysia. Publisher Copyright: This journal is {\textcopyright} The Royal Society of Chemistry. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

year = "2020",

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doi = "10.1039/d0ra00643b",

language = "English",

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AU - Junaid, Ahmad

AU - Lim, Felicia Phei Lin

AU - Chuah, Lay Hong

AU - Dolzhenko, Anton V.

N1 - Funding Information: This work is supported by the Ministry of Higher Education, Malaysia under the Fundamental Research Grant Scheme, grant number FRGS/1/2018/STG01/MUSM/02/2. The work is also partially supported by the Bridging Grant from the School of Pharmacy, Monash University Malaysia. Publisher Copyright: This journal is © The Royal Society of Chemistry. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2020/3/25

Y1 - 2020/3/25

N2 - A library of 126 compounds with a 6,N2-diaryl-1,3,5-triazine-2,4-diamine scaffold was prepared using a one-pot, microwave-assisted method from readily available cyanoguanidine, aromatic aldehydes and arylamines. The three-component condensation of these reagents in the presence of hydrochloric acid was followed by the treatment with a base, which promoted a rearrangement of the dihydrotriazine ring and its dehydrogenative aromatization. The antiproliferative properties of the prepared compounds were evaluated using three breast cancer cell lines. The most promising results were obtained in the growth inhibition of the triple negative MDA-MB231 breast cancer cells. The active compounds were also selective against cancer cells and did not affect growth of the non-cancerous MCF-10A breast cell line. Analyzing the structure-activity relationship within the series, we built a 3D-QSAR model for the further design of more potent anticancer compounds.

AB - A library of 126 compounds with a 6,N2-diaryl-1,3,5-triazine-2,4-diamine scaffold was prepared using a one-pot, microwave-assisted method from readily available cyanoguanidine, aromatic aldehydes and arylamines. The three-component condensation of these reagents in the presence of hydrochloric acid was followed by the treatment with a base, which promoted a rearrangement of the dihydrotriazine ring and its dehydrogenative aromatization. The antiproliferative properties of the prepared compounds were evaluated using three breast cancer cell lines. The most promising results were obtained in the growth inhibition of the triple negative MDA-MB231 breast cancer cells. The active compounds were also selective against cancer cells and did not affect growth of the non-cancerous MCF-10A breast cell line. Analyzing the structure-activity relationship within the series, we built a 3D-QSAR model for the further design of more potent anticancer compounds.

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6, N-2-Diaryl-1,3,5-triazine-2,4-diamines: synthesis, antiproliferative activity and 3D-QSAR modeling

Abstract

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New Strategy for the Efficient and Safe Preparation of Carbendazim and its Analogues as Agents for Crop Protection with a Potential for Repurposing as Anticancer Therapeutics

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