Design, Synthesis and Biological Evaluation of Novel 4-(4-Methoxynaphthalen-1-yl)-5-arylpyrimidin-2-amines as Tubulin Polymerization Inhibitors
A novel series of 4-(4-methoxynaphthalen-1-yl)-5-arylpyrimidin-2-amines were designed, synthesized, and evaluated for their anticancer activities. Most of the synthesized compounds exhibited moderate to high antiproliferative activity in comparison to the standard drug cisplatin. Among them, 5i bear...
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| Published in | Chemical & pharmaceutical bulletin Vol. 68; no. 12; pp. 1184 - 1192 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
TOKYO
The Pharmaceutical Society of Japan
01.12.2020
Pharmaceutical Society of Japan Pharmaceutical Soc Japan Japan Science and Technology Agency |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0009-2363 1347-5223 1347-5223 |
| DOI | 10.1248/cpb.c20-00575 |
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| Abstract | A novel series of 4-(4-methoxynaphthalen-1-yl)-5-arylpyrimidin-2-amines were designed, synthesized, and evaluated for their anticancer activities. Most of the synthesized compounds exhibited moderate to high antiproliferative activity in comparison to the standard drug cisplatin. Among them, 5i bearing ethoxy at the 4-position of the phenyl was found to be the most active on MCF-7 and HepG2 cancer cell lines, with IC50 values of 3.77 ± 0.36 and 3.83 ± 0.26 µM, respectively. Further mechanism study shown that 5i potently inhibited tubulin polymerization, induced cell cycle arrest at G2/M phase and cell apoptosis in MCF-7 cell line. Furthermore, molecular modeling study suggested that 5i probably binds to the colchicine site of tubulin. |
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| AbstractList | A novel series of 4-(4-methoxynaphthalen-1-yl)-5-arylpyrimidin-2-amines were designed, synthesized, and evaluated for their anticancer activities. Most of the synthesized compounds exhibited moderate to high antiproliferative activity in comparison to the standard drug cisplatin. Among them, 5i bearing ethoxy at the 4-position of the phenyl was found to be the most active on MCF-7 and HepG2 cancer cell lines, with IC50 values of 3.77 ± 0.36 and 3.83 ± 0.26 µM, respectively. Further mechanism study shown that 5i potently inhibited tubulin polymerization, induced cell cycle arrest at G2/M phase and cell apoptosis in MCF-7 cell line. Furthermore, molecular modeling study suggested that 5i probably binds to the colchicine site of tubulin.A novel series of 4-(4-methoxynaphthalen-1-yl)-5-arylpyrimidin-2-amines were designed, synthesized, and evaluated for their anticancer activities. Most of the synthesized compounds exhibited moderate to high antiproliferative activity in comparison to the standard drug cisplatin. Among them, 5i bearing ethoxy at the 4-position of the phenyl was found to be the most active on MCF-7 and HepG2 cancer cell lines, with IC50 values of 3.77 ± 0.36 and 3.83 ± 0.26 µM, respectively. Further mechanism study shown that 5i potently inhibited tubulin polymerization, induced cell cycle arrest at G2/M phase and cell apoptosis in MCF-7 cell line. Furthermore, molecular modeling study suggested that 5i probably binds to the colchicine site of tubulin. A novel series of 4-(4-methoxynaphthalen-1-yl)-5-arylpyrimidin-2-amines were designed, synthesized, and evaluated for their anticancer activities. Most of the synthesized compounds exhibited moderate to high antiproliferative activity in comparison to the standard drug cisplatin. Among them, 5i bearing ethoxy at the 4-position of the phenyl was found to be the most active on MCF-7 and HepG2 cancer cell lines, with IC50 values of 3.77 ± 0.36 and 3.83 ± 0.26 µM, respectively. Further mechanism study shown that 5i potently inhibited tubulin polymerization, induced cell cycle arrest at G2/M phase and cell apoptosis in MCF-7 cell line. Furthermore, molecular modeling study suggested that 5i probably binds to the colchicine site of tubulin. Graphical Abstract A novel series of 4-(4-methoxynaphthalen-1-yl)- 5-arylpyrimidin-2-amines were designed, synthesized, and evaluated for their anticancer activities. Most of the synthesized compounds exhibited moderate to high antiproliferative activity in comparison to the standard drug cisplatin. Among them, 5i bearing ethoxy at the 4-position of the phenyl was found to be the most active on MCF-7 and HepG2 cancer cell lines, with IC50 values of 3.77 +/- 0.36 and 3.83 +/- 0.26 mu M, respectively. Further mechanism study shown that 5i potently inhibited tubulin polymerization, induced cell cycle arrest at G2/M phase and cell apoptosis in MCF-7 cell line. Furthermore, molecular modeling study suggested that 5i probably binds to the colchicine site of tubulin. A novel series of 4-(4-methoxynaphthalen-1-yl)-5-arylpyrimidin-2-amines were designed, synthesized, and evaluated for their anticancer activities. Most of the synthesized compounds exhibited moderate to high antiproliferative activity in comparison to the standard drug cisplatin. Among them, 5i bearing ethoxy at the 4-position of the phenyl was found to be the most active on MCF-7 and HepG2 cancer cell lines, with IC50 values of 3.77+-0.36 and 3.83+-0.26μM, respectively. Further mechanism study shown that 5i potently inhibited tubulin polymerization, induced cell cycle arrest at G2/M phase and cell apoptosis in MCF-7 cell line. Furthermore, molecular modeling study suggested that 5i probably binds to the colchicine site of tubulin. A novel series of 4-(4-methoxynaphthalen-1-yl)-5-arylpyrimidin-2-amines were designed, synthesized, and evaluated for their anticancer activities. Most of the synthesized compounds exhibited moderate to high antiproliferative activity in comparison to the standard drug cisplatin. Among them, 5i bearing ethoxy at the 4-position of the phenyl was found to be the most active on MCF-7 and HepG2 cancer cell lines, with IC50 values of 3.77 ± 0.36 and 3.83 ± 0.26 µM, respectively. Further mechanism study shown that 5i potently inhibited tubulin polymerization, induced cell cycle arrest at G2/M phase and cell apoptosis in MCF-7 cell line. Furthermore, molecular modeling study suggested that 5i probably binds to the colchicine site of tubulin. |
| Author | Wang, Guangcheng Li, Yongjun Peng, Zhiyun Liu, Wenjing |
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| Keywords | POTENTIAL ANTICANCER AGENTS PYRIMIDINE-DERIVATIVES naphthalene MECHANISMS IDENTIFICATION pyrimidine tubulin polymerization inhibitor BINDING anticancer |
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| References_xml | – reference: 9) Kuppens I. E. L. M., Curr. Clin. Pharmacol., 1, 57–70 (2006). – reference: 17) Farghaly A. M., Med. Chem. Res., 28, 360–379 (2019). – reference: 22) Keating G. M., Am. J. Cardiovasc. Drugs, 16, 453–460 (2016). – reference: 29) Wang G., Liu W., Gong Z., Huang Y., Li Y., Peng Z., J. Enzyme Inhib. Med. Chem., 35, 139–144 (2020). – reference: 5) Jordan M. A., Wilson L., Nat. Rev. Cancer, 4, 253–265 (2004). – reference: 20) Farag A. K., Hassan A. H. E., Ahn B. S., Park K. D., Roh E. J., J. Enzyme Inhib. Med. Chem., 35, 311–324 (2020). – reference: 27) Romagnoli R., Oliva P., Salvador M. K., Camacho M. E., Padroni C., Brancale A., Ferla S., Hamel E., Ronca R., Grillo E., Bortolozzi R., Rruga F., Mariotto E., Viola G., Eur. J. Med. Chem., 181, 21 (2019). – reference: 3) Amos L. A., Org. Biomol. Chem., 2, 2153–2160 (2004). – reference: 12) Okazaki S., Mizuhara T., Shimura K., Murayama H., Ohno H., Oishi S., Matsuoka M., Fujii N., Bioorg. Med. 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| Snippet | A novel series of 4-(4-methoxynaphthalen-1-yl)-5-arylpyrimidin-2-amines were designed, synthesized, and evaluated for their anticancer activities. Most of the... A novel series of 4-(4-methoxynaphthalen-1-yl)- 5-arylpyrimidin-2-amines were designed, synthesized, and evaluated for their anticancer activities. Most of the... |
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| SubjectTerms | Amines anticancer Anticancer properties Apoptosis Biotechnology Cell cycle Chemistry Chemistry, Medicinal Chemistry, Multidisciplinary Cisplatin Colchicine Life Sciences & Biomedicine Molecular modelling naphthalene Pharmacology & Pharmacy Physical Sciences Polymerization pyrimidine Science & Technology Tubulin tubulin polymerization inhibitor Tumor cell lines |
| Title | Design, Synthesis and Biological Evaluation of Novel 4-(4-Methoxynaphthalen-1-yl)-5-arylpyrimidin-2-amines as Tubulin Polymerization Inhibitors |
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