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Synthesis and Histone Deacetylase Inhibitory Activity of New Benzamide Derivatives
Open accessAbstract
Newly synthesized benzamide derivatives were evaluated for their inhibitory activity against histone deacetylase. The structure of these derivatives was unrelated to the known inhibitors, and IC(50) values of the active compounds were in the range of 2-50 microM. Structure-activity relationship on the benzanilide moiety showed that the 2'-substituent, an amino or hydroxy group, was indispensable for inhibitory activity. Although the electronic influence of the substituent in the anilide moiety showed only a small effect on inhibitory activity, the steric factor in the anilide moiety, especially at positions 3'and 4', played an important role in interaction with the enzyme. Among these benzamide derivatives, MS-275 (1), which showed significant antitumor activity in vivo, has been selected for further investigation.
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Cited by
Histone deacetylases and cancer: causes and therapies
Marks, P. A., Rifkind, R. A., Richon, V. M., Breslow, R., Miller, T., & Kelly, W. K. (2001) · Nature reviews. Cancer · doi:10.1038/35106079 · Cited by 1,866
Targeting epigenetic regulators for cancer therapy: mechanisms and advances in clinical trials
Cheng, Y., He, C., Wang, M., Ma, X., Mo, F., Yang, S., Han, J., & Wei, X. (2019) · Signal Transduction and Targeted Therapy · doi:10.1038/s41392-019-0095-0 · Cited by 1,097
Grozinger, C. M., & Schreiber, S. L. (2002) · Chemistry & Biology · doi:10.1016/s1074-5521(02)00092-3 · Cited by 537
CLINICAL DEVELOPMENT OF HISTONE DEACETYLASE INHIBITORS AS ANTICANCER AGENTS
Drummond, D. C., Noble, C. O., Kirpotin, D. B., Guo, Z., Scott, G. K., & Benz, C. C. (2005) · Annual Review of Pharmacology and Toxicology · doi:10.1146/annurev.pharmtox.45.120403.095825 · Cited by 494
(2003) · PubMed · Cited by 465
Metadata
- Authors
- Suzuki, T., Ando, T., Tsuchiya, K., Fukazawa, N., Saito, A., Mariko, Y., Yamashita, T., & Nakanishi, O.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1999-06-30
- Volume
- 42
- Issue
- 15
- Pages
- 3001-3003
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2057916687
- Cited by
- 293
- References
- 0
- FWCI
- 1.20
- Type
- journal article
- Language
- en
- Open access
- green
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- Suzuki, T., Ando, T., Tsuchiya, K., Fukazawa, N., Saito, A., Mariko, Y., Yamashita, T., & Nakanishi, O. (1999). Synthesis and Histone Deacetylase Inhibitory Activity of New Benzamide Derivatives. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm980565u
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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