Synthesis and Histone Deacetylase Inhibitory Activity of New Benzamide Derivatives
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 IC50 values of the active compounds were in the range of 2−50 μM. Structure−activity relationship on the ben...
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| Published in | Journal of medicinal chemistry Vol. 42; no. 15; pp. 3001 - 3003 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
29.07.1999
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
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| Abstract | 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 IC50 values of the active compounds were in the range of 2−50 μM. 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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| AbstractList | 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 IC50 values of the active compounds were in the range of 2−50 μM. 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. 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 sub(50) values of the active compounds were in the range of 2-50 mu M. 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. 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. 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 IC50 values of the active compounds were in the range of 2-50 mu M. 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. |
| Author | Suzuki, Tsuneji Nakanishi, Osamu Mariko, Yukiyasu Yamashita, Takashi Ando, Tomoyuki Tsuchiya, Katsutoshi Fukazawa, Nobuyuki Saito, Akiko |
| Author_xml | – sequence: 1 givenname: Tsuneji surname: Suzuki fullname: Suzuki, Tsuneji – sequence: 2 givenname: Tomoyuki surname: Ando fullname: Ando, Tomoyuki – sequence: 3 givenname: Katsutoshi surname: Tsuchiya fullname: Tsuchiya, Katsutoshi – sequence: 4 givenname: Nobuyuki surname: Fukazawa fullname: Fukazawa, Nobuyuki – sequence: 5 givenname: Akiko surname: Saito fullname: Saito, Akiko – sequence: 6 givenname: Yukiyasu surname: Mariko fullname: Mariko, Yukiyasu – sequence: 7 givenname: Takashi surname: Yamashita fullname: Yamashita, Takashi – sequence: 8 givenname: Osamu surname: Nakanishi fullname: Nakanishi, Osamu |
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| Cites_doi | 10.1073/pnas.96.8.4592 10.1016/S0968-0004(97)01018-9 |
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| Keywords | Antineoplastic agent Acyltransferases Enzyme Nitrogen heterocycle Transferases Enzyme inhibitor Organic carbamate Histone acetyltransferase In vitro Pyridine derivatives Amine Structure activity relation Six membered ring Benzamide derivatives Carboxamide Aromatic compound Chemical synthesis Arylamine |
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| References | Wade, PA (WOS:A1997WU99700008) 1997; 22 YOSHIDA, M (WOS:A1990EA85700073) 1990; 265 KIJIMA, M (WOS:A1993MD34800039) 1993; 268 Saito, A (WOS:000079766500070) 1999; 96 KRUH, J (WOS:A1982ND07200001) 1982; 42 Kijima M. (jm980565ub00004/jm980565ub00004_1) 1993; 268 Yoshida M. (jm980565ub00003/jm980565ub00003_1) 1990; 265 Saito A. (jm980565ub00005/jm980565ub00005_1) 1999; 96 Wade P. A. (jm980565ub00001/jm980565ub00001_1) 1997; 22 Kruh J (jm980565ub00002/jm980565ub00002_1) 1982; 42 |
| References_xml | – volume: 96 start-page: 4592 year: 1999 ident: WOS:000079766500070 article-title: A synthetic inhibitor of histone deacetylase, MS-27-275, with marked in vivo antitumor activity against human tumors publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA contributor: fullname: Saito, A – volume: 265 start-page: 17174 year: 1990 ident: WOS:A1990EA85700073 article-title: POTENT AND SPECIFIC-INHIBITION OF MAMMALIAN HISTONE DEACETYLASE BOTH INVIVO AND INVITRO BY TRICHOSTATIN-A publication-title: JOURNAL OF BIOLOGICAL CHEMISTRY contributor: fullname: YOSHIDA, M – volume: 268 start-page: 22429 year: 1993 ident: WOS:A1993MD34800039 article-title: TRAPOXIN, AN ANTITUMOR CYCLIC TETRAPEPTIDE, IS AN IRREVERSIBLE INHIBITOR OF MAMMALIAN HISTONE DEACETYLASE publication-title: JOURNAL OF BIOLOGICAL CHEMISTRY contributor: fullname: KIJIMA, M – volume: 42 start-page: 65 year: 1982 ident: WOS:A1982ND07200001 article-title: EFFECTS OF SODIUM-BUTYRATE, A NEW PHARMACOLOGICAL AGENT, ON CELLS IN CULTURE publication-title: MOLECULAR AND CELLULAR BIOCHEMISTRY contributor: fullname: KRUH, J – volume: 22 start-page: 128 year: 1997 ident: WOS:A1997WU99700008 article-title: Histone acetylation: Chromatin in action publication-title: TRENDS IN BIOCHEMICAL SCIENCES contributor: fullname: Wade, PA – volume: 265 start-page: 17179 year: 1990 ident: jm980565ub00003/jm980565ub00003_1 publication-title: J. Biol. Chem. contributor: fullname: Yoshida M. – volume: 42 start-page: 82 year: 1982 ident: jm980565ub00002/jm980565ub00002_1 publication-title: Mol. Cell. Biochem. contributor: fullname: Kruh J – volume: 268 start-page: 22435 year: 1993 ident: jm980565ub00004/jm980565ub00004_1 publication-title: J. Biol. Chem. contributor: fullname: Kijima M. – volume: 96 start-page: 4597 year: 1999 ident: jm980565ub00005/jm980565ub00005_1 publication-title: Proc. Natl. Acad. Sci. U.S.A. doi: 10.1073/pnas.96.8.4592 contributor: fullname: Saito A. – volume: 22 start-page: 132 year: 1997 ident: jm980565ub00001/jm980565ub00001_1 publication-title: Trends Biochem. Sci. doi: 10.1016/S0968-0004(97)01018-9 contributor: fullname: Wade P. A. |
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| Snippet | Newly synthesized benzamide derivatives were evaluated for their inhibitory activity against histone deacetylase. The structure of these derivatives was... |
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| SubjectTerms | Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology benzamide Benzamides - chemical synthesis Benzamides - chemistry Benzamides - pharmacology Biological and medical sciences Chemistry, Medicinal Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology General aspects histone deacetylase Histone Deacetylase Inhibitors Humans Life Sciences & Biomedicine Medical sciences Pharmacology & Pharmacy Pharmacology. Drug treatments Pyridines - chemical synthesis Pyridines - chemistry Pyridines - pharmacology Science & Technology Structure-Activity Relationship |
| Title | Synthesis and Histone Deacetylase Inhibitory Activity of New Benzamide Derivatives |
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