N-(benzyloxy)-4-hydroxybenzamide | 732308-76-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(benzyloxy)-4-hydroxybenzamide
• 英文别名: 4-hydroxy-N-phenylmethoxybenzamide
• CAS: 732308-76-8
• 化学式: C₁₄H₁₃NO₃
• mdl: MFCD20760619
• 分子量: 243.262
• InChiKey: CJQBHMBYMZIHQZ-UHFFFAOYSA-N

物化性质

• 熔点：
  46-48 °C
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(benzyloxy)-4-hydroxybenzamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以99%的产率得到4,N-二羟基苯甲酰胺
  参考文献：
  名称：

  Inhibitors of the FEZ-1 metallo-β-lactamase

  摘要：

  Metallo-beta-lactamases (MBLs) catalyze the hydrolysis of beta-lactams including penicillins, cephalosporins and carbapenems. Starting from benzohydroxamic acid (1) structure-activity studies led to the identification of selective inhibitors of the FEZ-1 MBL, e.g., 2,5-substituted benzophenone hydroxamic acid 17 has a K-i of 6.1 +/- 0.71 mu M against the FEZ-1 MBL but does not significantly inhibit the IMP-1, Bell, CphA or L1 MBLs. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.053
• 作为产物：
  描述：

  4-(allyloxy)-N-(benzyloxy)benzamide 在 四(三苯基膦)钯 四氢吡咯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以56%的产率得到N-(benzyloxy)-4-hydroxybenzamide
  参考文献：
  名称：

  Inhibitors of the FEZ-1 metallo-β-lactamase

  摘要：

  Metallo-beta-lactamases (MBLs) catalyze the hydrolysis of beta-lactams including penicillins, cephalosporins and carbapenems. Starting from benzohydroxamic acid (1) structure-activity studies led to the identification of selective inhibitors of the FEZ-1 MBL, e.g., 2,5-substituted benzophenone hydroxamic acid 17 has a K-i of 6.1 +/- 0.71 mu M against the FEZ-1 MBL but does not significantly inhibit the IMP-1, Bell, CphA or L1 MBLs. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.053

文献信息

• [EN] CARBAMIC ACID COMPOUNDS COMPRISING AN ESTER OR KETONE LINKAGE AS HDAC INHIBITORS<br/>[FR] COMPOSES D'ACIDE CARBAMIQUE COMPRENANT UNE LIAISON ESTER OU CETONE, UTILISES COMME INHIBITEURS DE L'HISTONE DESACETYLASE
  申请人：TOPOTARGET UK LTD

  公开号：WO2004065354A1

  公开（公告）日：2004-08-05

  This invention pertains to certain carbamic acid compounds of the formula (I), which inhibit HDAC (histone deacetylase) activity: wherein: J is a linking functional group and is independently: -O-C(=O)- or -C(=O)-O- or - C(=O)-; Cy is a cyclyl group and is independently: C3-20carbocyclyl, C3-20heterocyclyl, or C5-20aryl; and is optionally substituted; Q1 is a cyclyl leader group, and is independently a divalent bidentate group obtained by removing two hydrogen atoms from a ring carbon atom of a saturated monocyclic hydrocarbon having from 4 to 7 ring atoms, or by removing two hydrogen atoms from a ring carbon atom of saturated monocyclic heterocyclic compound having from 4 to 7 ring atoms including 1 nitrogen ring atom or 1 oxygen ring atom; and is optionally substituted; Q2 is an acid leader group, and is independently: C1-8alkylene; and is optionally substituted; or: Q2 is an acid leader group, and is independently: C5-20arylene; C5-20arylene-C1-7alkylene; C1-7alkylene-C5-20arylene; or C1-7alkylene-C5-20arylene-C1-7alkylene; and is optionally substituted; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HDAC,and in the treatment of conditions mediated by HDAC, cancer, proliferative conditions, psoriasis, etc.

  这项发明涉及某些具有以下式(I)的氨甲酸化合物，其抑制HDAC（组蛋白去乙酰化酶）活性：其中：J是一个连接的功能基团，独立地为：-O-C(=O)-或-C(=O)-O-或-C(=O)-；Cy是一个环烷基团，独立地为：C3-20碳环烷基、C3-20杂环烷基或C5-20芳基；并且可以选择性地被取代；Q1是一个环烷基领头基团，独立地是通过从具有4至7个环原子的饱和单环碳氢化合物的环碳原子中去除两个氢原子获得的双价双齿基团，或者通过从具有4至7个环原子，包括1个氮环原子或1个氧环原子的饱和单环杂环化合物的环碳原子中去除两个氢原子获得的双价双齿基团；并且可以选择性地被取代；Q2是一个酸领头基团，独立地为：C1-8烷基烯；并且可以选择性地被取代；或者：Q2是一个酸领头基团，独立地为：C5-20芳基烯；C5-20芳基烯-C1-7烷基烯；C1-7烷基烯-C5-20芳基烯；或C1-7烷基烯-C5-20芳基烯-C1-7烷基烯；并且可以选择性地被取代；以及其药学上可接受的盐、溶剂化合物、酰胺、酯、醚、化学保护形式和前药。本发明还涉及包括这种化合物的药物组合物，以及在体内外使用这种化合物和组合物来抑制HDAC，并用于治疗由HDAC介导的疾病、癌症、增殖性疾病、牛皮癣等。
• Carbamic acid compounds comprising an ester or ketone linkage as hdac inhibitors
  申请人：Finn W Paul

  公开号：US20060058282A1

  公开（公告）日：2006-03-16

  This invention pertains to certain carbamic acid compounds of the formula (I), which inhibit HDAC (histone deacetylase) activity: wherein: J is a linking functional group and is independently: —O—C(═O)— or —C(═O)—O— or —C(═O)—; Cy is a cyclyl group and is independently: C 3-20 carbocyclyl, C 3-20 heterocyclyl, or C 5-20 aryl; and is optionally substituted; Q 1 is a cyclyl leader group, and is independently a divalent bidentate group obtained by removing two hydrogen atoms from a ring carbon atom of a saturated monocyclic hydrocarbon having from 4 to 7 ring atoms, or by removing two hydrogen atoms from a ring carbon atom of saturated monocyclic heterocyclic compound having from 4 to 7 ring atoms including 1 nitrogen ring atom or 1 oxygen ring atom; and is optionally substituted; Q 2 is an acid leader group, and is independently: C 1-8 alkylene; and is optionally substituted; or: Q 2 is an acid leader group, and is independently: C 5-20 arylene; C 5-20 arylene-C 1-7 alkylene; C 1-7 alkylene-C 5-20 arylene; or C 1-7 alkylene-C 5-20 arylene-C 1-7 alkylene; and is optionally substituted; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HDAC, and in the treatment of conditions mediated by HDAC, cancer, proliferative conditions, psoriasis, etc.

  该发明涉及一类具有以下式子(I)的碳酰胺化合物，其抑制HDAC（组蛋白去乙酰化酶）活性：其中：J是连接功能基团，独立地为：—O—C(═O)—或—C(═O)—O—或—C(═O)—；Cy是环基团，独立地为：C3-20碳环基、C3-20杂环基或C5-20芳基；并且可以选择性地被取代；Q1是环基领导基团，独立地为从具有4至7个环原子的饱和单环烃或包括1个氮环原子或1个氧环原子的饱和单环杂环化合物的环碳原子上去除两个氢原子而得到的二价双齿基团；并且可以选择性地被取代；Q2是酸基领导基团，独立地为：C1-8烷基；并且可以选择性地被取代；或：Q2是酸基领导基团，独立地为：C5-20芳基、C5-20芳基-C1-7烷基、C1-7烷基-C5-20芳基或C1-7烷基-C5-20芳基-C1-7烷基；并且可以选择性地被取代；以及其药学上可接受的盐、溶剂化物、酰胺、酯、醚、化学保护形式和前药。本发明还涉及包含这样的化合物的制药组合物，以及这样的化合物和组合物的使用，无论是在体外还是体内，用于抑制HDAC，以及用于治疗由HDAC介导的疾病，如癌症、增生性疾病、牛皮癣等。
• Carbamic acid compounds comprising an ester or ketone linkage as HDAC inhibitors
  申请人：Topotarget UK Limited

  公开号：US07465719B2

  公开（公告）日：2008-12-16

  This invention pertains to certain carbamic acid compounds of the formula (I), which inhibit HDAC (histone deacetylase) activity: wherein: J is a linking functional group and is independently:—O —C(═O)— or —C(═O)—O — or —C(═O)—; Cy is a cyclyl group and is independently: C3-20carbocyclyl, C3-20heterocyclyl, or C5-20aryl; and is optionally substituted; Q1 is a cyclyl leader group, and is independently a divalent bidentate group obtained by removing two hydrogen atoms from a ring carbon atom of a saturated monocyclic hydrocarbon having from 4 to 7 ring atoms, or by removing two hydrogen atoms from a ring carbon atom of saturated monocyclic heterocyclic compound having from 4 to 7 ring atoms including 1 nitrogen ring atom or 1 oxygen ring atom; and is optionally substituted; Q2 is an acid leader group, and is independently: C1-8alkylene; and is optionally substituted; or: Q2 is an acid leader group, and is independently: C5-20arylene; C5-20arylene-C1-7alkylene; C1-7alkylene-C5-20arylene; or C1-7alkylene-C5-20aryleneC1-7alkylene; and is optionally substituted; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HDAC,and in the treatment of conditions mediated by HDAC, cancer, proliferative conditions, psoriasis, etc.

  本发明涉及一些具有以下化学式(I)的碳酰胺类化合物，其抑制HDAC（组蛋白去乙酰化酶）活性： 其中：J是连接功能基，独立地为：—O—C(═O)—或—C(═O)—O—或—C(═O)—；Cy是环烷基团，独立地为：C3-20碳环烷基、C3-20杂环烷基或C5-20芳基；并且可选择性地被取代；Q1是环烷基团，独立地为由饱和的单环烃类碳环原子上去除两个氢原子或由含有4至7个环原子的饱和单环杂环化合物的环碳原子上去除两个氢原子获得的二价双齿基团；并且可选择性地被取代；Q2是酸性基团，独立地为：C1-8烷基；并且可选择性地被取代；或：Q2是酸性基团，独立地为：C5-20芳基、C5-20芳基-C1-7烷基、C1-7烷基-C5-20芳基或C1-7烷基-C5-20芳基-C1-7烷基；并且可选择性地被取代；以及其药学上可接受的盐、溶剂化合物、酰胺、酯、醚、化学保护形式和前药。本发明还涉及包含这种化合物的制药组合物以及在体内外中使用这种化合物和组合物来抑制HDAC，并用于治疗由HDAC介导的疾病，如癌症、增生性疾病、牛皮癣等。
• CARBAMIC ACID COMPOUNDS COMPRISING AN ESTER OR KETONE LINKAGE AS HDAC INHIBITORS
  申请人：TopoTarget UK Limited

  公开号：EP1583736A1

  公开（公告）日：2005-10-12
• US7465719B2
  申请人：——

  公开号：US7465719B2

  公开（公告）日：2008-12-16