5-(3-furyl)-N-{4-[(hydroxyamino)carbonyl]benzyl}-3-(4-hydroxyphenyl)-1H-pyrrole-2-carboxamide | 1279698-23-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-(3-furyl)-N-{4-[(hydroxyamino)carbonyl]benzyl}-3-(4-hydroxyphenyl)-1H-pyrrole-2-carboxamide
• 英文别名: 5-(furan-3-yl)-N-[[4-(hydroxycarbamoyl)phenyl]methyl]-3-(4-hydroxyphenyl)-1H-pyrrole-2-carboxamide
• CAS: 1279698-23-5
• 化学式: C₂₃H₁₉N₃O₅
• 分子量: 417.421
• InChiKey: QTDGOLQQCBXUSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  128
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 4-[({[5-(3-furyl)-3-(4-hydroxyphenyl)-1H-pyrrol-2-yl]carbonyl}amino)methyl]benzoate 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 26.0h， 以94%的产率得到5-(3-furyl)-N-{4-[(hydroxyamino)carbonyl]benzyl}-3-(4-hydroxyphenyl)-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  [EN] NEW HISTONE DEACETYLASE INHIBITORS BASED SIMULTANEOUSLY ON TRISUBSTITUTED 1H-PYRROLES AND AROMATIC AND HETEROAROMATIC SPACERS
  [FR] NOUVEAUX INHIBITEURS D'HISTONE DÉSACÉTYLASE BASÉS À LA FOIS SUR DES 1H-PYRROLES TRISUBSTITUÉS ET DES GROUPES ESPACEURS AROMATIQUES ET HÉTÉROAROMATIQUES

  摘要：

  本发明涉及从三取代1H-吡咯环和芳香环衍生的化合物，其具有以下式（I）：其中：R1和R2独立地代表一个可选择取代的C6-C10芳基基团或一个可选择取代的杂环基团；A和M独立地代表一个亚甲基基团或一个单键，此时相邻的芳香环将直接连接到酰胺基团；Y=Z基团表示一起和不明确地表示一个氧原子、硫原子、顺式-乙烯基团、亚胺基团或一个带有sp2-杂化碳原子的甲基基团；X不明确地表示一个甲基基团、一个顺式-乙烯基团或一个氮原子；W表示一个羟基、一个可选择取代的C1-C6烷基基团、一个可选择取代的杂环基团或一个可选择取代的C6-C10芳基基团；或其盐、溶剂化合物或前药，以及其制备方法和用于治疗癌症的用途。

  公开号：

  WO2011039353A1

文献信息

• [EN] NEW HISTONE DEACETYLASE INHIBITORS BASED SIMULTANEOUSLY ON TRISUBSTITUTED 1H-PYRROLES AND AROMATIC AND HETEROAROMATIC SPACERS<br/>[FR] NOUVEAUX INHIBITEURS D'HISTONE DÉSACÉTYLASE BASÉS À LA FOIS SUR DES 1H-PYRROLES TRISUBSTITUÉS ET DES GROUPES ESPACEURS AROMATIQUES ET HÉTÉROAROMATIQUES
  申请人：IKERCHEM S L

  公开号：WO2011039353A1

  公开（公告）日：2011-04-07

  The present invention refers to compounds derived from trisubstituted 1H- pyrrole rings and aromatic rings, which have the following formula (I): wherein: R1 and R2 represent, independently, an optionally substituted C6-C10 aryl radical or an optionally substituted heteroaryl radical; A and M represent, independently, a methylene group or a single bond, in which case the adjacent aromatic ring would be attached directly to the amide group; the Y=Z group represents together and indistinctly an oxygen atom, a sulfur atom, a cis-vinylidene group, an imino group, or a methine group with a sp2- hybridized carbon atom; X represents indistinctly a methine group, a cis-vinylidene group or a nitrogen atom; and W represents a hydroxyl group, an optionally substituted C1-C6 alkyl group, an optionally substituted heteroaryl group or an optionally substituted C6-C10 aryl group; or a salt, solvate or prodrug thereof, as well as to the process for their preparation and the use thereof for the treatment of cancer.

  本发明涉及从三取代1H-吡咯环和芳香环衍生的化合物，其具有以下式（I）：其中：R1和R2独立地代表一个可选择取代的C6-C10芳基基团或一个可选择取代的杂环基团；A和M独立地代表一个亚甲基基团或一个单键，此时相邻的芳香环将直接连接到酰胺基团；Y=Z基团表示一起和不明确地表示一个氧原子、硫原子、顺式-乙烯基团、亚胺基团或一个带有sp2-杂化碳原子的甲基基团；X不明确地表示一个甲基基团、一个顺式-乙烯基团或一个氮原子；W表示一个羟基、一个可选择取代的C1-C6烷基基团、一个可选择取代的杂环基团或一个可选择取代的C6-C10芳基基团；或其盐、溶剂化合物或前药，以及其制备方法和用于治疗癌症的用途。
• Histone deacetylase inhibitors based simultaneously on trisubstituted 1H-pyrroles and aromatic and heteroaromatic spacers
  申请人：Cossío Mora Fernando Pedro

  公开号：US08685992B2

  公开（公告）日：2014-04-01

  The present invention refers to compounds derived from trisubstituted 1H-pyrrole rings and aromatic rings, which have the following formula (I): wherein: R1 and R2 represent, independently, an optionally substituted C6-C10 aryl radical or an optionally substituted heteroaryl radical; A and M represent, independently, a methylene group or a single bond, in which case the adjacent aromatic ring would be attached directly to the amide group; the Y═Z group represents together and indistinctly an oxygen atom, a sulfur atom, a cis-vinylidene group, an imino group, or a methine group with a sp2-hybridized carbon atom; X represents indistinctly a methine group, a cis-vinylidene group or a nitrogen atom; and W represents a hydroxyl group, an optionally substituted C1-C6 alkyl group, an optionally substituted heteroaryl group or an optionally substituted C6-C10 aryl group; or a salt, solvate or prodrug thereof, as well as to the process for their preparation and the use thereof for the treatment of cancer.

  本发明涉及由三取代1H-吡咯环和芳香环衍生的化合物，其具有以下式子(I)： 其中：R1和R2独立地表示可选取代的C6-C10芳基基团或可选取代的杂环基团；A和M独立地表示亚甲基基团或单键，此时相邻的芳香环将直接连接到酰胺基团上；Y═Z基团表示一起和不明显的氧原子、硫原子、顺式-乙烯基基团、亚胺基或带有sp2杂化碳原子的甲基基团；X不明显地表示一个甲基基团、顺式-乙烯基基团或氮原子；W表示一个羟基、可选取代的C1-C6烷基基团、可选取代的杂环基团或可选取代的C6-C10芳基基团；或其盐、溶剂化合物或前药。本发明还涉及其制备过程及其用于治疗癌症的用途。
• New histone deacetylase inhibitors based simultaneously on trisubstituted 1h-pyrroles and aromatic and heteroaromatic spacers
  申请人：Ikerchem, S.L.

  公开号：EP2305643A1

  公开（公告）日：2011-04-06

  The present invention refers to compounds derived from trisubstituted 1H-pyrrole rings and aromatic rings, which have the following formula (I): as well as to the procedure for their preparation and the use thereof for the treatment of cancer by inhibiting histone deacetylases and the therapeutic use of biological processes related to the mentioned inhibition.

  本发明指的是由三取代的 1H 吡咯环和芳香环衍生的化合物，它们具有下式 (I)： 以及它们的制备方法和通过抑制组蛋白去乙酰化酶治疗癌症的用途，以及与上述抑制有关的生物过程的治疗用途。
• COMPOUNDS FOR THE TREATMENT OF AUTOIMMUNE DISEASES
  申请人：QUIMATRYX, S.L

  公开号：EP3318256A1

  公开（公告）日：2018-05-09

  The present invention refers to the use of compounds derived from trisubstituted 1H-pyrrole rings and aromatic rings, which have the following formula (I): wherein R1 and R2 represent, independently of each other: an optionally substituted phenyl ring, or an optionally substituted 5-membered heteroaromatic ring; one of R3 and R4 is H and the other represents a group wherein W is OH or an ortho-aniline group; each A, independently of each other, represents a -CH2- group or is absent; =Y-Y= is =HC-CH=, =N-CH=, or =HC-N=; or a salt or solvate thereof, in the prevention or treatment of an autoimmune disease.

  本发明是指使用由三取代的 1H 吡咯环和芳香环衍生的化合物，这些化合物具有下式 (I)： 其中 R1 和 R2 各自代表 任选取代的苯基环，或 任选取代的 5 元杂芳环； R3 和 R4 中的一个是 H，另一个代表 其中 W 是 OH 或正苯胺基团； 每个 A 独立地代表-CH2-基团或不存在；=Y-Y= 是 =HC-CH=、=N-CH= 或 =HC-N=； 或其盐或溶液、 用于预防或治疗自身免疫性疾病。
• [EN] COMPOUNDS FOR THE TREATMENT OF AUTOIMMUNE DISEASES<br/>[FR] COMPOSÉS POUR LE TRAITEMENT DE MALADIES AUTO-IMMUNES
  申请人：QUIMATRYX S L

  公开号：WO2018087082A1

  公开（公告）日：2018-05-17

  The present invention refers to the use of compounds derived from trisubstituted 1H-pyrrole rings and aromatic rings, which have the following formula (I); wherein R1and R2 represent, independently of each other: an optionally substituted phenyl ring, or an optionally substituted 5-membered heteroaromatic ring; one of R3 and R4 is H and the other represents a (A) group wherein W is OH or an ortho-aniline group; each A, independently of each other, represents a -CH2- group or is absent; =Y-Y= is =HC-CH=, =N-CH=, or =HC-N=; or a salt or solvate thereof, in the prevention or treatment of an autoimmune disease.