methyl 5-(bromomethyl)benzofuran-2-carboxylate | 82788-35-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: methyl 5-(bromomethyl)benzofuran-2-carboxylate
• 英文别名: 5-bromomethylbenzofuran-2-carboxylic acid methyl ester；Methyl-5-bromomethyl-benzofuran-2-carboxylate；Methyl 5-(bromomethyl)-1-benzofuran-2-carboxylate
• CAS: 82788-35-0
• 化学式: C₁₁H₉BrO₃
• mdl: MFCD20233634
• 分子量: 269.095
• InChiKey: AWCPGVQAHZGMBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5-(bromomethyl)benzofuran-2-carboxylate 在 sodium azide 、 palladium on activated charcoal 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 Methyl 5-(aminomethyl)-1-benzofuran-2-carboxylate
  参考文献：
  名称：

  Benzofused hydroxamic acids: Useful fragments for the preparation of histone deacetylase inhibitors. Part 2: 7-Fluorobenzothiophenes and benzofurans

  摘要：

  In the search for a new class of histone deacetylase inhibitors, we prepared a series of very simple benzofused hydroxamic acids to find an anchoring fragment of minimal molecular weight: they showed very good ligand efficiencies. Following these findings, classical fragment growing work was performed to increase binding energy and selective cytotoxicity. In the second phase of the work, information from the SARs of the benzothiophene series and data available in literature, we explored the in vitro pharmacological properties of the 6-substituted-7-fluoro-benzothiophene hydroxamates and the 5-susbtituted-benzofuran hydroxamates. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.02.007
• 作为产物：
  描述：

  5-甲基苯并呋喃-2-羧酸 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 1,4-二氧六环 、 四氯化碳 为溶剂， 生成 methyl 5-(bromomethyl)benzofuran-2-carboxylate
  参考文献：
  名称：

  Benzofused hydroxamic acids: Useful fragments for the preparation of histone deacetylase inhibitors. Part 2: 7-Fluorobenzothiophenes and benzofurans

  摘要：

  In the search for a new class of histone deacetylase inhibitors, we prepared a series of very simple benzofused hydroxamic acids to find an anchoring fragment of minimal molecular weight: they showed very good ligand efficiencies. Following these findings, classical fragment growing work was performed to increase binding energy and selective cytotoxicity. In the second phase of the work, information from the SARs of the benzothiophene series and data available in literature, we explored the in vitro pharmacological properties of the 6-substituted-7-fluoro-benzothiophene hydroxamates and the 5-susbtituted-benzofuran hydroxamates. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.02.007

文献信息

• Inhibitors of histone deacetylase
  申请人：Delorme Daniel

  公开号：US06897220B2

  公开（公告）日：2005-05-24

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  本发明涉及组蛋白去乙酰化酶的抑制。本发明提供了用于抑制组蛋白去乙酰化酶酶活性的化合物和方法。本发明还提供了用于治疗细胞增殖性疾病和状况的药物组合物和方法。
• [EN] ECTONUCLEOTIDASE INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS D'ÉCTONUCLÉOTIDASE ET LEURS MÉTHODES D'UTILISATION
  申请人：CALITHERA BIOSCIENCES INC

  公开号：WO2018119284A1

  公开（公告）日：2018-06-28

  The invention relates to novel heterocyclic compounds and pharmaceutical preparations thereof. The invention further relates to methods of treating or preventing cancer using the novel heterocyclic compounds of the invention.

  这项发明涉及新颖的杂环化合物及其制药制剂。该发明还涉及使用该发明的新颖杂环化合物治疗或预防癌症的方法。
• [EN] NOVEL COMPOUNDS AS HISTONE DEACETYLASE 6 INHIBITORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME<br/>[FR] NOUVEAUX COMPOSÉS EN TANT QU'INHIBITEURS DE L'HISTONE DÉSACÉTYLASE 6 ET COMPOSITIONS PHARMACEUTIQUES LES COMPRENANT
  申请人：CHONG KUN DANG PHARM CORP

  公开号：WO2015137750A1

  公开（公告）日：2015-09-17

  The present invention relates to novel compounds having histone deacetylase 6 (HDAC6) inhibitory activity, isomers thereof, or pharmaceutically acceptable salts thereof, the use thereof for the preparation of therapeutic medicaments, pharmaceutical compositions comprising the same, a method of treating disease using the composition, and methods for preparing the novel compounds. The novel compounds according to the present invention have histone deacetylase 6 (HDAC6) inhibitory activity, and are effective for the prevention or treatment of HDAC6-associated diseases, including cancer, inflammatory diseases, autoimmune diseases, neurological diseases and neurodegenerative disorders.

  本发明涉及具有组蛋白去乙酰化酶6（HDAC6）抑制活性的新化合物，其异构体或其药用盐，其用于制备治疗药物的用途，包括相同的药物组成部分的药物组合物，使用该组合物治疗疾病的方法，以及制备新化合物的方法。根据本发明的新化合物具有组蛋白去乙酰化酶6（HDAC6）抑制活性，并且对于预防或治疗HDAC6相关疾病（包括癌症、炎症性疾病、自身免疫疾病、神经系统疾病和神经退行性疾病）有效。
• Heterocyclic thromboxane synthetase inhibitors and pharmaceutical
  申请人：Pfizer Inc.

  公开号：US04410539A1

  公开（公告）日：1983-10-18

  Heterocyclic thromboxane synthetase inhibitors of the formula ##STR1## wherein R.sup.1, which is attached to the 2-, 3- or 4-position, is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, hydroxy or C.sub.1 -C.sub.4 alkoxy; Y, which is attached to the 2- or 3-position, is --COOH, --COO(C.sub.1 -C.sub.4 alkyl) or --CONH.sub.2 ; X is O, S, NH, N(C.sub.1 -C.sub.4 alkyl) or N(benzyl); and R, which is attached to the 5-, 6- or 7-position, is a group of the formula ##STR2## or (3- or 4-pyridyl)-Z.sup.2 - wherein Z.sup.1 is --CH.sub.2 --, --CH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 O-- and Z.sup.2 is --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 O-- or --OCH.sub.2 --; and their pharmaceutically acceptable salts; processes for their preparation, and pharmaceutical compositions containing them.

  杂环血栓素合成酶抑制剂的化学式为##STR1##其中R.sup.1，连接到2-、3-或4-位置，是氢、卤素、C.sub.1 -C.sub.4烷基、羟基或C.sub.1 -C.sub.4烷氧基；Y，连接到2-或3-位置，是--COOH、--COO(C.sub.1 -C.sub.4烷基)或--CONH.sub.2；X为O、S、NH、N(C.sub.1 -C.sub.4烷基)或N(苄基)；R，连接到5-、6-或7-位置，是化学式##STR2##或(3-或4-吡啶基)-Z.sup.2-其中Z.sup.1为--CH.sub.2 --、--CH.sub.2 CH.sub.2 --或--CH.sub.2 CH.sub.2 O--，Z.sup.2为--CH.sub.2 --、--CH.sub.2 CH.sub.2 --、--CH.dbd.CH--、--CH.sub.2 O--或--OCH.sub.2 --；以及它们的药学上可接受的盐；它们的制备方法和含有它们的药物组合物。
• ECTONUCLEOTIDASE INHIBITORS AND METHODS OF USE THEREOF
  申请人：Chen Lijing

  公开号：US20180072742A1

  公开（公告）日：2018-03-15

  The invention relates to novel heterocyclic compounds and pharmaceutical preparations thereof. The invention further relates to methods of treating or preventing cancer using the novel heterocyclic compounds of the invention.

  该发明涉及新颖的杂环化合物及其药物制剂。该发明还涉及使用该新颖杂环化合物治疗或预防癌症的方法。