methyl 6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-2-carboxylate | 721926-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: methyl 6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-2-carboxylate
• 英文别名: methyl 6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-2-carboxyIate；methyl 6-methyl-5,7-dihydro-4H-thieno[2,3-c]pyridine-2-carboxylate
• CAS: 721926-88-1
• 化学式: C₁₀H₁₃NO₂S
• 分子量: 211.285
• InChiKey: MYXWZJICHAFRCV-UHFFFAOYSA-N

物化性质

• 沸点：
  336.9±42.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-2-carboxylate 在 1-氯乙基氯甲酸酯 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 23.5h， 生成 Methyl 6-(2,2-dimethyl-1-oxopropyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-2-carboxylate
  参考文献：
  名称：

  Potent Histone Deacetylase Inhibitors Derived from 4-(Aminomethyl)-N-hydroxybenzamide with High Selectivity for the HDAC6 Isoform

  摘要：

  A screen for HDAC6 inhibitors identified acyl derivatives of 4-(aminomethyl)-N-hydroxybenzamide as potent leads with unexpected selectivity over the other subtypes. We designed and synthesized constrained heterocyclic analogues such as tetrahydroisoquinolines that show further enhanced HDAC6 selectivity and inhibitory activity in cellular assays. Selectivity may be attributed to the benzylic spacer more effectively accessing the wider channel of HDAC6 compared to other HDAC subtypes as well as hydrophobic capping groups interacting with the protein surface near the rim of the active site.

  DOI：

  10.1021/jm400385r
• 作为产物：
  描述：

  3-氟-4-吡啶甲醛 在 platinum(IV) oxide 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 54.5h， 生成 methyl 6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-2-carboxylate
  参考文献：
  名称：

  Potent Histone Deacetylase Inhibitors Derived from 4-(Aminomethyl)-N-hydroxybenzamide with High Selectivity for the HDAC6 Isoform

  摘要：

  A screen for HDAC6 inhibitors identified acyl derivatives of 4-(aminomethyl)-N-hydroxybenzamide as potent leads with unexpected selectivity over the other subtypes. We designed and synthesized constrained heterocyclic analogues such as tetrahydroisoquinolines that show further enhanced HDAC6 selectivity and inhibitory activity in cellular assays. Selectivity may be attributed to the benzylic spacer more effectively accessing the wider channel of HDAC6 compared to other HDAC subtypes as well as hydrophobic capping groups interacting with the protein surface near the rim of the active site.

  DOI：

  10.1021/jm400385r

文献信息

• SUBSTITUTED PYRROLIDINE AMIDES, THE PRODUCTION THEREOF, AND THE USE THEREOF AS MEDICATIONS
  申请人：Gerlach Kai

  公开号：US20100099664A1

  公开（公告）日：2010-04-22

  The object of the present invention is novel substituted pyrrolidine amides of the general formula (I) in which D, L. E, G, J, M, L 1 , L 2 , R 4 , and R 5 are defined as in the specification, the tautomers, enantiomers, diastereomers, mixtures, and salts thereof, particularly physiologically tolerated salts with inorganic or organic acids or bases having valuable properties.

  本发明的对象是新颖的取代吡咯烷酰胺，其具有通式(I)，其中D、L、E、G、J、M、L1、L2、R4和R5如说明书所述定义，包括其互变异构体、对映异构体、非对映异构体、混合物以及盐，特别是具有宝贵性质的与无机或有机酸或碱的生理耐受盐。
• [EN] SUBSTITUTED HYDROXAMIC ACIDS AND USES THEREOF<br/>[FR] ACIDES HYDROXAMIQUES SUBSTITUÉS ET LEURS UTILISATIONS
  申请人：MILLENNIUM PHARM INC

  公开号：WO2010151317A1

  公开（公告）日：2010-12-29

  This invention provides compounds of formula (/): wherein R1, R2, G, n, p and q have values as described in the specification, useful as inhibitors of HDAC6. The invention also provides pharmaceutical compositions comprising the compounds of the invention and methods of using the compositions in the treatment of proliferative, inflammatory, infectious, neurological or cardiovascular diseases or disorders.

  这项发明提供了式(/)的化合物：其中R1、R2、G、n、p和q的取值如规范中所述，可用作HDAC6的抑制剂。该发明还提供了包括该发明化合物的药物组合物，以及在治疗增殖性、炎症性、传染性、神经系统或心血管疾病或紊乱中使用这些组合物的方法。
• Substituted hydroxamic acids and uses thereof
  申请人：Blackburn Christopher

  公开号：US20110046157A1

  公开（公告）日：2011-02-24

  This invention provides compounds of formula (I): wherein R 1 , R 2 , G, n, p and q have values as described in the specification, useful as inhibitors of HDAC6. The invention also provides pharmaceutical compositions comprising the compounds of the invention and methods of using the compositions in the treatment of proliferative, inflammatory, infectious, neurological or cardiovascular diseases or disorders.

  本发明提供了式(I)的化合物： 其中R1、R2、G、n、p和q的值如说明书所述，可用作HDAC6的抑制剂。该发明还提供了包括该发明中的化合物的制药组合物以及使用该组合物治疗增生性、炎症性、感染性、神经系统或心血管疾病或紊乱的方法。
• Substituted pyrrolidine amides, the production thereof, and the use thereof as medications
  申请人：Boehringer Ingelheim International GmbH

  公开号：US08309542B2

  公开（公告）日：2012-11-13

  The object of the present invention is novel substituted pyrrolidine amides of the general formula (I) in which D, L. E, G, J, M, L1, L2, R4, and R5 are defined as in the specification, the tautomers, enantiomers, diastereomers, mixtures, and salts thereof, particularly physiologically tolerated salts with inorganic or organic acids or bases having valuable properties.

  本发明的对象是一种新的取代吡咯烷酰胺，其通式为（I），其中D、L、E、G、J、M、L1、L2、R4和R5如规范中所定义，其互变异构体、对映异构体、顺反异构体、混合物和盐，特别是与无机或有机酸或碱物理上耐受的盐具有有价值的性质。
• SUBSTITUTED HYDROXAMIC ACIDS AND USES THEREOF
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US20140329836A1

  公开（公告）日：2014-11-06

  This invention provides compounds of formula (I): wherein R 1 , R 2 , G, n, p and q have values as described in the specification, useful as inhibitors of HDAC6. The invention also provides pharmaceutical compositions comprising the compounds of the invention and methods of using the compositions in the treatment of proliferative, inflammatory, infectious, neurological or cardiovascular diseases or disorders.

  本发明提供了式(I)的化合物：其中R1、R2、G、n、p和q的值如规范所述，可用作HDAC6的抑制剂。本发明还提供了包含本发明化合物的制药组合物和使用该组合物治疗增生性、炎症性、感染性、神经系统或心血管疾病或障碍的方法。