3-(4-ethylbenzyl)pyridin-2-ol | 866606-91-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(4-ethylbenzyl)pyridin-2-ol
• 英文别名: 3-[(4-ethylphenyl)methyl]-1H-pyridin-2-one
• CAS: 866606-91-9
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: GVUMFMGCMQLAGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-ethylbenzyl)pyridin-2-ol 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 1,2-二氯乙烷 作用下， 以 顺-1,2-二氯乙烯 、 甲醇 、 乙腈 为溶剂， 生成 3-[(4-ethylphenyl)methyl]-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]pyridin-2-one
  参考文献：
  名称：

  N-glucosides as human sodium-dependent glucose cotransporter 2 (hSGLT2) inhibitors

  摘要：

  Inhibition of renal sodium-dependent glucose cotransporter 2 (SGLT2) increases urinary glucose excretion (UGE), and thus reduces blood glucose levels in hyperglycemia. A series of N-glucosides was synthesized for biological evaluation as human SGLT2 (hSGLT2) inhibitors. Among these compounds, N-glucoside 9d possessing an indole core structure showed good in vitro activity (IC50 = 7.1 nM against hSGLT2). Furthermore, 9d exhibited favorable in vivo potency with regard to UGE in rats based on good pharmacokinetic profiles. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.042
• 作为产物：
  描述：

  2-benzyloxy-3-pyridyl 4-ethylphenyl ketone 在 sodium tetrahydroborate 、 盐酸 、 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 、 甲醇 为溶剂， 以27%的产率得到3-(4-ethylbenzyl)pyridin-2-ol
  参考文献：
  名称：

  N-glucosides as human sodium-dependent glucose cotransporter 2 (hSGLT2) inhibitors

  摘要：

  Inhibition of renal sodium-dependent glucose cotransporter 2 (SGLT2) increases urinary glucose excretion (UGE), and thus reduces blood glucose levels in hyperglycemia. A series of N-glucosides was synthesized for biological evaluation as human SGLT2 (hSGLT2) inhibitors. Among these compounds, N-glucoside 9d possessing an indole core structure showed good in vitro activity (IC50 = 7.1 nM against hSGLT2). Furthermore, 9d exhibited favorable in vivo potency with regard to UGE in rats based on good pharmacokinetic profiles. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.042

文献信息

• [EN] NOVEL COMPOUNDS HAVING INHIBITORY ACTIVITY AGAINST SODIUM-DEPENDANT TRANSPORTER<br/>[FR] NOUVEAUX COMPOSES POSSEDANT UNE ACTIVITE INHIBITRICE DIRIGEE CONTRE LE TRANSPORTEUR DEPENDANT DU SODIUM
  申请人：TANABE SEIYAKU CO

  公开号：WO2005012326A1

  公开（公告）日：2005-02-10

  A compound of the formula (I) wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is -(CH2)n- (n is 1 or 2); a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  化合物的式子（I）其中环A和环B为：（1）环A是可选取代的不饱和单环杂环，环B是可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环，（2）环A是可选取代的苯环，环B是可选取代的不饱和单环杂环或可选取代的不饱和融合杂双环，或（3）环A是可选取代的不饱和融合杂双环，环B独立地是可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；X是碳原子或氮原子；Y是-(CH2)n-（n为1或2）；其药物可接受的盐或前药。
• Novel compounds
  申请人：Nomura Sumihiro

  公开号：US20050233988A1

  公开（公告）日：2005-10-20

  A compound of the formula: wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is —(CH 2 ) n — (n is 1 or 2); a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  一种化合物，其化学式为：其中环A和环B分别为：（1）环A为可选取代的不饱和单环杂环，环B为可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；（2）环A为可选取代的苯环，环B为可选取代的不饱和单环杂环或可选取代的不饱和融合杂双环；或（3）环A为可选取代的不饱和融合杂双环，环B独立地为可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；X为碳原子或氮原子；Y为—（CH2）n—（n为1或2）；其药学上可接受的盐或其前药。
• GLUCOPYRANOSIDE COMPOUND
  申请人：NOMURA Sumihiro

  公开号：US20120258913A1

  公开（公告）日：2012-10-11

  A compound of the formula: wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is —(CH 2 ) n — (n is 1 or 2); or a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  一种化合物的公式：其中环A和环B是：(1) 环A是一个可选取代的不饱和单环杂环，环B是一个可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环，(2) 环A是一个可选取代的苯环，环B是一个可选取代的不饱和单环杂环或可选取代的不饱和融合杂双环，或(3) 环A是一个可选取代的不饱和融合杂双环，环B是独立的可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；X是一个碳原子或氮原子；Y是—(CH2)n—(n为1或2)；或其药学上可接受的盐或前药。
• Glucopyranoside compound
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：US08202984B2

  公开（公告）日：2012-06-19

  A compound of the formula: wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is —(CH2)n— (n is 1 or 2); or a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  该化合物的化学式为：其中环A和环B分别为：（1）环A是可选取代的不饱和单环杂环，环B是可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环，（2）环A是可选取代的苯环，环B是可选取代的不饱和单环杂环或可选取代的不饱和融合杂双环，或（3）环A是可选取代的不饱和融合杂双环，环B是独立的可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；X是碳原子或氮原子；Y是—(CH2)n—（n为1或2）；或其药学上可接受的盐或前药。
• BENZYLPHENYL GLUCOPYRANOSIDE DERIVATIVE
  申请人：Honda Takeshi

  公开号：US20090137499A1

  公开（公告）日：2009-05-28

  The present invention relates to a benzylphenyl glucopyranoside derivative having an excellent inhibitory effect on human SGLT1 and/or SGLT2 activity. There is provided a compound or a pharmacologically acceptable salt thereof represented by the following general formula (I): wherein R 1 represents a hydrogen atom, an amino group, a hydroxy C 1 -C 6 alkyl group, etc.; R 2 represents a hydrogen atom, etc.; R 3 represents a C 1 -C 6 alkyl group, a hydroxy C 1 -C 6 alkyl group, etc.; R 4 represents a hydrogen atom, a C 2 -C 7 acyl group, etc.; R 5 , R 6 , R 7 , and R 8 are the same or different and each represents a hydrogen atom or a C 1 -C 6 alkyl group, provided that R 5 , R 6 , R 7 and R 8 are not hydrogen atoms at the same time; n is 0 to 4; and X is CH or N.

  本发明涉及一种对人类SGLT1和/或SGLT2活性具有优异抑制作用的苯甲基苯基葡萄糖吡喃糖苷衍生物。提供了一种化合物或其药理学上可接受的盐，其代表以下通式（I）： 其中，R1代表氢原子，氨基，羟基C1-C6烷基等；R2代表氢原子等；R3代表C1-C6烷基，羟基C1-C6烷基等；R4代表氢原子，C2-C7酰基等；R5，R6，R7和R8相同或不同，每个代表氢原子或C1-C6烷基，但要求R5，R6，R7和R8同时不是氢原子；n为0到4；X为CH或N。