(5-bromo-2-chlorophenyl)(6-ethylpyridin-3-yl)methanone | 842136-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5-bromo-2-chlorophenyl)(6-ethylpyridin-3-yl)methanone
• 英文别名: 5-Bromo-2-chlorophenyl 6-ethyl-3-pyridyl ketone；(5-bromo-2-chlorophenyl)-(6-ethylpyridin-3-yl)methanone
• CAS: 842136-65-6
• 化学式: C₁₄H₁₁BrClNO
• 分子量: 324.604
• InChiKey: MXIJVFAJLXFSPX-UHFFFAOYSA-N

物化性质

• 沸点：
  424.0±45.0 °C(Predicted)
• 密度：
  1.463±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5-bromo-2-chlorophenyl)(6-ethylpyridin-3-yl)methanone 在 一水合肼 、 potassium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 1.5h， 以64.2%的产率得到5-(5-bromo-2-chlorobenzyl)-2-ethylpyridine
  参考文献：
  名称：

  Discovery of Canagliflozin, a Novel C-Glucoside with Thiophene Ring, as Sodium-Dependent Glucose Cotransporter 2 Inhibitor for the Treatment of Type 2 Diabetes Mellitus

  摘要：

  We discovered that C-glucosides 4 bearing a heteroaromatic ring formed metabolically more stable inhibitors for sodium-dependent glucose cotransporter 2 (SGLT2) than the O-glucoside, 2 (T-1095). A novel thiophene derivative 4b-3 (canagliflozin) was a highly potent and selective SGLT2 inhibitor and showed pronounced anti-hyperglycemic effects in high-fat diet fed KK (HF-KK) mice.

  DOI：

  10.1021/jm100332n
• 作为产物：
  描述：

  (5-bromo-2-chlorophenyl)(6-bromopyridin-3-yl)methanone 、 三乙基铝 在 四(三苯基膦)钯 、 cerium(III) chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以61.9%的产率得到(5-bromo-2-chlorophenyl)(6-ethylpyridin-3-yl)methanone
  参考文献：
  名称：

  Discovery of Canagliflozin, a Novel C-Glucoside with Thiophene Ring, as Sodium-Dependent Glucose Cotransporter 2 Inhibitor for the Treatment of Type 2 Diabetes Mellitus

  摘要：

  We discovered that C-glucosides 4 bearing a heteroaromatic ring formed metabolically more stable inhibitors for sodium-dependent glucose cotransporter 2 (SGLT2) than the O-glucoside, 2 (T-1095). A novel thiophene derivative 4b-3 (canagliflozin) was a highly potent and selective SGLT2 inhibitor and showed pronounced anti-hyperglycemic effects in high-fat diet fed KK (HF-KK) mice.

  DOI：

  10.1021/jm100332n

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：US20120058941A1

  公开（公告）日：2012-03-08

  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.

  该化合物的分子式为：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可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）；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。
• Novel compounds having inhibitory activity against sodium-dependant glucose transporter
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP2514756A1

  公开（公告）日：2012-10-24

  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); a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  式中的化合物： 其中环 A 和环 B 是(1) 环 A 是被任选取代的不饱和单环杂环，环 B 是被任选取代的不饱和单环杂环、被任选取代的不饱和融合杂环或被任选取代的苯环环 B 是任选取代的不饱和单环杂环或任选取代的不饱和融合杂环，或 (3) 环 A 是任选取代的不饱和融合杂环，环 B 独立地是任选取代的不饱和单环杂环、任选取代的不饱和融合杂环或任选取代的苯环；X 是碳原子或氮原子； Y 是-(CH2)n-(n 是 1 或 2)； 其药学上可接受的盐，或其原药。