7-氨基-8-甲基喹啉-3-甲醛 | 521074-55-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 7-氨基-8-甲基喹啉-3-甲醛
• 英文名称: 7-amino-8-methylquinoline-3-carboxaldehyde
• 英文别名: 7-amino-8-methyl-quinoline-3-carbaldehyde；7-amino-8-methylquinoline-3-carbaldehyde
• CAS: 521074-55-5
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: QUWSKHBEAJXBPT-UHFFFAOYSA-N

物化性质

• 密度：
  1.266

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  56
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  7-氨基-8-甲基喹啉-3-甲醛 在 三乙酰氧基硼氢化钠 、 三乙胺 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 4.5h， 生成 4-(2-cyclopropylethoxy)-N-[8-methyl-3-(pyrrolidin-1-ylmethyl)quinolin-7-yl]benzamide
  参考文献：
  名称：

  Synthesis, Structure–Activity Relationship, and Pharmacological Studies of Novel Melanin-Concentrating Hormone Receptor 1 Antagonists 3-Aminomethylquinolines: Reducing Human Ether-a-go-go-Related Gene (hERG) Associated Liabilities

  摘要：

  Recently, we discovered 3-aminomethylquinoline derivative 1, a selective, highly potent, centrally acting, and orally bioavailable human MCH receptor 1 (hMCHR1) antagonist, that inhibited food intake in F344 rats with diet-induced obesity (DIO). Subsequent investigation of 1 was discontinued because 1 showed potent hERG K+ channel inhibition in a patch-clamp study. To decrease hERG K+ channel inhibition, experiments with ligand-based drug designs based on 1 and a docking study were conducted. Replacement of the terminal p-fluorophenyl group with a cyclopropylmethoxy group, methyl group introduction on the benzylic carbon at the 3-position of the quinoline core, and employment of a [2-(acetylamino)ethyl]amino group as the amine portion eliminated hERG K+ channel inhibitory activity in a patch-clamp study, leading to the discovery of N-{3-[(1R)-1-{[2-(acetylamino)ethyl]amino}ethyl]-8-methylquinolin-7-yl}-4-(cyclopropylmethoxy)benzamide (R)-10h. The compound (R)-10h showed potent inhibitory activity against hMCHR1 and dose-dependently suppressed food intake in a 2-day study on DIO-F344 rats. Furthermore, practical chiral synthesis of (R)-10h was performed to determine the molecule's absolute configuration.

  DOI：

  10.1021/jm300167z
• 作为产物：
  描述：

  2,6-二氨基甲苯 、 2-dimethylaminomethylene-1,3-bis(dimethylimmonio)propane bistetrafluoroborate 在 盐酸 、 水 、 potassium carbonate 作用下， 以 异丙醇 、 水 、 乙酸乙酯 为溶剂， 反应 21.0h， 生成 7-氨基-8-甲基喹啉-3-甲醛
  参考文献：
  名称：

  EP1447402

  摘要：

  公开号：

文献信息

• HETEROCYCLIC COMPOUND
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2261213A1

  公开（公告）日：2010-12-15

  The present invention provides to a compound having melanin-concentrating hormone receptor antagonistic action and low toxicity, and useful as a agent for the prophylaxis or treatment of obesity and the like. The present invention relates to a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof.

  本发明提供了一种具有黑色素浓集激素受体拮抗作用和低毒性的化合物，可用作预防或治疗肥胖等疾病的药剂。本发明涉及一种由下式（I）表示的化合物：其中每个符号如规范中定义的，或其盐。
• Quinoline compound
  申请人：Ishihara Yuji

  公开号：US20050209213A1

  公开（公告）日：2005-09-22

  A compound, which has a melanin-concentrating hormone antagonistic action and useful as an agent for preventing or treating obesity, and which is represented by the formula: wherein Ar is a cyclic group optionally having substituent(s); X is a bond or a spacer having a main chain of 1 to 6 atoms; R 1 and R 2 are the same or different and each is a hydrogen atom or a hydrocarbon group optionally having substituent(s), or R 1 and R 2 may form, together with the adjacent nitrogen atom, a nitrogen-containing heterocycle optionally having substituent(s); Y is a divalent hydrocarbon group optionally having substituent(s) (except CO); R 3 is a hydrogen atom or a hydrocarbon group optionally having substituent(s); and ring A and ring B may further have substituents, and when ring B further has a substituent, the substituent may be linked to R 1 to form a ring, or a salt thereof, or a prodrug thereof, is provided.

  一种化合物，具有黑色素浓缩激素拮抗作用，可用作预防或治疗肥胖症的药物，其化学式为：其中，Ar是一个环状基团，可以有取代基；X是1到6个原子的主链的键或空隙；R1和R2相同或不同，分别是氢原子或烃基，可以有取代基，或者R1和R2可以与相邻的氮原子一起形成含氮杂环，可以有取代基；Y是一个双价的烃基，可以有取代基（除CO）；R3是氢原子或烃基，可以有取代基；环A和环B还可以有取代基，当环B还有取代基时，取代基可以与R1连接形成一个环，或其盐，或其前药。
• Heterocyclic compound
  申请人：Murata Toshiki

  公开号：US20110015225A1

  公开（公告）日：2011-01-20

  The present invention provides to a compound having melanin-concentrating hormone receptor antagonistic action and low toxicity, and useful as a agent for the prophylaxis or treatment of obesity and the like. The present invention relates to a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof.

  本发明提供了一种具有黑色素浓聚激素受体拮抗作用和低毒性的化合物，可用作预防或治疗肥胖等疾病的药剂。本发明涉及一种由公式（I）表示的化合物，其中每个符号如规范中所定义，或其盐。
• QUINOLINE COMPOUND
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1447402A1

  公开（公告）日：2004-08-18

  A compound, which has a melanin-concentrating hormone antagonistic action and useful as an agent for preventing or treating obesity, and which is represented by the formula:    wherein Aris a cyclic group optionally having substituent(s) ; Xis a bond or a spacer having a main chain of 1 to 6 atoms; R1 and R2are the same or different and each is a hydrogen atom or a hydrocarbon group optionally having substituent(s), or R1 and R2 may form, together with the adjacent nitrogen atom, a nitrogen-containing heterocycle optionally having substituent(s); Yis a divalent hydrocarbon group optionally having substituent(s) (except CO); R3is a hydrogen atom or a hydrocarbon group optionally having substituent(s); and ring A and ring Bmay further have substituents, and when ring B further has a substituent, the substituent may be linked to R1 to form a ring, or a salt thereof, or a prodrug thereof, is provided.

  一种化合物，具有拮抗黑色素浓缩激素的作用，可作为预防或治疗肥胖症的药物，由式表示： 式中 Ar 是一个环状基团，可选择具有取代基； X 是主链为 1 至 6 个原子的键或间隔物； R1 和 R2 相同或不同，各自为氢原子或任选具有取代基的烃基，或 R1 和 R2 可与邻近的氮原子一起形成任选具有取代基的含氮杂环； Y 是可选具有取代基的二价烃基（CO 除外）； R3 是氢原子或可选具有取代基的烃基；以及 环 A 和环 B 可进一步具有取代基，当环 B 进一步具有取代基时，该取代基可与 R1 连接形成一个环、 或其盐或其原药。
• US7183415B2
  申请人：——

  公开号：US7183415B2

  公开（公告）日：2007-02-27