4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine-3-carboxylic acid | 185540-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine-3-carboxylic acid
• 英文别名: 3-carboxy-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine；4-(3-methoxyphenyl)-2-oxo-1H-1,8-naphthyridine-3-carboxylic acid
• CAS: 185540-06-1
• 化学式: C₁₆H₁₂N₂O₄
• 分子量: 296.282
• InChiKey: LFLJBVVVTUZBKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  88.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine-3-carboxylic acid 生成 N-[4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-[2-tert-butyl-5-(morpholinomethyl)phenyl]urea
  参考文献：
  名称：

  Naphthyridine derivatives

  摘要：

  化合物的分子式（I）：其中环A是取代或未取代的吡啶环，Y是取代或未取代的烷基等，R1是氢，或取代或未取代的烷基等，R2是氢或较低的烷基，R3是较低的烷基，Z是1）—D1—Q【D1是直链键或二价的C1-8碳氢化合物等，Q是羟基，羧基等。】，或2）—D2M—E—W【D2是直链键或二价的C1-8碳氢化合物等，M是氧，硫等，E是直链键或二价的C1-8碳氢化合物等，W是羟基，羧基等。】，或其前药，或其药用上可接受的盐，该化合物具有酰辅酶A：胆固醇酰基转移酶（ACAT）抑制活性，并且可用作治疗高脂血症和动脉粥样硬化的药物。

  公开号：

  US06420381B1
• 作为产物：
  描述：

  N-{3-[hydroxy(3-methoxyphenyl)methyl]pyridin-2-yl}pivalamide 在 吡啶 、 盐酸 、 manganese(IV) oxide 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and structure–activity relationship studies on a novel series of naphthylidinoylureas as inhibitors of acyl-CoA:cholesterol O -acyltransferase (ACAT)

  摘要：

  The synthesis and structure-activity relationships of N-phenyl-N'-[3-(4-phenylnaphthylidinoyl)]urea derivatives 3 as a novel structural class of potent ACAT inhibitors is described. A 3-methoxy group substituted on the naphthylidinone 4-phenyl ring, together with a 1-N-(n)butyl substitution, SM-32504 (3m), gave a potent ACAT inhibitor, in vitro, respectively. The most potent compound, SM-32504 (3m), decreased the serum cholesterol level significantly in a high fat and high cholesterol-fed mouse model. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.045

文献信息

• NOVEL NAPHTHYRIDINE DERIVATIVES
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0842933A1

  公开（公告）日：1998-05-20

  Naphthyridine derivative of the formula: wherein Ring A is substituted or unsubstituted pyridine, X is ―N(R2)―CO― (R2 is H, alkyl, substituted alkyl, etc.), Z is a direct bond, ―NH―, C1-C2 alkylene, or ―CH=CH―, Y is alkyl, substituted alkyl, aromatic group or substituted aromatic group, etc., B is alkyl, substituted alkyl, aromatic group or substituted aromatic group, or an acid addition salt thereof, these compounds having acyl-CoA: cholesterol acyl transferase inhibitory activity, and being useful as an agent for prophylaxis or treatment of hyperlipidemia, atherosclerosis, and related diseases thereof.

  式中的萘啶衍生物： 其中环 A 是取代或未取代的吡啶，X 是-N(R2)-CO-（R2 是 H、烷基、取代的烷基等），Z 是直接键、-NH-、C1-C2 亚烷基或-CH=CH-，Y 是烷基、取代的烷基、芳香基团或取代的芳香基团等、B 是烷基、取代的烷基、芳香基团或取代的芳香基团，或其酸加成盐，这些化合物具有酰基-CoA：胆固醇酰基转移酶抑制活性，可用作预防或治疗高脂血症、动脉粥样硬化及其相关疾病的药物。
• NAPHTHYRIDINE DERIVATIVES
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：EP1104763A1

  公开（公告）日：2001-06-06

  A compound of the formula (I): wherein Ring A is substituted or unsubstituted pyridine ring, Y is substituted or unsubstituted alkyl, etc., R1 is hydrogen, or substituted or unsubstituted alkyl, etc., R2 is hydrogen or lower alkyl, R3 is lower alkyl, Z is 1)―D1―Q [D1 is direct bond or divalent C1-8 hydrocarbon, etc.; Q is hydroxy, carboxyl, etc.], or 2) ―D2―M―E―W [D2 is direct bond or divalent C1-8 hydrocarbon, etc., M is oxygen, sulfur, etc., E is direct bond or divalent C1-8 hydrocarbon, etc., W is hydroxyl, carboxyl, etc.], or a prodrug thereof, or a pharmaceutically acceptable salt of the same, which exhibits acyl-CoA: cholesterol acyl transferase (ACAT) inhibitory activity, and is useful as an agent for treatment of hyperlipidemia and atherosclerosis.

  式(I)的化合物： 其中环 A 是取代或未取代的吡啶环，Y 是取代或未取代的烷基等，R1 是氢或取代或未取代的烷基等，R2 是氢或低级烷基，R3 是低级烷基，Z 是 1)-D1-Q [D1 是直接键或二价 C1-8 碳氢化合物等；Q 是羟基、羧基等]，或 2) -D2-M-E-W [D2 为直接键或二价 C1-8 碳氢化合物等；M 为氧、硫等；E 为直接键或二价 C1-8 碳氢化合物等；W 为羟基、羧基等]、 或其原药，或其药学上可接受的盐，具有酰基-CoA：胆固醇酰基转移酶（ACAT）抑制活性，可作为治疗高脂血症和动脉粥样硬化的药物。
• US5843957A
  申请人：——

  公开号：US5843957A

  公开（公告）日：1998-12-01
• US6420381B1
  申请人：——

  公开号：US6420381B1

  公开（公告）日：2002-07-16
• Naphthyridine derivatives
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：US06420381B1

  公开（公告）日：2002-07-16

  A compound of the formula (I): wherein Ring A is substituted or unsubstituted pyridine ring, Y is substituted or unsubstituted alkyl, etc., R1 is hydrogen, or substituted or unsubstituted alkyl, etc., R2 is hydrogen or lower alkyl, R3 is lower alkyl, Z is 1) —D1—Q [D1 is direct bond or divalent C1-8 hydrocarbon, etc., Q is hydroxy, carboxyl, etc.], or 2) —D2M—E—W [D2 is direct bond or divalent C1-8 hydrocarbon, etc., M is oxygen, sulfur, etc., E is direct bond or divalent C1-8 hydrocarbon, etc., W is hydroxyl, carboxyl, etc.], or a prodrug thereof, or a pharmaceutically acceptable salt of the same, which exhibits acyl-CoA: cholesterol acyl transferase (ACAT) inhibitory activity, and is useful as an agent for treatment of hyperlipidemia and atherosclerosis.

  化合物的分子式（I）：其中环A是取代或未取代的吡啶环，Y是取代或未取代的烷基等，R1是氢，或取代或未取代的烷基等，R2是氢或较低的烷基，R3是较低的烷基，Z是1）—D1—Q【D1是直链键或二价的C1-8碳氢化合物等，Q是羟基，羧基等。】，或2）—D2M—E—W【D2是直链键或二价的C1-8碳氢化合物等，M是氧，硫等，E是直链键或二价的C1-8碳氢化合物等，W是羟基，羧基等。】，或其前药，或其药用上可接受的盐，该化合物具有酰辅酶A：胆固醇酰基转移酶（ACAT）抑制活性，并且可用作治疗高脂血症和动脉粥样硬化的药物。