1-methyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine-3-carboxylic acid | 185540-05-0

• 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: 1-methyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine-3-carboxylic acid
• 英文别名: 4-(3-methoxyphenyl)-1-methyl-2-oxo-1,8-naphthyridine-3-carboxylic acid
• CAS: 185540-05-0
• 化学式: C₁₇H₁₄N₂O₄
• 分子量: 310.309
• InChiKey: OPKPAJQJJYVQPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-methyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine-3-carboxylic acid 在 二苯基膦叠氮化物 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-[1-methyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,4-difluorophenyl)urea
  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
• 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 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-methyl-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

• Naphthyridine derivatives
  申请人：Sumitomo Pharmaceuticals Company, Ltd.

  公开号：US05843957A1

  公开（公告）日：1998-12-01

  Naphthyridine derivative of the formula: ##STR1## wherein Ring A is substituted or unsubstituted pyridine, X is --N(R.sup.2)--CO--(R.sup.2 is H, alkyl, substituted alkyl, etc.), Z is a direct bond, --NH--, C.sub.1 -C.sub.2 alkylene, or --CH.dbd.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.

  公式为：##STR1##其中环A是取代或未取代的吡啶，X为--N(R.sup.2)--CO--(R.sup.2为H，烷基，取代烷基等)，Z为直接键，--NH--，C.sub.1 -C.sub.2烷基或--CH.dbd.CH--，Y为烷基，取代烷基，芳香基或取代芳香基等，B为烷基，取代烷基，芳香基或取代芳香基等，或其酸加成盐。这些化合物具有酰基辅酶A：胆固醇酰基转移酶抑制活性，可用作预防或治疗高脂血症、动脉硬化及相关疾病的药物。
• 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。
• US5843957A
  申请人：——

  公开号：US5843957A

  公开（公告）日：1998-12-01
• Synthesis and structure–activity relationship studies on a novel series of naphthylidinoylureas as inhibitors of acyl-CoA:cholesterol O -acyltransferase (ACAT)
  作者：Satoshi Ohnuma、Masami Muraoka、Katsuhisa Ioriya、Naohito Ohashi

  DOI：10.1016/j.bmcl.2003.12.045

  日期：2004.3

  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.