1-butyl-3-ethoxycarbonyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine | 239099-70-8

• 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-butyl-3-ethoxycarbonyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine
• 英文别名: ethyl 1-butyl-4-(3-methoxyphenyl)-2-oxo-1,8-naphthyridine-3-carboxylate
• CAS: 239099-70-8
• 化学式: C₂₂H₂₄N₂O₄
• 分子量: 380.444
• InChiKey: VVUVCKYFNULUJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-butyl-3-ethoxycarbonyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine 在 sodium hydroxide 、 二苯基膦叠氮化物 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[1-butyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)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：

  在 吡啶 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-butyl-3-ethoxycarbonyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine
  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

• Preparation of pyridone derivatives using phthalimido containing starting material
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：US06300500B1

  公开（公告）日：2001-10-09

  A process for preparing a pyridone derivative (4), which comprises reacting the compound (1) with a hypochlorite or a hypobromite or with lead tetraacetate to give the compound (2), and reacting the compound (2) with the compound (3). Said process is preferably especially from the standpoint of safety. wherein R1 is hydrogen, alkyl, substituted alkyl, etc.; Y1 is hydrogen, alky, substituted alky, etc.; Y2 and Y3 are indenpently hydrogen, halogen, etc.; and L is alkyl, substituted alky, etc.

  制备吡啶酮衍生物（4）的方法包括将化合物（1）与次氯酸盐或次溴酸盐或四乙酰基铅反应，得到化合物（2），然后将化合物（2）与化合物（3）反应。所述方法在安全方面尤其偏好。其中R1为氢、烷基、取代烷基等；Y1为氢、烷基、取代烷基等；Y2和Y3分别为氢、卤素等；L为烷基、取代烷基等。
• Pyridone derivatives and process for preparing the same
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：US20010051732A1

  公开（公告）日：2001-12-13

  A process for preparing a pyridone derivative ( 4 ), which comprises reacting the compound ( 1 ) with a hypochlorite or a hypobromite or with lead tetraacetate to give the compound ( 2 ), and reacting the compound ( 2 ) with the compound ( 3 ). Said process is preferably especially from the standpoint of safety. 1 wherein R 1 is hydrogen, alkyl, substituted alkyl, etc.; Y 1 is hydrogen, alky, substituted alky, etc.; Y 2 and Y 3 are indenpently hydrogen, halogen, etc.; and L is alkyl, substituted alkyl, etc.

  一种制备吡啶酮衍生物（4）的方法，包括将化合物（1）与次氯酸盐或次溴酸盐或四乙酸铅反应以得到化合物（2），并将化合物（2）与化合物（3）反应。从安全角度考虑，该方法是首选的。其中R1为氢、烷基、取代烷基等；Y1为氢、烷基、取代烷基等；Y2和Y3独立地为氢、卤素等；L为烷基、取代烷基等。
• PYRIDONE DERIVATIVES AND PROCESS FOR PRODUCING THE SAME
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：EP1086948A1

  公开（公告）日：2001-03-28

  A process for producing a pyridone derivative represented by general formula (4), characterized by reacting a compound represented by general formula (1) with a hypochlorite or hypobromite or with lead tetraacetate to give a compound represented by general formula (2) and reacting this compound with a compound represented by general formula (3). The process is preferable especially from the standpoint of safety. In said formulae, R1 represents hydrogen, alkyl, substituted alkyl, etc.; Y1 represents hydrogen, alkyl, substituted alkyl, etc.; Y2 and Y3 each independently represents hydrogen, halogeno, etc.; and L represents alkyl, substituted alkyl, etc.

  一种生产通式(4)所代表的吡啶酮衍生物的工艺，其特征是将通式(1)所代表的化合物与次氯酸盐或次溴酸盐或四乙酸铅反应，得到通式(2)所代表的化合物，再将该化合物与通式(3)所代表的化合物反应。从安全角度考虑，该工艺更可取。在上述通式中，R1 代表氢、烷基、取代烷基等；Y1 代表氢、烷基、取代烷基等；Y2 和 Y3 各自独立地代表氢、卤素等；L 代表烷基、取代烷基等。
• US6300500B1
  申请人：——

  公开号：US6300500B1

  公开（公告）日：2001-10-09
• US6452008B2
  申请人：——

  公开号：US6452008B2

  公开（公告）日：2002-09-17