1-Benzothiazol-2-yl-7-chloro-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester | 108118-78-1

• 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: 1-Benzothiazol-2-yl-7-chloro-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 1-(1,3-benzothiazol-2-yl)-7-chloro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylate
• CAS: 108118-78-1
• 化学式: C₁₈H₁₁ClFN₃O₃S
• 分子量: 403.821
• InChiKey: DKRXDZKHRSOIIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-Benzothiazol-2-yl-7-chloro-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester 在 20percent aq. HCl 作用下， 以 乙腈 为溶剂， 生成 7-(3-Amino-pyrrolidin-1-yl)-1-benzothiazol-2-yl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid; hydrochloride
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Novel 7-Substituted 1,4-Dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic Acids as Antitumor Agents. Part 1

  摘要：

  In an attempt to search for clinically useful antitumor agents, we have discovered that a series of 1,1-disubstituted-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids possessed moderate cytotoxic activity.,We investigated the structure-activity relationships in this series of compounds by changing N-1 and C-7 positions and the core ring structure itself and evaluated the synthesized compounds against several murine and human tumor cell lines. These modifications led us to the following findings. (1) The 2-thiazolyl group at the N-1 position of the naphthyridine structure is the best substituent for antitumor activity. (2) Regarding core ring structure, the naphthyridine derivative is the most active followed by pyridopyrimidine analogue. (3) At the C-7 position, -aminopyrrolidine derivatives are more effective than other amines or thioether derivatives. Finally, the trans-3-amino-4-methoxypyrrolidinyl derivative (43j), and the 3-amino-3-methylpyrrolidinyl derivative (43f) as well as 3-aminopyrrolidinyl derivative (AT-3639, 1) were determined to be effective in in vitro and in vivo antitumor assays, and their activity was comparable to that of etoposide.

  DOI：

  10.1021/jm010057b
• 作为产物：
  描述：

  ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate 在 乙酸酐 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 1-Benzothiazol-2-yl-7-chloro-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Novel 7-Substituted 1,4-Dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic Acids as Antitumor Agents. Part 1

  摘要：

  In an attempt to search for clinically useful antitumor agents, we have discovered that a series of 1,1-disubstituted-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids possessed moderate cytotoxic activity.,We investigated the structure-activity relationships in this series of compounds by changing N-1 and C-7 positions and the core ring structure itself and evaluated the synthesized compounds against several murine and human tumor cell lines. These modifications led us to the following findings. (1) The 2-thiazolyl group at the N-1 position of the naphthyridine structure is the best substituent for antitumor activity. (2) Regarding core ring structure, the naphthyridine derivative is the most active followed by pyridopyrimidine analogue. (3) At the C-7 position, -aminopyrrolidine derivatives are more effective than other amines or thioether derivatives. Finally, the trans-3-amino-4-methoxypyrrolidinyl derivative (43j), and the 3-amino-3-methylpyrrolidinyl derivative (43f) as well as 3-aminopyrrolidinyl derivative (AT-3639, 1) were determined to be effective in in vitro and in vivo antitumor assays, and their activity was comparable to that of etoposide.

  DOI：

  10.1021/jm010057b

文献信息

• Heterocyclic substituted 1,4-dihydri-4-0x9-1,8-naphthyridine analogs
  申请人：Whitten P. Jeffrey

  公开号：US20050004160A1

  公开（公告）日：2005-01-06

  The present invention relates to 1,4-dihydro-4-oxo-1,8-napthpyridine analogs of the formula and pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein A, X, W and Y are substituents. The present invention relates to methods for using such compounds.

  本发明涉及式 1,4-二氢-4-氧代-1,8-萘吡啶类似物及其药物可接受的盐类、酯类和原药，其中 A、X、W 和 Y 为取代基。 及其药学上可接受的盐、酯和原药，其中A、X、W和Y为取代基。本发明涉及使用此类化合物的方法。
• Heterocyclic substituted 1,4-dihydro-4-oxo-1,8-naphthpyridine analogs
  申请人：Whitten P. Jeffrey

  公开号：US20070010512A1

  公开（公告）日：2007-01-11

  The present invention relates to 1,4-dihydro-4-oxo-1,8-napthpyridine analogs of the formula and pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein A, X, W and Y are substituents. The present invention also relates to methods for using such compounds.
• US7163948B2
  申请人：——

  公开号：US7163948B2

  公开（公告）日：2007-01-16