[1-(3-Fluoro-6-formyl-5-oxo-8-thiazol-2-yl-5,8-dihydro-[1,8]naphthyridin-2-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester | 727739-69-7

• 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-(3-Fluoro-6-formyl-5-oxo-8-thiazol-2-yl-5,8-dihydro-[1,8]naphthyridin-2-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester
• CAS: 727739-69-7
• 化学式: C₂₁H₂₂FN₅O₄S
• 分子量: 459.501
• InChiKey: ASNMJDHKQXZYBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  106.42
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  [1-(3-Fluoro-6-formyl-5-oxo-8-thiazol-2-yl-5,8-dihydro-[1,8]naphthyridin-2-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester 在 盐酸 作用下， 以81%的产率得到7-(3-aminopyrrolidin-1-yl)-6-fluoro-4-oxo-1-(1,3-thiazol-2-yl)-1,8-naphthyridine-3-carbaldehyde;hydrochloride
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 3-substituted 1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridines as novel antitumor agents

  摘要：

  In order to obtain clinically useful antitumor agent, we have designed and synthesized various 3-substituted 1,4-dihydro4-oxo-1,(2-thiazolyl)-1,8-naphthyridines, and evaluated their cytotoxic activity. The series of novel 3-substituted derivatives synthesized in this study showed good antitumor activity against murine P388 leukemia. Particularly, the 3-formyl 1,8-naphthyridine displayed an antitumor activity equal to that of the 3-carboxy 1,8-naphthyridine against murine and human tumor cell lines as well as in vivo test for mouse leukemia. These results demonstrate that the carboxy group at the C-3 position of 1,8-naphthyridine ring is not essential for antitumor activity. In addition, the trend of cytotoxic activity for the 3-substituted 1,8-naphthyridines was different from that of antibacterial activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.011
• 作为产物：
  描述：

  在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 生成 [1-(3-Fluoro-6-formyl-5-oxo-8-thiazol-2-yl-5,8-dihydro-[1,8]naphthyridin-2-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 3-substituted 1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridines as novel antitumor agents

  摘要：

  In order to obtain clinically useful antitumor agent, we have designed and synthesized various 3-substituted 1,4-dihydro4-oxo-1,(2-thiazolyl)-1,8-naphthyridines, and evaluated their cytotoxic activity. The series of novel 3-substituted derivatives synthesized in this study showed good antitumor activity against murine P388 leukemia. Particularly, the 3-formyl 1,8-naphthyridine displayed an antitumor activity equal to that of the 3-carboxy 1,8-naphthyridine against murine and human tumor cell lines as well as in vivo test for mouse leukemia. These results demonstrate that the carboxy group at the C-3 position of 1,8-naphthyridine ring is not essential for antitumor activity. In addition, the trend of cytotoxic activity for the 3-substituted 1,8-naphthyridines was different from that of antibacterial activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.011