ethyl 7-(ethylthio)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate | 84424-21-5

• 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: ethyl 7-(ethylthio)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate
• 英文别名: ethyl 7-ethylthio-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate；ethyl 7-ethylsulfanyl-6-fluoro-4-oxo-1H-1,8-naphthyridine-3-carboxylate
• CAS: 84424-21-5
• 化学式: C₁₃H₁₃FN₂O₃S
• 分子量: 296.322
• InChiKey: JNZPZWUGEHLMJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 7-(ethylthio)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 在 盐酸 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 4.5h， 生成 6-fluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(3-methylamino-1-pyrrolidinyl)-4-oxo-1,8-naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  吡啶酮羧酸作为抗菌剂。4. 7-（3-氨基-1-吡咯烷基）-1-乙基-6-氟-1,4-二氢-4-氧代-1,8-萘啶-3-羧酸及其类似物的合成及抑菌活性。

  摘要：

  用1-取代的7-氯-，7-（乙基磺酰基）-和7-（甲苯磺酰氧基）-制备在C-7具有氨基和/或羟基取代的环状氨基的标题化合物（28-56）。 6-氟-1,4-二氢-4-氧代-1,8-萘啶-3-羧酸及其乙酯（3-7）与环状胺，例如3-氨基吡咯烷。N-1取代基包括乙基，乙烯基和2-氟乙基。作为体外和体内抗菌筛选的结果，三种化合物，1-乙基和1-乙烯基-7-（3-氨基-1-吡咯烷基）-6-氟-1,4-二氢-4-氧代-发现1,8-萘啶-3-羧酸（33a和33b）和1-乙烯基-7- [3-（甲基氨基）-1-吡咯烷基]类似物34b具有比依诺沙星（2）更高的活性。值得进一步的生物学研究。讨论了构效关系。

  DOI：

  10.1021/jm00378a004
• 作为产物：
  描述：

  Diethyl 2-[[(6-ethylsulfanyl-5-fluoropyridin-2-yl)amino]methylidene]propanedioate 以75%的产率得到
  参考文献：
  名称：

  MATSUMOTO, JUN-ICHI;MIYAMOTO, TERUYUKI;MINAMIDA, AKIRA;NISHIMURA, YOSHIRO+, J. HETEROCYCL. CHEM., 1984, 21, N 3, 673-679

  摘要：

  DOI：

文献信息

• Synthesis of fluorinated pyridines by the balz-schiemann reaction. An alternative route to enoxacin, a new antibacterial pyridonecarboxylic acid
  作者：Jun-Ichi Matsumoto、Teruyuki Miyamoto、Akira Minamida、Yoshiro Nishimura、Hiroshi Egawa、Haruki Nishimura

  DOI：10.1002/jhet.5570210309

  日期：1984.5

  Fluorination of the 2,6-disubstituted 3-aminopyridines 5 and 12 by the Balz-Schiemann reaction is described. 2,6-Dichloro-3-pyridinediazonium tetrafluoroborate (6) and 2-substituted 6-acetylamino-3-pyridinediazonium tetrafluoroborates 13 were heated with or without a solvent to give the corresponding fluorinated pyridines 7 and 14, respectively, in good yields. 2-Substituted 6-acetylamino-3-fluoropyridines

  描述了通过Balz-Schiemann反应对2，6-二取代的3-氨基吡啶5和12的氟化。2,6-二氯-3- pyridinediazonium四氟硼酸盐（6）和2-取代的6-乙酰氨基-3- pyridinediazonium四氟硼酸盐13用或不用溶剂加热，得到相应的氟化吡啶7和14分别，以良好产率。通过已知方法将2-取代的6-乙酰氨基-3-氟吡啶（14）转化为一系列的7-取代的1-乙基-6-氟-1,4-二氢-4-氧代-1,8-萘啶- 3-羧酸21包括新的潜在抗菌剂依诺沙星[1-乙基-6-氟-1,4-二氢-4-氧代-7-（1-哌嗪基）-1,8-萘啶-3-羧酸[（2）] 。
• Naphthyridine derivatives and their use as anti-bacterials
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US04382937A1

  公开（公告）日：1983-05-10

  A 1,8-naphthyridine compound of the formula ##STR1## wherein R is a vinyl or 2-fluoroethyl group, and R.sub.1 and R.sub.2 are the same or different and each represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, and the esters thereof and salts thereof. For example, 7-(3-amino-1-pyrrolidinyl)-6-fluoro-1,4-dihydro-4-oxo-1-vinyl-1,8-naphthyr idine-3-carboxylic acid and nontoxic salts thereof, which are covered by the aforesaid compound, are useful as an antibacterial agent.

  化合物为1,8-萘啶类化合物，其化学式为##STR1##其中R是乙烯或2-氟乙基基团，R.sub.1和R.sub.2相同或不同，每个代表氢原子或具有1到4个碳原子的低级烷基基团，其酯类和盐类。例如，7-(3-氨基-1-吡咯烷基)-6-氟-1,4-二氢-4-氧代-1-乙烯基-1,8-萘啶-3-羧酸及其无毒盐，这些化合物被用作抗菌剂。
• 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
  作者：Kyoji Tomita、Yasunori Tsuzuki、Koh-ichiro Shibamori、Masanori Tashima、Fumie Kajikawa、Yuji Sato、Shigeki Kashimoto、Katsumi Chiba、Katsuhiko Hino

  DOI：10.1021/jm010057b

  日期：2002.12.1

  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.
• EGAWA, HIROSHI;MIYAMOTO, TERUYUKI;MINAMIDA, AKIRA;NISHIMURA, YOSHIRO;OKAD+, J. MED. CHEM., 1984, 27, N 12, 1543-1548
  作者：EGAWA, HIROSHI、MIYAMOTO, TERUYUKI、MINAMIDA, AKIRA、NISHIMURA, YOSHIRO、OKAD+

  DOI：——

  日期：——
• US4382937A
  申请人：——

  公开号：US4382937A

  公开（公告）日：1983-05-10