Ethyl 4,9b-diaza-5,6-difluoro-8,9b-dihydro-8-oxo-1-thia-1H-cyclopentaphenalene-9-carboxylate | 158898-68-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: Ethyl 4,9b-diaza-5,6-difluoro-8,9b-dihydro-8-oxo-1-thia-1H-cyclopentaphenalene-9-carboxylate
• 英文别名: ethyl 5,6-difluoro-9-oxo-12-thia-3,14-diazatetracyclo[6.5.2.04,15.011,14]pentadeca-1(13),2,4(15),5,7,10-hexaene-10-carboxylate
• CAS: 158898-68-1
• 化学式: C₁₅H₈F₂N₂O₃S
• 分子量: 334.303
• InChiKey: VZGUCWVSKVXEKH-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：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 Ethyl 4,9b-diaza-5,6-difluoro-8,9b-dihydro-8-oxo-1-thia-1H-cyclopentaphenalene-9-carboxylate 生成 4,9b-Diaza-8,9b-dihydro-6-fluoro-5-(4-methyl-1-piperazinyl)-8-oxo-1-thia-1H-cyclopentaphenalene-9-carboxylic acid hydrochloride
  参考文献：
  名称：

  Synthesis of New DNA Gyrase Inhibitors: Application of the DMSO Oxidation to the Conversion of the Amine into the Imine

  摘要：

  A novel type of pyridonecarboxylic acid with a planar thiazolopyrazine-incorporated tetracyclic skeleton, 4,9b-diaza-8,9b-dihydro-6-fluoro-5-(4-methyl-1-piperazinyl)-8-oxo-1-thia-1H-yclopenta[cd]phenalene-9-carboxylic acid (3), was prepared. Compound 3 was a potent inhibitor of DNA gyrase and exhibited attractive antibacterial activity against both Gram-positive and Gram-negative bacteria. In the course of the synthetic studies, we have found a new oxidation method of the amine 4 to the imine 5 with DMSO activated by trifluoroacetic anhydride or oxalyl chloride. The DMSO/trifluoroacetic anhydride method gave the byproduct 8, an unusual (methylthio)methyl adduct. The DMSO/oxalyl chloride method gave the byproducts 9 and 10, a (methylthio)methyl ester, and a halogen adduct, respectively. The mechanisms of these oxidations are also discussed.

  DOI：

  10.1021/jo00099a042
• 作为产物：
  描述：

  Diethyl (6,7-difluoro-1H,4H-thiazolo<3,4-a>quinoxalin-1-ylidene)malonate 在 PPA 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 反应 3.0h， 生成 Ethyl 4,9b-diaza-5,6-difluoro-8,9b-dihydro-8-oxo-1-thia-1H-cyclopentaphenalene-9-carboxylate
  参考文献：
  名称：

  Synthesis of New DNA Gyrase Inhibitors: Application of the DMSO Oxidation to the Conversion of the Amine into the Imine

  摘要：

  A novel type of pyridonecarboxylic acid with a planar thiazolopyrazine-incorporated tetracyclic skeleton, 4,9b-diaza-8,9b-dihydro-6-fluoro-5-(4-methyl-1-piperazinyl)-8-oxo-1-thia-1H-yclopenta[cd]phenalene-9-carboxylic acid (3), was prepared. Compound 3 was a potent inhibitor of DNA gyrase and exhibited attractive antibacterial activity against both Gram-positive and Gram-negative bacteria. In the course of the synthetic studies, we have found a new oxidation method of the amine 4 to the imine 5 with DMSO activated by trifluoroacetic anhydride or oxalyl chloride. The DMSO/trifluoroacetic anhydride method gave the byproduct 8, an unusual (methylthio)methyl adduct. The DMSO/oxalyl chloride method gave the byproducts 9 and 10, a (methylthio)methyl ester, and a halogen adduct, respectively. The mechanisms of these oxidations are also discussed.

  DOI：

  10.1021/jo00099a042

文献信息

• Synthesis of New DNA Gyrase Inhibitors: Application of the DMSO Oxidation to the Conversion of the Amine into the Imine
  作者：Yoshikazu Jinbo、Hirosato Kondo、Masahiro Taguchi、Fumio Sakamoto、Goro Tsukamoto

  DOI：10.1021/jo00099a042

  日期：1994.10

  A novel type of pyridonecarboxylic acid with a planar thiazolopyrazine-incorporated tetracyclic skeleton, 4,9b-diaza-8,9b-dihydro-6-fluoro-5-(4-methyl-1-piperazinyl)-8-oxo-1-thia-1H-yclopenta[cd]phenalene-9-carboxylic acid (3), was prepared. Compound 3 was a potent inhibitor of DNA gyrase and exhibited attractive antibacterial activity against both Gram-positive and Gram-negative bacteria. In the course of the synthetic studies, we have found a new oxidation method of the amine 4 to the imine 5 with DMSO activated by trifluoroacetic anhydride or oxalyl chloride. The DMSO/trifluoroacetic anhydride method gave the byproduct 8, an unusual (methylthio)methyl adduct. The DMSO/oxalyl chloride method gave the byproducts 9 and 10, a (methylthio)methyl ester, and a halogen adduct, respectively. The mechanisms of these oxidations are also discussed.