N-cyclopropylisatoic anhydride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: N-cyclopropylisatoic anhydride
• 英文别名: 1-cyclopropyl-1H-benzo[d][1,3]oxazine-2,4-dione；N-(cyclopropyl)isatoic anhydride；1-Cyclopropyl-3,1-benzoxazine-2,4-dione
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: CDIMXYCIMOFKTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-cyclopropylisatoic anhydride 在 盐酸 、 sodium hydride 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Disorders:  Structure−Activity Relationship

  摘要：

  Roquinimex-related 3-quinolinecarboxamide derivatives were prepared and evaluated for treatment of autoimmune disorders. The compounds were tested in mice for their inhibitory effects on disease development in the acute experimental autoimmune encephalomyelitis model and selected compounds in the beagle dog for induction of proinflammatory reaction. Structure-activity relationships are discussed. Compound 8c, laquinimod, showed improved potency and superior toxicological profile compared to the lead compound roquinimex (1b, Linomide) and was selected for clinical studies (currently in phase II).

  DOI：

  10.1021/jm031044w
• 作为产物：
  描述：

  2-氟苯腈 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 乙醇 、 异丙醇 为溶剂， 反应 73.0h， 生成 N-cyclopropylisatoic anhydride
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Disorders:  Structure−Activity Relationship

  摘要：

  Roquinimex-related 3-quinolinecarboxamide derivatives were prepared and evaluated for treatment of autoimmune disorders. The compounds were tested in mice for their inhibitory effects on disease development in the acute experimental autoimmune encephalomyelitis model and selected compounds in the beagle dog for induction of proinflammatory reaction. Structure-activity relationships are discussed. Compound 8c, laquinimod, showed improved potency and superior toxicological profile compared to the lead compound roquinimex (1b, Linomide) and was selected for clinical studies (currently in phase II).

  DOI：

  10.1021/jm031044w

文献信息

• Synthesis and Antibacterial Evaluation of a New Series of N-Alkyl-2-alkynyl/(E)-alkenyl-4-(1H)-quinolones
  作者：Abraham Wube、Juan-David Guzman、Antje Hüfner、Christina Hochfellner、Martina Blunder、Rudolf Bauer、Simon Gibbons、Sanjib Bhakta、Franz Bucar

  DOI：10.3390/molecules17078217

  日期：——

  To gain further insight into the structural requirements of the aliphatic group at position 2 for their antimycobacterial activity, some N-alkyl-4-(1H)-quinolones bearing position 2 alkynyls with various chain length and triple bond positions were prepared and tested for in vitro antibacterial activity against rapidly-growing strains of mycobacteria, the vaccine strain Mycobacterium bovis BCG, and

  为了进一步了解 2 位脂肪族基团的抗分枝杆菌活性的结构要求，一些 N-烷基-4-(1H)-喹诺酮类在 2 位具有不同链长和三键位置的炔基被制备和测试。对快速生长的分枝杆菌菌株、疫苗菌株牛分枝杆菌 BCG 和耐甲氧西林金黄色葡萄球菌菌株 EMRSA-15 和 -16 的体外抗菌活性。还评估了化合物对结核分枝杆菌的 ATP 依赖性 MurE 连接酶的抑制作用。对偶发分枝杆菌和耻垢分枝杆菌的最低 MIC 值为 0.5 mg/L (1.2–1.5 µM)。这些化合物在 100 µM 浓度下对人肺成纤维细胞系 MRC-5 没有或只有微弱的毒性。喹诺酮衍生物对流行的 MRSA 菌株（EMRSA-15 和 -16）表现出显着的活性，MIC 值为 2–128 mg/L（5.3–364.7 µM），对牛分枝杆菌 BCG 的 MIC 值为 25 mg/L (66.0–77.4 µM)。此外，这些化合物抑制结核分枝杆菌的
• Pharmacologically active tricyclic quinazolinones
  申请人：Sandoz, Inc.

  公开号：US03969506A1

  公开（公告）日：1976-07-13

  The compounds are biologically active tricyclic quinazolinones of the class of imidazo[2,1-b]quinazolin-5-ones, pyrimido[2,1-b]quinazolin-6-ones and diazepino[2,1-b]quinazolin-7-ones, useful, for example, as bronchodilator agents. Processes for preparation of said compounds include the reaction of a N-carboxy anthranilic anhydride (an isatoic anhydride) with a cyclic pseudothiourea such as 2-organomercapto-4,5-dihydroimidazole or 2-organomercapto-3,4,5,6-tetrahydropyrimidine.

  这些化合物属于咪唑[2,1-b]喹唑啉-5-酮、嘧啶并[2,1-b]喹唑啉-6-酮和二氮杂[2,1-b]喹唑啉-7-酮的三环喹唑啉酮类，具有生物活性，例如可作为支气管扩张剂。制备这些化合物的方法包括将N-羧基蒽醌酐（异酰亚胺）与环状伪硫脲反应，例如与2-有机硫醇基-4,5-二氢咪唑或2-有机硫醇基-3,4,5,6-四氢嘧啶反应。
• Yoshino, Yasufumi; Kurahashi, Takuya; Matsubara, Seijiro, Journal of the American Chemical Society, 2009, vol. 131, p. 7494 - 7495
  作者：Yoshino, Yasufumi、Kurahashi, Takuya、Matsubara, Seijiro

  DOI：——

  日期：——
• US3969506A
  申请人：——

  公开号：US3969506A

  公开（公告）日：1976-07-13
• Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Disorders:  Structure−Activity Relationship
  作者：Stig Jönsson、Gunnar Andersson、Tomas Fex、Tomas Fristedt、Gunnar Hedlund、Karl Jansson、Lisbeth Abramo、Ingela Fritzson、Olga Pekarski、Anna Runström、Helena Sandin、Ingela Thuvesson、Anders Björk

  DOI：10.1021/jm031044w

  日期：2004.4.1

  Roquinimex-related 3-quinolinecarboxamide derivatives were prepared and evaluated for treatment of autoimmune disorders. The compounds were tested in mice for their inhibitory effects on disease development in the acute experimental autoimmune encephalomyelitis model and selected compounds in the beagle dog for induction of proinflammatory reaction. Structure-activity relationships are discussed. Compound 8c, laquinimod, showed improved potency and superior toxicological profile compared to the lead compound roquinimex (1b, Linomide) and was selected for clinical studies (currently in phase II).