吡啶并[3,2-e][1,3]苯并噻唑-2-胺 | 141890-75-7

• 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
• 中文名称: 吡啶并[3,2-e][1,3]苯并噻唑-2-胺
• 中文别名: 7-(2-氨基甲基吗啉代)-1-环丙基-6,8-二氟-1,4-二氢-4-羰基-3-喹啉羧酸
• 英文名称: thiazolo<4,5-f>quinolin-2-amine
• 英文别名: 2-aminothiazolo[4,5-f]quinoline；thiazolo[4,5-f]quinolin-2-ylamine；Thiazolo[4,5-f]chinolin-2-ylamin；Thiazolo(4,5-f)quinolin-2-amine；[1,3]thiazolo[4,5-f]quinolin-2-amine
• CAS: 141890-75-7
• 化学式: C₁₀H₇N₃S
• 分子量: 201.252
• InChiKey: BMHGKKHBROMCAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,5-二氢吡啶并[3,2-e][1,3]苯并噻唑-2-胺 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 吡啶并[3,2-e][1,3]苯并噻唑-2-胺
  参考文献：
  名称：

  Assessment of mutagenic potential in a series of compounds structurally related to 2-amino-3-methylimidazo [4,5-f]quinoline (IQ)

  摘要：

  The bacterial mutagenicity of a series of compounds related to the mutagen 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) was determined in the Ames test using Salmonella strain TA-1538. Thiazolo[4,5-f]quinoline-2-amine 3 and its 4,5-dihydro derivative 4, where the N(3)-Me moiety of IQ has been replaced by a sulfur atom, were both potent mutagens. A structure-mutagenicity study was performed in a group of aminothiazole compounds related to 3. In addition to the aromatic NH2 group, a fully aromatic tricyclic structure is required for mutagenicity. Enzymatic oxidation can provide the required aromaticity to partially reduced analogues, but more extensively reduced compounds, or compounds where the central ring cannot be oxidized, are not mutagenic.

  DOI：

  10.1016/0223-5234(93)90085-s

文献信息

• An expedient synthesis of novel 2-substituted thiazolo[4,5-f]isoquinolines/quinolines and benzo[1,2-d:4,3-d']bisthiazoles and their potential as inhibitors of COX-1 and COX-2
  作者：Manas Chakrabarty、Ajanta Mukherji、Sulakshana Karmakar、Ratna Mukherjee、Kenichiro Nagai、Athina Geronikaki、Pitta Eleni

  DOI：10.3998/ark.5550190.0011.b22

  日期：——

  efficient, general synthesis of 2-substituted thiazolo[4,5-f]isoquinolines, thiazolo[4,5-f]quinolines and benzo[1,2-d:4,3-d′]bisthiazoles has been accomplished from 5nitroisoquinoline/quinoline and 6-nitrobenzothiazole, respectively, and all the products have been thoroughly identified spectroscopically (IR, H and C NMR, LR/ HR EI/ FAB/ ESI-MS). The synthesis of thiazolo[4,5-f]isoquinolines constitutes the

  2-取代的噻唑并[4,5-f]异喹啉、噻唑并[4,5-f]喹啉和苯并[1,2-d:4,3-d']双噻唑的高效、通用合成已由5硝基异喹啉完成/喹啉和 6-硝基苯并噻唑，所有产品均已通过光谱（IR、H 和 C NMR、LR/HR EI/FAB/ESI-MS）彻底鉴定。噻唑并[4,5-f]异喹啉的合成是此类杂芳烃的首次合成。对涵盖所有三种类型的 18 种化合物进行了 COX-1 和 COX-2 抑制筛选，其中一些表现出中等活性。
• Kasida et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 553,554
  作者：Kasida et al.

  DOI：——

  日期：——
• Assessment of mutagenic potential in a series of compounds structurally related to 2-amino-3-methylimidazo [4,5-f]quinoline (IQ)
  作者：JC Jaen、ML Kropko、JC Theiss、S Wold、BW Caprathe、LD Wise

  DOI：10.1016/0223-5234(93)90085-s

  日期：1993.1

  The bacterial mutagenicity of a series of compounds related to the mutagen 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) was determined in the Ames test using Salmonella strain TA-1538. Thiazolo[4,5-f]quinoline-2-amine 3 and its 4,5-dihydro derivative 4, where the N(3)-Me moiety of IQ has been replaced by a sulfur atom, were both potent mutagens. A structure-mutagenicity study was performed in a group of aminothiazole compounds related to 3. In addition to the aromatic NH2 group, a fully aromatic tricyclic structure is required for mutagenicity. Enzymatic oxidation can provide the required aromaticity to partially reduced analogues, but more extensively reduced compounds, or compounds where the central ring cannot be oxidized, are not mutagenic.