3-chloro-4-cyanobenzo<1,6>naphthyridine | 104802-98-4

• 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: 3-chloro-4-cyanobenzo<1,6>naphthyridine
• 英文别名: 3-chloro-4-cyanobenzo-1,6-naphthyridine；3-chlorobenzo[b][1,6]naphthyridine-4-carbonitrile；3-chloro-4-cyanobenzo[b][1,6]naphthyridine
• CAS: 104802-98-4
• 化学式: C₁₃H₆ClN₃
• 分子量: 239.664
• InChiKey: FDXPJUZQXQATBN-UHFFFAOYSA-N

物化性质

• 熔点：
  300 °C (decomp)
• 沸点：
  485.6±25.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 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：
  49.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-4-cyanobenzo<1,6>naphthyridine 在 potassium hexacyanoferrate(III) 作用下， 以 水 、 异丙醇 为溶剂， 反应 60.75h， 生成 3-chloro-4-cyano-10-(1H-indol-3-yl)benzo[b][1,6]naphthyridine
  参考文献：
  名称：

  摘要：

  Two routes to consecutive functionalization of 3-chloro-4-cyanobenzo[b][1,6]naphthyridine (1a) at positions 3 and 10 were developed. Oxidation of compound la with m-chloro-perbenzoic acid in acetone leads to 3-chloro-4-cyano-10-oxobenzo[b][1,6]naphthyridine, while in acetic acid, the reactiongives 3-chloro-4-cyano-10-(3-chlorobenzoyloxy)-5-hydroxy-5,10-dihydrobenzo[b][1,6]naphthyridine. The reactions of la with some C-nucleophiles give sigma-adducts at position 10. The reactions of N,N-dimethylamide acetals with chloride la leads to 4-cyano-3-dimethylaminobenzo[b][1,6]naphthyridine.

  DOI：

  10.1023/a:1024725811506
• 作为产物：
  描述：

  4-anilino-5-formyl-2-oxo-1,2-dihydropyridine-3-carbonitrile 在 三乙胺盐酸盐 、 三氯氧磷 作用下， 反应 1.0h， 以90%的产率得到3-chloro-4-cyanobenzo<1,6>naphthyridine
  参考文献：
  名称：

  [EN] CPAP-TUBULIN MODULE
  [FR] MODULE DE TUBULINE CPAP

  摘要：

  这项发明涉及具有一般式（1）或其生理上可接受的盐的CPAP-微管蛋白抑制剂；以及它们作为抗癌治疗药物的用途。

  公开号：

  WO2017097928A1

文献信息

• CPAP-tubulin module
  申请人：UNIVERSITAET ZU KOELN

  公开号：US10875856B2

  公开（公告）日：2020-12-29

  The invention relates to CPAP-tubulin inhibitors having the general formula (1) or a physiologically acceptable salt thereof; and their use as cancer therapeutics.

  本发明涉及具有通式（1）或其生理上可接受的盐的 CPAP-微管蛋白抑制剂；以及它们作为癌症治疗剂的用途。
• ——
  作者：A. S. Ivanov、N. Z. Tugusheva、N. P. Solov"eva、V. G. Granik

  DOI：10.1023/a:1021636632164

  日期：——

  The reactions of 3-chloro-4-cyanobenzo[b][1,6]naphthyridine (4) with S-, C-, and N-nucleophiles afford stable sigma-adducts at position 10. In the base-catalyzed reactions of compound 4 with thiols, the resulting sigma-complexes are rearranged into sulfides 14a-c. Sulfides 14b,c undergo the Thorpe-Ziegler cyclization to give 1-aminobenzo[b]thieno[2,3-h][1,6]naphthyridine derivatives 15a,b. The reaction of naphthyridine 4 with aniline affords a mixture of sigma-adducts of the C-N and C-C types, while those with aliphatic amines yield 3-amino derivatives 17a-c. In the presence of H2O2, benzonaphthyridine 4 adds peroxycarboxylic acids to give compounds 8a,b. In alkaline medium, adduct 8a is rearranged into 4-aminopyridine-3-carbaldehyde derivative 10.
• Synthesis and biological activity of mono- and tricyclic derivatives of 2-amino-3-cyanopyridine
  作者：N. Z. Tugusheva、L. V. Ershov、V. G. Granik、G. Ya. Shvarts、R. D. Syubaev、M. D. Mashkovskii

  DOI：10.1007/bf00776332

  日期：1986.7
• ——
  作者：E. Yu. Khmel'nitskaya、A. S. Ivanov、N. Z. Tugusheva、N. B. Grigor'ev、V. G. Granik

  DOI：10.1023/a:1024917609689

  日期：——

  The elect roreduction of benzo[b][1,6]naphthyridine derivatives in anhydrous media by the polarographic method was studied. It is found that the first step of the process is the transfer of an electron to position 10 of the molecule, which is consistent with the addition of nucleophilic reagents to this particular position of the tricyclic system in question.
• Acetals of lactams and acid amides. 47. Investigation of the behavior of substituted 6-(?-dimethylamino) vinyl-4-pyrimidinones in acidic media. Synthesis of 3-cyano-4-anilino-5-formyl-2-pyridone and 3-chloro-4-cyanobenzo[b] [1,6]-naphthyridine
  作者：N. Z. Yalysheva、N. P. Solov'eva、V. V. Chistyakov、Yu. N. Sheinker、V. G. Granik

  DOI：10.1007/bf01175070

  日期：1986.8