4-cyano-3-(phenylthio)benzo[b][1,6]naphthyridine | 370844-73-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-cyano-3-(phenylthio)benzo[b][1,6]naphthyridine
• 英文别名: Benzo[b][1,6]naphthyridine-4-carbonitrile, 3-(phenylthio)-；3-phenylsulfanylbenzo[b][1,6]naphthyridine-4-carbonitrile
• CAS: 370844-73-8
• 化学式: C₁₉H₁₁N₃S
• 分子量: 313.382
• InChiKey: GYGNTBSGPUFNTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吲哚 、 4-cyano-3-(phenylthio)benzo[b][1,6]naphthyridine 以 正丁醇 为溶剂， 反应 6.0h， 以80%的产率得到4-cyano-10-(1H-indol-3-yl)-3-phenylthiobenzo[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：

  1-Phenyl-4-oxo-5-cyano-6-(β-dimethylaminovinyl)-1,4-dihydropyrimidine 在 水 、 sodium acetate 、 溶剂黄146 、 三氯氧磷 作用下， 以 异丙醇 为溶剂， 反应 25.5h， 生成 4-cyano-3-(phenylthio)benzo[b][1,6]naphthyridine
  参考文献：
  名称：

  摘要：

  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.

  DOI：

  10.1023/a:1021636632164

文献信息

• [EN] CPAP-TUBULIN MODULE<br/>[FR] MODULE DE TUBULINE CPAP
  申请人：UNIVERSITÄT ZU KÖLN

  公开号：WO2017097928A1

  公开（公告）日：2017-06-15

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

  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。
• 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、L. M. Alekseeva、V. G. Granik

  DOI：10.1023/a:1024725811506

  日期：——

  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.
• ——
  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.