4-methyl-6,7-(methylenedioxy)-9-[(3,4,5-trimethoxyphenyl)amino]-3a,4-dihydrofuro[3,4-b]quinolin-1(3H)-one | 1020667-77-9

• 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: 4-methyl-6,7-(methylenedioxy)-9-[(3,4,5-trimethoxyphenyl)amino]-3a,4-dihydrofuro[3,4-b]quinolin-1(3H)-one
• 英文别名: 2-Methyl-8-(3,4,5-trimethoxyanilino)-5,12,14-trioxa-2-azatetracyclo[7.7.0.03,7.011,15]hexadeca-1(16),7,9,11(15)-tetraen-6-one
• CAS: 1020667-77-9
• 化学式: C₂₂H₂₂N₂O₇
• 分子量: 426.426
• InChiKey: ZAPBNTPVZIULKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  87.7
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-methyl-6,7-(methylenedioxy)-1-oxo-9-[(3,4,5-trimethoxyphenyl)amino]-1,3-dihydrofuro[3,4-b]quinolin-4-ium trifluoromethanesulfonate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以80%的产率得到4-methyl-6,7-(methylenedioxy)-9-[(3,4,5-trimethoxyphenyl)amino]-3a,4-dihydrofuro[3,4-b]quinolin-1(3H)-one
  参考文献：
  名称：

  Design and Effective Synthesis of the First 4-Aza-2,3-didehydropodophyllotoxin Rigid Aminologue: A N-Methyl-4-[(3,4,5-trimethoxyphenyl)amino)]-1,2-dihydroquinoline-lactone

  摘要：

  [GRPAHICS]The first N1-alkyl-4-amino- 1,2-dihydroquinoline-lactone has been prepared by a five-step sequence in a 51 % overall yield via the corresponding furo[3,4-b]quinolin- 1 (3H)-one. A new practical synthesis of this intermediate was carried out using versatile, commercially available starting materials and constitutes the shortest and highest yielding route. These synthetic pathways could be widened with a view toward the preparation of different substituted derivatives, which could be considered as rigid aminologues of 4-aza-2,3-dide-hydropodophyllotoxins.

  DOI：

  10.1021/jo800166b

文献信息

• [EN] WATER SOLUBLE 4-AZAPODOPHYLLOTOXIN ANALOGS<br/>[FR] ANALOGUES DE 4-AZAPODOPHYLLOTOXINE SOLUBLES DANS L'EAU
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2015107119A1

  公开（公告）日：2015-07-23

  The present invention relates to 4-azapodophyllotoxin analogs of formula (I) in which X, R1, R2, R3, R4 and Ar are as defined in claim 1, preferably a pharmaceutically acceptable salt thereof, optionally in the form of a solvate, a composition comprising said analogs, their use as medicament, in particular for the treatment of cancer, and a process for their preparation.

  本发明涉及公式（I）中的4-azapodophyllotoxin类似物，其中X，R1，R2，R3，R4和Ar如权利要求1所定义，优选为药学上可接受的盐，可选地为溶剂化合物形式，包括所述类似物的组合物，它们作为药物的用途，特别是用于治疗癌症，以及它们的制备方法。
• WATER SOLUBLE 4-AZAPODOPHYLLOTOXIN ANALOGS
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)

  公开号：US20160333022A1

  公开（公告）日：2016-11-17

  The present invention relates to 4-azapodophyllotoxin analogs of formula (I) in which X, R 1 , R 2 , R 3 , R 4 and Ar are as defined in claim 1, preferably a pharmaceutically acceptable salt thereof, optionally in the form of a solvate, a composition comprising said analogs, their use as medicament, in particular for the treatment of cancer, and a process for their preparation.

  本发明涉及式（I）的4-氮杂青蒿琥酯类似物，其中X，R1，R2，R3，R4和Ar如权利要求1所定义，优选为其药学上可接受的盐，可选地为溶剂化合物形式，包括所述类似物的组合物，其用途作为药物，特别是用于治疗癌症，以及它们的制备方法。
• US9783547B2
  申请人：——

  公开号：US9783547B2

  公开（公告）日：2017-10-10