9-(3,4,5-trimethoxyphenyl)-5,6,7,9-tetrahydro-8H-[1,3]dioxolo[4,5-g]pyrrolo[3,4-b]quinolin-8-one | 476359-65-6

• 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: 9-(3,4,5-trimethoxyphenyl)-5,6,7,9-tetrahydro-8H-[1,3]dioxolo[4,5-g]pyrrolo[3,4-b]quinolin-8-one
• 英文别名: 6,7-methylenedioxy-9-(3,4,5-trimethoxyphenyl)-2,3,4,9-tetrahydropyrrolo[3,4-b]quinolin-1(1H)-one；8-(3,4,5-Trimethoxyphenyl)-12,14-dioxa-2,5-diazatetracyclo[7.7.0.03,7.011,15]hexadeca-1(16),3(7),9,11(15)-tetraen-6-one
• CAS: 476359-65-6
• 化学式: C₂₁H₂₀N₂O₆
• 分子量: 396.4
• InChiKey: GETMSPZIIJLCJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  87.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  tert-butyl 8-oxo-9-(3,4,5-trimethoxyphenyl)-5,6,8,9-tetrahydro-7H-[1,3]dioxolo[4,5-g]pyrrolo[3,4-b]quinoline-7-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以90%的产率得到9-(3,4,5-trimethoxyphenyl)-5,6,7,9-tetrahydro-8H-[1,3]dioxolo[4,5-g]pyrrolo[3,4-b]quinolin-8-one
  参考文献：
  名称：

  Insecticidal heterolignans—Tubuline polymerization inhibitors with activity against chewing pests

  摘要：

  Starting from natural product podophyllotoxin 1 substituted heterolignans were identified with promising insecticidal in vivo activity. The impact of substitution in each segment of the core structure was investigated in a detailed SAR study, and variation of substituents in both aromatic moieties afforded derivatives 5 and 43 with broad insecticidal activity against lepidopteran and coleopteran species. In vitro measurements supported by modeling studies indicate that heterolignans 3-134 act as tubuline polymerization inhibitors interacting with the colchicine-binding site. Insect specific structure-activity effects were observed showing that the insecticidal SAR described herein differs from reported cytotoxicity studies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.042

文献信息

• Tricyclic dihydroquinoline derivatives,method for preparing same and pharmaceutical compositions containing same
  申请人：——

  公开号：US20040198981A1

  公开（公告）日：2004-10-07

  Compound of formula (I): 1 wherein: 2 represents a single or double bond, 3 represents a ring system selected from 4 R 6a , R 6b , R 6c , R 6d , X and Y are as defined in the description, R 1 represents a hydrogen atom or a group selected from aryl, heteroaryl, cycloalkyl, optionally substituted alkyl, and COR 8 wherein R 8 is as defined in the description, R 2 , R 3 , R 4 and R 5 , which may be the same or different, each represent: a hydrogen atom, a halogen atom, an alkyl group,. an alkoxy group, a hydroxy group, a polyhaloalkyl group, a nitro group, an optionally substituted amino group, a group of formula 5 wherein m represents an integer such that 1≦m≦4, or R 2 with R 3 , or R 3 with R 4 , or R 4 with R 5 , form, together with the carbon atoms carrying them, an optionally substituted, 5- to 12-membered, mono- or bi-cyclic, aromatic or non-aromatic group optionally containing 1 or 2 hetero atoms selected from O, S and N, R 10 represents a hydrogen atom or an alkyl group, Ar represents an aryl, heteroaryl or arylalkyl group, its optical isomers, addition salts thereof with a pharmaceutically acceptable acid, and hydrates and solvates thereof.

  化合物的式子（I）：其中：代表单键或双键，代表从R6a，R6b，R6c，R6d选择的环系统，X和Y的定义在描述中，R1代表氢原子或从aryl，heteroaryl，cycloalkyl，可选择的取代烷基和COR8中选择的基团，其中R8在描述中定义，R2，R3，R4和R5，可以相同也可以不同，每个代表：氢原子，卤原子，烷基，烷氧基，羟基，多卤代烷基，硝基，可选择的取代氨基，式子5中m代表整数，使得1≤m≤4，或R2与R3，或R3与R4，或R4与R5，与携带它们的碳原子一起形成，一个可选择取代的，含有1或2个从O，S和N选择的杂原子的，5到12个成员的，单环或双环的，芳香或非芳香基团，R10代表氢原子或烷基，Ar代表芳基，杂原芳基或芳基烷基，它的光学异构体，与药学上可接受的酸形成的加合盐，以及其水合物和溶剂合物。
• NOUVEAUX DERIVES TRICYCLIQUES DE DIHYDRO-QUINOLEINES, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT
  申请人：Les Laboratoires Servier

  公开号：EP1389210A1

  公开（公告）日：2004-02-18
• [EN] TRICYCLIC DIHYDRO-QUINOLINE DERIVATIVES, METHOD FOR PREPARING SAME AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME<br/>[FR] NOUVEAUX DERIVES TRICYCLIQUES DE DIHYDRO-QUINOLEINES, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT
  申请人：SERVIER LAB

  公开号：WO2002094835A1

  公开（公告）日：2002-11-28

  Composé de formule (I), dans laquelle: - (a) représente une liaison simple ou double, - (b) représente un cycle choisi parmi (i), (ii), (iii), (iv), (v), (vi) et (vii). Les composés de l'invention, outre le fait qui'ils soient nouveaux, présentent des propriétés antitumorales très intéressantes.