5-(2-dimethylaminoethoxy)-2-nitrobenzaldehyde | 478287-47-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(2-dimethylaminoethoxy)-2-nitrobenzaldehyde
• 英文别名: 5-(2-Dimethylaminoethoxy)-2-nitrobenzaidehyde；5-[2-(dimethylamino)ethoxy]-2-nitrobenzaldehyde
• CAS: 478287-47-7
• 化学式: C₁₁H₁₄N₂O₄
• 分子量: 238.243
• InChiKey: USLPRYCBDKMZGO-UHFFFAOYSA-N

物化性质

• 沸点：
  390.7±37.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(2-dimethylaminoethoxy)-2-nitrobenzaldehyde 在 sodium hydroxide 、 氢气 、 三溴化硼 、 镍 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 90.0 ℃ 、506.62 kPa 条件下， 反应 3.75h， 生成 1,7-dihydroxy-10H-isoindolo[2,1-a]indol-10-one
  参考文献：
  名称：

  New ligands at the melatonin binding site MT3

  摘要：

  The third melatonin binding site, MT3 is a non-classical one since it is not a seven transmembrane domains receptor, but an enzyme, quinone reductase 2. A major concern for the study of the physiological role of this site is the lack of specific ligands, permitting to more accurately dissect the pathways linked to the activation of MT3. Indeed, in the course of finding new ligands, we identified a new series of compounds with affinity to the binding site in the nM range, particularly 2,3-dimethoxy 7-hydroxy 10-methyl 5H 10H indeno(1,2-b)indol-10-one (DMHMIO), with a Ki of 190 pM. Based on slightly different and novel synthons compared to most of the compounds used in melatonin pharmacology studies, these compounds offer new perspective for the description of the melatonin pathways, so much more by not having any affinity towards the MTI and MT2 'classical' melatonin receptors. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.12.002
• 作为产物：
  描述：

  5-羟基-2-硝基苯甲醛 、 2-氯-N,N-二甲基乙胺 在 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以50%的产率得到5-(2-dimethylaminoethoxy)-2-nitrobenzaldehyde
  参考文献：
  名称：

  New ligands at the melatonin binding site MT3

  摘要：

  The third melatonin binding site, MT3 is a non-classical one since it is not a seven transmembrane domains receptor, but an enzyme, quinone reductase 2. A major concern for the study of the physiological role of this site is the lack of specific ligands, permitting to more accurately dissect the pathways linked to the activation of MT3. Indeed, in the course of finding new ligands, we identified a new series of compounds with affinity to the binding site in the nM range, particularly 2,3-dimethoxy 7-hydroxy 10-methyl 5H 10H indeno(1,2-b)indol-10-one (DMHMIO), with a Ki of 190 pM. Based on slightly different and novel synthons compared to most of the compounds used in melatonin pharmacology studies, these compounds offer new perspective for the description of the melatonin pathways, so much more by not having any affinity towards the MTI and MT2 'classical' melatonin receptors. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.12.002

文献信息

• New indenoindolone compounds
  申请人：——

  公开号：US20030125369A1

  公开（公告）日：2003-07-03

  Compound of formula (I): 1 wherein R represents hydrogen, optionally substituted alkyl or alkenyl, R 1 to R 8 , which may be identical or different, each represents hydrogen, optionally substituted alkyl, hydroxy, acyloxy, optionally substituted amino, carboxy, optionally substituted alkoxy, or alkenyloxy, or one of R 1 to R 8 forms, with another of R 1 to R 8 that is adjacent, an alkylenedioxy group, X represents oxygen or NR 16 wherein R 16 represents hydrogen, alkyl, aryl or arylalkyl, R 9 represents hydrogen, aryl, heteroaryl, or optionally substituted, saturated or unsaturated alkyl, isomers thereof, and addition salts thereof with a pharmaceutically acceptable acid or base. Medicinal products containing the same which are useful as anti-cancer agents.

  化合物的分子式（I）如下： 其中R代表氢，可选择地取代的烷基或烯基，R1至R8，可以相同也可以不同，每个代表氢，可选择地取代的烷基，羟基，酰氧基，可选择地取代的氨基，羧基，可选择地取代的烷氧基，或烯基氧基，或者R1至R8中的一个与相邻的另一个R1至R8形成烷二氧基基团，X代表氧或NR16，其中R16代表氢，烷基，芳基或芳基烷基，R9代表氢，芳基，杂芳基，或可选择地取代的饱和或不饱和烷基，其异构体，以及其与药用酸或碱的可接受盐。含有该化合物的药物制剂可用作抗癌剂。
• Indenoindolone compounds
  申请人：Les Laboratoires Servier

  公开号：US06627650B2

  公开（公告）日：2003-09-30

  A compound of formula (I): wherein: R represents hydrogen, optionally substituted alkyl or alkenyl, R1 to R8, which may be identical or different, each represents hydrogen, optionally substituted alkyl, hydroxy, acyloxy, optionally substituted amino, carboxy, optionally substituted alkoxy, or alkenyloxy, or one of R1 to R8 forms, with another of R1 to R8 that is adjacent, an alkylenedioxy group, X represents oxygen or NR16 wherein R16 represents hydrogen, alkyl, aryl or arylalkyl, R9 represents hydrogen, aryl, heteroaryl, or optionally substituted, saturated or unsaturated alkyl, an isomer thereof, or an addition salt thereof with a pharmaceutically acceptable acid or base. Medicinal products containing the same which are useful as anti-cancer agents.

  化合物的化学式(I)：其中：R代表氢，可选取代的烷基或烯基，R1到R8，它们可以相同也可以不同，每个代表氢，可选取代的烷基，羟基，酰氧基，可选取代的氨基，羧基，可选取代的烷氧基或烯氧基，或者R1到R8中的一个与相邻的另一个R1到R8形成烷二氧基基团，X代表氧或NR16，其中R16代表氢，烷基，芳基或芳基烷基，R9代表氢，芳基，杂芳基，或可选取代的饱和或不饱和烷基的同分异构体，或其与药学上可接受的酸或碱形成的加合物。含有该化合物的药物可用作抗癌剂。
• Dérivés d'indénoindolones, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：Les Laboratoires Servier

  公开号：EP1266887B1

  公开（公告）日：2005-08-17
• US6627650B2
  申请人：——

  公开号：US6627650B2

  公开（公告）日：2003-09-30
• New ligands at the melatonin binding site MT3
  作者：Marie-Françoise Boussard、Sandrine Truche、Anne Rousseau-Rojas、Sylvie Briss、Sophie Descamps、Monique Droual、Michel Wierzbicki、Gilles Ferry、Valérie Audinot、Philippe Delagrange、Jean A. Boutin

  DOI：10.1016/j.ejmech.2005.12.002

  日期：2006.3

  The third melatonin binding site, MT3 is a non-classical one since it is not a seven transmembrane domains receptor, but an enzyme, quinone reductase 2. A major concern for the study of the physiological role of this site is the lack of specific ligands, permitting to more accurately dissect the pathways linked to the activation of MT3. Indeed, in the course of finding new ligands, we identified a new series of compounds with affinity to the binding site in the nM range, particularly 2,3-dimethoxy 7-hydroxy 10-methyl 5H 10H indeno(1,2-b)indol-10-one (DMHMIO), with a Ki of 190 pM. Based on slightly different and novel synthons compared to most of the compounds used in melatonin pharmacology studies, these compounds offer new perspective for the description of the melatonin pathways, so much more by not having any affinity towards the MTI and MT2 'classical' melatonin receptors. (c) 2006 Elsevier SAS. All rights reserved.