2-氨基-4,5-二乙氧基苯甲酸甲酯 | 20197-71-1

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氨基-4,5-二乙氧基苯甲酸甲酯
• 英文名称: 2-amino-4,5-diethoxymethylbenzoate
• 英文别名: 4,5-diethoxy-2-aminobenzoic acid methyl ester；3,4-Diaethoxy-6-aminobenzoesaeure-methylester；methyl 2-amino-4,5-diethoxybenzoate
• CAS: 20197-71-1
• 化学式: C₁₂H₁₇NO₄
• mdl: MFCD00089595
• 分子量: 239.271
• InChiKey: WYHBJUPMCJWBDD-UHFFFAOYSA-N

物化性质

• 沸点：
  369.0±37.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  2-氨基-4,5-二乙氧基苯甲酸甲酯 在 sodium hydroxide 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.5h， 生成 4-氯-6,7-二乙氧基喹唑啉
  参考文献：
  名称：

  Anilinodialkoxyquinazolines:  Screening Epidermal Growth Factor Receptor Tyrosine Kinase Inhibitors for Potential Tumor Imaging Probes

  摘要：

  The epidermal growth factor receptor (EGFR), a long-standing drug development target, is also a desirable target for imaging. Sixteen dialkoxyquinazoline analogues, suitable for labeling with positron-emitting isotopes, have been synthesized and evaluated in a battery of in vitro assays to ascertain their chemical and biological properties. These characteristics provided the basis for the adoption of a selection schema to identify lead molecules for labeling and in vivo evaluation. A new EGER tyrosine kinase radiometric binding assay revealed that all of the compounds possessed suitable affinity (IC50 = 0.4-51 nM) for the EGFR tyrosine kinase. All of the analogues inhibited ligand-induced EGFR tyrosine phosphorylation (IC50 = 0.8-20 nM). The HPLC-estimated octanol/water partition coefficients ranged from 2 to 5.5. Four compounds, 4-(2'-fluoroanilino)- and 4-(3'-fluoroanilino)-6,7-diethoxyquinazoline as well as 4-(3'chloroanilino)- and 4-(3'-bromoanilino)-6,7-dimethoxyquinazoline, possess the best combination of characteristics that warrant radioisotope labeling and further evaluation in tumor-bearing mice.

  DOI：

  10.1021/jm050607w

文献信息

• Substituted 3-cyano quinolines
  申请人：American Cyanamid Company

  公开号：US06002008A1

  公开（公告）日：1999-12-14

  This invention provides compounds having the formula: ##STR1## wherein: X is cycloalkyl which may be optionally substituted; or is a pyridinyl, pyrimidinyl, or phenyl ring; wherein the pyridinyl, pyrimidinyl, or phenyl ring may be optionally substituted; n is 0-1; Y is --NH--, --O--, --S--, or --NR--; R is alkyl of 1-6 carbon atoms; R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are each, independently, hydrogen, halogen, alkyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, hydroxymethyl, halomethyl, alkanoyloxy, alkenoyloxy, alkynoyloxy, alkanoyloxymethyl, alkenoyloxymethyl, alkynoyloxymethyl, alkoxymethyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylsulfonamido, alkenylsulfonamido, alkynylsulfonamido, hydroxy, trifluoromethyl, cyano, nitro, carboxy, carboalkoxy, carboalkyl, phenoxy, phenyl, thiophenoxy, benzyl, amino, hydroxyamino, alkoxyamino, alkylamino, dialkylamino, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalkyl, phenylamino, benzylamino, ##STR2## R.sub.5 is alkyl which may be optionally substituted, or phenyl which may be optionally substituted; R.sub.6 is hydrogen, alkyl, or alkenyl; R.sub.7 is chloro or bromo R.sub.8 is hydrogen, alkyl, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalkyl, N-cycloalkylaminoalkyl, N-cycloalkyl-N-alkylaminoalkyl, N,N-dicycloalkylaminoalkyl, morpholino-N-alkyl, piperidino-N-alkyl, N-alkyl-piperidino-N-alkyl, azacycloalkyl-N-alkyl, hydroxyalkyl, alkoxyalkyl, carboxy, carboalkoxy, phenyl, carboalkyl+, chloro, fluoro, or bromo; Z is amino, hydroxy, alkoxy, alkylamino, dialkylamino, morpholino, piperazino, N-alkylpiperazino, or pyrrolidino; m=1-4,q=1-3, and p=0-3; any of the substituents R.sub.1, R.sub.2, R.sub.3, or R.sub.4 that are located on contiguous carbon atoms can together be the divalent radical --O--C(R.sub.8).sub.2 --O--; or a pharmaceutically acceptable salt thereof with the proviso that when Y is --NH--, R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are hydrogen, and n is 0, X is not 2-methylphenyl, which are inhibitors of protein tyrosine kinase.

  这项发明提供了具有以下结构的化合物：##STR1## 其中：X是环烷基，可以选择性地被取代；或者是吡啶基、嘧啶基或苯环；其中吡啶基、嘧啶基或苯环可以选择性地被取代；n为0-1；Y为--NH--、--O--、--S--或--NR--；R为1-6个碳原子的烷基；R.sub.1、R.sub.2、R.sub.3和R.sub.4分别独立地是氢、卤素、烷基、烯基、炔基、烯氧基、炔氧基、羟甲基、卤甲基、烷酰氧基、烯酰氧基、炔酰氧基、烷酰氧甲基、烯酰氧甲基、炔酰氧甲基、烷氧甲基、烷氧基、烷基硫、烷基亚砜基、烷基磺酰基、烷基磺酰胺基、烯基磺酰胺基、炔基磺酰胺基、羟基、三氟甲基、氰基、硝基、羧基、羧基烷氧基、羧基烷基、苯氧基、苯基、噻吩氧基、苄基、氨基、羟氨基、烷氧氨基、烷基氨基、二烷基氨基、氨基烷基、N-烷基氨基烷基、N,N-二烷基氨基烷基、苯基氨基、苄氨基、##STR2## R.sub.5是可以选择性取代的烷基，或者是可以选择性取代的苯基；R.sub.6是氢、烷基或烯基；R.sub.7是氯或溴；R.sub.8是氢、烷基、氨基烷基、N-烷基氨基烷基、N,N-二烷基氨基烷基、N-环烷基氨基烷基、N-环烷基-N-烷基氨基烷基、N,N-二环烷基氨基烷基、吗啉-N-烷基、哌啶-N-烷基、N-烷基-哌啶-N-烷基、氮杂环烷基-N-烷基、羟基烷基、烷氧基烷基、羧基、羧基烷氧基、苯基、羧基+、氯、氟或溴；Z是氨基、羟基、烷氧基、烷基氨基、二烷基氨基、吗啉基、哌嗪基、N-烷基哌嗪基或吡咯烷基；m=1-4，q=1-3，p=0-3；任何位于相邻碳原子上的R.sub.1、R.sub.2、R.sub.3或R.sub.4取代基可以共同形成二价基团--O--C(R.sub.8).sub.2 --O--；或其药学上可接受的盐，但当Y为--NH--时，R.sub.1、R.sub.2、R.sub.3和R.sub.4为氢，n为0时，X不是2-甲基苯基，这些化合物是蛋白酪氨酸激酶的抑制剂。
• Method of treating or inhibiting colonic polyps
  申请人：American Cyanamid Company

  公开号：US06384051B1

  公开（公告）日：2002-05-07

  This invention provides a method of treating or inhibiting colonic polyps which comprises providing a compound of formula 1 wherein: R1, R2, R3, R4, X, Y, and n are as defined hereinbefore, or a pharmaceutically acceptable salt thereof.

  本发明提供了一种治疗或抑制结肠息肉的方法，包括提供如下公式1的化合物： 其中： R1、R2、R3、R4、X、Y和n如前文所定义，或其药用可接受的盐。
• Substituted 3-cyanoquinolines
  申请人：American Cyanamid Company

  公开号：US06288082B1

  公开（公告）日：2001-09-11

  This invention provides compounds of formula I having the structure wherein G1, G2, R1, R4, Z, n, and X are defined in the specification or a pharmaceutically acceptable salt thereof which are useful as antineoplastic agents and in the treatment of polycystic kidney disease.

  这项发明提供了具有结构的化合物I的公式，其中G1、G2、R1、R4、Z、n和X在规范中定义，或其药用盐，这些化合物可用作抗肿瘤剂，并用于多囊肾病的治疗。
• Design, synthesis, and biological evaluation of substituted 2,3-dihydro-1H-cyclopenta[b]quinolin-9-ylamine related compounds as fructose-1,6-bisphosphatase inhibitors
  作者：Michela Rosini、Francesca Mancini、Andrea Tarozzi、Francesco Colizzi、Vincenza Andrisano、Maria L. Bolognesi、Patrizia Hrelia、Carlo Melchiorre

  DOI：10.1016/j.bmc.2006.07.059

  日期：2006.12

  In a search for structurally new inhibitors of fructose-1,6-bisphosphatase (F16BPase), substituted 2,3-dihydro-1H-cyclopenta[b]quinoline derivatives were synthesized. It has been shown that the 2,3-dihydro-1H-cyclopenta[b]quinoline moiety may represent a suitable scaffold for the synthesis of potent F16BPase inhibitors endowed with significantly lower EGFR tyrosine kinase inhibitory activity.

  为了寻找结构上新的果糖-1，6-双磷酸酶（F16BPase）抑制剂，合成了取代的2,3-二氢-1H-环戊[b]喹啉衍生物。已经显示出2，3-二氢-1H-环戊基[b]喹啉部分可以代表用于合成具有显着较低的EGFR酪氨酸激酶抑制活性的有效F16BPase抑制剂的支架。
• [EN] SUBSTITUTED 3-CYANOQUINOLINES AS PROTEIN TYROSINE KINASES INHIBITORS<br/>[FR] INHIBITEURS DE PROTEINES DE TYPE TYROSINE KINASES A BASE DE 3-CYANOQUINOLINES SUBSTITUEES
  申请人：AMERICAN CYANAMID CO

  公开号：WO2000018761A1

  公开（公告）日：2000-04-06

  This invention provides compounds of formula (1) wherein R1, G1, G2, R4, Z, X and n are defined herein, or a pharmaceutically acceptable salt thereof, which are useful as antineoplastic agents and in the treatment of polycystic kidney disease.

  该发明提供了式（1）的化合物，其中R1、G1、G2、R4、Z、X和n在此定义，或其药学上可接受的盐，可用作抗肿瘤剂以及多囊肾病的治疗。