diethyl 2-(4-formylphenoxy)malonate | 159560-93-7

• 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: diethyl 2-(4-formylphenoxy)malonate
• 英文别名: Diethyl 2-(4-formylphenoxy)propanedioate
• CAS: 159560-93-7
• 化学式: C₁₄H₁₆O₆
• 分子量: 280.277
• InChiKey: ZGZOLSPBOBHGLF-UHFFFAOYSA-N

物化性质

• 沸点：
  393.5±27.0 °C(predicted)
• 密度：
  1.210±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  吡咯 、 4-[2-(2-甲氧基乙氧基)乙氧基]苯甲醛 、 diethyl 2-(4-formylphenoxy)malonate 在 三氟化硼乙醚 、 原乙酸三乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 、
  参考文献：
  名称：

  Soluble Tetraarylporphyrin−Platinum Conjugates as Cytotoxic and Phototoxic Antitumor Agents

  摘要：

  A series of asymmetric tetraarylporphyrins was synthesized from pyrrole, para-substituted oligo- or poly(ethylene glycol) monomethyl ether benzaldehyde and from 4-hydroxybenzaldehyde etherified with diethyl bromomalonate according to the Lindsey method. After hydrolysis of the tetraarylporphyrin esters, the resulting carboxylic acid groups were used to bind platinum fragments. In comparison to analogous hematoporphyrin-platinum conjugates, the title compounds are characterized by a 30 nm bathochromic shift of their absorption bands. The antiproliferative activity of 18 platinum complexes (1, 5, and 10 muM) differing in solubility, type of the platinum fragment, and the corresponding tetraarylporphyrin ligands were studied on TCC-SUP transitional bladder cancer cells in the dark and after irradiation (lambda = 600-730 nm; 24 J/cm(2)). The most active compounds were among the tetraarylporphyrin-platinum conjugates bearing the diammine and (RR/SS)-trans-1,2-diaminocyclohexane ligands.

  DOI：

  10.1021/jm0110690
• 作为产物：
  描述：

  对羟基苯甲醛 、 溴代丙二酸二乙酯 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以71%的产率得到diethyl 2-(4-formylphenoxy)malonate
  参考文献：
  名称：

  Soluble Tetraarylporphyrin−Platinum Conjugates as Cytotoxic and Phototoxic Antitumor Agents

  摘要：

  A series of asymmetric tetraarylporphyrins was synthesized from pyrrole, para-substituted oligo- or poly(ethylene glycol) monomethyl ether benzaldehyde and from 4-hydroxybenzaldehyde etherified with diethyl bromomalonate according to the Lindsey method. After hydrolysis of the tetraarylporphyrin esters, the resulting carboxylic acid groups were used to bind platinum fragments. In comparison to analogous hematoporphyrin-platinum conjugates, the title compounds are characterized by a 30 nm bathochromic shift of their absorption bands. The antiproliferative activity of 18 platinum complexes (1, 5, and 10 muM) differing in solubility, type of the platinum fragment, and the corresponding tetraarylporphyrin ligands were studied on TCC-SUP transitional bladder cancer cells in the dark and after irradiation (lambda = 600-730 nm; 24 J/cm(2)). The most active compounds were among the tetraarylporphyrin-platinum conjugates bearing the diammine and (RR/SS)-trans-1,2-diaminocyclohexane ligands.

  DOI：

  10.1021/jm0110690

文献信息

• Novel, water-soluble porphyrin platinum compounds with high tumor selectivity and their use for the treatment of benign and malignant tumor diseases
  申请人：——

  公开号：US20040023942A1

  公开（公告）日：2004-02-05

  The invention relates to novel, water-soluble porphyrin platinum compounds of the tetraarylporphyrin platinum derivatives type or of the hematoporphyrin platinum derivatives type with high tumor selectivity and their use for the treatment of benign and malignant tumor diseases. In particular, the compounds are suitable for photodynamic anti-tumor therapy.
• US7087214B2
  申请人：——

  公开号：US7087214B2

  公开（公告）日：2006-08-08
• [EN] ARYLETHANOLAMINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF OBESITY AND HYPERGLYCAEMIA<br/>[FR] DERIVES D'ARYLETHANOLAMINE ET UTILISATION DE CES DERNIERS DANS LE TRAITEMENT DE L'OBESITE DE L'HYPERGLYCEMIE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1994024090A1

  公开（公告）日：1994-10-27

  (EN) A compound of formula (I) or a salt, ester or amide thereof, or a solvate thereof, wherein, R0 represents a substituted or unsubstituted aryl group; R1 represents hydrogen or an alkyl group; R2 represents a moiety of formula (a), wherein R4 represents a moiety (CH2)nCO2H wherein n is zero or an integer in the range of from 1 to 3 and R5 represents a moiety (CH2)pCO2H, (CH2)pOH, (CH2)pCN, (CH2)pCOCH3 or (CH2)pNH2 wherein p is zero or an integer in the range of from 1 to 3; and R3 represents hydrogen, halogen, alkyl or alkoxy; a process for the preparation of such a compound, a pharmaceutical composition comprising such a compound and the use of such a compound in medicine.(FR) Composé de la formule (I) ou sel, ester, amide ou solvate de ce dernier. Dans cette formule R0 représente un groupe aryle substitué ou non; R1 représente hydrogène ou un groupe aryle; R2 représente une fraction de formule (a). Dans cette formule R4 représente une fraction (CH2)nCO2H où n représente zéro ou un entier compris entre 1 et 3, et R5 représente une fraction (CH2)pCO2H, (CH2)pOH, (CH2)pCN, (CH2)pCOCH3 ou (CH2)pNH2 où p représente zéro ou un entier compris entre 1 et 3; R3 représente hydrogène, halogène, alkyle or alcoxy. Cette invention concerne également un procédé de préparation de ce composé, une composition pharmaceutique renfermant ledit composé ainsi que son utilisation en médecine.
• Soluble Tetraarylporphyrin−Platinum Conjugates as Cytotoxic and Phototoxic Antitumor Agents
  作者：Christian Lottner、Karl-Christian Bart、Günther Bernhardt、Henri Brunner

  DOI：10.1021/jm0110690

  日期：2002.5.1

  A series of asymmetric tetraarylporphyrins was synthesized from pyrrole, para-substituted oligo- or poly(ethylene glycol) monomethyl ether benzaldehyde and from 4-hydroxybenzaldehyde etherified with diethyl bromomalonate according to the Lindsey method. After hydrolysis of the tetraarylporphyrin esters, the resulting carboxylic acid groups were used to bind platinum fragments. In comparison to analogous hematoporphyrin-platinum conjugates, the title compounds are characterized by a 30 nm bathochromic shift of their absorption bands. The antiproliferative activity of 18 platinum complexes (1, 5, and 10 muM) differing in solubility, type of the platinum fragment, and the corresponding tetraarylporphyrin ligands were studied on TCC-SUP transitional bladder cancer cells in the dark and after irradiation (lambda = 600-730 nm; 24 J/cm(2)). The most active compounds were among the tetraarylporphyrin-platinum conjugates bearing the diammine and (RR/SS)-trans-1,2-diaminocyclohexane ligands.