meso-1,2-bis(4-methoxy-2-methylphenyl)ethylenediamine | 111086-47-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: meso-1,2-bis(4-methoxy-2-methylphenyl)ethylenediamine
• 英文别名: (1R,2S)/(1S,2R)-1,2-bis(4-methoxy-2-methylphenyl)ethylenediamine；(1R,2S)-1,2-bis(4-methoxy-2-methylphenyl)ethane-1,2-diamine
• CAS: 111086-47-6
• 化学式: C₁₈H₂₄N₂O₂
• 分子量: 300.401
• InChiKey: WFSMJQUJRDFMAQ-HDICACEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  meso-1,2-bis(4-methoxy-2-methylphenyl)ethylenediamine 在 氢溴酸 作用下， 以 乙腈 为溶剂， 反应 50.17h， 生成 d,l-1,2-bis(2-methyl-4-hydroxyphenyl)ethylenediamine
  参考文献：
  名称：

  Ring-substituted [1,2-bis(4-hydroxyphenyl)ethylenediamine]dichloroplatinum(II) complexes: compounds with a selective effect on the hormone-dependent mammary carcinoma

  摘要：

  [1,2-Bis(4-hydroxyphenyl)ethylenediamine]dichloroplatinum (II) complexes with one substituent in the 2-position (CH3, CF3, F, Cl, Br, I: meso- and d,l-1-PtCl2, meso-(3-5)-PtCl2, meso-(7 and 8)-PtCl2) or two substituents in the 2,6-positions (CH3, Cl: meso-2-PtCl2, meso- and d,l-6-PtCl2) in both benzene rings were synthesized and tested for estrogenic and cytotoxic activities. Two complexes (meso-6-PtCl2 and meso-7-PtCl2) possess both effects. In comparative tests on estrogen receptor positive and negative mammary tumors in cell culture (MCF 7, ER+ and MDA-MB 231, ER-) and in animals (MXT, ER+ and MXT, ER-, mouse), meso-6-PtCl2 shows a selective effect on the estrogen receptor positive mammary carcinoma. A further increase of efficacy was achieved with the water-soluble (sulfato)platinum(II) derivative (meso-6-PtSO4). On the DMBA-induced hormone dependent mammary carcinoma of the SD rat, meso-6-PtSO4 is significantly more active than its ligand (meso-6) and cisplatin.

  DOI：

  10.1021/jm00396a012
• 作为产物：
  描述：

  间甲基苯甲醚 在 硫酸 、 溴 、 溴化乙啶 、 铁粉 、 magnesium 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 4.0h， 生成 meso-1,2-bis(4-methoxy-2-methylphenyl)ethylenediamine
  参考文献：
  名称：

  Ring-substituted [1,2-bis(4-hydroxyphenyl)ethylenediamine]dichloroplatinum(II) complexes: compounds with a selective effect on the hormone-dependent mammary carcinoma

  摘要：

  [1,2-Bis(4-hydroxyphenyl)ethylenediamine]dichloroplatinum (II) complexes with one substituent in the 2-position (CH3, CF3, F, Cl, Br, I: meso- and d,l-1-PtCl2, meso-(3-5)-PtCl2, meso-(7 and 8)-PtCl2) or two substituents in the 2,6-positions (CH3, Cl: meso-2-PtCl2, meso- and d,l-6-PtCl2) in both benzene rings were synthesized and tested for estrogenic and cytotoxic activities. Two complexes (meso-6-PtCl2 and meso-7-PtCl2) possess both effects. In comparative tests on estrogen receptor positive and negative mammary tumors in cell culture (MCF 7, ER+ and MDA-MB 231, ER-) and in animals (MXT, ER+ and MXT, ER-, mouse), meso-6-PtCl2 shows a selective effect on the estrogen receptor positive mammary carcinoma. A further increase of efficacy was achieved with the water-soluble (sulfato)platinum(II) derivative (meso-6-PtSO4). On the DMBA-induced hormone dependent mammary carcinoma of the SD rat, meso-6-PtSO4 is significantly more active than its ligand (meso-6) and cisplatin.

  DOI：

  10.1021/jm00396a012

文献信息

• (4<i>R</i>,5<i>S</i>)/(4<i>S</i>,5<i>R</i>)-4,5-Bis(4-hydroxyphenyl)-2-imidazolines:  Ligands for the Estrogen Receptor with a Novel Binding Mode
  作者：Ronald Gust、Roland Keilitz、Kathrin Schmidt、Moriz von Rauch

  DOI：10.1021/jm020809h

  日期：2002.8.1

  The 1,2-diarylethane pharmacophor takes a Z-stilbene-like structure with pseudoaxially oriented phenyl rings at the planar heterocyclic ring. Because of this unusual spatial structure, the (4R,5S)/(4S,5R)-4,5-bis(4-hydroxyphenyl)-2-imidazolines have to be assigned to a second class of estrogenically active compounds (type II estrogens). In contrast to type I estrogens, e.g., estradiol (E2), diethylstilbestrol

  通过甲氧基取代的（1R，2S）/（1S，2R）反应合成（4R，5S）/（4S，5R）-4,5-双（4-羟苯基）-2-咪唑啉1-7 -1,2-二芳基乙二胺1b-7b与原甲酸三乙酯，然后用BBr（3）裂解。使用[（3）H]-雌二醇的竞争实验测试了所有化合物的雌激素受体（ER）结合，并使用经质粒ERE（ERE）稳定转染的ER阳性MCF-7-2a乳腺癌细胞通过萤光素酶测定法测试了所有化合物的基因激活。 wtc）luc。2-咪唑啉的相对结合亲和力很低（RBA <0.1％）。然而，在萤光素酶测定中，4-7具有完全的激动活性。相对转录能力以5（2,2'-I）<6（2,6-Cl（2），2'-F）<4（2,2'-Cl）<7（2,6）的顺序增加-Cl（2），2'-Cl）。这些数据与光谱学和分子建模研究一起用于研究咪唑啉配体所采用的优选结合方式。1，2-二芳基乙烷药效基团具有在平面杂环上具有拟轴向取向的苯环的Z
• KARL, JOHANN;SCHONENBERGER, HELMUT, ARCH. PHARM., 321,(1988) N 7, C. 405-410
  作者：KARL, JOHANN、SCHONENBERGER, HELMUT

  DOI：——

  日期：——