N-(4-ethoxyphenyl)methanimine | 1314977-96-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(4-ethoxyphenyl)methanimine
• CAS: 1314977-96-2
• 化学式: C₉H₁₁NO
• mdl: MFCD11226441
• 分子量: 149.192
• InChiKey: OPXMQOBEPISHKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-ethoxyphenyl)methanimine 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 、 水 、 异丙醇 为溶剂， 反应 122.0h， 生成 4-N-(4-ethoxyphenyl)-4-N-methyl-9H-pyrimido[4,5-b]indole-2,4-diamine
  参考文献：
  名称：

  Synthesis of N4-(substituted phenyl)-N4-alkyl/desalkyl-9H-pyrimido[4,5-b]indole-2,4-diamines and identification of new microtubule disrupting compounds that are effective against multidrug resistant cells

  摘要：

  A series of fourteen N-4-(substituted phenyl)-N-4-alkyl/clesalkyl-9H-pyrimido[4,5-b]indole-2,4-diamines was synthesized as potential microtubule targeting agents. The synthesis involved a Fisher indole cyclization of 2-amino-6-hydrazinylpyrimidin-4(3H)-one with cyclohexanone, followed by oxidation, chlorination and displacement with appropriate anilines. Compounds 6, 14 and 15 had low nanomolar potency against MDA-MB-435 tumor cells and depolymerized microtubules. Compound 6 additionally had nanomolar GI(50) values against 57 of the NCI 60-tumor panel cell lines. Mechanistic studies showed that 6 inhibited tubulin polymerization and [H-3]colchicine binding to tubulin. The most potent compounds were all effective in cells expressing P-glycoprotein or the 0111 isotype of tubulin, which have been associated with clinical drug resistance. Modeling studies provided the potential interactions of 6, 14 and 15 within the colchicine site. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.010
• 作为产物：
  描述：

  聚合甲醛 、 对乙氧基苯胺 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 N-(4-ethoxyphenyl)methanimine
  参考文献：
  名称：

  Synthesis of N4-(substituted phenyl)-N4-alkyl/desalkyl-9H-pyrimido[4,5-b]indole-2,4-diamines and identification of new microtubule disrupting compounds that are effective against multidrug resistant cells

  摘要：

  A series of fourteen N-4-(substituted phenyl)-N-4-alkyl/clesalkyl-9H-pyrimido[4,5-b]indole-2,4-diamines was synthesized as potential microtubule targeting agents. The synthesis involved a Fisher indole cyclization of 2-amino-6-hydrazinylpyrimidin-4(3H)-one with cyclohexanone, followed by oxidation, chlorination and displacement with appropriate anilines. Compounds 6, 14 and 15 had low nanomolar potency against MDA-MB-435 tumor cells and depolymerized microtubules. Compound 6 additionally had nanomolar GI(50) values against 57 of the NCI 60-tumor panel cell lines. Mechanistic studies showed that 6 inhibited tubulin polymerization and [H-3]colchicine binding to tubulin. The most potent compounds were all effective in cells expressing P-glycoprotein or the 0111 isotype of tubulin, which have been associated with clinical drug resistance. Modeling studies provided the potential interactions of 6, 14 and 15 within the colchicine site. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.010

文献信息

• [EN] METHOD FOR PRODUCING N-METHYL-PARA-PHENETIDINE<br/>[FR] PROCÉDÉ DE PRODUCTION DE N-MÉTHYL-PARA-PHÉNÉTIDINE<br/>[RU] СПОСОБ ПОЛУЧЕНИЯ N-МЕТИЛ-ПАРА-ФЕНЕТИДИНА
  申请人：OBSCHESTVO S OGRANICHENNOI OTVETSTVENNOSTYU IFOTOP

  公开号：WO2018048319A1

  公开（公告）日：2018-03-15

  Изобретение относится к химическим технологическим процессам и, в частности, к жидкофазным каталитическим способам получения в присутствии водорода алкилированного пара-фенетидина, используемого в качестве химического вещества или добавок к бензину для повышения его октанового числа. Техническим результатом заявленной группы изобретений является повышение выхода Ν-метил-пара-фенетидина и снижение выхода диметилпроизводного. Способ получения Ν-метил-пара-фенетидина в жидкой фазе включает алкилирование пара-фенетидина формалином при раздельной, одновременной их подаче в смеситель, расположенный в реакторе непосредственно перед зоной каталитического восстановления, с образованием промежуточного азометина - 4-этокси-N-фенилметанимина, с последующим его восстановлением на гидрирующем катализаторе при температуре 20-120°С, в среде водорода при повышенном давлении и последующим выделением целевого продукта - Ν-метил-пара-фенетидина.
• Synthesis of N4-(substituted phenyl)-N4-alkyl/desalkyl-9H-pyrimido[4,5-b]indole-2,4-diamines and identification of new microtubule disrupting compounds that are effective against multidrug resistant cells
  作者：Aleem Gangjee、Nilesh Zaware、Ravi Kumar Vyas Devambatla、Sudhir Raghavan、Cara D. Westbrook、Nicholas F. Dybdal-Hargreaves、Ernest Hamel、Susan L. Mooberry

  DOI：10.1016/j.bmc.2012.12.010

  日期：2013.2

  A series of fourteen N-4-(substituted phenyl)-N-4-alkyl/clesalkyl-9H-pyrimido[4,5-b]indole-2,4-diamines was synthesized as potential microtubule targeting agents. The synthesis involved a Fisher indole cyclization of 2-amino-6-hydrazinylpyrimidin-4(3H)-one with cyclohexanone, followed by oxidation, chlorination and displacement with appropriate anilines. Compounds 6, 14 and 15 had low nanomolar potency against MDA-MB-435 tumor cells and depolymerized microtubules. Compound 6 additionally had nanomolar GI(50) values against 57 of the NCI 60-tumor panel cell lines. Mechanistic studies showed that 6 inhibited tubulin polymerization and [H-3]colchicine binding to tubulin. The most potent compounds were all effective in cells expressing P-glycoprotein or the 0111 isotype of tubulin, which have been associated with clinical drug resistance. Modeling studies provided the potential interactions of 6, 14 and 15 within the colchicine site. (C) 2012 Elsevier Ltd. All rights reserved.