3-[4-(2-Ethoxy-2-oxoethoxy)phenyl]adamantane-1-carboxylic acid | 1192322-56-7

• 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: 3-[4-(2-Ethoxy-2-oxoethoxy)phenyl]adamantane-1-carboxylic acid
• CAS: 1192322-56-7
• 化学式: C₂₁H₂₆O₅
• 分子量: 358.434
• InChiKey: PTLHCNVUZRDPOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,7-二甲氧基-1,2,3,4-四氢异喹啉 、 3-[4-(2-Ethoxy-2-oxoethoxy)phenyl]adamantane-1-carboxylic acid 在 sodium cyanide 、 1-丙基磷酸酐 、 三乙胺 作用下， 以66%的产率得到(4-[3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbonyl)adamantan-1-yl]phenoxy)acetic acid ethyl ester
  参考文献：
  名称：

  A novel class of highly potent multidrug resistance reversal agents: Disubstituted adamantyl derivatives

  摘要：

  Novel disubstituted adamantyl derivatives were synthesized and evaluated in a P-glycoprotein dependent multidrug resistance cancer cell line. The hit to lead optimization provided potent MDR reversal agents. Some potent adamantyl derivatives were more than 10-fold more potent than verapamil without considerable intrinsic cytotoxicity. The 3-trifluorophenyl derivative 14f did not affect the metabolism of CYP450 3A4, whereas most of MDR revertants had a weak inhibitory effect. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.127
• 作为产物：
  描述：

  3-(4-ethoxycarbonylmethoxyphenyl)adamantane-1-carboxylic acid benzylester 在 1% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 以99%的产率得到3-[4-(2-Ethoxy-2-oxoethoxy)phenyl]adamantane-1-carboxylic acid
  参考文献：
  名称：

  A novel class of highly potent multidrug resistance reversal agents: Disubstituted adamantyl derivatives

  摘要：

  Novel disubstituted adamantyl derivatives were synthesized and evaluated in a P-glycoprotein dependent multidrug resistance cancer cell line. The hit to lead optimization provided potent MDR reversal agents. Some potent adamantyl derivatives were more than 10-fold more potent than verapamil without considerable intrinsic cytotoxicity. The 3-trifluorophenyl derivative 14f did not affect the metabolism of CYP450 3A4, whereas most of MDR revertants had a weak inhibitory effect. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.127

文献信息

• [EN] NOVEL DI-SUBSTITUTED PHENOXYACETYL-BASED COMPOUND OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PRODUCTION METHOD FOR SAME AND PHARMACEUTICAL COMPOSITION FOR SUPPRESSING MULTIPLE DRUG RESISTANCE COMPRISING SAME AS AN ACTIVE INGREDIENT<br/>[FR] NOUVEAU COMPOSÉ À BASE DE PHÉNOXYACÉTYLE DISUBSTITUÉ OU SON SEL PHARMACEUTIQUEMENT ACCEPTABLE, SON PROCÉDÉ DE FABRICATION, ET COMPOSITION PHARMACEUTIQUE DE SUPPRESSION DE MULTIRÉSISTANCE AUX MÉDICAMENTS QUI CONTIENT CE COMPOSÉ EN TANT QUE PRINCIPE AC
  申请人：KOREA RES INST OF BIOSCIENCE

  公开号：WO2011014009A2

  公开（公告）日：2011-02-03

  본 발명은 신규 이치환된 페녹시아세틸계 화합물, 이의 제조방법 및 이를 유효성분으로 함유하는 다약제내성 억제용 약학적 조성물에 관한 것으로, 본 발명에 따른 신규 이치환된 페녹시아세틸계 화합물은 다약제내성의 주요 원인인 P-당단백질(P-glycoprotein, Pgp)의 과발현에 대한 억제활성 및 항암제와의 병용투여시 항암활성의 증가를 나타내어 항암제에 대한 다약제내성 극복제제, 치료제 또는 조절제로 이용될 수 있으며, 항암제의 효과를 증진시켜 암환자의 생존률을 높일 수 있고, 병용투여하는 항암제의 용량을 줄여 정상세포에 대한 부작용을 감소시킬 수 있으므로 항암치료에 유용하게 사용될 수 있다.
• A novel class of highly potent multidrug resistance reversal agents: Disubstituted adamantyl derivatives
  作者：Kyung Hoon Min、Yan Xia、Eun Kyung Kim、Yinglan Jin、Navneet Kaur、Eun Seon Kim、Dae Kyong Kim、Hwa Young Jung、Yongseok Choi、Mi-Kyung Park、Yong Ki Min、Kiho Lee、Kyeong Lee

  DOI：10.1016/j.bmcl.2009.07.127

  日期：2009.9

  Novel disubstituted adamantyl derivatives were synthesized and evaluated in a P-glycoprotein dependent multidrug resistance cancer cell line. The hit to lead optimization provided potent MDR reversal agents. Some potent adamantyl derivatives were more than 10-fold more potent than verapamil without considerable intrinsic cytotoxicity. The 3-trifluorophenyl derivative 14f did not affect the metabolism of CYP450 3A4, whereas most of MDR revertants had a weak inhibitory effect. (C) 2009 Elsevier Ltd. All rights reserved.