(4-[3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbonyl)adamantan-1-yl]phenoxy)acetic acid ethyl ester | 1192322-58-9

• 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: (4-[3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbonyl)adamantan-1-yl]phenoxy)acetic acid ethyl ester
• 英文别名: ethyl 2-[4-[3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbonyl)-1-adamantyl]phenoxy]acetate
• CAS: 1192322-58-9
• 化学式: C₃₂H₃₉NO₆
• 分子量: 533.665
• InChiKey: MULHENGOAFAECW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4-[3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbonyl)adamantan-1-yl]phenoxy)acetic acid ethyl ester 在 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-(4-(3-(6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)adamantan-1-yl)phenoxy)-1-(4-methylpiperazin-1-yl)ethanone
  参考文献：
  名称：

  KR102274238

  摘要：

  公开号：
• 作为产物：
  描述：

  3-溴-1-金刚烷甲酸 在 aluminum (III) chloride 、 三溴化硼 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (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：

  KR102274238

  摘要：

  公开号：

文献信息

• DISUBSTITUTED ADAMANTYL DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION FOR SUPPRESSING CANCER GROWTH COMPRISING SAME AS ACTIVE INGREDIENT
  申请人：Onecuregen Co., Ltd.

  公开号：EP4098647A1

  公开（公告）日：2022-12-07

  The present invention relates to: a disubstituted adamantyl derivative or a pharmaceutically acceptable salt thereof, and an anticancer pharmaceutical composition and a kit containing same as an active ingredient. The disubstituted adamantyl derivative according to the present invention suppresses the growth of cancer cells by targeting mitochondria ETC complex I and damaging the metabolism of cancer cells, and thus can be useful as an anticancer pharmaceutical composition that is a powerful therapeutic agent for cancer dependent on oxidative phosphorylation for producing ATP.

  本发明涉及：一种二取代金刚烷基衍生物或其药学上可接受的盐，以及含有其作为活性成分的抗癌药物组合物和试剂盒。根据本发明的二取代金刚烷基衍生物通过靶向线粒体 ETC 复合物 I 和破坏癌细胞的新陈代谢来抑制癌细胞的生长，因此可作为一种抗癌药物组合物，对依赖氧化磷酸化产生 ATP 的癌症具有强大的治疗作用。
• 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.
• [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.
• [EN] DISUBSTITUTED ADAMANTYL DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION FOR SUPPRESSING CANCER GROWTH COMPRISING SAME AS ACTIVE INGREDIENT<br/>[FR] DÉRIVÉ D'ADAMANTYLE DISUBSTITUÉ OU SON SEL PHARMACEUTIQUEMENT ACCEPTABLE, ET COMPOSITION PHARMACEUTIQUE POUR EMPÊCHER LA CROISSANCE DU CANCER LE CONTENANT COMME PRINCIPE ACTIF<br/>[KO] 이치환 아다만틸 유도체, 이의 약학적으로 허용가능한 염 및 이를 유효성분으로 포함하는 암 성장 억제용 약학적 조성물
  申请人：UNIV DONGGUK IND ACAD COOP

  公开号：WO2021149900A1

  公开（公告）日：2021-07-29

  본 발명은 이치환 아다만틸 유도체 또는 이의 약학적으로 허용가능한 염, 및 이를 유효성분으로 함유하는 항암용 약학적 조성물과 키트에 관한 것으로, 본 발명에 따른 이치환 아다만틸 유도체는 미토콘드리아 ETC 복합체 I을 표적화하고 암 세포 대사를 손상시킴으로써 암 세포의 성장을 억제하는바, ATP 생성을 위한 산화적 인산화에 의존하는 암에 대한 강력한 치료제로서 항암용 약학적 조성물로 유용하게 사용될 수 있다.