Methyl 3-(2-(4-(3-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-adamantan-1-yl)phenoxy)acetamido)benzoate | 1192322-77-2

• 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: Methyl 3-(2-(4-(3-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-adamantan-1-yl)phenoxy)acetamido)benzoate
• 英文别名: methyl 3-[[2-[4-[3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbonyl)-1-adamantyl]phenoxy]acetyl]amino]benzoate
• CAS: 1192322-77-2
• 化学式: C₃₈H₄₂N₂O₇
• 分子量: 638.761
• InChiKey: KSJCPBCGKSFACD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  47
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl 3-(2-(4-(3-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-adamantan-1-yl)phenoxy)acetamido)benzoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 3-[[2-[4-[3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbonyl)-1-adamantyl]phenoxy]acetyl]amino]benzoic 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
• 作为产物：
  描述：

  6,7-二甲氧基-1,2,3,4-四氢异喹啉 、 3-{4-[(3-methoxycarbonylphenylaminoformyl)-methoxy]-phenyl}-adamantane-1-carboxylic acid 在 1-丙基磷酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Methyl 3-(2-(4-(3-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-adamantan-1-yl)phenoxy)acetamido)benzoate
  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] 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.