6-((4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-ynyl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)(methyl)amino)hexanoic acid | 1129547-80-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 6-((4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-ynyl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)(methyl)amino)hexanoic acid
• 英文别名: 17β-hydroxy-11β-[4-(5-carboxy-N-methylpentylamino)-phenyl]-17α-(1-propinyl)-estra-4,9-dien-3-one；6-N-methyl-N-[4'-[17β-hydroxy-3-oxo-17α-(1-propynyl)estra-4,9-dien-11β-yl]phenyl]aminohexanoic acid；17beta-Hydroxy-11beta-[4-(5-carboxy-N-methylpentylamino)-phenyl]-17alpha-(1-propinyl)-estra-4,9-dien-3-one；6-[4-[(8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-prop-1-ynyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-11-yl]-N-methylanilino]hexanoic acid
• CAS: 1129547-80-3
• 化学式: C₃₄H₄₃NO₄
• 分子量: 529.72
• InChiKey: VETSLXUNGBDAPY-BWQSSOLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[5-[(3,4-二氢-4-氧代-1-酞嗪基)甲基]-2-氟苯甲酰基]哌嗪 、 6-((4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-ynyl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)(methyl)amino)hexanoic acid 在 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 生成 4-(4-fluoro-3-(4-(6-((4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-ynyl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)(methyl)amino)hexanoyl)piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one
  参考文献：
  名称：

  [EN] ANTI-CANCER NUCLEAR HORMONE RECEPTOR-TARGETING COMPOUNDS
  [FR] COMPOSÉS CIBLANT DES RÉCEPTEURS HORMONAUX NUCLÉAIRES ANTICANCÉREUX

  摘要：

  该披露涉及抗癌化合物，这些化合物是公式Al、A2、A3或A4的抗癌PARP抑制剂，通过连接剂与类固醇结合，从而使类固醇将该共轭物靶向到细胞核，以及其制备和使用的方法。

  公开号：

  WO2021097046A1
• 作为产物：
  描述：

  米非司酮 在 碘 、 碳酸氢钠 、 calcium oxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 17.0h， 生成 6-((4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-ynyl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)(methyl)amino)hexanoic acid
  参考文献：
  名称：

  [EN] ANTI-CANCER NUCLEAR HORMONE RECEPTOR-TARGETING COMPOUNDS
  [FR] COMPOSÉS CIBLANT DES RÉCEPTEURS HORMONAUX NUCLÉAIRES ANTICANCÉREUX

  摘要：

  该披露涉及抗癌化合物，这些化合物是公式Al、A2、A3或A4的抗癌PARP抑制剂，通过连接剂与类固醇结合，从而使类固醇将该共轭物靶向到细胞核，以及其制备和使用的方法。

  公开号：

  WO2021097046A1

文献信息

• Syntheses and Antigestagenic Activity of Mifepristone Derivatives
  作者：Claudia Hödl、Katrin Raunegger、Rainer Strommer、Gerhard F. Ecker、Olaf Kunert、Sonja Sturm、Christoph Seger、Ernst Haslinger、Rudolf Steiner、Wolfgang S. L. Strauss、Hans-Wolfgang Schramm

  DOI：10.1021/jm800985z

  日期：2009.3.12

  A series of mifepristone derivatives with different "linker groups" in position 4' of the phenyl ring in the 11 beta-position of the steroid scaffold (2-41) have been synthesized. Their antigestagenic activites were determined in a cell-based assay (alkali phosphatase assay in T47-D breast cancer cells) and compared with that of the parent compound mifepristone. SAR and QSAR studies reveal the influence of both lipophilicity and partial charge based van der Waals surface area descriptors on biological activity. Within the series of compounds described in this study, three n-mifepristone derivatives are identified with considerably high antigestagenic activity. These compounds are regarded as useful starting materials for the synthesis of either physiologically stable or cleavable progesterone receptor-binding conjugates for therapeutic or diagnostic purposes.
• Synthesis, in vitro progesterone receptors affinity of gadolinium containing mifepristone conjugates and estimation of binding sites in human breast cancer cells
  作者：Pijus Saha、Claudia Hödl、Wolfgang S.L. Strauss、Rudolf Steiner、Walter Goessler、Olaf Kunert、Alexander Leitner、Ernst Haslinger、H. Wolfgang Schramm

  DOI：10.1016/j.bmc.2010.01.048

  日期：2010.3

  Novel gadolinium-based mifepristone conjugates were synthesised using various synthetic routes. Moderate antiprogestagenic activity of the new conjugates was observed in human breast cancer cells (T47-D cells) using AP (alkaline phosphatase) assay. The amount of incorporated Gd determined by inductively coupled plasma mass spectroscopy (ICPMS) indicates the number of binding sites per cell. These conjugates might be important compounds to develop receptor-targeted MRI contrast agents as well as other anti-breast cancer therapeutics. (C) 2010 Elsevier Ltd. All rights reserved.
• ANTI-CANCER NUCLEAR HORMONE RECEPTOR-TARGETING COMPOUNDS
  申请人：Nuvation Bio Inc.

  公开号：US20210214316A1

  公开（公告）日：2021-07-15

  The disclosure relates to anti-cancer compounds derived from nuclear steroid receptor binders, to products containing the same, as well as to methods of their use and preparation.
• [EN] ANTI-CANCER NUCLEAR HORMONE RECEPTOR-TARGETING COMPOUNDS<br/>[FR] COMPOSÉS CIBLANT DES RÉCEPTEURS HORMONAUX NUCLÉAIRES ANTICANCÉREUX
  申请人：NUVATION BIO INC

  公开号：WO2021097046A1

  公开（公告）日：2021-05-20

  The disclosure relates to anti-cancer compounds which are anti-cancer PARP inhibitors of formula Al, A2, A3 or A4 conjugated by a linker to a steroid, whereby the steroid targets the conjugate to the nucleus, as well as to methods for their preparation and use. (I)

  该披露涉及抗癌化合物，这些化合物是公式Al、A2、A3或A4的抗癌PARP抑制剂，通过连接剂与类固醇结合，从而使类固醇将该共轭物靶向到细胞核，以及其制备和使用的方法。