(8S,9S,13S,14S,17S)-4-氨基-13-甲基-6,7,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-3,17-二醇 | 6301-88-8

• 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
• 中文名称: (8S,9S,13S,14S,17S)-4-氨基-13-甲基-6,7,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-3,17-二醇
• 英文名称: 4-Aminoestratriene-3,17beta-diol
• 英文别名: 4-aminoestra-1,3,5(10)-triene-3,17β-diol；4-aminoestradiol；4-Aminoestra-1,3,5(10)-triene-3,17beta-diol；(8R,9S,13S,14S,17S)-4-amino-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 6301-88-8
• 化学式: C₁₈H₂₅NO₂
• 分子量: 287.402
• InChiKey: DIDANTCTDBQPRP-ZHIYBZGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8S,9S,13S,14S,17S)-4-氨基-13-甲基-6,7,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-3,17-二醇 在 盐酸 、 sodium periodate 、 溶剂黄146 作用下， 生成 4-羟雌二醇
  参考文献：
  名称：

  Convenient large scale preparation of catechol estrogens

  摘要：

  2-Hydroxyestrone, 2-hydroxyestradiol-17beta, 2-hydroxy-17alpha-ethynylestradiol, 2-hydroxyestriol, 4-hydroxyestrone, 4-hydroxyestradiol-17beta, 4-hydroxy-17alpha-ethynylestradiol and 4-hydroxyestriol are prepared on a preparative scale from the corresponding aminophenols using a new inverse oxidation procedure. By the synthesis described both the 2- and 4-hydroxylated estrogens are available in high yields.

  DOI：

  10.1016/0039-128x(76)90010-6
• 作为产物：
  描述：

  4-Nitroestratriene-3,17beta-diol 在 sodium hydroxide 、 sodium hydrogensulfite 作用下， 生成 (8S,9S,13S,14S,17S)-4-氨基-13-甲基-6,7,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-3,17-二醇
  参考文献：
  名称：

  Convenient large scale preparation of catechol estrogens

  摘要：

  2-Hydroxyestrone, 2-hydroxyestradiol-17beta, 2-hydroxy-17alpha-ethynylestradiol, 2-hydroxyestriol, 4-hydroxyestrone, 4-hydroxyestradiol-17beta, 4-hydroxy-17alpha-ethynylestradiol and 4-hydroxyestriol are prepared on a preparative scale from the corresponding aminophenols using a new inverse oxidation procedure. By the synthesis described both the 2- and 4-hydroxylated estrogens are available in high yields.

  DOI：

  10.1016/0039-128x(76)90010-6

文献信息

• Synthesis and conversion of primary and secondary 2-aminoestradiols into A-ring-integrated benzoxazolone hybrids and their <i>in vitro</i> anticancer activity
  作者：Ferenc Kovács、Mohana K. Gopisetty、Dóra I. Adamecz、Mónika Kiricsi、Éva A. Enyedy、Éva Frank

  DOI：10.1039/d1ra01889b

  日期：——

  carbonyldiimidazole as a phosgene equivalent to introduce a carbonyl group with simultaneous ring-closure to give A-ring-fused oxazolone derivatives in high yields. The novel aminoestradiols and benzoxazolones were subjected to in vitro cytotoxicity analysis and were found to exert cancer cell specific activity.

  与其母体化合物相比，混合系统通常具有完全不同和改进的特性。为了将化学空间扩展到基于甾烷的分子杂化物，通过相应的 2-氨基苯酚中间体合成了许多具有组合芳环的雌二醇衍生的苯并恶唑-2-酮。2-氨基雌二醇首先由雌酮在温和的反应条件下通过两步硝化/还原顺序制备。随后用不同芳醛进行的还原胺化以良好的收率提供了仲 2-氨基雌二醇衍生物。通过紫外-可见分光光度滴定法研究了氨基雌二醇在水溶液中的质子解离过程，以揭示它们在生理 pH 值下的实际化学形式。确定的 p K1和p K 2值归因于+ NH 3或+ NH 2 R 和OH 部分，并且都因氨基的不同R 取代基而变化。接下来，伯和仲 2-氨基雌二醇与作为光气等价物的羰基二咪唑反应，以引入羰基并同时闭环，以高收率得到 A-环稠合恶唑酮衍生物。对新型氨基雌二醇和苯并恶唑酮进行体外细胞毒性分析，发现它们具有癌细胞特异性活性。
• Biomarkers for prostate cancer and methods using the same
  申请人：Metabolon Inc.

  公开号：EP2560006A2

  公开（公告）日：2013-02-20

  Methods for identifying and evaluating suites of biochemical and/or gene entities useful as biomarkers for early predication of prostate cancer, disease grading, target identification/validation, and monitoring of drug efficacy are provided. Also provided are suites of small molecule entities as biomarkers for prostate cancer

  本研究提供了鉴定和评估可用作前列腺癌早期预测、疾病分级、靶点鉴定/验证和药物疗效监测的生物标记物的生化和/或基因实体组的方法。此外，还提供了作为前列腺癌生物标记物的小分子实体套件。
• Biomarkers for cardiovascular diseases and methods using the same
  申请人：Metabolon, Inc.

  公开号：US10175233B2

  公开（公告）日：2019-01-08

  Biomarkers relating to cardiovascular disease, including atherosclerosis and cardiomyopathy, are provided, as well as methods for using such biomarkers as biomarkers for cardiovascular disease. In addition, methods for modulating the respective disorders or conditions of a subject are also provided. Also provided are suites of small molecule entities as biomarkers for cardiovascular disease, including atherosclerosis and cardiomyopathy.

  本研究提供了与心血管疾病（包括动脉粥样硬化和心肌病）有关的生物标志物，以及将此类生物标志物用作心血管疾病生物标志物的方法。此外，还提供了调节受试者相应疾病或状况的方法。还提供了作为心血管疾病（包括动脉粥样硬化和心肌病）生物标志物的成套小分子实体。
• BIOMARKERS FOR PROSTATE CANCER AND METHODS USING THE SAME
  申请人：Metabolon Inc.

  公开号：EP2061899B1

  公开（公告）日：2012-08-29
• BIOMARKERS FOR PRE-DIABETES AND METHODS USING THE SAME
  申请人：Metabolon, Inc.

  公开号：EP2164977B1

  公开（公告）日：2013-10-30