16β-amino-3-methoxy-estra-1,3,5(10)-triene | 90702-80-0

• 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: 16β-amino-3-methoxy-estra-1,3,5(10)-triene
• 英文别名: 16beta-Amino-3-methoxy-estra-1,3,5(10)-triene；(8S,9S,13R,14S,16S)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-16-amine
• CAS: 90702-80-0
• 化学式: C₁₉H₂₇NO
• 分子量: 285.429
• InChiKey: KJWLAEWLUXLIOM-QHWILLEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  对甲基肉桂醛 、 16β-amino-3-methoxy-estra-1,3,5(10)-triene 以 甲醇 为溶剂， 反应 4.0h， 以61%的产率得到((8S,9S,13R,14S,16S)-3-Methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-16-yl)-[(E)-3-p-tolyl-prop-2-en-(E)-ylidene]-amine
  参考文献：
  名称：

  Steroid imines as chiral ligands. Diastereoselective formation of (1-azadiene)Fe(CO)3 complexes by sterically tuning the ligand coordination spheres

  摘要：

  The condensation of steroid amines with alpha,beta-unsaturated aldehydes leads to the formation of chiral 1-azadiene ligands with a steroid core attached to nitrogen. If the azadiene chain is situated at the D-ring of the steroid at C-16 or C-17, respectively, the two diastereotopic faces of the ligand may be discriminated by different neighbouring substituents and their configuration. The reaction of these ligands with Fe-2(CO)(9) produces mixtures of diastereomeric (1-azadiene)Fe(CO)(3) complexes. By increasing the steric demands of the neighbouring groups it is possible to improve the diastereoselectivity of this complexation reaction from 1:1 mixtures using the least sterically hindered ligands to complete diastereoselectivity using the azadiene derived from cinnamaldehyde and 16 beta-amino-3-methoxy-estra-1,3,5(10)-triene-17 beta-ol. In addition, the molecular structure of [17 beta-(3-phenyl-prop-2-enyliden)-amino-3-methoxy-estra-1,3,5(10)-triene]Fe(CO)(3) was determined by X-ray structure analysis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00281-5
• 作为产物：
  描述：

  16β-hydroxy-3-methoxyestra-1,3,5(10)-triene 在 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 叠氮化锂 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.5h， 生成 16β-amino-3-methoxy-estra-1,3,5(10)-triene
  参考文献：
  名称：

  衍生自邻近类固醇氨基醇和胺的新型（N-二茂铁基甲基）胺和（N-二茂铁基甲基）亚胺：合成，分子结构和生物学活性。

  摘要：

  合成了具有潜在生物活性和潜在兴趣的新型甾族（N-二茂铁基甲基）胺类，作为金属配合物的手性配体。体外筛选了新化合物作为抗菌剂的潜力。描述了新的甾族二茂铁的合成，包括两个X射线晶体结构和生物学分析。16-（二茂铁基甲基）氨基雌激素4a-d，7b和10b表现出出色的广泛抗菌活性，特别是对分枝杆菌和多重耐药葡萄球菌。因此，它们可以被认为是新的引线结构。相反，类似的3α-（二茂铁基甲基）氨基-胆甾烷12仅具有弱活性。研究了四种异构氨基醇1a-d（方案1）与二茂铁甲醛的反应。具有16 / 17-反式构型的1b和1c几乎定量地产生（E）-席夫碱2b和2c（方案2）。与反式化合物相反，顺式构型的氨基醇1a和1d的缩合提供了席夫碱（分别为2a和2d）及其相应的1,3-恶唑烷（分别为3a和3d）的互变异构混合物。通过在乙醇中用硼氢化钠还原互变异构体混合物和均匀的席夫碱，以优异的产率获得了新型的（N-二茂铁基甲

  DOI：

  10.1016/s0039-128x(98)00062-2

文献信息

• DERIVATIVES OF STEROID BENZYLAMINES, HAVING AN ANTIPARASITIC ANTIBACTERIAL, ANTIMYCOTIC AND/OR ANTIVIRAL ACTION
  申请人：Becker Katja

  公开号：US20130266645A1

  公开（公告）日：2013-10-10

  The present invention relates to compounds derived from steroids of the general formula (I) wherein L represents a linker and R # represents a steroid residue, the use of compounds of the general formula (I) in medicine and for the prophylaxis and/or the treatment of infectious diseases. Furthermore described are pharmaceutical compositions containing at least one compound of the general formula (I). A further aspect of the invention relates to the synthesis of said compounds of the general formula (I).

  本发明涉及一般式(I)的类固醇衍生物，其中L代表连接剂，R#代表类固醇残基，以及一般式(I)化合物在医学中的使用以及用于传染病的预防和/或治疗。此外，还描述了包含至少一种一般式(I)化合物的药物组合物。本发明的另一个方面涉及一般式(I)化合物的合成。
• Derivatives of steroid benzylamines, having an antiparasitic antibacterial, antimycotic and/or antiviral action
  申请人：Becker Katja

  公开号：US09382288B2

  公开（公告）日：2016-07-05

  The present invention relates to compounds derived from steroids of the general formula (I) wherein L represents a linker and R# represents a steroid residue, the use of compounds of the general formula (I) in medicine and for the prophylaxis and/or the treatment of infectious diseases. Furthermore described are pharmaceutical compositions containing at least one compound of the general formula (I). A further aspect of the invention relates to the synthesis of said compounds of the general formula (I).

  本发明涉及一种源自类固醇的化合物，其一般式为（I），其中L代表连接剂，R#代表类固醇残基，该一般式（I）的化合物在医学上的使用以及用于预防和/或治疗传染病。此外，还描述了至少含有一种一般式（I）化合物的制药组合物。本发明的另一个方面涉及所述一般式（I）化合物的合成。
• DERIVATE VON STEROIDBENZYLAMINEN MIT ANTIPARASITÄRER, ANTIBAKTERIELLER, ANTIMYKOTISCHER UND/ODER ANTIVIRALER WIRKUNG
  申请人：Justus-Liebig-Universität Giessen

  公开号：EP2625190B1

  公开（公告）日：2021-07-14
• US9382288B2
  申请人：——

  公开号：US9382288B2

  公开（公告）日：2016-07-05
• Steroid imines as chiral ligands. Diastereoselective formation of (1-azadiene)Fe(CO)3 complexes by sterically tuning the ligand coordination spheres
  作者：Daniel Berger、Manuela Dubs、Angela Göbel、Wolfgang Imhof、Manuela Kötteritzsch、Matthias Rost、Bruno Schönecker

  DOI：10.1016/s0957-4166(99)00281-5

  日期：1999.7

  The condensation of steroid amines with alpha,beta-unsaturated aldehydes leads to the formation of chiral 1-azadiene ligands with a steroid core attached to nitrogen. If the azadiene chain is situated at the D-ring of the steroid at C-16 or C-17, respectively, the two diastereotopic faces of the ligand may be discriminated by different neighbouring substituents and their configuration. The reaction of these ligands with Fe-2(CO)(9) produces mixtures of diastereomeric (1-azadiene)Fe(CO)(3) complexes. By increasing the steric demands of the neighbouring groups it is possible to improve the diastereoselectivity of this complexation reaction from 1:1 mixtures using the least sterically hindered ligands to complete diastereoselectivity using the azadiene derived from cinnamaldehyde and 16 beta-amino-3-methoxy-estra-1,3,5(10)-triene-17 beta-ol. In addition, the molecular structure of [17 beta-(3-phenyl-prop-2-enyliden)-amino-3-methoxy-estra-1,3,5(10)-triene]Fe(CO)(3) was determined by X-ray structure analysis. (C) 1999 Elsevier Science Ltd. All rights reserved.