(8R,9S,13S,14S,17S)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diyl bis(2,2-dimethylpropanoate) | 28275-50-5

• 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: (8R,9S,13S,14S,17S)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diyl bis(2,2-dimethylpropanoate)
• 英文别名: 3.17β-dipivaloyloxy-estratriene-(1.3.5(10))；Oestratrien-(1.3.5(10))-diyl-(3.17β)-dipivalat；3.17β-Dipivaloyloxy-oestratrien-(A)；3.17β-Dipivaloyloxy-oestratrien-(1.3.5(10))；(8R)-3.17c-Dipivaloyloxy-13c-methyl-(8rH.9tH.14tH)-7.8.9.11.12.13.14.15.16.17-decahydro-6H-cyclopenta[a]phenanthren；estradiol 3,17-dipivaloate；[(8R,9S,13S,14S,17S)-3-(2,2-dimethylpropanoyloxy)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] 2,2-dimethylpropanoate
• CAS: 28275-50-5
• 化学式: C₂₈H₄₀O₄
• 分子量: 440.623
• InChiKey: JZKRVXZGYCKHMB-YMEVAXIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (8R,9S,13S,14S,17S)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diyl bis(2,2-dimethylpropanoate) 、 对甲苯磺酰胺 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以34%的产率得到(8R,9S,13S,14S,17S)-13-methyl-6-((4-methylphenyl)sulfonamido)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diyl bis(2,2-dimethylpropanoate)
  参考文献：
  名称：

  Halogen-Bond-Induced Consecutive C_sp³–H Aminations via Hydrogen Atom Transfer Relay Strategy

  摘要：

  The utilization of a halogen bond in a number of chemical fields is well-known. Surprisingly, the incorporation of this useful noncovalent interaction in chemical reaction engineering is rare. We disclose here an uncommon use of halogen bonding to induce intermolecular C-sp(3)-H amination while enabling a hydrogen atom transfer relay strategy to access privileged pyrrolidine structures directly from alkanes. Mechanistic studies support the presence of multiple halogen bond interactions at distinct reaction stages.

  DOI：

  10.1021/acs.orglett.0c00081
• 作为产物：
  描述：

  雌二醇 、 三甲基乙酰氯 以 吡啶 、 二氯甲烷 为溶剂， 以61%的产率得到(8R,9S,13S,14S,17S)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diyl bis(2,2-dimethylpropanoate)
  参考文献：
  名称：

  HYDROXYLATION ACTIVATED DRUG RELEASE

  摘要：

  本发明涉及一种前药，其芳香族氧化，特别是它们的酶促芳香族羟化，导致通过释放药物基团来激活它们。它特别涉及抗肿瘤前药，以及那些特别被P-450酶CYP1B1的羟化活性激活的前药。

  公开号：

  US20020037296A1

文献信息

• Sterols. LXVIII. Highly Branched Aliphatic Esters of Estrone and α-Estrodiol
  作者：Russell E. Marker、Ewald. Rohrmann

  DOI：10.1021/ja01876a504

  日期：1939.7
• US6794384B1
  申请人：——

  公开号：US6794384B1

  公开（公告）日：2004-09-21
• [EN] HYDROXYLATION ACTIVATED DRUG RELEASE<br/>[FR] LIBERATION DE MEDICAMENTS ACTIVEE PAR HYDROXYLATION
  申请人：——

  公开号：WO1999040944A2

  公开（公告）日：1999-08-19

  [EN] The present invention concerns prodrugs whose aromatic oxidation, particularly their enzymatic aromatic hydroxylation, results in their activation by the release of a drug moiety. It particularly concerns anti-tumour prodrugs and those which are specifically activated by the hydroxylation activity of the P-450 enzyme CYP1B1. Also provided are methods of detection of aromatic oxidation activity.
  [FR] L'invention concerne des promédicaments dont l'oxydation aromatique, en particulier, l'hydroxylation aromatique, enzymatique, produit leur activation par libération d'une fraction de médicament. L'invention concerne, en particulier, des promédicaments antitumoraux ainsi que ceux activés, de manière spécifique, par l'activité d'hydroxylation de l'enzyme CYP1B1 de P-450. L'invention concerne également des techniques de détection d'activité d'oxydation aromatique.
• Halogen-Bond-Induced Consecutive C_sp³–H Aminations via Hydrogen Atom Transfer Relay Strategy
  作者：Fan Wu、Jeewani P. Ariyarathna、Navdeep Kaur、Nur-E Alom、Maureen L. Kennell、Omar H. Bassiouni、Wei Li

  DOI：10.1021/acs.orglett.0c00081

  日期：2020.3.20

  The utilization of a halogen bond in a number of chemical fields is well-known. Surprisingly, the incorporation of this useful noncovalent interaction in chemical reaction engineering is rare. We disclose here an uncommon use of halogen bonding to induce intermolecular C-sp(3)-H amination while enabling a hydrogen atom transfer relay strategy to access privileged pyrrolidine structures directly from alkanes. Mechanistic studies support the presence of multiple halogen bond interactions at distinct reaction stages.
• HYDROXYLATION ACTIVATED DRUG RELEASE
  申请人：——

  公开号：US20020037296A1

  公开（公告）日：2002-03-28

  The present invention concerns prodrugs whose aromatic oxidation, particularly their enzymatic aromatic hydroxylation, results in their activation by the release of a drug moiety. It particularly concerns anti-tumour prodrugs and those which are specifically activated by the hydroxylation activity of the P-450 enzyme CYP1B1.

  本发明涉及一种前药，其芳香族氧化，特别是它们的酶促芳香族羟化，导致通过释放药物基团来激活它们。它特别涉及抗肿瘤前药，以及那些特别被P-450酶CYP1B1的羟化活性激活的前药。