2-ethyl-3-O-benzyl-17β-(2-methoxyethyl) 17-deoxyestrone | 767351-87-1

• 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: 2-ethyl-3-O-benzyl-17β-(2-methoxyethyl) 17-deoxyestrone
• 英文别名: (8S,9S,13R,14S,17R)-2-ethyl-17-(2-methoxyethyl)-13-methyl-3-phenylmethoxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene
• CAS: 767351-87-1
• 化学式: C₃₀H₄₀O₂
• 分子量: 432.646
• InChiKey: UCNNNTMNJNZNAR-PYOUBREUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethyl-3-O-benzyl-17β-(2-methoxyethyl) 17-deoxyestrone 在 5%-palladium/activated carbon 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 以97%的产率得到2-ethyl-3-hydroxy-17β-(2-methoxyethyl)estra-1,3,5(10)-triene
  参考文献：
  名称：

  [EN] OESTROGEN DERIVATIVES AS INHIBITORS OF STEROID SULPHATASE
  [FR] DERIVES ESTROGENES UTILISES EN TANT QU'INHIBITEURS DE STEROIDE SULFATASE

  摘要：

  本发明提供一种化合物，包括一种甾体环系统和一个可选的基团R1，所述基团R1从以下任一基团中选择：-OH、磺酸酯基团、膦酸酯基团、硫代膦酸酯基团、磺酸基团或磺酰胺基团；其中所述甾体环系统的D环通过一个公式-L-R3的基团R2取代，其中L是一个可选的连接基团，R3选择自一个亚硝酸盐基团、醇基团、酯基团、醚基团、胺基团和烯烃基团中的一个或组成一个，条件是当R3是或包含一个醇基团时，L存在；以及所述甾体环系统的A环在位置2或4处被一个基团R4取代，其中R4是一个烃基团。

  公开号：

  WO2004085459A1
• 作为产物：
  描述：

  (3-benzyloxy-2-ethyl-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)-acetic acid ethyl ester 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.25h， 生成 2-ethyl-3-O-benzyl-17β-(2-methoxyethyl) 17-deoxyestrone
  参考文献：
  名称：

  Structure–Activity Relationships of C-17-Substituted Estratriene-3-O-sulfamates as Anticancer Agents

  摘要：

  The synthesis and antiproliferative activities of analogues of 2-substituted estradiol-3,17-O,O-bis-sulfamates (E2bisMATEs) are discussed. Modifications of the C-17 substituent confirm that an H-bond acceptor is essential for high activity; its optimal linkage to C-17 and the local environment in which it resides are defined. In the non-sulfamoylated series 17 beta-acyl substitution delivers 48b, the most potent compound identified to date. In the sulfamate series a number of permutations of linker and H-bond acceptor deliver excellent activity, with 55, 61, 65, 49a, and 49b proving especially promising. The in vivo potential of these compounds was explored in the NCI hollow fiber assay and also in a mouse Matrigel model of antiangiogenesis in which 49 and 55 show significant inhibitory activity.

  DOI：

  10.1021/jm200483x

文献信息

• [EN] OESTROGEN DERIVATIVES AS INHIBITORS OF STEROID SULPHATASE<br/>[FR] DERIVES ESTROGENES UTILISES EN TANT QU'INHIBITEURS DE STEROIDE SULFATASE
  申请人：STERIX LTD

  公开号：WO2004085459A1

  公开（公告）日：2004-10-07

  The present invention provides a compound comprising a steroidal ring system and an optional group R1 selected from any one of -OH, a sulphamate group, a phosphonate group, a thiophosphonate group, a sulphonate group or a sulphonamide group; wherein the D ring of the steroidal ring system is substituted by a group R2 of the formula -L-R3, wherein L is an optional linker group and R3 is selected from groups which are or which comprise one of a nitrite group, an alcohol, an ester, an ether, an amine and an alkene, provided that when R3 is or comprises an alcohol, L is present; and wherein the A ring of the steroidal ring system is substituted at position 2 or 4 with a group R4, wherein R4 is a hydrocarbyl group.

  本发明提供一种化合物，包括一种甾体环系统和一个可选的基团R1，所述基团R1从以下任一基团中选择：-OH、磺酸酯基团、膦酸酯基团、硫代膦酸酯基团、磺酸基团或磺酰胺基团；其中所述甾体环系统的D环通过一个公式-L-R3的基团R2取代，其中L是一个可选的连接基团，R3选择自一个亚硝酸盐基团、醇基团、酯基团、醚基团、胺基团和烯烃基团中的一个或组成一个，条件是当R3是或包含一个醇基团时，L存在；以及所述甾体环系统的A环在位置2或4处被一个基团R4取代，其中R4是一个烃基团。
• US7893284B2
  申请人：——

  公开号：US7893284B2

  公开（公告）日：2011-02-22
• Structure–Activity Relationships of C-17-Substituted Estratriene-3-<i>O</i>-sulfamates as Anticancer Agents
  作者：Fabrice Jourdan、Mathew P. Leese、Wolfgang Dohle、Eric Ferrandis、Simon P. Newman、Surinder Chander、Atul Purohit、Barry V. L. Potter

  DOI：10.1021/jm200483x

  日期：2011.7.14

  The synthesis and antiproliferative activities of analogues of 2-substituted estradiol-3,17-O,O-bis-sulfamates (E2bisMATEs) are discussed. Modifications of the C-17 substituent confirm that an H-bond acceptor is essential for high activity; its optimal linkage to C-17 and the local environment in which it resides are defined. In the non-sulfamoylated series 17 beta-acyl substitution delivers 48b, the most potent compound identified to date. In the sulfamate series a number of permutations of linker and H-bond acceptor deliver excellent activity, with 55, 61, 65, 49a, and 49b proving especially promising. The in vivo potential of these compounds was explored in the NCI hollow fiber assay and also in a mouse Matrigel model of antiangiogenesis in which 49 and 55 show significant inhibitory activity.