3,17β-dihydroxy-11β-[9-(4,4,5,5,5-pentafluoropentane-1-sulfinyl)nonyl]-estra-1,3,5(10)-triene | 151555-65-6

• 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: 3,17β-dihydroxy-11β-[9-(4,4,5,5,5-pentafluoropentane-1-sulfinyl)nonyl]-estra-1,3,5(10)-triene
• 英文别名: (11I(2),17I(2))-11-[9-[(4,4,5,5,5-Pentafluoropentyl)sulfinyl]nonyl]estra-1,3,5(10)-triene-3,17-diol；(8S,9S,11S,13S,14S,17S)-13-methyl-11-[9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl]-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 151555-65-6
• 化学式: C₃₂H₄₇F₅O₃S
• 分子量: 606.781
• InChiKey: GLJFFZDAMFZFTM-FXFJOQCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (8S,9S,11S,13S,14S,17S)-13-methyl-11-[9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl]-17-phenylmethoxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以56%的产率得到3,17β-dihydroxy-11β-[9-(4,4,5,5,5-pentafluoropentane-1-sulfinyl)nonyl]-estra-1,3,5(10)-triene
  参考文献：
  名称：

  Effect of Fluorination on the Pharmacological Profile of 11β Isomers of Fulvestrant in Breast Carcinoma Cells

  摘要：

  We describe the synthesis of an 11 beta isomer 3 of the steroidal antiestrogen fulvestrant 2. Partial fluorination of the 11 beta side chain in 3 leads to 4, which still shows strong antiproliferative activity on MCF-7 cells. However, unlike 2 and 3, compound 4 fails to down-regulate estrogen receptor alpha (ER alpha). This result suggests that ER alpha down-regulation is not a sine qua non condition for the antitumor activity of steroidal antiestrogens.

  DOI：

  10.1021/jm801154q

文献信息

• [EN] NOVEL 19-NOR STEROIDS HAVING A THIOCARBON-CONTAINING CHAIN IN THE 11BETA POSITION, A METHOD FOR PREPARING SAME AND INTERMEDIATES THEREFOR, MEDICINAL USES THEREOF AND COMPOSITIONS CONTAINING SAID STEROIDS
  申请人：ROUSSEL-UCLAF

  公开号：WO1993013123A1

  公开（公告）日：1993-07-08

  (EN) Compounds of formula (I), wherein R17 and R'17 are such that: either R17 and R'17 together form ketone, hydrazono, oxime or methylene, or R17 is hydroxyl, hydroxymethyl or acyloxy and R'17 is hydrogen, alkyl or optionally substitued alkenyl or alkynyl; R3 is hydrogen or alkyl; R16 is hydrogen, halogen or alkyl; m is 0, 1 or 2; X, Y and Z are such that: X is methylene, arylene or arylenoxy bonded to the steroid by a carbon atom; Y is a saturated or unsaturated straight or branched aliphatic chain which is optionally interrupted by oxygen; and Z is aryl, arylalkyl or straight or branched alkyl; addition salts thereof, a preparation method therefor, medicinal uses thereof, compositions containing said compounds, and resulting novel intermediates.(FR) L'invention a pour objet les composés de formule (I) dans laquelle R17 et R'17 sont tels que: soit R17 et R'17 forment ensemble une cétone, hydrazono, oxime, méthylène; soit R17 est hydroxyle, hydroxyméthyle, acyloxy et R'17 représente un hydrogène, un alkyle, alcényle ou alcynyle éventuellement substitués; R3 est hydrogène, alkyle; R16 est hydrogène, halogène, alkyle; m a la valeur 0, 1 ou 2; X, Y et Z sont tels que: X représente un méthylène, un arylène ou arylénoxy lié au stéroïde par un atome de carbone; Y représente une chaîne aliphatique linéaire ou ramifiée, saturée ou insaturée éventuellement interrompue par oxygène, Z représente un alkyle linéaire ou ramifié, ou un aryle ou arylalkyle, et les sels d'addition de ceux-ci, leur préparation, leur application comme médicaments, les compositions les renfermant et les nouveaux intermédiaires obtenus.

  化合物的公式(I)，其中R17和R'17的取值如下：R17和R'17可以组成酮、肼酮、肟或亚甲基；或者R17为羟基、羟甲基或酰氧基，而R'17为氢、烷基或者是可选取代烯基或炔基；R3为氢或烷基；R16为氢、卤素或烷基；m的取值为0、1或2；X、Y和Z的取值如下：X为与类固醇通过碳原子相连的亚甲基、芳基或芳基氧；Y为饱和或不饱和的直链或支链脂肪链，可以被氧中断；Z为芳基、芳基烷基或者是直链或支链烷基；该化合物的加成盐、制备方法、药用途径、含有该化合物的组合物以及由此得到的新型中间体。
• New 19-Nor steroids having a thiocarbonated chain in position 11beta, their preparation process and the intermediates of this process, their use as medicaments and compositions
  申请人：Roussel Uclaf

  公开号：US20020072624A1

  公开（公告）日：2002-06-13

  Novel compounds having a formula selected from the group consisting of 1 wherein the substituents are defined as in the specification which are intermediates for the production of vinyl compounds having a remarkable anti-estrogenic and anti-proliferative activity.

  具有以下式子之一的新化合物，其中取代基如说明书中所定义，它们是生产具有显著抗雌激素和抗增殖活性的乙烯基化合物的中间体：1（此处省略图式）
• NOUVEAUX 19-NOR STEROIDES AYANT EN POSITION 11BETA UNE CHAINE THIOCARBONEE, LEUR PROCEDE DE PREPARATION ET LES INTERMEDIAIRES DE CE PROCEDE, LEUR APPLICATION COMME MEDICAMENTS ET LES COMPOSITIONS
  申请人：HOECHST MARION ROUSSEL

  公开号：EP0623140B1

  公开（公告）日：1998-04-22
• US6281204B1
  申请人：——

  公开号：US6281204B1

  公开（公告）日：2001-08-28
• US6596885B2
  申请人：——

  公开号：US6596885B2

  公开（公告）日：2003-07-22