3,3-[2,2-dimethyl-1,3-propanediylbis(oxy)]-5α,10α-epoxy-estr-9(11)-en-17β-ol | 104068-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 3,3-[2,2-dimethyl-1,3-propanediylbis(oxy)]-5α,10α-epoxy-estr-9(11)-en-17β-ol
• 英文别名: 3,3-(2,2-dimethyl-trimethylenedioxy)-5,10α-epoxy-5α-estr-9(11)-en-17β-ol；3,3-(2,2-dimethyl-trimethylenedioxy)-5α,10α-epoxy-9(11)-estren-17β-ol；5α,10α-epoxy-3,3-(2,2-dimethyltrimethylenedioxy)-9(11)-estren-17β-ol；5α-10α-epoxy-3,3-(2,2-dimethyltrimethylenedioxy)-9(11)-estren-17β-ol；5alpha,10alpha-epoxy-3,3-(2,2-dimethyltrimethylenedioxy)-9(11)-estren-17beta-ol；(1'R,5'S,6'S,9'S,10'S,13'R)-5,5,5'-trimethylspiro[1,3-dioxane-2,15'-18-oxapentacyclo[11.4.1.01,13.02,10.05,9]octadec-2-ene]-6'-ol
• CAS: 104068-77-1
• 化学式: C₂₃H₃₄O₄
• 分子量: 374.521
• InChiKey: VUAXZABSVFJVOM-SSKYMUOVSA-N

物化性质

• 沸点：
  515.5±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3-[2,2-dimethyl-1,3-propanediylbis(oxy)]-5α,10α-epoxy-estr-9(11)-en-17β-ol 在 zirconium(IV) tert-butoxide 、 三氯乙醛 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以71%的产率得到3,3-(2,2-dimethyltrimethylene-1,3-dioxy)-5α-hydroxyestra-1(10),9-dien-17-one
  参考文献：
  名称：

  Zirconium Alkoxide Catalyzed Oppenauer Oxidation Using Chloral as the Hydride Acceptor

  摘要：

  Oppenauer氧化法的新变体以氯醛作为氢化物受体，以Zr(O-t-BU)4或SiO2/Zr(O-n-Pr)x（用于高活性羰基产品）作为催化剂。反应在温和条件下（20°C）进行，Zr(O-t-Bu)4的用量低于化学计量（通常为20%）。初级和次级烯丙醇被高转化率地转化为相应的羰基化合物。

  DOI：

  10.1055/s-1996-4381

文献信息

• 11&bgr; LONG-CHAIN SUBSTITUTED ESTRATRIENES, METHOD FOR THEIR PRODUCTION, PHARMACEUTICAL PREPARATIONS CONTAINING SAID 11&bgr; LONG-CHAIN SUBSTITUTED ESTATRIENES, AND THEIR USE FOR PRODUCING MEDICAMENTS
  申请人：Schering Aktiengesellschaft

  公开号：US06790842B1

  公开（公告）日：2004-09-14

  This invention describes a 11&bgr;-long-chain-substituted estratriene of general formula (I), in which R11 is a long-chain radical that has a nitrogen atom and optionally a sulfur atom, which in addition can be functionalized in the terminal position with a perfluoroalkyl group or an optionally substituted arly radical. The compound can have antiestrogenic or tissue-selective estrogenic properties and be suitable for the production of pharmaceutical agents.

  该发明描述了一种通式（I）中的11β-长链取代雌三烯，其中R11是一个具有氮原子和可选的硫原子的长链基团，此外，该基团的末端位置可以被全氟烷基团或可选取代的芳基基团官能化。该化合物可以具有抗雌激素或组织选择性雌激素特性，并适用于制备药用剂。
• Steroidal Affinity Labels of the Estrogen Receptor. 3. Estradiol 11β-<i>n-</i>Alkyl Derivatives Bearing a Terminal Electrophilic Group:  Antiestrogenic and Cytotoxic Properties
  作者：Carole Lobaccaro、Jean-François Pons、Marie-Josèphe Duchesne、Gilles Auzou、Michel Pons、François Nique、Georges Teutsch、Jean-Louis Borgna

  DOI：10.1021/jm970019l

  日期：1997.7.1

  4-hydroxytamoxifen. In conclusion, the synthesized electrophilic estradiol 11 beta-ethyl and 11 beta-butyl derivatives (i) were not efficient affinity labels of the estrogen receptor and (ii) did not display significant cytotoxicity in estrogen-sensitive mammary tumor cells. However, since these derivatives displayed high affinity for the estrogen receptor, they could be used to prepare potential cytotoxic agents

  为了开发雌激素受体的甾体亲和力标记物的新系列，带有11β的雌二醇的六种亲电子的11β-乙基（C2），11β-丁基（C4）或11β-癸基（C10）衍生物-末端的亲电官能团，即溴（C4），（甲基磺酰基）氧基（C2和C4），溴乙酰胺基（C2和C4）和（对甲苯磺酰基）氧基（C10）被合成。它们与雌激素受体结合的亲和常数范围为雌二醇的亲和常数的0.4-37％。（i）相对于11个β-烷基臂的亲和力增加的顺序是乙基<丁基，而（ii）相对于亲电官能团的顺序是溴乙酰胺基<溴<（甲基磺酰基）氧基。无论使用哪种条件，包括将受体长时间暴露于各种pH值（7-9）和温度（0-25摄氏度）下，11β-乙基和11β-丁基化合物（如果有）标记的受体亲和力的程度低于10％。这与使用11个β-（（甲苯磺酰氧基）癸基）雌二醇获得的结果形成鲜明对比，后者以60％至90％的受体激素结合位点标记EC50约为10 nM。使用MVLN细胞
• PROGESTERONE RECEPTOR ANTAGONISTS
  申请人：Schwede Wolfgang

  公开号：US20130072464A1

  公开（公告）日：2013-03-21

  The invention relates to 17-hydroxy-17-pentafluoroethyl-estra-4,9(10)-dien-11-aryl derivatives of formula I with progesterone-antagonizing action and methods of production thereof, use thereof for the treatment and/or prevention of diseases and use thereof for producing medicinal products for the treatment and/or prevention of diseases, in particular uterine fibroids (myomata, uterine leiomyomata), endometriosis, heavy menstrual bleeding, meningiomata, hormone-dependent breast cancers and menopause-associated complaints or for fertility control and emergency contraception.

  该发明涉及公式I的17-羟基-17-五氟乙基-雌甾-4,9(10)-二烯-11-芳基衍生物，具有孕酮拮抗作用及其生产方法，用于治疗和/或预防疾病以及用于生产用于治疗和/或预防疾病的药品，特别是子宫肌瘤（肌瘤、子宫平滑肌瘤）、子宫内膜异位症、月经过多、脑膜瘤、激素依赖性乳腺癌和更年期相关的不适或用于生育控制和紧急避孕。
• 19,11 .beta.-bridged steroids, their manufacture and pharmaceutical
  申请人：Schering Aktiengesellschaft

  公开号：US05095129A1

  公开（公告）日：1992-03-10

  New 19,11.beta.-bridged steroids of the general formula I ##STR1## where R.sup.1 stands for a methyl or ethyl radical, R.sup.2 for a hydrogen or chlorine atom or a C.sub.1 -C.sub.4 -alkyl radical, B and G, which are the same or different, respectively for a hydrogen atom, a C.sub.1 -C.sub.4 -alkyl radical or, together, for a second bond between the carbon atoms 6 and 7, B and R.sup.2 together for a methylene or an ethylene group, Z for the radical of a pentagonal or hexagonal ring, which is possibly substituted and possibly unsaturated, V stands for a possibly substituted carbocyclic or heterocyclic aryl radical, the ring A for ##STR2## M and N together meaning a second bond or M a hydrogen atom and N a hydroxy group, X means an oxygen atom, two hydrogen atoms or a hydroxyimino grouping N.about.OH, R.sup.3 and D, which are the same or different, respectively a hydrogen atom, a nitrile radical or a C.sub.1 -C.sub.4 -alkyl radical or, together, a methylene or ethylene group, E a hydrogen atom or a C.sub.1 -C.sub.4 -alkyl radical, D and E together meaning a second bond between carbon atoms 1 and 2 or together a methylene group ##STR3## with R.sup.11 in the meaning of a hydrogen atom or a C.sub.1 -C.sub.8 -alkyl radical, are described as well as their pharmaceutically tolerated addition salts with acids. The new compounds possess valuable pharmacological properties.

  新的19,11-β-桥联类固醇的一般公式为I，其中R.sup.1代表甲基或乙基基团，R.sup.2代表氢原子或氯原子或C.sub.1-C.sub.4-烷基基团，B和G分别代表氢原子、C.sub.1-C.sub.4-烷基基团，或者一起代表碳原子6和7之间的第二键，B和R.sup.2一起代表亚甲基或乙烯基团，Z代表可能被取代和可能不饱和的五角形或六角形环的基团，V代表可能被取代的碳环或杂环芳基团，环A代表M和N一起意味着第二键，或者M是氢原子，N是羟基，X代表氧原子、两个氢原子或羟氧亚胺基团N.about.OH，R.sup.3和D分别代表氢原子、腈基团或C.sub.1-C.sub.4-烷基基团，或者一起代表亚甲基或乙烯基团，E代表氢原子或C.sub.1-C.sub.4-烷基基团，D和E一起代表碳原子1和2之间的第二键或一起代表亚甲基基团，其中R.sup.11的含义是氢原子或C.sub.1-C.sub.8-烷基基团，以及它们与酸形成的药物耐受性加合盐。这些新化合物具有有价值的药理学性质。
• 11.beta.-phenyl-14.beta.H steroids
  申请人：Schering Aktiengesellschaft

  公开号：US05244886A1

  公开（公告）日：1993-09-14

  New 11.beta.-phenyl-14.beta.H-steroids of general formula (I), where Z is an oxygen atom or the hydroxyimino-grouping N.about.OH, and M and N are either jointly a second compound or L is a hydrogen atom and M is an .alpha.-permanent hydroxy group and either A and B together are a second compound and D is a hydrogen atom, where R.sup.1 is a five or six-part heteroalkyl residue or a cycloalkyl, cycloalkenyl or aryl residue or A is a hydrogen atom and B and D together are a methylene bridge, where R.sup.1 besides the aforementioned residues may be a possibly substituted hydrocarbon residue with up to 10 C atoms, a possibly substituted amino group, a hydroxy or C.sub.1-8 alkoxy, mercapto or thioalkyl group, R.sup.2 is a methyl or ethyl residue, and R.sup.3 /R.sup.4 represents the usual combination of substituents on the C17 atom in steroid chemistry, having antigestagenic and other properties.

  新的11-β-苯基-14-β-H类固醇的一般化学式（I），其中Z是氧原子或羟亚胺基团N.OH，M和N要么共同是第二化合物，要么L是氢原子，M是α-永久羟基，A和B一起是第二化合物，D是氢原子，其中R^1是五个或六个部分的杂烷基残基或环烷基、环烯烃基或芳基残基，或A是氢原子，B和D一起是亚甲基桥，R^1除了上述残基外，还可能是具有最多10个碳原子的可能被取代的烃基残基，可能被取代的氨基团，羟基或C1-8烷氧基，巯基或硫代烷基团，R^2是甲基或乙基残基，R^3/R^4代表类固醇化学中C17原子上的取代基的常见组合，具有抗孕激素和其他性质。