3,7β-dihydroxy-estra-1,3,5(10)-trien-17-one | 2487-47-0

• 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: 3,7β-dihydroxy-estra-1,3,5(10)-trien-17-one
• 英文别名: 3,7β-Dihydroxy-oestra-1,3,5(10)-trien-17-on；3.7β-Dihydroxy-oestratrien-(A)-on-(17)；3,7β-dihydroxy-1,3,5(10)-estratrien-17-one；7β-hydroxyestrone；3,7beta-Dihydroxy-estra-1,3,5(10)-trien-17-one；(7S,8R,9S,13S,14S)-3,7-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 2487-47-0
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: MXXBVPDRVYYYJY-WBOSRHFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,7β-dihydroxy-estra-1,3,5(10)-trien-17-one 、 溴甲苯 在 lithium hydroxide 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 0.5h， 以87%的产率得到3-benzyloxy-7-β-hydroxy-estra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  18 Norsteroids as selectively active estrogens

  摘要：

  本发明涉及新型18-去甾体（戈纳三烯）的一般式（I），其中R1、R2、R3、R6、R7、R8、R9、R11、R11'、R14、R15、R15'、R16、R17和R17'在说明书中所述，以及将所述化合物用作药物活性成分。这些化合物在大鼠前列腺的雌激素受体制备中体外表现出高亲和力，在大鼠子宫的雌激素受体制备中也表现出高亲和力。这些化合物在体内与子宫相比对骨骼具有优先活性和/或在刺激5HT2a受体和转运分子的表达方面具有显着活性。本发明还涉及所述化合物的生产、治疗用途和所述化合物的制剂形式。本发明还涉及基于戈纳三烯分子骨架的类固醇的应用，以治疗雌激素缺乏引起的疾病和疾病，并且还涉及将所述戈纳三烯结构组分用于分离以产生与子宫相比增强雌激素活性的化合物的总结构中的应用。

  公开号：

  US06958327B1
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 3,7β-dihydroxy-estra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  Pearlman; Wintersteiner, Journal of Biological Chemistry, 1939, vol. 130, p. 35,42

  摘要：

  DOI：

文献信息

• 7-Hydroxyestradiols
  申请人：Schering Aktiengesellschaft

  公开号：US04011314A1

  公开（公告）日：1977-03-08

  7-Hydroxyestradiols of the formula ##STR1## wherein R.sub.1 is hydrogen, acyl, alkyl, cycloalkyl, an oxygenated saturated heterocyclic group or hydrocarbylsulfonyl; R.sub.2 and R.sub.3 each are hydrogen, acyl, oxygenated saturated heterocyclic group or R.sub.2 is hydrocarbylsulfonyl and R.sub.4 is alkyl, alkenyl, chlorinated alkenyl, alkynyl or chlorinated alkynyl, are useful for treating estrogen deficiency symptoms.

  公式为##STR1##的7-羟基雌二醇，其中R.sub.1是氢、酰基、烷基、环烷基、含氧饱和杂环基团或烃基磺酰基；R.sub.2和R.sub.3分别是氢、酰基、含氧饱和杂环基团或R.sub.2是烃基磺酰基，R.sub.4是烷基、烯基、氯代烯基、炔基或氯代炔基，可用于治疗雌激素缺乏症状。
• New 2-substituted estra-1,3,5(10)-trien-17-ones as inhibitors of 17beta-hydroxy steroid dehydrogenase type 1
  申请人：Hillisch Alexander

  公开号：US20060009434A1

  公开（公告）日：2006-01-12

  The invention relates to new 2-substituted estra-1,3,5(10)-trien-17-ones of general formula I in which R 2 means a saturated or unsaturated C 1 -C 8 -alkyl group, a C 1 -C 5 -alkyloxy group, an aralkyl radical or alkylaryl radical, a radical —O—C n F m H o , whereby n=1, 2, 3, 4, 5 or 6, m≧1 and m+o=2n+1, or a group CH 2 XY, in which X stands for an oxygen atom and Y stands for an alkyl radical with 1 to 4 carbon atoms, as well as a halogen atom or a nitrile group, R 13 means a hydrogen atom or a methyl group, R 16 means a hydrogen atom or a fluorine atom, Z means an oxygen atom or a sulfur atom, R 3 and R 5 , in each case independently of one another, mean an α- or β-position hydrogen atom, R 4 and R 6 , in each case independently of one another, mean an α- or β-position hydrogen atom, a C 1 -C 5 -alkyl group, a C 1 -C 5 -alkyloxy group, a C 1 -C 5 -acyl group or a hydroxy group or an aralkyl radical or alkylaryl radical, R 3 and R 4 together mean an oxygen atom, R 5 and R 6 together mean an oxygen atom, R 7 and R 8 in each case mean a hydrogen atom or together a CH 2 group, as well as their pharmaceutically acceptable salts, their manufacture and use as medicaments for prophylaxis and therapy of estrogen-dependent diseases that can be influenced by the inhibition of 17β-hydroxy steroid dehydrogenase type 1.

  本发明涉及一般式I的新2-取代的酮类化合物，其中R2代表饱和或不饱和的C1-C8烷基基团，C1-C5烷氧基团，芳基烷基基团或烷基芳基基团，基团—O—CnFmHo，其中n=1、2、3、4、5或6，m≥1且m+o=2n+1，或基团CH2XY，其中X代表氧原子，Y代表具有1至4个碳原子的烷基基团，以及卤原子或腈基团，R13代表氢原子或甲基基团，R16代表氢原子或氟原子，Z代表氧原子或硫原子，R3和R5分别独立地表示α或β位的氢原子，R4和R6分别独立地表示α或β位的氢原子，C1-C5烷基基团，C1-C5烷氧基团，C1-C5酰基团，羟基或芳基烷基基团或烷基芳基基团，R3和R4一起表示氧原子，R5和R6一起表示氧原子，R7和R8分别表示氢原子或一起表示一个CH2基团，以及它们的药学上可接受的盐，它们的制备和用作预防和治疗由于17β-羟基类固醇脱氢酶类型1的抑制而可影响的雌激素依赖性疾病的药物。
• 18-nor steroids as selectively active estrogens
  申请人：Hillisch Alexander

  公开号：US20050282791A1

  公开（公告）日：2005-12-22

  This invention describes the new 18-nor steroids (gonatrienes) of general formula (I), in which R 1 , R 2 , R 3 , R 6 , R 7 , R 8 , R 9 , R 11 , R 11 ′, R 14 , R 15 , R 15 , R 16 , R 17 and R 17 ′ have the meanings that are indicated in the description, as pharmaceutical active ingredients that have in vitro a higher affinity to estrogen receptor preparations of rat prostates than to estrogen receptor preparations of rat uteri and in vivo a preferential action on bone in comparison to the uterus, and/or pronounced action relative to the stimulation of the expression of 5HT2a-receptors and transporters, their production, their therapeutic use and pharmaceutical dispensing forms that contain the new compounds. The invention further describes the use of steroids, on which the gonatriene skeleton is based, for treatment of estrogen-deficiency-induced diseases and conditions as well as the use of the gonatriene structural part in the total structures of compounds that have a dissociation in favor of their estrogenic action on bone in comparison to the uterus.

  本发明描述了一种新的18-去甾体（gonatrienes），其通式为（I），其中R1、R2、R3、R6、R7、R8、R9、R11、R11'、R14、R15、R15'、R16、R17和R17'具有说明书中指示的含义，作为具有体外比大鼠子宫雌激素受体制备更高亲和力和体内对骨骼具有优先作用而非子宫的药物活性成分，以及明显作用于5HT2a受体和转运体表达的刺激，它们的生产、治疗用途和含有新化合物的制药分配形式。本发明进一步描述了基于gonatriene骨架的类固醇的用途，用于治疗雌激素缺乏引起的疾病和病况，以及将gonatriene结构部分用于总结构中具有有利于它们在骨骼中的雌激素作用而非子宫的化合物的解离。
• Steroids. XCIX. Synthesis of Ring B Oxygenated Estrogens¹
  作者：J. Iriarte、H. J. Ringold、Carl Djerassi

  DOI：10.1021/ja01555a052

  日期：1958.11
• [DE] NEUE 2-SUBSTITUIERTE ESTRA-1,3,5(10)-TRIEN-17-ONE ALS INHIBITOREN DER 17ß-HYDROXYSTEROIDDEHYDROGENASE TYP 1<br/>[EN] NOVEL 2-SUBSTITUTED ESTRA-1,3,5(10)-TRIEN-17-ONES USED IN THE FORM OF INHIBITORS OF 17ß-HYDROXYSTEROIDDEHYDROGENASE OF TYPE 1<br/>[FR] NOUVELLES OESTRA-1,3,5(10)-TRIENE-17-ONES 2-SUBSTITUEES, UTILISEES COMME INHIBITEURS DE LA 17ß-HYDROXYSTEROIDE-DEHYDROGENASE DE TYPE 1
  申请人：SCHERING AG

  公开号：WO2006003013A3

  公开（公告）日：2006-06-22