hydroxy-17β 19-norandostrene-1 one-3 | 73991-16-9

• 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: hydroxy-17β 19-norandostrene-1 one-3
• 英文别名: 17β-hydroxy-5α-estr-1-ene-3-one；17β-hydroxy-5α-estr-1-en-3-one；17β-Hydroxy-5αH-1-oestren-3-on；17beta-Hydroxy-5alpha-estr-1-en-3-one；(5S,8R,9S,10R,13S,14S,17S)-17-hydroxy-13-methyl-5,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-4H-cyclopenta[a]phenanthren-3-one
• CAS: 73991-16-9
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: NIWPDWMHVDBOFT-PNOKGRBDSA-N

物化性质

• 熔点：
  146-147 °C
• 沸点：
  421.2±45.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  hydroxy-17β 19-norandostrene-1 one-3 、 氰化钾 在 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,5S,8R,9S,10S,13S,14S,17S)-17-Hydroxy-13-methyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthrene-1-carbonitrile
  参考文献：
  名称：

  丙酮控制的逆向氢化氰化立体电子

  摘要：

  双环和类固醇系列中类似的β-氰基酮对逆向氢氰化反应表现出不同的行为。可以调用立体电子效应来解释这种差异。

  DOI：

  10.1016/s0040-4039(00)93624-4
• 作为产物：
  描述：

  1β,17β-Dihydroxy-5α-oestran-3-on 在 盐酸 作用下， 以 丙酮 为溶剂， 生成 hydroxy-17β 19-norandostrene-1 one-3
  参考文献：
  名称：

  Bolt,C.C. et al., Recueil des Travaux Chimiques des Pays-Bas, 1965, vol. 84, p. 626 - 632

  摘要：

  DOI：

文献信息

• Stereoisomerically pure 17.alpha.-ethynyl-estra-2-en-17.beta.-ol and the
  申请人：SRI International

  公开号：US05116830A1

  公开（公告）日：1992-05-26

  This invention relates to a stereoisomerically pure .DELTA..sup.2 compound of the formula (I): ##STR1## wherein: R.sup.1 is hydrogen or --(C.dbd.O)--R.sup.2, wherein: R.sup.2 is an organic substituent selected from the group consisting of alkyls, alkenyls, alkynyls, cycloalkyls, cycloalkylalkylenes, haloalkyls, aryls, haloaryls and arylalkylenes, and their product by the process of: (a) reacting the 17.beta.-hydroxy group of 17.beta.-hydroxy-5.alpha.-estr-1-en-3-one with dihydropyran to produce the 3-keto-17.beta.-ether; (b) reducing the 3-keto-17.beta.-ether product of step (a) with lithium in ammonia; (c) reacting the product of step (b) with dialkyl chlorophosphate to produce the 3-substituted phosphate; (d) reducing the product of step (c) with lithium and ammonia to produce the .DELTA..sup.2 -protected-17.beta.-ether product; (e) hydrolysis of the produce of step (d) to product the .DELTA..sup.2 -17.beta.-hydroxy compound; (f) oxidizing the 17.beta.-hydroxy product of step (e) to produce the 17-keto compound; (g) reacting the 17-keto derivative of step (f) with acetylene magnesium halide to produce the compound of formula I where R.sup.1 is hydrogen; and (h) optionally reacting the product of step (g) with an acyl halide The invention described herein was made in the course of work under a contract from the U.S. National Institutes of Health No. NOl-HD-2809 of the Department of Health and Human Resources.

  本发明涉及一种立体异构纯度的.DELTA..sup.2化合物，化学式为（I）：##STR1##其中：R.sup.1是氢或--(C.dbd.O)--R.sup.2，其中：R.sup.2是从烷基、烯基、炔基、环烷基、环烷烯基、卤代烷基、芳基、卤代芳基和芳基烯基等基团中选择的有机取代基，以及通过以下过程得到的产物：(a)将17.beTA.-羟基-17.beTA.-羟基-5.alpha.-雌甾-1-烯-3-酮与二氢吡喃反应，产生3-酮-17.beTA.-醚；(b)用氨中的锂还原步骤（a）中的3-酮-17.beTA.-醚产物；(c)将步骤（b）中的产物与二烷基氯磷酸酯反应，产生3-取代磷酸酯；(d)用氨中的锂还原步骤（c）中的产物，产生.DELTA..sup.2-保护的-17.beTA.-醚产物；(e)水解步骤（d）的产物，得到.DELTA..sup.2-17.beTA.-羟基化合物；(f)将步骤（e）中的17.beTA.-羟基产物氧化，得到17-酮化合物；(g)将步骤（f）中的17-酮衍生物与乙炔镁卤化物反应，得到化合物的化学式I，其中R.sup.1是氢；以及（h）可选择性地将步骤（g）的产物与酰卤反应。本发明是在美国国家卫生研究院卫生与人力资源部门的合同N01-HD-2809的合同下进行的工作过程中完成的。
• ESTRATRIENE DERIVATIVES COMPRISING HETEROCYCLIC BIOISOSTERES FOR THE PHENOLIC A-RING
  申请人：Blume Thorsten

  公开号：US20110190246A1

  公开（公告）日：2011-08-04

  The present invention is directed to novel pyrazolo-estrien and triazolo-estrien-derivatives, pharmaceutical compositions containing them and their use in the treatment or prevention of disorders and diseases mediated by an estrogen receptor such as hot flashes, vaginal dryness, osteopenia, osteoporosis, hyperlipidemia, loss of cognitive function, degenerative brain diseases, cardiovascular diseases, cerebrovascular diseases, hormone sensitive cancers and hyperplasia (in tissues including breast, endometrium, and cervix in women and prostate in men), endometriosis, uterine fibroids, osteoarthritis; and as contraceptive agents either alone or in combination with a progestogen or progestogen antagonist. The compounds of the invention are selective estrogen receptor modulators.

  本发明涉及新型吡唑酮-雌甾烯和三唑酮-雌甾烯衍生物，包含它们的制药组合物以及它们在治疗或预防由雌激素受体介导的疾病和疾病中的应用，例如潮热、阴道干燥、骨质疏松、骨质疏松症、高脂血症、认知功能丧失、退行性脑疾病、心血管疾病、脑血管疾病、激素敏感性癌症和增生（包括女性乳房、子宫内膜和宫颈以及男性前列腺组织），子宫内膜异位症、子宫肌瘤、骨关节炎；以及作为避孕剂，单独使用或与孕激素或孕激素拮抗剂组合使用。本发明的化合物是选择性雌激素受体调节剂。
• Estratriene derivatives comprising heterocyclic bioisosteres for the phenolic a-ring
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：EP2147924A1

  公开（公告）日：2010-01-27

  The present invention is directed to novel pyrazolo-estrien and triazolo-estrien-derivatives, pharmaceutical compositions containing them and their use in the treatment or prevention of disorders and diseases mediated by an estrogen receptor such as hot flashes, vaginal dryness, osteopenia, osteoporosis, hyperlipidemia, loss of cognitive function, degenerative brain diseases, cardiovascular diseases, cerebrovascular diseases, hormone sensitive cancers and hyperplasia (in tissues including breast, endometrium, and cervix in women and prostate in men), endometriosis, uterine fibroids, osteoarthritis; and as contraceptive agents either alone or in combination with a progestogen or progestogen antagonist. The compounds of the invention are selective estrogen receptor modulators.

  本发明涉及新型吡唑-雌三烯和三唑-雌三烯衍生物、含有它们的药物组合物，以及它们在治疗或预防由雌激素受体介导的紊乱和疾病中的用途，如潮热、阴道干燥、骨质疏松、骨质疏松症、高脂血症、认知功能丧失、脑退化性疾病、心血管疾病、脑血管疾病、激素敏感性癌症和增生（组织中包括乳腺、子宫内膜和子宫颈）、高脂血症、认知功能丧失、退化性脑部疾病、心血管疾病、脑血管疾病、对激素敏感的癌症和增生（女性组织包括乳腺、子宫内膜和宫颈，男性组织包括前列腺）、子宫内膜异位症、子宫肌瘤、骨关节炎；以及作为避孕药物单独使用或与孕激素或孕激素拮抗剂联合使用。本发明的化合物是选择性雌激素受体调节剂。
• Bioavailable prodrugs of androgenic steroids and related method
  申请人：——

  公开号：US20030134830A1

  公开（公告）日：2003-07-17

  A compound is provided for increasing the concentration of a parent androgen in a subject in vivo. The parent androgen has a skeletal structure including a 1 position and a 17 position, a 17&bgr;-hydroxy group comprising a 17&bgr;-hydroxy oxygen appended to the 17 position, and a 17&bgr;-hydroxy hydrogen appended to the 17&bgr;-hydroxy oxygen. The compound includes a substrate having the skeletal structure of the parent androgen. It includes a 1 position and a 17 position corresponding to the 1 and 17 positions respectively of the parent androgen. The substrate has a carbon-carbon double bond at the 1 position. The compound also has a promoiety appended to the 17&bgr;-hydroxy oxygen of the substrate as a substitute for the 17&bgr;-hydroxy hydrogen of the parent androgen. The promoiety includes, and preferably consists of, an alkylcarbonate ester. A related method also is provided.

  本发明提供了一种化合物，用于提高体内受试者体内母体雄激素的浓度。母体雄激素的骨架结构包括1位和17位，17&bgr;-羟基包括与17位相连的17&bgr;-羟基氧和与17&bgr;-羟基氧相连的17&bgr;-羟基氢。该化合物包括具有母体雄激素骨架结构的底物。它包括一个 1 位和一个 17 位，分别对应于母体雄激素的 1 位和 17 位。底物在 1 位上有一个碳碳双键。该化合物还有一个原基附加在底物的 17&bgr;-羟基氧上，以替代母体雄激素的 17&bgr;-羟基氢。原基包括，最好是烷基碳酸酯。还提供了一种相关的方法。
• Composition and method for increasing in vivo androgen concentration
  申请人：——

  公开号：US20030134828A1

  公开（公告）日：2003-07-17

  A composition is provided including a first prohormone for increasing the concentration of a Class I parent androgen in a subject in vivo, and a second prohormone for increasing the concentration of a Class II parent androgen in the subject in vivo. The first prohormone includes a first carbon-carbon double bond at the 1 position, and a first 17&bgr;-hydroxy oxygen appended to the 17 position. The first prohormone further includes a first 17-position promoiety is appended to the first 17&bgr;-hydroxy oxygen as a substitute for the 17&bgr;-hydroxy hydrogen of the Class I parent androgen. The second prohormone includes a second carbon-carbon double bond at the 4 position and a second 17&bgr;-hydroxy oxygen appended to the 17 position. The second prohormone also includes a second 17-position promoiety appended to the second 17&bgr;-hydroxy oxygen as a substitute for the 17&bgr;-hydroxy hydrogen of the Class II parent androgen.

  提供了一种组合物，其中包括用于增加体内受试者体内第一类母体雄激素浓度的第一种原激素，以及用于增加体内受试者体内第二类母体雄激素浓度的第二种原激素。第一种原激素包括位于 1 位的第一碳碳双键，以及附加到 17 位的第一 17&bgr;-羟基氧。第一种原激素还包括与第一17&bgr;-羟基氧相连的第一17位原基，作为第一类母雄激素的17&bgr;-羟基氢的替代物。第二种原激素包括位于 4 位的第二个碳碳双键和附加到 17 位的第二个 17&bgr;-羟基氧。第二种原激素还包括与第二17&bgr;-羟基氧相连的第二17位原基，作为第二类母雄激素的17&bgr;-羟基氢的替代物。