5-androstene-3β-17β-diol-19-one 3,17-diacetate | 2951-52-2

• 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: 5-androstene-3β-17β-diol-19-one 3,17-diacetate
• 英文别名: 19-oxo-5-androstene-3β,17β-diol diacetate；19-oxoandrost-5-ene-3β,17β-diyl diacetate；19-oxo-3β,17β-androst-5-ene diol diacetate；3β,17β-Diacetoxy-androsten-(5)-aldehyd-(19)；19-Oxo-androst-5-en-3β,17β-diol-diacetat；19-Oxo-androst-5-en-3β,17-diol-3,17-diacetat；19-Oxo-3beta, 17beta-androst-5ene diol diacetate；[(3S,8S,9S,10S,13S,14S,17S)-17-acetyloxy-10-formyl-13-methyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 2951-52-2
• 化学式: C₂₃H₃₂O₅
• 分子量: 388.504
• InChiKey: VZZVDHGDRPQCMC-HXWZHSPTSA-N

物化性质

• 熔点：
  150-152 °C
• 沸点：
  480.0±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-androstene-3β-17β-diol-19-one 3,17-diacetate 在 palladium on activated charcoal chromium(VI) oxide 、 硫酸 、 氢气 作用下， 生成 19(R)-Acetoxy-19-methyl-5α-androstandion-(3,17)
  参考文献：
  名称：

  甾体新戊基系统的转化。第四部分 的甲基锂的反应的产物的立体化学与Δ 5 -19-醛

  摘要：

  研究了甲基锂与3β，17β-二乙酰氧基和5-5-en-19-al的反应以及衍生产物的某些转化。该反应仅形成19 R-醇，并通过转化为17β-乙酰氧基-3α-甲氧基-19-甲基-5α-雄烷氧基3,19-氧化物（9d）证明了其立体化学。在环氧乙烷形成过程中观察到涉及1，5-氢化物离子转移的还原-氧化反应。

  DOI：

  10.1039/j39680001740
• 作为产物：
  描述：

  5α-Chlor-6β,19-epoxyandrostan-3β,17β,19-triol-3,17-diacetat 在 溶剂黄146 、 锌 作用下， 生成 5-androstene-3β-17β-diol-19-one 3,17-diacetate
  参考文献：
  名称：

  C-19功能性类固醇。十一。C-19醛的一些反应。

  摘要：

  DOI：

  10.1021/jo01279a036

文献信息

• [EN] ESTROGEN RECEPTOR MODULATORS<br/>[FR] MODULATEURS DES RÉCEPTEURS DES ESTROGÈNES
  申请人：MERCK & CO INC

  公开号：WO2006012333A1

  公开（公告）日：2006-02-02

  The present invention relates to compounds and derivatives thereof, their synthesis, and their use as estrogen receptor modulators. The compounds of the instant invention are ligands for estrogen receptors and as such may be useful for treatment or prevention of a variety of conditions related to estrogen functioning including: bone loss, bone fractures, osteoporosis, metastatic bone disease, Paget’s disease, periodontal disease, cartilage degeneration, endometriosis, uterine fibroid disease, hot flashes, increased levels of LDL cholesterol, cardiovascular disease, impairment of cognitive functioning, cerebral degenerative disorders, restenosis, gynecomastia, vascular smooth muscle cell proliferation, obesity, incontinence, inflammation, inflammatory bowel disease, sexual dysfunction, hypertension, retinal degeneration and cancer, in particular of the breast, uterus and prostate.

  本发明涉及化合物及其衍生物，它们的合成以及它们作为雌激素受体调节剂的用途。本发明的化合物是雌激素受体的配体，因此可能对治疗或预防与雌激素功能相关的各种疾病具有用处，包括：骨质流失、骨折、骨质疏松症、转移性骨病、帕盖特病、牙周病、软骨退化、子宫内膜异位症、子宫肌瘤病、潮热、低密度脂蛋白胆固醇水平升高、心血管疾病、认知功能障碍、脑退行性疾病、再狭窄、男性乳腺发育、血管平滑肌细胞增殖、肥胖、失禁、炎症、炎症性肠病、性功能障碍、高血压、视网膜退行性疾病和癌症，特别是乳腺、子宫和前列腺癌。
• Synthesis and evaluation of 10β-substituted 4-estrene-3,17-diones as inhibitors of human placental microsomal aromatase
  作者：Patrick A. Marcotte、Cecil H. Robinson

  DOI：10.1016/0039-128x(82)90151-9

  日期：1982.3

  Abstract This paper describes the synthesis of a series of new 10β-substituted 4-estrene-3,17-dione analogs ( 1–8 ). These compounds, together with a number of known analogs ( 9–14 ), have been evaluated as reversible or irreversible inhibitors of human placental microsomal aromatase. The best reversible inhibitor is the 10β-vinyl compound ( 9 ). The only compounds causing irreversible inhibition of

  摘要 本文描述了一系列新的 10β-取代的 4-estrene-3,17-dione 类似物的合成 (1-8)。这些化合物与许多已知的类似物 (9-14) 一起被评估为人类胎盘微粒体芳香酶的可逆或不可逆抑制剂。最好的可逆抑制剂是 10β-乙烯基化合物 (9)。引起芳香酶不可逆抑制的唯一化合物是 10β-炔丙基化合物 (1) 和 10β-二氟甲基化合物 (12)。
• Steroid Series. XVI. The Preparation of 3α, 5α-Cyclo-6β, 19-oxidosteroids and its Conversion to 19-Oxygenated Steroid Derivatives
  作者：Katsumi Tanabe、Rinji Takasaki、Kiyoshi Sakai、Ryozo Hayashi、Yasuhiro Morisawa、Teruo Hashimoto

  DOI：10.1248/cpb.15.15

  日期：——

  3α, 5α-Cyclo-6β, 19-oxidosteroid (II) was synthesized by the lead tetraacetate oxidation of 3α, 5α-cyclo-6β-hydroxysteroid (I) in benzene. The acid-catalysed solvolysis of the oxide (II) afforded 3α, 5α-cyclo-19-hydroxy-6β-substituted steroid (XVI) and/or Δ5-19-hydroxy-3β-substituted steroid (XVII), depending upon the reaction conditions employed. Oxidation of the oxide (II) with Jones reagent gave 3α, 5α-cyclo-6β, 19-dioxosteroid (XIX) with two equivalent molar oxidant, and 3α, 5α-cyclo-6-oxosteroid-19-oic acid (XX) with the excess reagent.

  3α, 5α-环-6β, 19-氧化类固醇(II)是通过四乙酸铅在苯中氧化3α, 5α-环-6β-羟基类固醇(I)合成的。氧化物(II)的酸催化溶剂解提供3α，5α-环-19-羟基-6β-取代的类固醇(XVI)和/或Δ5-19-羟基-3β-取代的类固醇(XVII)，取决于反应采用的条件。用琼斯试剂氧化氧化物(II)，得到3α，5α-环-6β，19-二氧类固醇(XIX)和两个当量摩尔氧化剂，以及3α，5α-环-6-氧类固醇-19-油酸(XX)多余的试剂。
• Estrogen receptor modulators
  申请人：Blizzard A. Timothy

  公开号：US20070099880A1

  公开（公告）日：2007-05-03

  The present invention relates to compounds and derivatives thereof, their synthesis, and their use as estrogen receptor modulators. The compounds of the instant invention are ligands for estrogen receptors and as such may be useful for treatment or prevention of a variety of conditions related to estrogen functioning including: bone loss, bone fractures, osteoporosis, metastatic bone disease, Paget's disease, periodontal disease, cartilage degeneration, endometriosis, uterine fibroid disease, hot flashes, increased levels of LDL cholesterol, cardiovascular disease, impairment of cognitive functioning, cerebral degenerative disorders, restenosis, gynecomastia, vascular smooth muscle cell proliferation, obesity, incontinence, inflammation, inflammatory bowel disease, sexual dysfunction, hypertension, retinal degeneration and cancer, in particular of the breast, uterus and prostate.

  本发明涉及化合物及其衍生物、它们的合成以及它们作为雌激素受体调节剂的用途。本发明的化合物是雌激素受体的配体，因此可能有助于治疗或预防与雌激素功能相关的各种疾病，包括：骨质流失、骨折、骨质疏松症、转移性骨病、佩吉特病、牙周病、软骨退化、子宫内膜异位症、子宫肌瘤病、潮热、低密度脂蛋白胆固醇水平升高、心血管疾病、认知功能障碍、脑退行性疾病、再狭窄、男性乳房发育、血管平滑肌细胞增殖、肥胖、失禁、炎症、炎症性肠病、性功能障碍、高血压、视网膜退化和癌症，特别是乳腺、子宫和前列腺癌。
• Estrogen Receptor Modulators
  申请人：Blizzard A. Timothy

  公开号：US20070203102A1

  公开（公告）日：2007-08-30

  The present invention relates to compounds and derivatives thereof, their synthesis, and their use as estrogen receptor modulators. The compounds of the instant invention are ligands for estrogen receptors and as such may be useful for treatment or prevention of a variety of conditions related to estrogen functioning including: bone loss, bone fractures, osteoporosis, metastatic bone disease, Paget's disease, periodontal disease, cartilage degeneration, endometriosis, uterine fibroid disease, hot flashes, increased levels of LDL cholesterol, cardiovascular disease, impairment of cognitive functioning, cerebral degenerative disorders, restenosis, gynecomastia, vascular smooth muscle cell proliferation, obesity, incontinence, inflammation, inflammatory bowel disease, sexual dysfunction, hypertension, retinal degeneration and cancer, in particular of the breast, uterus and prostate.

  本发明涉及化合物及其衍生物、它们的合成以及它们作为雌激素受体调节剂的用途。本发明的化合物是雌激素受体的配体，因此可能用于治疗或预防与雌激素功能相关的各种疾病，包括：骨质流失、骨折、骨质疏松症、转移性骨病、帕吉特病、牙周病、软骨退化、子宫内膜异位症、子宫肌瘤病、潮热、低密度脂蛋白胆固醇水平升高、心血管疾病、认知功能障碍、脑退行性疾病、再狭窄、男性乳房发育、血管平滑肌细胞增殖、肥胖、失禁、炎症、炎性肠病、性功能障碍、高血压、视网膜退化和癌症，特别是乳腺癌、子宫癌和前列腺癌。