(3beta,7beta,17beta)-雄甾-5-烯-3,7,17-三醇 | 2697-85-0

• 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
• 中文名称: (3beta,7beta,17beta)-雄甾-5-烯-3,7,17-三醇
• 中文别名: 5-雄烯-3Β,7Β,17Β-三醇
• 英文名称: 5-androstene-3β,7β,17β-triol
• 英文别名: 3β,7β,17β-trihydroxyandrost-5-ene；Androst-5-ene-3beta,7beta,17beta-triol；HE 2200；3β,7β,17β-trihydroxy-androst-5-en；androst-5-ene-3β,7β,17β-triol；5-androsten-3β,7β,17β-triol；Reversionex；(3S,7R,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7,17-triol
• CAS: 2697-85-0
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: OEVZKEVBDIDVOI-YSZCXEEOSA-N

物化性质

• 熔点：
  235-237℃
• 沸点：
  474.3±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

制备方法与用途

3b,7a,17a-三羟基雄甾-5-烯是从专利US20030060425中提取的免疫调节剂。

反应信息

• 作为反应物：
  描述：

  (3beta,7beta,17beta)-雄甾-5-烯-3,7,17-三醇 在 钯 作用下， 以to yield 3β,7β,17β-trihydroxy-5α-androstane (CIX)的产率得到5α-androstane-3β,7β,17β-triol
  参考文献：
  名称：

  Compositions containing corticosteroids or analogues thereof and

  摘要：

  3.beta.,17.beta.-雄烯二醇（".beta.AED"）和3.beta.，7.beta.，17.beta.-雄烯三醇（".beta.AET"）可用于抵消氢化可的松和其他皮质类固醇的抗增殖和免疫抑制作用（即作为缓冲剂来抵消这些类固醇的淋巴抑制反应）。.beta.AED和.beta.AET是类固醇，介导免疫反应，为身体提供免疫下调保护。描述了一种测试.beta.AED和.beta.AET的类似物以比较这些类似物作为缓冲氢化可的松和其他皮质类固醇的某些效应（包括免疫反应和增殖效应）的有效性的方法。通过向淋巴细胞的细胞培养基中添加.beta.AET和.beta.AED及其类似物来产生细胞因子，包括尤其是IL-3。

  公开号：

  US05387583A1
• 作为产物：
  描述：

  7-酮基去氢表雄酮 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 以88%的产率得到(3beta,7beta,17beta)-雄甾-5-烯-3,7,17-三醇
  参考文献：
  名称：

  C19-Steroids as androgen receptor modulators: Design, discovery, and structure-activity relationship of new steroidal androgen receptor antagonists

  摘要：

  Dehydroepiandrosterone (DHEA), the most abundant steroid in human circulating blood, is metabolized to sex hormones and other C-19-steroids. Our previous collaborative study demonstrated that androst-5-ene-3 beta,17 beta-diol (Adiol) and androst-4-ene-3,17-dione (Adione), metabolites of DHEA, can activate androgen receptor (AR) target genes. Adiol is maintained at a high concentration in prostate cancer tissue; even after androgen deprivation therapy and its androgen activity is not inhibited by the antiandrogens currently used to treat prostate cancer patients. We have synthesized possible metabolites of DHEA and several synthetic analogues and evaluated their role in androgen receptor transactivation to identify AR modulators. Steroids with low androgenic potential in PC-3 cell lines were evaluated for anti-dihydrotestosterone (DHT) and anti-Adiol activity. We discovered three potent antiandrogens: 3 beta-acetoxyandrosta-1,5-diene-17-one 17-ethylene ketal (ADEK), androsta-1,4-diene-3,17-dione 17-ethylene ketal (OAK), and 3 beta-hydroxyandrosta-5,16-diene (HAD) that antagonized the effects of DHT as well as of Adiol on the growth of LNCaP cells and on the expression of prostate-specific antigen (PSA). In vivo tests of these compounds will reveal their potential as potent antiandrogens for the treatment of prostate cancer. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.022

文献信息

• Novel derivatives of androstane and androstene with ascorbic acid and use thereof in treating or preventing various conditions, diseases, and disorders
  申请人：FORBES MEDI-TECH INC.

  公开号：US20030232797A1

  公开（公告）日：2003-12-18

  The present invention provides novel derivatives comprising compounds in the androstane and androstene series, coupled with ascorbic acid, including salts thereof, and represented by one or more of the general formulae: 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 may individually be chosen from hydrogen, OH, carbonyl, and an ascorbyl moiety; and R 7 may be hydrogen or any halogen.

  本发明提供了包括雄烷和雄烯系列化合物与抗坏血酸结合的新颖衍生物，包括其盐，并由下列一个或多个通式表示： 其中R1、R2、R3、R4、R5、R6可以分别选择为氢、OH、羰基和抗坏血酸基团；R7可以是氢或任何卤素。
• Hydroxylation of DHEA, androstenediol and epiandrosterone by Mortierella isabellina AM212. Evidence indicating that both constitutive and inducible hydroxylases catalyze 7α- as well as 7β-hydroxylations of 5-ene substrates
  作者：Teresa Kołek、Natalia Milecka、Alina Świzdor、Anna Panek、Agata Białońska

  DOI：10.1039/c1ob05350g

  日期：——

  underwent effective hydroxylation; 5-ene substrates – DHEA and androstenediol – were transformed into a mixture of 7α- and 7β- allyl alcohols, while epiandrosterone was converted into 7α- (mainly), 11α- and 9α- monohydroxy derivatives. Ketoconazole and cycloheximide inhibition studies suggest the presence of constitutive and substrate-induced hydroxylases in M. isabellina. On the basis of time course analysis

  DHEA的转型过程， 雄烯二醇 和 表雄甾酮在黄被孢霉AM212文化的影响。所提到的底物进行了有效的羟基化。5烯底物– DHEA和雄烯二醇 –被转化为7α-和7β-烯丙醇的混合物，而 表雄甾酮 被转化为7α-（主要是），11α-和9α-单羟基衍生物。 酮康唑和环己酰亚胺的抑制研究表明，伊萨贝拉霉中存在组成型和底物诱导的羟化酶。在时间过程的基础上分析脱氢表雄酮和雄烯二醇，烯丙基C中的氧化7 -H α和C 7 -H β键由相同的酶是一个合理的假设。
• Hydroxylation of DHEA and its analogues by Absidia coerulea AM93. Can an inducible microbial hydroxylase catalyze 7α- and 7β-hydroxylation of 5-ene and 5α-dihydro C19-steroids?
  作者：Natalia Milecka-Tronina、Teresa Kołek、Alina Świzdor、Anna Panek

  DOI：10.1016/j.bmc.2013.11.050

  日期：2014.1

  coerulea AM93. DHEA and androstenediol were transformed to the mixture of allyl 7-hydroxy derivatives, while EpiA and 5α-androstan-3,17-dione were converted mainly to 7α- and 7β-alcohols accompanied by 9α- and 11α-hydroxy derivatives. On the basis of (i) time course analysis of hydroxylation of the abovementioned substrates, (ii) biotransformation with resting cells at different pH, (iii) enzyme inhibition

  在本文中，我们着重研究了Absidia coerulea AM93对DHEA，雄烯二醇，表雄甾酮和5α-雄烷-3,17-二酮进行7-羟基化的过程。除此之外，我们提出了对蓝藻中类固醇的羟基化的初步分析。AM93。DHEA和雄烯二醇被转化为烯丙基7-羟基衍生物的混合物，而EpiA和5α-雄烷-3,17-二酮主要转化为7α-和7β-醇，并伴有9α-和11α-羟基衍生物。基于（i）上述底物羟基化的时程分析，（ii）在不同pH下静息细胞的生物转化，（iii）酶抑制分析以及（iv）底物C–H键之间的几何关系经历羟基化和辅因子结合的活性氧原子，但假定相同的酶可催化氧化ç 7 -H α以及为C 7 -H β在-5-烯和5α二氢C键19-类固醇。在底物的结构和羟基化的区域选择性之间观察到的相关性表明，正常的结合酶-底物复合物中可能发生7β-羟基化，而在反向反向结合复合物中则发生7α-羟基化。
• Combination of dehydroepiandrosterone or dehydroepiandrosterone-sulfate with a lipoxygenase inhibitor for treatment of asthma or chronic obstructive pulmonary disease
  申请人：Robinson B. Cynthia

  公开号：US20050090455A1

  公开（公告）日：2005-04-28

  A pharmaceutical or veterinary composition, comprises a first active agent selected from a dehydroepiandrosterone and/or dehydroepiandrosterone-sulfate, or a salt thereof, and a second active agent comprising a lipoxygenase inhibitor for the treatment of asthma, chronic obstructive pulmonary disease, or other respiratory diseases. The composition is provided in various formulations and in the form of a kit. The products of this patent are applied to the prophylaxis and treatment of asthma, chronic obstructive pulmonary disease, or other respiratory diseases.

  一种药物或兽药组合物，包括从去氢表雄酮和/或去氢表雄酮硫酸盐中选择的第一活性成分，以及包括一种脂氧合酶抑制剂的第二活性成分，用于治疗哮喘、慢性阻塞性肺病或其他呼吸系统疾病。该组合物以各种配方形式提供，并以套装形式提供。该专利的产品用于预防和治疗哮喘、慢性阻塞性肺病或其他呼吸系统疾病。
• Blood cell deficiency treatment method
  申请人：——

  公开号：US20030083231A1

  公开（公告）日：2003-05-01

  The invention relates to the use of compounds to treat a number of conditions, such as thrombocytopenia, neutropenia or the delayed effects of radiation therapy. Compounds that can be used in the invention include methyl-2,3,4-trihydroxy-1-O-(7,17-dioxoandrost-5-ene-3&bgr;-yl)-&bgr;-D-glucopyranosiduronate, 16&agr;,3&agr;-dihydroxy-5&agr;-androstan-17-one or 3,7,16,17-tetrahydroxyandrost-5-ene, 3,7,16,17-tetrahydroxyandrost-4-ene,3,7,16,17-tetrahydroxyandrost-1-ene or 3,7,16,17-tetrahydroxyandrostane that can be used in the treatment method.

  该发明涉及使用化合物治疗多种疾病，如血小板减少症、中性粒细胞减少症或放疗延迟效应。可以用于该发明的化合物包括甲基-2,3,4-三羟基-1-O-(7,17-二氧代雄烯-3β-基)-β-D-葡糖吡喃糖醛酸酯、16α,3α-二羟基-5α-雄甾酮-17-酮或3,7,16,17-四羟基雄烷-5-烯、3,7,16,17-四羟基雄烷-4-烯、3,7,16,17-四羟基雄烷-1-烯或3,7,16,17-四羟基雄烷可用于治疗方法中。