3β-butyroxyandrost-5-en-17-one | 15253-51-7

• 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: 3β-butyroxyandrost-5-en-17-one
• 英文别名: (3S,10R,13S)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl butyrate；dehydroepiandrosterone 3-butyrate；3β-butanoyloxyandrost-5-en-17-one；17-oxoandrost-5-ene-3β-yl butanoate；[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] butanoate
• CAS: 15253-51-7
• 化学式: C₂₃H₃₄O₃
• 分子量: 358.521
• InChiKey: GOXSYMHOEHYILT-VYAQIDIUSA-N

物化性质

• 沸点：
  450.93°C (rough estimate)
• 密度：
  1.0030 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-butyroxyandrost-5-en-17-one 在 mercury(II) trifluoroacetate 、 碳酸氢钠 作用下， 生成 3β-butyroxy-6β-hydroxyandrost-4-en-17-one
  参考文献：
  名称：

  δ5-类固醇与三氟乙酸汞(II)反应的范围和局限性

  摘要：

  摘要 研究了C-3 取代基对雄性5-烯与三氟乙酸汞(II) 在二氯甲烷中反应（改性Treibs 氧化）的影响。3β-Acyloxyandrost-5-en-17-ones 得到 3β-acyloxy-6β-hydroxyandrost-4-en-17-ones 伴随着 3β-acyloxy-6-chloromercuriandrost-5-en-17-ones。3β-Acetoxy-6β-trifluoroacetoxyandrost-4-en-17-one 和 3β-acetoxy-4β-trifluoroacetoxyandrost-5-en-17-one 是反应的中间体。氯汞类固醇的形成表明溶剂参与了反应。以 3α-acetoxyandrost-5-en-17-one 作为底物，观察到产物分布的完全逆转。3β-Haloandrost-5-en-17-ones 的主要产物反映了卤化物的

  DOI：

  10.1016/s0039-128x(98)00076-2
• 作为产物：
  描述：

  (3S,8R,9S,10R,13S,14S)-3-Chloro-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one 在 吡啶 、 mercury(II) trifluoroacetate 、 碳酸氢钠 、 对甲苯磺酰氯 作用下， 反应 30.0h， 生成 3β-butyroxyandrost-5-en-17-one
  参考文献：
  名称：

  δ5-类固醇与三氟乙酸汞(II)反应的范围和局限性

  摘要：

  摘要 研究了C-3 取代基对雄性5-烯与三氟乙酸汞(II) 在二氯甲烷中反应（改性Treibs 氧化）的影响。3β-Acyloxyandrost-5-en-17-ones 得到 3β-acyloxy-6β-hydroxyandrost-4-en-17-ones 伴随着 3β-acyloxy-6-chloromercuriandrost-5-en-17-ones。3β-Acetoxy-6β-trifluoroacetoxyandrost-4-en-17-one 和 3β-acetoxy-4β-trifluoroacetoxyandrost-5-en-17-one 是反应的中间体。氯汞类固醇的形成表明溶剂参与了反应。以 3α-acetoxyandrost-5-en-17-one 作为底物，观察到产物分布的完全逆转。3β-Haloandrost-5-en-17-ones 的主要产物反映了卤化物的

  DOI：

  10.1016/s0039-128x(98)00076-2

文献信息

• Esters of Dehydroepiandrosterone (DHEA) as Probes for the Active Site of Type 3 17β-Hydroxysteroid Dehydrogenase (17β-HSD3)
  作者：Moniola S. Olusanjo、Caroline P. Owen、Sabbir Ahmed

  DOI：10.2174/157018010791163505

  日期：2010.6.1

  We report the use of steroid-based compounds as probes for the active site of 17β-hydroxysteroid dehydrogenase, in particular, type 3 (17β-HSD3). Results suggest that the compounds were good inhibitors of 17β-HSD3 – a number were extremely potent with respect to the standard compounds used.

  我们报告了使用基于类固醇的化合物作为 17β-羟基类固醇脱氢酶活性位点的探针，特别是 3 型（17β-HSD3）。结果表明，这些化合物是 17β-HSD3 的良好抑制剂——其中一些化合物相对于所使用的标准化合物非常有效。
• New steroidal lactones as 5α-reductase inhibitors and antagonists for the androgen receptor
  作者：Mariana Garrido、Eugene Bratoeff、Dulce Bonilla、Juan Soriano、Yvonne Heuze、Marisa Cabeza

  DOI：10.1016/j.jsbmb.2011.07.001

  日期：2011.11

  of these steroids was demonstrated in in vivo as well as in vitro experiments. In the in vivo experiments, we measured the activity of ten new steroidal derivatives on the weight of the prostate and seminal vesicle glands of gonadectomized hamsters treated with testosterone. For the in vitro studies, we determined the IC(50) values by measuring the concentration of the steroidal derivatives that inhibits

  这项研究报告了几种新的甾体内酯的合成：5α，6β-二溴17a-氧杂-D-高雄甾烷-3β-基-3'-草戊酸（11），5α，6β-二溴17a-氧杂-D-高雄甾烷-3β-丙酸基酯（12），5α，6β-二溴17a-氧杂-D-高雄甾烷3β-基丁酸（13），5α，6β-二溴17a-氧杂-D-高雄甾烷-3β-基-戊酸酯（14），5α，6β-二溴17a-氧杂-D-高雄甾烷3β-基己酸（15），17a-氧杂-D-高纯甾烷5-en-17-一个3β-基-3 -草酸戊酯（16），17a-草酸-D-高锰酸-5-en-17-一3β-丙酸基酯（17），17a-草酸-D-高纯铜-5-en-17-one-3β-丁酸丁酯（18），17a-氧杂-D-均雄酮5-en-17-一个3β-戊酸丁酯（19）和17a-氧杂-D-均丁烯酮5-en-17-一个3β-己酸己酯（20）具有抗雄激素的治疗​​潜力。这些类固醇的生物学作用已在体内以及体外实验中得到证实。在体内实验中
• The Effects of the Steroids 5-Androstenediol and Dehydroepiandrosterone and Their Synthetic Derivatives on the Viability of K562, HeLa, and Wi-38 Cells and the Luminol-Stimulated Chemiluminescence of Peripheral Blood Mononuclear Cells from Healthy Volunteers
  作者：Mikhail N. Sokolov、Vladimir V. Rozhkov、Maria E. Uspenskaya、Darya N. Ulchenko、Vladimir I. Shmygarev、Vladimir M. Trukhan、Andrei V. Churakov、Nikolay L. Shimanovsky、Tatiana A. Fedotcheva

  DOI：10.3390/biom14030373

  日期：——

  toward HeLa and K562 human cancer cells. The maximum cytostatic effect during long-term incubation for five days with HeLa and K562 cells was demonstrated by the propionic esters of the steroids: DHEA 3-propionate and 5-AED 3,17-dipropionate. These compounds stimulated the growth of normal Wi-38 cells by 30–50%, which indicates their cytoprotective properties toward noncancerous cells. The synthesized

  为了评价3-C和17-C取代基在DHEA和5-AED分子的细胞毒性和细胞保护作用中的作用，使用相应的酸酐或酰基氯通过酯化合成它们的衍生物。结果，获得了七种化合物：四种DHEA衍生物（DHEA 3-丙酸酯、DHEA 3-丁酸酯、DHEA 3-乙酸酯、DHEA 3-甲基磺酸酯）和三种5-AED衍生物（5-AED 3-丁酸酯、5-AED 3,17-二丙酸、5-AED 3,17-二丁酸）。所有这些化合物均对 HeLa 和 K562 人类癌细胞表现出微摩尔细胞毒活性。 HeLa 和 K562 细胞长期孵育五天期间，类固醇的丙酸酯（DHEA 3-丙酸酯和 5-AED 3,17-二丙酸酯）证明了最大的细胞抑制作用。这些化合物刺激正常 Wi-38 细胞的生长 30-50%，这表明它们对非癌细胞具有细胞保护特性。合成的类固醇衍生物通过减少健康志愿者外周血单核细胞产生的活性氧（ROS）而表现出抗氧化活性，正如
• New ester derivatives of dehydroepiandrosterone as 5α-reductase inhibitors
  作者：Yazmín Arellano、Eugene Bratoeff、Mariana Garrido、Juan Soriano、Yvonne Heuze、Marisa Cabeza

  DOI：10.1016/j.steroids.2011.05.015

  日期：2011.11

  The aim of this study was to synthesize different ester derivatives of dehydroepiandrosterone with therapeutic potential as antiandrogens.The biological effect of these steroids was demonstrated in in vivo as well as in vitro experiments. In the in vivo experiments, we measured the activity of seven steroids on the weight of the prostate and seminal vesicles of gonadectomized hamsters treated with testosterone. For the in vitro studies, we determined the IC(50) values by measuring the concentration of the steroidal derivatives that inhibits 50% of the activity of 5 alpha-reductase present in human prostate and also its binding capacity to the androgen receptors (AR) obtained from rat's prostate cytosol. The results from these experiments indicated that compounds 7 5 alpha,6 beta-dibromo-3 beta-propanoyloxyandrostan-17-one, 8 5 alpha,6 beta-dibromo-3 beta-butanoyloxyandrostan-17-one and 9 5 alpha,6 beta-dibromo-3 beta-(3'-oxapentanoyloxy)-androstan-17-one, significantly decreased the weight of the prostate and seminal vesicles as compared to testosterone treated animals: this reduction of the weight of these glands was comparable to that produced by Finasteride 11. On the other hand, compounds 4 3 beta-acetoxyandrost-5-en-17-one, 5 3 beta-hexanoyloxyandrost-5-en-17-one 6 3 beta-(3'-oxapentanoyloxy)-androst-5-en-17-one, 7 and 12 dehydroepiandrosterone, (commercially available) inhibited the enzyme 5 alpha-reductase. Compounds 4, 5, 6, 8 and 9 (IC(50) values of 5.2 +/- 1.2, 0.049 +/- 0.002, 6.4 +/- 1.1, 0.10 +/- 0.045, and 6.8 +/- 0.9 nM, respectively) exhibited the highest inhibitory activity. However, none of these compounds binds to the AR. (C) 2011 Elsevier Inc. All rights reserved.
• THERAPEUTIC USES AND DELIVERY SYSTEMS OF DEHYDROEPIANDROSTERONE
  申请人：ENDORECHERCHE INC.

  公开号：EP0680327B1

  公开（公告）日：2004-09-15