17-oxoandrost-5-ene-3β-yl pentanoate | 7642-68-4

• 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: 17-oxoandrost-5-ene-3β-yl pentanoate
• 英文别名: 3β-pentanoyloxyandrostan-17-one；5,6-Dehydroisoandrosteron-valerat；3beta-Pentanoyloxyandrost-5-en-17-one；[(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] pentanoate
• CAS: 7642-68-4
• 化学式: C₂₄H₃₆O₃
• 分子量: 372.548
• InChiKey: XAFPTAQBZXAXLR-IGJOJHROSA-N

物化性质

• 沸点：
  461.97°C (rough estimate)
• 密度：
  0.9937 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  5
• 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：

  17-oxoandrost-5-ene-3β-yl pentanoate 在 水 、 溴 、 magnesium monoperoxyphthalate 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 17-oxo-D-homoandrost-5-ene-3β-yl pentanoate
  参考文献：
  名称：

  新的甾体内酯作为雄激素受体的5α-还原酶抑制剂和拮抗剂。

  摘要：

  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

  DOI：

  10.1016/j.jsbmb.2011.07.001
• 作为产物：
  描述：

  去氢表雄酮 、 正戊酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以96.1%的产率得到17-oxoandrost-5-ene-3β-yl pentanoate
  参考文献：
  名称：

  新的甾体内酯作为雄激素受体的5α-还原酶抑制剂和拮抗剂。

  摘要：

  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

  DOI：

  10.1016/j.jsbmb.2011.07.001

文献信息

• 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
• Conjugated Neuroactive Steroid Compositions And Methods Of Use
  申请人：Marx Christine

  公开号：US20130245253A1

  公开（公告）日：2013-09-19

  The present disclosure provides modified neuroactive steroids. The modified neuroactive steroids may comprise, consist of, or consist essentially of a therapeutic agent and/or a modifying moiety. The modified neuroactive steroid can have modified characteristics as compared to native neuroactive steroids that do not include a modifying moiety and/or therapeutic agent. The modified neuroactive steroid may be, for example, modified pregnenolone, pregnenolone metabolites, allopregnanolone, and/or allopregnanolone metabolites. The modified neuroactive steroids can be used to treat, prevent and/or ameliorating a phenotypic state of interest in a subject.
• [EN] CONJUGATED NEUROACTIVE STEROID COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSITIONS DE STÉROÏDE NEUROACTIF CONJUGUÉ ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV DUKE

  公开号：WO2011120044A1

  公开（公告）日：2011-09-29

  The present disclosure provides modified neuroactive steroids. The modified neuroactive steroids may comprise, consist of, or consist essentially of a therapeutic agent and/or a modifying moiety. The modified neuroactive steroid can have modified characteristics as compared to native neuroactive steroids that do not include a modifying moiety and/or therapeutic agent. The modified neuroactive steroid may be, for example, modified pregnenolone, pregnenolone metabolites, allopregnanolone, and/or allopregnanolone metabolites. The modified neuroactive steroids can be used to treat, prevent and/or ameliorating a phenotypic state of interest in a subject.
• 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