androst-5-ene-3,7,17-trione 3,17-diethylene diketal | 122623-16-9

• 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: androst-5-ene-3,7,17-trione 3,17-diethylene diketal
• 英文别名: 3,3:17,17-bis(ethylenedioxy)-5-androsten-7-one；(20S,7R)-7,20-dimethyldispiro[1,3-dioxolane-2,5’-tetracyclo[8.7.0.0^2,7.0^11,15]heptadecane-14’,2"-1,3-dioxolane]-12-en-14-one；3,3,17,17-diethylenedioxyandrost-5-ene-7-one；3,3:17,17-bis(ethylendioxy)androst-5-ene-7-one
• CAS: 122623-16-9
• 化学式: C₂₃H₃₂O₅
• 分子量: 388.504
• InChiKey: ZCKVJCRUBHRHDF-WJRACZLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  androst-5-ene-3,7,17-trione 3,17-diethylene diketal 在 盐酸 、 硫酸 、 硝酸 、 tin(ll) chloride 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 50.5h， 生成 7-(4'-aminobenzyl)-4,6-androstadiene-3,17-dione
  参考文献：
  名称：

  Synthesis and biochemical studies of 7-substituted 4,6-androstadiene-3,17-diones as aromatase inhibitors

  摘要：

  Inhibitors of aromatase, the cytochrome P-450 enzyme complex responsible for the biosynthesis of estrogens, may be useful as therapeutic agents for the treatment of estrogen-dependent disease states such as breast and endometrial cancer. Several 7 alpha-thio-substituted androstenediones have proven to be potent inhibitors of aromatase in vitro and in vivo. Recent research efforts have focused on designing aromatase inhibitors with both substitution at C-7 and extended linear conjugation in rings A and B of the steroid nucleus. The targeted compounds, 7-substituted 4,6-androstadiene-3,17-diones 4-10, were prepared by the addition of either Grignard or lithium reagents to 3,3:17,17-bis(ethylenedioxy)-5-androsten-7-one (3). Inhibitory activities of the compounds were evaluated in vitro by enzyme kinetic studies employing the microsomal fraction isolated from human term placenta. 7-Benzyl- and 7-phenethyl-4,6-androstadiene-3,17-dione analogues are effective inhibitors with apparent Ki's of 60.9-174 nM, while the 7-phenyl analogue exhibited an apparent Ki of 1.424 microM. Thus, several 7-substituted 4,6-androstadiene-3,17-diones were prepared and exhibited good competitive inhibition of aromatase in vitro in human placental microsomes.

  DOI：

  10.1021/jm00163a017
• 作为产物：
  描述：

  雄烯二酮 在 叔丁基过氧化氢 、 重铬酸吡啶 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 53.0h， 生成 androst-5-ene-3,7,17-trione 3,17-diethylene diketal
  参考文献：
  名称：

  Synthesis of Some Novel 3,3-Ethylenedioxyandrost-7β-Acyloxy-5-Ene-17-One Derivatives as Potent Aromatase Inhibitors

  摘要：

  3,3,17,17-二亚乙基二氧基雄甾-5-烯由雄烯二酮酮化而得，雄烯二酮与 PDC 和 t-BuOOH 氧化生成 3,3,17,17-二亚乙基二氧基雄甾-5-烯-7-酮。在 CeCl3.6H2O 的存在下，NaBH4 对 3,3,17,17-二亚乙二氧基雄-5-烯-7-酮进行立体选择性还原，得到 3,3,17,17-二亚乙二氧基-7β-羟基雄-5-烯，用对甲苯磺酸对其进行脱保护，得到 3,3-亚乙二氧基雄-5-烯-7β-羟基和雄-4,6-二烯-3,17-二酮。通过酯化反应，从 3,3-亚乙二氧基雄-5-烯-7β-羟基得到了一系列雄烯二酮衍生物。通过质谱、1H NMR、13C NMR 和 HRMS 确认了它们的结构。

  DOI：

  10.3184/174751911x13129058638242

文献信息

• AMINO DERIVATIVES OF ANDROSTANES AND ANDROSTENES AS MEDICAMENTS FOR CARDIOVASCULAR DISORDERS
  申请人：Cerri Alberto

  公开号：US20110053902A1

  公开（公告）日：2011-03-03

  Compounds of formula (I) wherein: the groups are as defined in the description, are useful for the preparation of medicaments for the treatment of cardiovascular disorders, in particular heart failure and hypertension. The compounds are inhibitors of the enzymatic activity of the Na + , K + -ATPase. Said compounds are used for the preparation of a medicament for the treatment of a disease caused by the hypertensive effects of endogenous ouabain, such as renal failure progression in autosomal dominant polycystic renal disease (ADPKD), preeclamptic hypertension and proteinuria and renal failure progression in patients with adducin polymorphisms.

  化合物的化学式（I），其中：所述基团如描述中所定义，可用于制备用于治疗心血管疾病，特别是心力衰竭和高血压的药物。这些化合物是Na+，K+-ATP酶活性的抑制剂。所述化合物用于制备一种药物，用于治疗由内源性欧巴因的高血压效应引起的疾病，例如在常染色体显性多囊肾病（ADPKD）中肾功能衰竭进展、妊娠期高血压和蛋白尿以及具有adducin多态性的患者中的肾功能衰竭进展。
• ANDROSTANE DERIVATIVES WITH ACTIVITY AS PURE OR PREDOMINANTLY PURE STIMULATORS OF SERCA2A FOR THE TREATMENT OF HEART FAILURE
  申请人：Windtree Therapeutics, Inc.

  公开号：EP3805243A1

  公开（公告）日：2021-04-14

  Compounds and compositions for the activation of SERCA2a are disclosed. In particular, provided are compounds that act as predominantly pure or pure SERCA2a activators while only moderately inhibiting the Na+/K+ ATPase. In general, the disclosed compounds are derivatives of androstane having the formula (I) Also disclosed herein are pharmaceutical compositions comprising one or more of the compounds of formula (I) for use for the treatment of heart failure.

  揭示了用于激活SERCA2a的化合物和组合物。具体来说，提供了作为主要纯或纯净的SERCA2a激活剂的化合物，同时仅在适度抑制Na+/K+ ATP酶。一般来说，所述的化合物是雄甾烷的衍生物，其化学式为(I)。本文还揭示了包含化学式(I)中的一个或多个化合物的药物组合物，用于治疗心力衰竭。
• STUDIES TOWARD THE SYNTHESIS OF CONTIGNASTEROL: FUNCTIONALIZATION OF THE STEROIDAL A,B RING SYSTEM
  作者：Christine Rogers、Yaping Shen、David Burgoyne、Edward Piers

  DOI：10.1081/scc-120012989

  日期：2002.1

  ABSTRACT The synthesis of androstane-3α,4β,6α,7β-tetrol-17-one (2), a potentially key intermediate for the preparation of contignasterol (1), was achieved by functionalization of the A,B-ring portion of the readily available androst-4-ene-3,17-dione (3).

  摘要雄甾烷-3α,4β,6α,7β-tetrol-17-one (2) 是制备 contignasterol (1) 的潜在关键中间体，其合成是通过 A,B 环部分的功能化实现的。容易获得的 androst-4-ene-3,17-dione (3)。
• AZAHETEROCYCLYL DERIVATIVES OF ANDROSTANES AND ANDROSTENES AS MEDICAMENTS FOR CARDIOVASCULAR DISORDERS
  申请人：Cerri Alberto

  公开号：US20090275542A1

  公开（公告）日：2009-11-05

  Compounds of formula (I) wherein: the groups are as defined in the description, are useful for the preparation of medicaments for the treatment of cardiovascular disorders, in particular heart failure and hypertension. The compounds are inhibitors of the enzymatic activity of the Na+, K+-ATPase. They are useful for the preparation of a medicament for the treatment of a disease caused by the hypertensive effects of endogenous ouabain, such as renal failure progression in autosomal dominant polycystic renal disease (ADPKD), preeclamptic hypertension and proteinuria and renal failure progression in patients with adducin polymorphisms.

  式(I)化合物，其中：所述基团如描述中定义的那样，对于制备治疗心血管疾病的药物，特别是心力衰竭和高血压是有用的。这些化合物是Na+，K+-ATPase酶活性的抑制剂。它们对于制备治疗内源性欧巴因引起的疾病的药物是有用的，例如：常染色体显性多囊肾病（ADPKD）中的肾功能衰竭进展、先兆子痫性高血压和蛋白尿，以及具有adducin多态性的患者的肾功能衰竭进展。
• AMINO DERIVATIVES OF BETA-HOMOANDROSTANES AND BETA-HETEROANDROSTANES
  申请人：Cerri Alberto

  公开号：US20090209506A1

  公开（公告）日：2009-08-20

  New aminoalkoxyimino derivatives at position 3 of substituted B-homoandrostanes and B-heteroandrostanes, processes for their preparation, and to pharmaceutical compositions containing them for the treatment of cardiovascular disorders, such as heart failure and hypertension. In particular compounds having the general formula (I) are described, where the radicals have the meanings described in detail in the application.

  本发明涉及在取代的B-同系异构体和B-杂环异构体的3位处的新的氨基烷氧基亚胺衍生物的制备方法，以及包含它们的制药组合物，用于治疗心血管疾病，如心力衰竭和高血压。特别地，本发明描述了具有通式（I）的化合物，其中基团的详细含义在申请中描述。