3-ethoxyandrosta-3,5,11-trien-17-one | 93519-11-0

• 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
• 英文名称: 3-ethoxyandrosta-3,5,11-trien-17-one
• 英文别名: Ethoxyandrosta-3,5,11-trien-17-one；3-ethoxy-androsta-3,5,11-trien-17-one；3-Aethoxy-androsta-3,5,11-trien-17-on；(8S,9S,10R,13S,14S)-3-ethoxy-10,13-dimethyl-1,2,7,8,9,14,15,16-octahydrocyclopenta[a]phenanthren-17-one
• CAS: 93519-11-0
• 化学式: C₂₁H₂₈O₂
• 分子量: 312.452
• InChiKey: IIQWQXGNJOSFJP-OEUJLIAZSA-N

物化性质

• 沸点：
  463.5±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-ethoxyandrosta-3,5,11-trien-17-one 在 吡啶 、 盐酸 、 sodium hydroxide 、 4 A molecular sieve 、 sodium ethanolate 、 sodium hydride 、 对甲苯磺酸 、 二甲基亚砜 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 25.67h， 生成 3-<7α-(acetylthio)-17β-hydroxy-3-oxoandrosta-4,11-dien-17α-yl>propionic acid γ-lactone
  参考文献：
  名称：

  醛固酮拮抗剂。2.11，12-脱氢戊二烯衍生物的合成和生物活性。

  摘要：

  合成了几种具有δ11-孕烷骨架，具有17-γ-螺内酯功能的类固醇衍生物，以评估其抗醛固酮活性并阐明其与盐皮质激素受体（MR）的结合亲和力与盐皮质激素和/或抗盐皮质激素活性之间的关系。虽然许多合成的化合物显示出对MR和醛固酮激动剂活性的强结合亲和力，但3-（17β-羟基-3-氧代雄甾烯1,4,6,11-四烯-17α-基）丙酸γ-内酯在体内试验中显示出良好的醛固酮拮抗剂活性。还发现其体内抗雄激素活性相对较弱。

  DOI：

  10.1021/jm00392a022
• 作为产物：
  描述：

  androsta-4,11-diene-3,17-dione 、 原甲酸三乙酯 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以67.6%的产率得到3-ethoxyandrosta-3,5,11-trien-17-one
  参考文献：
  名称：

  醛固酮拮抗剂。2.11，12-脱氢戊二烯衍生物的合成和生物活性。

  摘要：

  合成了几种具有δ11-孕烷骨架，具有17-γ-螺内酯功能的类固醇衍生物，以评估其抗醛固酮活性并阐明其与盐皮质激素受体（MR）的结合亲和力与盐皮质激素和/或抗盐皮质激素活性之间的关系。虽然许多合成的化合物显示出对MR和醛固酮激动剂活性的强结合亲和力，但3-（17β-羟基-3-氧代雄甾烯1,4,6,11-四烯-17α-基）丙酸γ-内酯在体内试验中显示出良好的醛固酮拮抗剂活性。还发现其体内抗雄激素活性相对较弱。

  DOI：

  10.1021/jm00392a022

文献信息

• Aldosterone-antagonistic steroids
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0115273A2

  公开（公告）日：1984-08-08

  Novel spironolactone derivatives characterized by the C11 - C12 double bond which have a potent aldosterone-antagonistic activity without causing potassium loss, used alone in diagnosis and improvement of condition of primary aldosteronism, or together with other drugs in treatment of essential or renal hypertension as well as cardiac or renal edema; prepared from 3,17-bis (ethylene-dioxy)-5,11- androstadiene.

  新型螺内酯衍生物，其特点是具有 C11 - C12 双键，具有强效的醛固酮拮抗活性，不会导致钾流失，可单独用于诊断和改善原发性醛固酮增多症，或与其他药物一起用于治疗原发性或肾性高血压以及心脏或肾脏水肿；由 3,17-双（乙烯二氧）-5,11-雄甾二烯制备而成。
• Glutathione conjugation of synthetic steroids in isolated rat hepatocytes
  作者：Junko Higaki、Takeaki Matsui、Yuji Ikenishi、Masaharu Hirata

  DOI：10.1016/0039-128x(89)90008-1

  日期：1989.9

  When designing steroid drugs with multiple double bonds, the influence of glutathione conjugation on the pharmacodynamics of drug action should be considered. We have examined the effect of canrenone, a mineralocorticoid receptor antagonist, on isolated rat hepatocytes and found that 1 mM canrenone injured the hepatocytes during shortterm incubation at 37 C, while an analogue of canrenone which bears 4 double bonds (delta 1,11-CAN) did not manifest such toxicity. To further pursue this, we prepared testosterone analogues comprising multiple double bonds as model compounds, and incubated them with freshly isolated rat hepatocytes. The viability of the hepatocytes was not influenced by any of the steroids, but some of them having a double bond at the C6-C7 position reduced the cellular glutathione levels. This was found to be due to conjugation of glutathione to the C7 position of the steroid molecule, and the rate of conjugation was accelerated when an additional double bond was introduced at C1-C2 or C11-C12 positions. The finding is interesting as glucuronidation or sulfation are common as conjugation processes of steroids.
• ——
  作者：KAMATA SUSUMU、 XAGA NOBUXIRO

  DOI：——

  日期：——
• US4502989A
  申请人：——

  公开号：US4502989A

  公开（公告）日：1985-03-05
• Remote sensing and GIS for locating favourable zones of lead-zinc-copper mineralization in Rajpura-Dariba area, Rajasthan, India
  作者：S. K. Srivastav、A. Bhattacharya、M. V. V. Kamaraju、G. Sreenivasa Reddy、A. K. Shrimal、D. S. Mehta、F. K. List、H. Burger

  DOI：10.1080/014311600750019877

  日期：2000.1

  This paper reports the results of a pilot study carried out in Rajpura-Dariba area, Rajasthan, for locating favourable zones of lead-zinc-copper (Pb-Zn-Cu) mineralization using remote sensing, Geographical Information System (GIS) and geostatistical modelling techniques. Remotely sensed data, both aerial and satellite, were used to update the existing geological map. ATLAS GIS software and multivariate geostatistical techniques were used to analyse and integrate different types of geological and geophysical datasets. The Favourability Index (FI) maps prepared during this study show the occurrence of three favourable zones for Pb-Zn-Cu mineralization. They are: (i) around and north of Rawan ka Khera; (ii) isolated spots between Ruppura and Bhupalsagar; and (iii) north of Dhani. Selective geochemical sampling and resistivity profiling carried out in these favourable zones indicated the presence of geochemical anomalies (anomalous concentrations of Zn and Cu) and low/moderate resistivity zones, respectively. Recent drilling carried out by the Department of Mines and Geology (DMG), Rajasthan, at about 2.5 km north of Rawan ka Khera (one of the predicted favourable zones) indicated evidence of Cu mineralization at a depth of about 70 m.