17α-ethynyldihydrotestosterone | 13611-97-7

• 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: 17α-ethynyldihydrotestosterone
• 英文别名: (5α,17α)-17-hydroxypregn-20-yn-3-one；17-Ethinyl-dihydrotestosterone；(5S,8R,9S,10S,13S,14S,17R)-17-ethynyl-17-hydroxy-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 13611-97-7
• 化学式: C₂₁H₃₀O₂
• 分子量: 314.468
• InChiKey: PVHMKHVQVIUQIP-JJFNZWTKSA-N

物化性质

• 溶解度：
  氯仿（少量溶解）、二氯甲烷（少量溶解）、甲醇（少量溶解）、吡啶

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  17α-ethynyldihydrotestosterone 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 various solvents 为溶剂， 反应 16.0h， 以65%的产率得到17β-hydroxy-17α-ethyl-5α-androstan-3-one
  参考文献：
  名称：

  用硼酸酯选择性处理甾体羟基：有效利用抗原C-3连接的甾体-蛋白质结合物和甾体硫酸盐标准物进行药物检测。

  摘要：

  作为硼酸酯的17alpha-烷基-5alpha-androstane-3beta，16beta，17beta三醇的临时保护是对其区域选择性功能化的有效方法。这已被应用于蛋白质-类固醇结合物7-10的合成，该蛋白-类固醇结合物的开发适用于针对澳大利亚赛马和其他体育比赛中禁止的类固醇的免疫测定。还报道了用作参考标准的类固醇硫酸盐缀合物42和44的合成。

  DOI：

  10.1039/b610499a
• 作为产物：
  描述：

  表雄酮 在 氢氧化钾 、 四丙基高钌酸铵 、 4 A molecular sieve 、 甲基锂 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 19.5h， 生成 17α-ethynyldihydrotestosterone
  参考文献：
  名称：

  A potential radioiodinated ligand for androgen receptor: 7.alpha.-methyl-17.alpha.-[2'-(E)-iodovinyl]-19-nortestosterone

  摘要：

  The presence of androgen receptor (AR) in prostate cancer has been linked to the androgen-dependent nature of the tumor and has also been shown to have prognostic significance; it also appears to be a positive prognostic indicator in breast cancer. However, due to the relatively low AR concentrations in most tumors and the inherently low specific activity of tritium, the assay of AR based on available H-3-ligands is not sensitive enough to measure accurately the amount of receptor in small specimens. A I-125-ligand like those available for the estrogen and progesterone receptors would be helpful, but development of such a ligand for AR has not been very successful. Although several androgen analogues containing iodine, bromine, or selenium have been synthesized specifically as potential probes for AR, none have shown any significant affinity or specificity for the receptor. We therefore undertook the synthesis of new potential AR ligands which could be radioiodinated, and determined their affinities for AR (from rat uterus and MCF-7 human breast cancer cells) by using a competition assay. We have examined both 5-alpha-dihydrotestosterone (5-alpha-DHT) and 19-nortestosterone analogues and have identified two such compounds which showed high AR affinity: (17-alpha,20E)-17-beta-hydroxy-21-iodo-5-alpha-pregn-20-en-3-one (17-alpha-((E)-iodovinyl)-5-alpha-DHT, 9) and 17-beta-hydroxy-7-alpha-methyl-(17-alpha,20E)-21-iodo-19-norpregna-4,20-dien-3-one (7-alpha-methyl-17-alpha-((E)-iodovinyl)-19-nortestosterone, 11). In fact, the affinity of the latter for human AR was found to be superior to that of 5-alpha-DHT itself. These iodovinyl analogues could be easily prepared in the radioiodinated form, and should prove to be extremely useful in assaying low levels of AR in small specimens.

  DOI：

  10.1021/jm00107a021

文献信息

• [EN] ANTI-CANCER NUCLEAR HORMONE RECEPTOR-TARGETING COMPOUNDS<br/>[FR] COMPOSÉS CIBLANT DES RÉCEPTEURS HORMONAUX NUCLÉAIRES ANTICANCÉREUX
  申请人：NUVATION BIO INC

  公开号：WO2019222272A1

  公开（公告）日：2019-11-21

  The disclosure relates to anti-cancer compounds derived from nuclear steroid receptor binders, to products containing the same, as well as to methods of their use and preparation.

  该披露涉及从核类固醇受体结合剂中衍生的抗癌化合物，以及含有这些化合物的产品，以及它们的使用和制备方法。
• Contragestational agents. 1. Steroidal-O-aryloximes
  作者：Allen F. Hirsch、George O. Allen、Benny Wong、Sandra Reynolds、Chris Exarhos、William Brown、Do Won Hahn

  DOI：10.1021/jm00222a002

  日期：1977.12

  The preparation of a series of O-aryloximes of various steroids by two different routes is described. These compounds were prepared by reacting a keto steroid with a substituted O-arylhydroxylamine in the presence of an acid catalyst or, alternatively, by the reaction of a steroidal oxime with a substituted aryl halide in the presence of a suitable base. These compounds were examined for their ability

  描述了通过两种不同的途径制备一系列各种类固醇的O-芳基肟。这些化合物是通过在酸催化剂的存在下使酮类固醇与取代的O-芳基羟胺反应或通过在合适的碱存在下使类固醇肟与取代的芳基卤反应来制备的。检查了这些化合物在雌性大鼠中中断植入后妊娠的能力。化合物的甾体基本结构为5α-雄甾烷，3-肟为对硝基苯基系列，具有最显着的避孕活性。当在妊娠第9-12天以2.5 mg / kg的剂量口服给予大鼠时，该系列中最活跃的化合物之一（16）被证明具有终止妊娠的能力。
• Synthesis and substance P receptor binding activity of androstano[3,2-b]pyrimido[1,2-a]benzimidazoles
  作者：Bhaskar R. Venepalli、Lisa D. Aimone、Kenneth C. Appell、Malcolm R. Bell、John A. Dority、Ramanuj Goswami、Patricia L. Hall、Virendra Kumar、Kristine B. Lawrence

  DOI：10.1021/jm00080a025

  日期：1992.1

  Several heterosteroids containing a dihydroethisterone skeleton were prepared and shown to displace substance P in a receptor binding assay. Further biochemical (kinetic and Scatchard analyses) and pharmacological evaluation (substance P-induced plasma extravasation and salivation in the rat) of a representative example in this series (5a) established that these compounds are competitive antagonists

  制备了几种含有二氢乙二酮骨架的杂类固醇，并在受体结合试验中显示出可取代物质P的性质。该系列（5a）中代表性实例的进一步生化（动力学和Scatchard分析）和药理评估（大鼠中P诱导的血浆渗出和唾液分泌）确定了这些化合物是P物质受体的竞争性拮抗剂。
• Antiandrogenic sulfonylsteroidopyrazoles and processes for preparation
  申请人：Sterling Drug Inc.

  公开号：US04684636A1

  公开（公告）日：1987-08-04

  1'-Sulfonylsteroido[3,2-c]pyrazoles, for example, (5.alpha.,17.alpha.)-1'-(methylsulfonyl)-1'H-pregn-20-yno[3,2-c]pyrazol-17 -ol, which are useful as antiandrogenic agents, and processes for preparation, method of use and compositions thereof are disclosed.

  本发明公开了1'-磺酰基类固醇[3,2-c]吡唑，例如，(5.alpha.，17.alpha.)-1'-(甲基磺酰基)-1'H-孕-20-炔[3,2-c]吡唑-17-醇，其作为抗雄激素剂有用，并公开了其制备方法、使用方法和组合物。
• [EN] AMINOSTEROID DERIVATIVES AND PROCESS FOR PRODUCING SAME<br/>[FR] DÉRIVÉS AMINOSTÉROÏDES ET LEUR PROCÉDÉ DE PRODUCTION
  申请人：UNIV LAVAL

  公开号：WO2017205964A8

  公开（公告）日：2018-12-06