[(7R,8R,9S,10R,13S,14S,17S)-17-(methoxymethoxy)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-yl]methyl acetate | 946835-11-6

• 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: [(7R,8R,9S,10R,13S,14S,17S)-17-(methoxymethoxy)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-yl]methyl acetate
• CAS: 946835-11-6
• 化学式: C₂₄H₃₆O₅
• 分子量: 404.547
• InChiKey: XOQGNFSKYZFRDV-PDGMGFRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(7R,8R,9S,10R,13S,14S,17S)-17-(methoxymethoxy)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-yl]methyl acetate 在 氨 、 lithium 作用下， 反应 1.25h， 以62%的产率得到(5S,7R,8R,9S,10S,13S,14S,17S)-7-(hydroxymethyl)-17-(methoxymethoxy)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  Synthesis of 7α-(Fluoromethyl)dihydrotestosterone and 7α-(Fluoromethyl)nortestosterone, Structurally Paired Androgens Designed To Probe the Role of Sex Hormone Binding Globulin in Imaging Androgen Receptors in Prostate Tumors by Positron Emission Tomography

  摘要：

  Although prostate cancer growth is regulated by androgens through the androgen receptor (AR), in vitro assays of AR levels in prostate tumors have limited prognostic value. This might be improved by direct measurement of tumor AR in vivo using positron emission tomography (PET) imaging with fluorine-18-labeled androgens. Most AR PET imaging agents have been designed to limit steroid binding to serum proteins, but there is evidence that binding to sex hormone binding globulin (SHBG) might enhance tumor uptake. To probe the role of SHBG in prostate tumor uptake of PET imaging agents, we have synthesized two fluoro steroids, 7 alpha-(fluoromethyl)dihydrotestosterone (7 alpha-FM-DHT) and 7 alpha-(fluoromethyl)nortestosterone (7 alpha-FM-norT), by a route amenable to their labeling with [F-18]fluoride ion. Both compounds have high affinity for AR, but 7 alpha-FM-norT has much lower affinity for SHBG. Thus, these two fluoro steroids are well matched in terms of their site of fluorine labeling, similarity of structure, and equivalent AR binding affinitybut contrasting SHBG bindingand therefore can be used as agents for evaluating the role of SHBG binding in the target tissue uptake of AR PET imaging agents in humans.

  DOI：

  10.1021/jo070328b
• 作为产物：
  描述：

  (7R,8R,9S,10R,13S,14S,17S)-17-(methoxymethoxy)-10,13-dimethylspiro[1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-3,2'-1,3-dithiolane]-7-carbonitrile 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 Ti⁽³⁺⁾*NO₃^(1-) 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 15.17h， 生成 [(7R,8R,9S,10R,13S,14S,17S)-17-(methoxymethoxy)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of 7α-(Fluoromethyl)dihydrotestosterone and 7α-(Fluoromethyl)nortestosterone, Structurally Paired Androgens Designed To Probe the Role of Sex Hormone Binding Globulin in Imaging Androgen Receptors in Prostate Tumors by Positron Emission Tomography

  摘要：

  Although prostate cancer growth is regulated by androgens through the androgen receptor (AR), in vitro assays of AR levels in prostate tumors have limited prognostic value. This might be improved by direct measurement of tumor AR in vivo using positron emission tomography (PET) imaging with fluorine-18-labeled androgens. Most AR PET imaging agents have been designed to limit steroid binding to serum proteins, but there is evidence that binding to sex hormone binding globulin (SHBG) might enhance tumor uptake. To probe the role of SHBG in prostate tumor uptake of PET imaging agents, we have synthesized two fluoro steroids, 7 alpha-(fluoromethyl)dihydrotestosterone (7 alpha-FM-DHT) and 7 alpha-(fluoromethyl)nortestosterone (7 alpha-FM-norT), by a route amenable to their labeling with [F-18]fluoride ion. Both compounds have high affinity for AR, but 7 alpha-FM-norT has much lower affinity for SHBG. Thus, these two fluoro steroids are well matched in terms of their site of fluorine labeling, similarity of structure, and equivalent AR binding affinitybut contrasting SHBG bindingand therefore can be used as agents for evaluating the role of SHBG binding in the target tissue uptake of AR PET imaging agents in humans.

  DOI：

  10.1021/jo070328b