17-(2-Iodovinyl)dihydrotestosterone | 129163-98-0

• 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: 17-(2-Iodovinyl)dihydrotestosterone
• 英文别名: (5S,8R,9S,10S,13S,14S,17R)-17-hydroxy-17-[(E)-2-iodoethenyl]-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 129163-98-0
• 化学式: C₂₁H₃₁IO₂
• 分子量: 442.38
• InChiKey: DWUIOIDQYOFBEC-GXDIAVKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 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

• 作为产物：
  描述：

  表雄酮 在 氢氧化钾 、 四丙基高钌酸铵 、 偶氮二异丁腈 、 4 A molecular sieve 、 甲基锂 、 碘 、 三正丁基氢锡 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 22.5h， 生成 17-(2-Iodovinyl)dihydrotestosterone
  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

• SALMAN, MOHAMMAD;CHAMNESS, GARY C., J. MED. CHEM., 34,(1991) N, C. 1019-1024
  作者：SALMAN, MOHAMMAD、CHAMNESS, GARY C.

  DOI：——

  日期：——
• A potential radioiodinated ligand for androgen receptor: 7.alpha.-methyl-17.alpha.-[2'-(E)-iodovinyl]-19-nortestosterone
  作者：Mohammad Salman、Gary C. Chamness

  DOI：10.1021/jm00107a021

  日期：1991.3

  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.