(7R,8R,9S,10R,13S,14S,17R)-17-羟基-17-[(E)-2-碘乙烯基]-7,13-二甲基-1,2,6,7,8,9,10,11,12,14,15,16-十二氢环戊烯并[a]菲-3-酮 | 131545-89-6

• 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
• 中文名称: (7R,8R,9S,10R,13S,14S,17R)-17-羟基-17-[(E)-2-碘乙烯基]-7,13-二甲基-1,2,6,7,8,9,10,11,12,14,15,16-十二氢环戊烯并[a]菲-3-酮
• 英文名称: E-7α-methyl-17α-(2'-iodovinyl)-19-nortestosterone
• 英文别名: Mivnt；(7R,8R,9S,10R,13S,14S,17R)-17-hydroxy-17-[(E)-2-iodoethenyl]-7,13-dimethyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 131545-89-6
• 化学式: C₂₁H₂₉IO₂
• 分子量: 440.365
• InChiKey: ZYZDMAJYGAZXEO-NOWBUFNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  曲托龙 在 偶氮二异丁腈 、 碘 、 三正丁基氢锡 作用下， 反应 24.5h， 生成 (7R,8R,9S,10R,13S,14S,17R)-17-羟基-17-[(E)-2-碘乙烯基]-7,13-二甲基-1,2,6,7,8,9,10,11,12,14,15,16-十二氢环戊烯并[a]菲-3-酮
  参考文献：
  名称：

  7α-Methyl-17α-(E-2'-[125I]iodovinyl)-19-nortestosterone: a new radioligand for the detection of androgen receptor

  摘要：

  We have synthesized two gamma-emitting, I-125-labeled steroids, E- and Z-7alpha-methyl-17alpha-(2'-[I-125]iodovinyl)-19-nortestosterone [I-125](E- and Z-MIVNT) for specific labeling of androgen receptors. [I-125]E- and [I-125]Z-MIVNT were synthesized stereospecifically from E- and Z-7alpha-methyl-17alpha-(2'-tri-n-butylstannyl-vinyl)-19-nortestosterone. The tin adducts were prepared by addition of tri-n-butyltin hydride to 7alpha-methyl-17alpha-ethynyl-19-nortestosterone, and after purification they were converted in high yield to the [I-125]MIVNT isomers by reaction with I-125 (generated in situ by oxidation of[I-125]iodide with chloramine T). The I-125-labeled products were purified by high-performance liquid chromatography, and their mass determined with an ultraviolet detector (specific activity of both, approximately 2,200 Ci/mmol). In rat prostate cytosol, [I-125]E-MIVNT bound with high affinity to a single class of binding sites. Nonspecific binding in the presence of 5alpha-dihydrotestosterone was relatively low, and compared favorably with that obtained in parallel studies with [H-3]methyltrienolone (R1881). The E-isomer bound prostate cytosol with at least twice the affinity of the Z-isomer; therefore, the interaction of the E-isomer with the androgen receptor as well as other steroid receptors was studied in greater detail. Complexes of the androgen receptor with [I-125]E-MIVNT as well as [H-3]R1881 dissociate very slowly at 4C (k(diss) for both = 0.04 h-1). Displacement studies showed that the interaction of[I-125]E-MIVNT with the androgen receptor is highly specific. Competition studies showed that unlabeled E-MIVNT binds poorly to other steroid receptors in rat tissue cytosols. These binding properties make [I-125]E-MIVNT a promising ligand for study of the androgen receptor, and [I-125] E-MIVNT a potential imaging agent for the detection of androgen-dependent tumors, such as prostate cancer.

  DOI：

  10.1016/0039-128x(93)90012-c