(17α,20E)-21-(tributylstannyl)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol | 82123-95-3

• 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,20E)-21-(tributylstannyl)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol
• 英文别名: (17α,20E)-21-(tri-n-butylstannyl)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol；17α-E-tri-n-butylstannylvinyl estradiol；(17α,20E)-21-(tri-n-butylstannyl)-19-norpregna-1,3,5(10)20-tetraene-3,17β-diol；(8R,9S,13S,14S,17R)-13-methyl-17-[(E)-2-tributylstannylethenyl]-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 82123-95-3
• 化学式: C₃₂H₅₂O₂Sn
• 分子量: 587.474
• InChiKey: OSJLWOIVHGBLDP-GRTMZFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.92
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (17α,20E)-21-(tributylstannyl)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol 在 碘 作用下， 以 氯仿 为溶剂， 以82.5%的产率得到[125I]-(E)-(Iodovinyl)estradiol
  参考文献：
  名称：

  Synthesis, receptor binding, and tissue distribution of (17.alpha.,20E)- and (17.alpha.,20Z)-21-[125I]Iodo-19-norpregna-1,3,5-(10),20-tetraene-3,17-diol

  摘要：

  The isomeric (17 alpha,20E)- and (17 alpha,20Z)-(iodovinyl)estradiol derivatives 3 and 6, and their no-carrier-added (nca) [125I]iodovinyl analogues, were tested for their relative target tissue retention and binding affinity for the estrogen receptor. The (iodovinyl)estradiols 3 and 6 were prepared via destannylation of the (17 alpha,20E)- and (17 alpha,20Z)-tributylstannyl precursors 2 and 4 with retention of configuration. Selective formation of the E or Z isomers 2 and 4 during the reaction of 17 alpha-ethynylestradiol 1a with tri-n-butyltin hydride was controlled by the presence or absence of the catalyst, the polarity of the solvent, and the reaction temperature. The nca [125I]iodovinyl analogues [125I]-3a and [125I]-6a were obtained in good radiochemical yield and high purity by treatment of 2a and 4a with [125I]NaI in the presence of H2O2 and chloroamine-T, respectively. Of the two isomeric iodovinyl derivatives 3 and 6, the 20Z isomer 6a exhibited the highest receptor binding affinity and the [125I]-6a gave the highest in vivo receptor-mediated target tissue uptake.

  DOI：

  10.1021/jm00118a013
• 作为产物：
  描述：

  19-去甲孕甾-1,3,5(10)-三烯-20-炔-3,17-二醇 生成 (17α,20E)-21-(tributylstannyl)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol
  参考文献：
  名称：

  PILLAI, K. M. R.;MCLAUGHLIN, W. H.;LAMBRECHT, R. M.;BLOOMER, W. D., J. LABELL. COMPOUNDS AND RADIOPHARM., 24,(1987) N 9, 1117-1122

  摘要：

  DOI：

文献信息

• Anti-proliferative activities of flavone–estradiol Stille-coupling adducts and of indanone-based compounds obtained by SnCl₄/Zn-catalysed McMurry cross-coupling reactions
  作者：Gulab Khushalrao Pathe、Naveen K. Konduru、Iram Parveen、Naseem Ahmed

  DOI：10.1039/c5ra15685h

  日期：——

  Flavone–estradiol adducts and indanophen based tamoxifen analogs are synthesized using SnCl₄–Zn reagent via McMurry reaction and evaluated in human cervical (HeLa) and breast cancer cells (MCF-7 and MDA-MB-231) for the anti-proliferative activity.

  使用SnCl₄–Zn试剂通过MCMurry反应合成黄酮-雌二醇加合物和基于indanophen的他莫昔芬类似物，并在人宫颈癌（HeLa）和乳腺癌细胞（MCF-7和MDA-MB-231）中评估其抗增殖活性。
• Synthesis of benzoylbenzamide derivatives of 17α-E-vinyl estradiol and evaluation as ligands for the estrogen receptor-α ligand binding domain
  作者：Robert N. Hanson、Emmett McCaskill、Edward Hua、Pakamas Tongcharoensirikul、Robert Dilis、Jessa L. Silver、Timothy A. Coulther、Mary Jo Ondrechen、David Labaree、Richard B. Hochberg

  DOI：10.1016/j.steroids.2019.02.003

  日期：2019.4

  A series consisting of substituted benzoylbenzamide derivatives of 17 alpha-E-vinyl estradiol 6a-i and 7a-d was prepared in good overall yields from the corresponding novel iodinated benzoylbenzamide precursors using Pd (0)-catalyzed Stille coupling. Biological evaluation using competitive binding assays indicated that all compounds were effective ligands for the ER alpha- and ER beta-LBD (RBA = 0.5-10.0% of estradiol). Most of the compounds expressed lower stimulatory (agonist) potency (RSA < 0.2-0.5%) compared to their binding affinity, however, the meta-substituted isomer 6h demonstrated a level of efficacy (RSA = 5.7%) comparable to its affinity (RBA = 9.5%). Docking studies of 6b, 6h, and 6i with the 2YAT crystal structure suggested that higher affinity and efficacy of 6h are due to an effective set of interactions with exposed receptor sidechains not observed with the ortho- and para- isomers. In this binding model, the terminal ring of the ligand is exposed to the solvent space, which would explain both the small variation in RBA values and the narrow SAR for the diverse structural features.
• Targeting the estrogen receptor with metal-carbonyl derivatives of estradiol
  作者：Robert N. Hanson、Rein Kirss、Emmett McCaskill、Edward Hua、Pakamas Tongcharoensirikul、Sandra L. Olmsted、David Labaree、Richard B. Hochberg

  DOI：10.1016/j.bmcl.2011.12.111

  日期：2012.2

  As part of our program to develop new probes for the estrogen receptor binding domain, we prepared and evaluated a novel 17 alpha-(rhenium tricarbonyl bipyridyl) vinyl estradiol complex. Preparation of the final compound was achieved using the Stille coupling between the preformed brominated rhenium tricarbonyl bipyridine complex and the tributylstannyl vinyl estradiol. Competitive receptor binding assays and stimulatory assays demonstrated that the final complex retained affinity and efficacy comparable to the corresponding pyridyl vinyl estradiol analog, but lower than that of the phenyl vinyl estradiol analog. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of 17α-E-20-(heteroaryl)norpregn-1,3,5(10),20 tetraene-3,17β-diols [17α-(heteroaryl)vinyl estradiols] as ligands for the estrogen receptor-α ligand binding domain (ERα-LBD)
  作者：Sandra L. Olmsted、Pakamas Tongcharoensirikul、Emmett McCaskill、Karla Gandiaga、David Labaree、Richard B. Hochberg、Robert N. Hanson

  DOI：10.1016/j.bmcl.2011.12.003

  日期：2012.1

  A series of 17 alpha-(heteroaryl)vinyi estradiols was prepared to evaluate the influence of heteroatom on the affinity and efficacy of estrogenic ligands for the estrogen receptor-alpha ligand binding domain (ER alpha-LBD). The products demonstrated reduced binding affinity compared to the parent 17 alpha-E-phenylvinyl estradiol, but the binding was relatively independent of the heteroatom. The greatest influence of the heteroatom was evident in the efficacy of the compounds as the thienyl derivatives 2f,g were more potent than either the pyridyl 2b-d or pyrimidinyl 2e analogs. The results suggest that a subtle interplay of interactions between the ligands and the receptor influences the biological response. (C) 2011 Elsevier Ltd. All rights reserved.
• HANSON, ROBERT N.;EL-WAKIL, HODA;MURPHY, FRANCIS;WILBUR, D. SCOTT, J. LABELL. COMPOUNDS AND RADIOPHARM., 27,(1989) N, C. 615-627
  作者：HANSON, ROBERT N.、EL-WAKIL, HODA、MURPHY, FRANCIS、WILBUR, D. SCOTT

  DOI：——

  日期：——