2'-(4-fluorophenyl)-21-(methansulfonyl)oxy-20-oxo-11β,17α-dihydroxy-pregn-4-eno[3,2-c]pyrazole | 540475-57-8

• 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: 2'-(4-fluorophenyl)-21-(methansulfonyl)oxy-20-oxo-11β,17α-dihydroxy-pregn-4-eno[3,2-c]pyrazole
• 英文别名: [2-[(1S,2R,13S,14S,17R,18S,20S)-7-(4-fluorophenyl)-17,20-dihydroxy-2,18-dimethyl-6,7-diazapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5,9-trien-17-yl]-2-oxoethyl] methanesulfonate
• CAS: 540475-57-8
• 化学式: C₂₉H₃₅FN₂O₆S
• 分子量: 558.671
• InChiKey: SEQZAIKCIJQWTQ-VVFCHSPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'-(4-fluorophenyl)-21-(methansulfonyl)oxy-20-oxo-11β,17α-dihydroxy-pregn-4-eno[3,2-c]pyrazole 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以85%的产率得到2'-(4-fluorophenyl)-21-iodo-20-oxo-11β,17α-dihydroxy-pregn-4-eno[3,2-c]pyrazole
  参考文献：
  名称：

  Synthesis of novel arylpyrazolo corticosteroids as potential ligands for imaging brain glucocorticoid receptors

  摘要：

  Corticosteroids regulate a variety of essential physiological functions, such as mineral balance and stress. The great interest in these steroids, especially the glucocorticoids, stems from roles they are thought to play in neuropsychiatric disorders, such as severe depression and anxiety.The development of glucocorticoid receptor (GR) ligands which are appropriately labeled with short-lived positron-emitting radioisotopes would allow the non-invasive in-vivo imaging and mapping of brain GRs by means of positron emission tomography (PET). In this context we have synthesized a series of novel arylpyrazolo steroids exhibiting different substitution patterns at the D-ring of the steroid skeleton, as ligands for brain GRs. Special attention was given to 4-fluorophenyl pyrazolo steroids, which are known to display high binding affinity toward the GR. The compounds were evaluated in a competitive radiometric receptor binding assay to determine their relative binding affinities (RBA) to the GR. Some compounds show good binding affinities of up to 56% in comparison to dexamethasone (100%). In initial experiments, selected candidates were labeled with the positron emitter fluorine-18 and in one case with the gamma-emitter iodine-131. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00171-x
• 作为产物：
  描述：

  在 甲酸 、 sodium acetate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 2'-(4-fluorophenyl)-21-(methansulfonyl)oxy-20-oxo-11β,17α-dihydroxy-pregn-4-eno[3,2-c]pyrazole
  参考文献：
  名称：

  甾体 C-21 杂芳基硫醚。第3部分：Pregn-4-eno-[3,2-c]吡唑稠合A环修饰类固醇作为选择性糖皮质激素受体调节剂（解离类固醇）

  摘要：

  与氢化可的松类似物相比，将 A 环吡唑修饰引入氢化可的松 C-21 杂芳基硫醚生成的化合物具有优异的反式阻抑效力（IL-8 抑制）。然而，这些化合物的转录反式激活活性明显高于相应的氢化可的松类似物。在所有评估的化合物中，喹喔啉硫醚修饰表现出最佳的整体体外分离效果。

  DOI：

  10.1016/j.bmcl.2012.03.015

文献信息

• Wuest, F.; Reul, J. M. H. M.; Rein, T., Journal of labelled compounds and radiopharmaceuticals, 2001, vol. 44, p. S12 - S14
  作者：Wuest, F.、Reul, J. M. H. M.、Rein, T.、Abel, A.、Stoecklin, G.

  DOI：——

  日期：——
• [EN] NOVEL [3,2-c] HETEROARYL STEROIDS AS GLUCOCORTICOID RECEPTOR AGONISTS, COMPOSITIONS AND USES THEREOF<br/>[FR] NOUVEAUX [3,2-C] HÉTÉROARYL STÉROÏDES EN TANT QU'AGONISTES DES RÉCEPTEURS GLUCOCORTICOÏDES, COMPOSITIONS ET UTILISATIONS DE CEUX-CI
  申请人：SCHERING CORP

  公开号：WO2010147947A3

  公开（公告）日：2011-03-03