2,2'-[(E)-1,2-ethenediyl]bis(5-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}benzenesulfonic acid) bis(1-methylethyl) ester | 299181-83-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,2'-[(E)-1,2-ethenediyl]bis(5-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}benzenesulfonic acid) bis(1-methylethyl) ester
• 英文别名: propan-2-yl 5-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[(E)-2-[4-(9H-fluoren-9-ylmethoxycarbonylamino)-2-propan-2-yloxysulfonylphenyl]ethenyl]benzenesulfonate
• CAS: 299181-83-2
• 化学式: C₅₀H₄₆N₂O₁₀S₂
• 分子量: 899.055
• InChiKey: KDGMESSXYMULPN-QURGRASLSA-N

物化性质

• 沸点：
  951.0±65.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  64
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  180
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,2'-[(E)-1,2-ethenediyl]bis(5-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}benzenesulfonic acid) bis(1-methylethyl) ester 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以77%的产率得到2,2'-[(E)-1,2-ethenediyl]bis[5-aminobenzenesulfonic acid], bis(1-methylethyl) ester
  参考文献：
  名称：

  Synthesis of (bis)Sulfonic acid, (bis)Benzamides as follicle-Stimulating hormone (FSH) antagonists

  摘要：

  Screening efforts identified (bis)sulfonic acid. (bis)benzamides (1-3) as compounds that interact with the follicle stimulating-hormone receptor (FSHR) and inhibit FSH-stimulated CAMP accumulation with IC50 values in the low micromolar range. Structure-activity relationship studies using novel analogues of 1-3 revealed that two phenylsulfonic acid moieties were necessary for activity and that the carbon-carbon double bond of the stilbene sub-series was the optimum spacer connecting these groups. Selected analogues (2, 14, and 50) were also able to block FSHR-dependent estradiol production in rat primary ovarian granulosa cells and progesterone secretion in a clonal mouse adrenal Y1 cell line. IC50 values for these compounds in these assays were in the low micromolar range. Optimization of the benzoic acid side chains of 1-3 led to gains in selectivity versus activity at the thyroid stimulating hormone (TSH) receptor (TSHR). For instance, while stilbene (bis)sulfonic acid congener 2 was only 10-fold selective for FSHR over TSHR, analogue 50 with an IC50 value of 0.9 muM in the FSHR-cAMP assay was essentially inactive at 30muM in the TSHR-cAMP assay. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00324-8
• 作为产物：
  描述：

  trans-4,4'-diaminostilbene-2,2'-disulfonic acid 在 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 生成 2,2'-[(E)-1,2-ethenediyl]bis(5-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}benzenesulfonic acid) bis(1-methylethyl) ester
  参考文献：
  名称：

  Synthesis of (bis)Sulfonic acid, (bis)Benzamides as follicle-Stimulating hormone (FSH) antagonists

  摘要：

  Screening efforts identified (bis)sulfonic acid. (bis)benzamides (1-3) as compounds that interact with the follicle stimulating-hormone receptor (FSHR) and inhibit FSH-stimulated CAMP accumulation with IC50 values in the low micromolar range. Structure-activity relationship studies using novel analogues of 1-3 revealed that two phenylsulfonic acid moieties were necessary for activity and that the carbon-carbon double bond of the stilbene sub-series was the optimum spacer connecting these groups. Selected analogues (2, 14, and 50) were also able to block FSHR-dependent estradiol production in rat primary ovarian granulosa cells and progesterone secretion in a clonal mouse adrenal Y1 cell line. IC50 values for these compounds in these assays were in the low micromolar range. Optimization of the benzoic acid side chains of 1-3 led to gains in selectivity versus activity at the thyroid stimulating hormone (TSH) receptor (TSHR). For instance, while stilbene (bis)sulfonic acid congener 2 was only 10-fold selective for FSHR over TSHR, analogue 50 with an IC50 value of 0.9 muM in the FSHR-cAMP assay was essentially inactive at 30muM in the TSHR-cAMP assay. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00324-8