2-methyl-5-nitro-benzenesulfonic acid, 2,2-dimethylpropyl ester | 299181-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methyl-5-nitro-benzenesulfonic acid, 2,2-dimethylpropyl ester
• 英文别名: 2,2-dimethylpropyl 2-methyl-5-nitrobenzenesulfonate
• CAS: 299181-86-5
• 化学式: C₁₂H₁₇NO₅S
• 分子量: 287.337
• InChiKey: SFSVUMPZAAPTKP-UHFFFAOYSA-N

物化性质

• 沸点：
  412.2±38.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methyl-5-nitro-benzenesulfonic acid, 2,2-dimethylpropyl ester 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 生成 dineopentyl 6,6'-(thiobis(methylene))bis(3-nitrobenzenesulfonate)
  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：

  新戊醇 、 2-甲基-5-硝基苯磺酰氯 在 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 以55%的产率得到2-methyl-5-nitro-benzenesulfonic acid, 2,2-dimethylpropyl 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

文献信息

• Aryl sulfonic acids and derivatives as FSH antagonists
  申请人：American Home Products Corporation

  公开号：US06355633B1

  公开（公告）日：2002-03-12

  This invention provides compounds of formula I having the structure wherein R1, Ar, Ar′, and Q are as defined in the specification, or a pharmaceutically acceptable salt thereof, which are useful as contraceptive agents.

  这项发明提供了具有结构的化合物I的公式，其中R1、Ar、Ar'和Q如规范中定义，或其药用可接受盐，这些化合物可用作避孕剂。
• Synthesis of (bis)Sulfonic acid, (bis)Benzamides as follicle-Stimulating hormone (FSH) antagonists
  作者：Jay Wrobel、Daniel Green、James Jetter、Wenling Kao、John Rogers、M Claudia Pérez、Jill Hardenburg、Darlene C Deecher、Francisco J López、Brian J Arey、Emily S Shen

  DOI：10.1016/s0968-0896(01)00324-8

  日期：2002.3

  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.