3-(benzenesulfonyl)-4-phenoxyfuroxan | 1237752-72-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(benzenesulfonyl)-4-phenoxyfuroxan
• 英文别名: 4-phenyloxy-3-phenylsulfonylfuroxan；3-(benzenesulfonyl)-2-oxido-4-phenoxy-1,2,5-oxadiazol-2-ium
• CAS: 1237752-72-5
• 化学式: C₁₄H₁₀N₂O₅S
• 分子量: 318.31
• InChiKey: UVZTYJQVZKHPTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(benzenesulfonyl)-4-phenoxyfuroxan 、 4-苯基丁酸 在 dipotassium peroxodisulfate 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 30.0h， 以75%的产率得到4-phenoxy-3-(3-phenylpropyl)furoxan
  参考文献：
  名称：

  通过自由基加成途径模块化合成碳取代的呋喃烷。基于“构建并报废”策略的脂肪族羧酸转化的有用工具。

  摘要：

  利用自由基化学，开发了在呋喃环上形成新的一般CC键的方法。通过利用呋喃喃的不稳定性，已证明了合成呋喃烷的多种转化。因此，这种发达的方法学不仅使呋喃喃的模块合成成为可能，而且使羧酸能够短时转化为各种官能团。

  DOI：

  10.1021/acs.orglett.0c00062
• 作为产物：
  描述：

  呋咱氮氧化物供体 、 苯酚 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以60%的产率得到3-(benzenesulfonyl)-4-phenoxyfuroxan
  参考文献：
  名称：

  Phenylsulfonylfuroxans as Modulators of Multidrug-Resistance-Associated Protein-1 and P-Glycoprotein

  摘要：

  A series of furoxan derivatives were studied for their ability to interact with P-gp and MRP1 transporters in MDCK cells overexpressing these proteins. 3-Phenylsulfonyl substituted furoxans emerged as the most interesting compounds. All of them were capable of inhibiting P-gp, and a few also were capable of inhibiting MRP1. Substituents at the 4-position of 3-phenylsulfonylfuroxan scaffold were able to modulate the selectivity and the intensity of inhibition. In some cases, they reverted MRP1 inhibitor activity, namely, they were capable of potentiating MRP1 dependent efflux. When compounds 16 and 17 were coadministered with doxorubicin, they restored a high degree of the activity of the antibiotic. Preliminary immunoblotting studies carried out on these two compounds indicate that they are capable of nitrating P-gp, which in this form is likely unable to efflux the antibiotic.

  DOI：

  10.1021/jm100066y

文献信息

• Modular Synthesis of Carbon-Substituted Furoxans via Radical Addition Pathway. Useful Tool for Transformation of Aliphatic Carboxylic Acids Based on “Build-and-Scrap” Strategy
  作者：Ryosuke Matsubara、Hojin Kim、Takaya Sakaguchi、Weibin Xie、Xufeng Zhao、Yuto Nagoshi、Chaoyu Wang、Masahiro Tateiwa、Akihiro Ando、Masahiko Hayashi、Masahiro Yamanaka、Takao Tsuneda

  DOI：10.1021/acs.orglett.0c00062

  日期：2020.2.7

  Utilizing radical chemistry, a new general C-C bond formation on the furoxan ring was developed. By taking advantage of the lability of furoxans, a wide variety of transformation of the synthesized furoxans have been demonstrated. Thus, this developed methodology enabled not only the modular synthesis of furoxans but also short-step transformations of carboxylic acids to a broad range of functional

  利用自由基化学，开发了在呋喃环上形成新的一般CC键的方法。通过利用呋喃喃的不稳定性，已证明了合成呋喃烷的多种转化。因此，这种发达的方法学不仅使呋喃喃的模块合成成为可能，而且使羧酸能够短时转化为各种官能团。
• Phenylsulfonylfuroxans as Modulators of Multidrug-Resistance-Associated Protein-1 and P-Glycoprotein
  作者：Roberta Fruttero、Marco Crosetti、Konstantin Chegaev、Stefano Guglielmo、Alberto Gasco、Francesco Berardi、Mauro Niso、Roberto Perrone、Maria Antonietta Panaro、Nicola Antonio Colabufo

  DOI：10.1021/jm100066y

  日期：2010.8.12

  A series of furoxan derivatives were studied for their ability to interact with P-gp and MRP1 transporters in MDCK cells overexpressing these proteins. 3-Phenylsulfonyl substituted furoxans emerged as the most interesting compounds. All of them were capable of inhibiting P-gp, and a few also were capable of inhibiting MRP1. Substituents at the 4-position of 3-phenylsulfonylfuroxan scaffold were able to modulate the selectivity and the intensity of inhibition. In some cases, they reverted MRP1 inhibitor activity, namely, they were capable of potentiating MRP1 dependent efflux. When compounds 16 and 17 were coadministered with doxorubicin, they restored a high degree of the activity of the antibiotic. Preliminary immunoblotting studies carried out on these two compounds indicate that they are capable of nitrating P-gp, which in this form is likely unable to efflux the antibiotic.