4-(benzo[b]thiophen-5-yl)phenyl benzenesulfonate

• 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: 4-(benzo[b]thiophen-5-yl)phenyl benzenesulfonate
• 英文别名: [4-(1-Benzothiophen-5-yl)phenyl] benzenesulfonate；[4-(1-benzothiophen-5-yl)phenyl] benzenesulfonate
• 化学式: C₂₀H₁₄O₃S₂
• 分子量: 366.461
• InChiKey: QTKBERKHOGSNQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-溴苯并[b]噻吩 在 [1,1'-二(二叔丁基膦)二茂铁]合二氯钯(II) 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 生成 4-(benzo[b]thiophen-5-yl)phenyl benzenesulfonate
  参考文献：
  名称：

  具有苯并呋喃或苯并噻吩核的磺酸盐和氨基磺酸盐衍生物作为有效的碳酸酐酶II / IX / XII抑制剂。

  摘要：

  在当前的工作中，我们报告发现了作为人碳酸酐酶（hCAs）II，IX和XII的有效抑制剂的新的苯并呋喃和苯并噻吩的磺酸盐和氨基磺酸衍生物。设计并合成了一组在稠合的苯并呋喃和苯并噻吩环上具有不同取代基的衍生物1a-t（R =烷基，环己基，芳基，NH2，NHMe或NMe2）。大多数衍生物作为纯化的hCAII，IX和XII同工型的抑制剂，其表现出比乙酰唑胺更高的效价。最有效的hCAII，hCAIX和hCAXII抑制剂为1g，1b和1d，IC50±SEM值分别为0.14±0.03、0.13±0.03和0.17±0.06 µM。此外，化合物1d和1n对hCAXII同工酶具有良好的抑制作用。

  DOI：

  10.1016/j.bmc.2019.07.026

文献信息

• Sulfonate and sulfamate derivatives possessing benzofuran or benzothiophene nucleus as potent carbonic anhydrase II/IX/XII inhibitors
  作者：Seyed-Omar Zaraei、Mohammed I. El-Gamal、Zainab Shafique、Sayyeda Tayyeba Amjad、Saifullah Afridi、Sumera Zaib、Hanan S. Anbar、Randa El-Gamal、Jamshed Iqbal

  DOI：10.1016/j.bmc.2019.07.026

  日期：2019.9

  discovery of new sulfonate and sulfamate derivatives of benzofuran- and benzothiophene as potent inhibitors of human carbonic anhydrases (hCAs) II, IX and XII. A set of derivatives, 1a-t, having different substituents on the fused benzofuran and benzothiophene rings (R = alkyl, cyclohexyl, aryl, NH2, NHMe, or NMe2) was designed and synthesized. Most of the derivatives exhibited higher potency than acetazolamide

  在当前的工作中，我们报告发现了作为人碳酸酐酶（hCAs）II，IX和XII的有效抑制剂的新的苯并呋喃和苯并噻吩的磺酸盐和氨基磺酸衍生物。设计并合成了一组在稠合的苯并呋喃和苯并噻吩环上具有不同取代基的衍生物1a-t（R =烷基，环己基，芳基，NH2，NHMe或NMe2）。大多数衍生物作为纯化的hCAII，IX和XII同工型的抑制剂，其表现出比乙酰唑胺更高的效价。最有效的hCAII，hCAIX和hCAXII抑制剂为1g，1b和1d，IC50±SEM值分别为0.14±0.03、0.13±0.03和0.17±0.06 µM。此外，化合物1d和1n对hCAXII同工酶具有良好的抑制作用。
• Evaluation of sulfonate and sulfamate derivatives possessing benzofuran or benzothiophene nucleus as inhibitors of nucleotide pyrophosphatases/phosphodiesterases and anticancer agents
  作者：Hanan S. Anbar、Randa El-Gamal、Saif Ullah、Seyed-Omar Zaraei、Mariya al-Rashida、Sumera Zaib、Julie Pelletier、Jean Sévigny、Jamshed Iqbal、Mohammed I. El-Gamal

  DOI：10.1016/j.bioorg.2020.104305

  日期：2020.11

  Ectonucleotidases are a broad family of ectoenzymes that play a crucial role in purinergic cell signaling. Ectonucleotide pyrophosphatases/phosphodiesterases (NPPs) belong to this group and are important drug targets. In particular, NPP1 and NPP3 are known to be druggable targets for treatment of impaired calcification disorders (including pathological aortic calcification) and cancer, respectively. In this study, we investigated a series of sulfonate and sulfamate derivatives of benzofuran and benzothiophene as potent and selective inhibitors of NPP1 and NPP3. Compounds 1c, 1g, 1n, and 1s are the most active NPP1 inhibitors (IC50 values in the range 0.12-0.95 mu M). Moreover, compounds 1e, 1f, 1j, and 1l are the most potent inhibitors of NPP3 (IC50 ranges from 0.12 to 0.95 mu M). Compound 1d, 1f and 1t are highly selective inhibitors of NPP1 over NPP3, whereas compounds 1m and 1s are found to be highly selective towards NPP3 over NPP1. Structure-activity relationship (SAR) study has been discussed in detailed. With the aid of molecular docking studies, a common binding mode of these compounds and suramin (the standard inhibitor) was revealed, where the sulfonate group acts as a cation-binding moiety that comes in close contact with the zinc ion of the active site. Moreover, cytotoxic evaluation against MCF-7 and HT-29 cancer cell lines revealed that compound 1r is the most cytotoxic towards MCF-7 cell line with IC50 value of 0.19 mu M. Compound 1r is more potent and selective against cancer cells than normal cells (WI-38) as compared to doxorubicin.