4-(benzo[b]thiophen-5-yl)phenol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 4-(benzo[b]thiophen-5-yl)phenol
• 英文别名: 4-(Benzo[b]thiophen-5-yl)phenol；4-(1-benzothiophen-5-yl)phenol
• 化学式: C₁₄H₁₀OS
• 分子量: 226.299
• InChiKey: JSBLFIMMOLWVIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(benzo[b]thiophen-5-yl)phenol 在 sodium hydride 、 氨基磺酰氯 作用下， 以 N,N-二甲基乙酰胺 、 mineral oil 为溶剂， 反应 0.25h， 以57%的产率得到4-(benzo[b]thiophen-5-yl)phenyl sulfamate
  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
• 作为产物：
  描述：

  5-溴苯并[b]噻吩 、 4-羟基苯硼酸 在 [1,1'-二(二叔丁基膦)二茂铁]合二氯钯(II) 、 caesium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 生成 4-(benzo[b]thiophen-5-yl)phenol
  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

• PIPERIDINE DERIVATIVES FOR GPR119 AGONIST
  申请人：CHONG KUN DANG PHARMACEUTICAL CORP.

  公开号：US20150166480A1

  公开（公告）日：2015-06-18

  The present invention relates to novel piperidine derivatives, stereoisomers thereof or pharmaceutically acceptable salts thereof; methods for preparing the compound; and pharmaceutical compositions comprising the compound. The novel piperidine derivatives, according to the present invention, having an effect as GPR119 agonist can be used for treatment of metabolic disorders, including diabetes mellitus (especially type II) and related disorders.

  本发明涉及新型的哌啶衍生物、它们的立体异构体或药用可接受的盐；制备该化合物的方法；以及包含该化合物的药物组合物。根据本发明，具有GPR119激动剂作用的新型哌啶衍生物可用于治疗代谢紊乱，包括糖尿病（尤其是II型）及相关疾病。
• [EN] PIPERIDINE DERIVATIVES FOR GPR119 AGONIST<br/>[FR] DÉRIVÉS DE PIPÉRIDINE AGONISTES DE GPR119
  申请人：CHONG KUN DANG PHARM CORP

  公开号：WO2013187646A1

  公开（公告）日：2013-12-19

  The present invention relates to novel piperidine derivatives, stereoisomers thereof or pharmaceutically acceptable salts thereof; methods for preparing the compound; and pharmaceutical compositions comprising the compound. The novel piperidine derivatives, according to the present invention, having an effect as GPR119 agonist can be used for treatment of metabolic disorders, including diabetes mellitus (especially type II) and related disorders.

  本发明涉及新型哌啶衍生物，其立体异构体或其药学上可接受的盐；制备该化合物的方法；以及包含该化合物的药物组合物。根据本发明，具有GPR119激动剂作用的新型哌啶衍生物可用于治疗代谢性疾病，包括糖尿病（特别是II型）及相关疾病。
• Electrochemical Reduction of Benzo[<i>b</i>]thiophene 1,<scp>1‐Dioxides</scp> with <scp>HFIP</scp> as Hydrogen Donor^†
  作者：Ming‐Zhong Guo、Mei‐Jin Mou、Zhuo Chen、Shao‐Fei Ni、Ming Li、Li‐Rong Wen、Lin‐Bao Zhang

  DOI：10.1002/cjoc.202300527

  日期：2024.3.15

  A straightforward electrochemical reduction of benzo[b]thiophene 1,1-dioxides with HFIP as the hydrogen donor has been reported in an undivided cell under metal-free conditions. Moreover, the tolerance of various functional groups and scaled-up experiments showed the practicability and potential applications of this methodology.

  据报道，在无金属条件下，在未分割的电池中，以 HFIP 作为氢供体，可以直接电化学还原苯并[ b ]噻吩 1,1-二氧化物。此外，各种官能团的耐受性和放大实验表明了该方法的实用性和潜在应用。
• 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.
• PIPERIDINE DERIVATIVES AS GPR119 AGONISTS
  申请人：Chong Kun Dang Pharmaceutical Corp.

  公开号：EP2858986B1

  公开（公告）日：2019-10-30