1-(5-hydroxy-1-benzothiophen-2-yl)ethan-1-one | 56363-81-6

• 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: 1-(5-hydroxy-1-benzothiophen-2-yl)ethan-1-one
• 英文别名: 1-(5-hydroxybenzo[b]thiophene-2-yl)ethanone；2-Acetyl-5-hydroxybenzothiophen；1-(5-hydroxy-benzo[b]thiophen-2-yl)-ethanone；1-(5-hydroxybenzo[b]thiophen-2-yl)ethan-1-one；1-(5-hydroxy-1-benzothiophen-2-yl)ethanone
• CAS: 56363-81-6
• 化学式: C₁₀H₈O₂S
• mdl: MFCD24717135
• 分子量: 192.238
• InChiKey: JUQUOEZMUSCAFN-UHFFFAOYSA-N

物化性质

• 熔点：
  190-191 °C(Solv: chloroform (67-66-3))
• 沸点：
  375.4±22.0 °C(Predicted)
• 密度：
  1.344±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO: 50mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  亚乙基硫脲 、 1-(5-hydroxy-1-benzothiophen-2-yl)ethan-1-one 在 苯基三甲基溴化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2-(5,6-dihydroimidazo[2,1-b]thiazol-3-yl)benzo[b]thiophen-4-ol hydrobromide
  参考文献：
  名称：

  Dihydroimidazo[2,1-b]thiazole and dihydro-5h-thiazolo[3,2-A]pyrimidines as antidepressant agents

  摘要：

  本发明涉及某些新颖的Formula (I)中的取代二氢咪唑[2,1-b]噻唑和二氢-5H-噻唑[3,2-a]嘧啶化合物，包括其对5-HT1A受体具有亲和力并抑制5-羟色胺和/或去甲肾上腺素的神经再摄取的药用盐，以及其制备方法，含有它们的药物组合物，以及它们在治疗抑郁症、焦虑症、精神病（例如精神分裂症）、迟发性运动障碍、肥胖症、药物成瘾、药物滥用、认知障碍、阿尔茨海默病、强迫性行为、恐慌发作、社交恐惧症、进食障碍（如暴食症、厌食症、吃零食和暴饮暴食）、非胰岛素依赖型糖尿病、高血糖、高脂血症、压力、作为戒烟辅助以及治疗和/或预防癫痫发作、癫痫等神经系统疾病以及存在神经损伤的情况（如中风、脑外伤、脑缺血、头部损伤和出血）中的用途。

  公开号：

  US20030166628A1
• 作为产物：
  描述：

  5-氨基苯并噻吩-2-羧酸甲酯 在 sodium hydrogensulfite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 49.0h， 生成 1-(5-hydroxy-1-benzothiophen-2-yl)ethan-1-one
  参考文献：
  名称：

  Hydroxybenzothiophene Ketones Are Efficient Pre-mRNA Splicing Modulators Due to Dual Inhibition of Dyrk1A and Clk1/4

  摘要：

  Dysregulated usage of pre-mRNA splicing sites contributes to the progression of cancer, neurodegenerative diseases, and viral infections. Serine/arginine-rich (SR) proteins play major roles in the splice site recognition and are largely regulated by phosphorylation. This provides an option for the pharmacological correction of aberrant splicing by inhibiting the relevant kinases. Cdc2-like kinases (Clks) and dual specificity tyrosine phosphorylation-regulated kinases (Dyrks) were both reported to phosphorylate numerous SR proteins in vitro and in vivo. In this study, we describe the discovery of new selective dual Clk/Dyrk1A/1B inhibitors, which are able to modulate alternative pre-mRNA splicing of model gene transcripts in cells with submicromolar potencies. The optimization process yielded a dual Clk and Dyrk inhibitor with exceptionally high ligand efficiency. Our results suggested that dual inhibition of both Clk1 and Dyrk1A increased the efficacy of pre-mRNA splicing modulation.

  DOI：

  10.1021/ml500059y

文献信息

• Synthesis of 2-Acylbenzo[<i>b</i>]thiophenes via Cu-Catalyzed α-C–H Functionalization of 2-Halochalcones Using Xanthate
  作者：Subramani Sangeetha、Govindasamy Sekar

  DOI：10.1021/acs.orglett.7b00462

  日期：2017.4.7

  An efficient protocol is described for the synthesis of 2-acylbenzo[b]thiophenes from easily accessible 2-iodochalcones through α-C–H functionalization using Cu(OAc)2 catalyst and xanthate as sulfur source. Less reactive 2-bromochalcones also yielded the corresponding 2-acylbenzothiophenes in good yield. The reaction proceeds via in situ incorporation of sulfur followed by copper-catalyzed cyclization

  描述了一种有效的规程，用于使用Cu（OAc）2催化剂和黄原酸酯作为硫源，通过α-C–H官能化，从易于获得的2-碘对二苯并呋喃中合成2-酰基苯并[ b ]噻吩。反应性较低的2-溴查耳酮也以良好的产率产生相应的2-酰基苯并噻吩。该反应通过硫的原位结合进行，然后进行铜催化的环化反应，生成没有外部酰基源的2-酰基苯并噻吩。合成的重要性通过1-（5-羟基苯并噻吩-2-基）乙酮的合成得到了展示，这是一种已知的mRNA前剪接调节剂。
• Anti-inflammatory phosphonate compounds
  申请人：Cannizzaro Carina

  公开号：US20060199788A1

  公开（公告）日：2006-09-07

  The invention is related to phosphorus substituted anti-inflammatory compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  该发明涉及磷取代的抗炎化合物、含有这些化合物的组合物、包括这些化合物的给药治疗方法，以及用于制备这些化合物的过程和中间体。
• ANTI-INFLAMMATORY PHOSPHONATE COMPOUNDS
  申请人：Cannizzaro Carina

  公开号：US20090247488A1

  公开（公告）日：2009-10-01

  The invention is related to phosphorus substituted anti-inflammatory compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  本发明涉及磷取代的抗炎化合物、含有这种化合物的组合物、包括给药这种化合物的治疗方法，以及用于制备这种化合物的有用过程和中间体。
• IRE-1alpha INHIBITORS
  申请人：Zeng Qingping

  公开号：US20130116247A1

  公开（公告）日：2013-05-09

  Compounds which directly inhibit IRE-1α activity in vitro, prodrugs, and pharmaceutically acceptable salts there-of. Such compounds and prodrugs are useful for treating diseases associated with the unfolded protein response or with regulated IRE1-dependent decay (RIDD) and can be used as single agents or in combination therapies.

  直接抑制IRE-1α活性的化合物、前药和其药学上可接受的盐。这些化合物和前药可用于治疗与未折叠蛋白应答或受调节的IRE1依赖性降解（RIDD）相关的疾病，并可作为单一药物或组合疗法使用。
• KRUBSACK A. J.; SEHGAL R.; LOONG W.-A.; SLACK W. E., J. ORG. CHEM. <JOCE-AH>, 1975, 40, NO 22, 3179-3182
  作者：KRUBSACK A. J.、 SEHGAL R.、 LOONG W.-A.、 SLACK W. E.

  DOI：——

  日期：——