3-((2-(methylthio)phenyl)ethynyl)pyridine | 924633-99-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-((2-(methylthio)phenyl)ethynyl)pyridine
• 英文别名: 3-[2-(2-methylsulfanylphenyl)ethynyl]pyridine
• CAS: 924633-99-8
• 化学式: C₁₄H₁₁NS
• 分子量: 225.314
• InChiKey: XKVDJPZMUKKVAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  380.4±22.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-((2-(methylthio)phenyl)ethynyl)pyridine 在 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 以82%的产率得到2-(3-pyridinyl)-3-bromobenzo[b]thiophene
  参考文献：
  名称：

  Halocyclization of 2-alkynylthioanisoles by cupric halides: synthesis of 2-substituted 3-halobenzo[b]thiophenes

  摘要：

  Reaction of 2-alkynylthioanisoles 3 with 2 equiv of CuX2 (X=Br or Cl) in refluxing CH3CN for 2.5 h gave the 2-substituted 3-halobenzo[b]thiophenes 4 in good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.068
• 作为产物：
  描述：

  3-溴吡啶 、 1-乙炔基-2-(甲硫基)苯 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以94%的产率得到3-((2-(methylthio)phenyl)ethynyl)pyridine
  参考文献：
  名称：

  Synthesis and cyclooxygenase inhibitory activities of linear 1-(methanesulfonylphenyl or benzenesulfonamido)-2-(pyridyl)acetylene regioisomers

  摘要：

  A group of 1-(aminosulfonylphenyl and methylsulfonylphenyl)-2-(pyridyl) acetylene regioisomers were designed such that a COX-2 SO2NH2 pharmacophore was located at the para-position of the phenyl ring, or a SO2Me pharmacophore was placed at the ortho-, meta- or para-position of the phenyl ring, on an acetylene template (scaffold). The point of attachment of the pyridyl ring to the acetylene linker was simultaneously varied (2-pyridyl, 3-pyridyl, 4-pyridyl, 3-methyl- 2-pyridyl) to determine the combined effects of positional, steric, and electronic substituent properties upon COX-1 and COX-2 inhibitory potency and COX isozyme selectivity. These target linear 1-(phenyl)-2-(pyridyl) acetylenes were synthesized via a palladium-catalyzed Sonogashira cross-coupling reaction. Structure-activity relationship (SAR) data (IC50 values) acquired by determination of the in vitro ability of the title compounds to inhibit the COX-1 and COX-2 isozymes showed that the position of the COX-2 SO2NH2 or SO2Me pharmacophore on the phenyl ring, and the point of attachment of the pyridyl ring to the acetylene linker, were either individual, or collective, determinants of COX-2 inhibitory potency and selectivity. A number of compounds discovered in this study, particularly 1-(4-aminosulfonylphenyl)-2-(3-methyl-2-pyridyl) acetylene (22), 1-(3-methanesulfonylphenyl)-2-(2-pyridyl) acetylene (27), 1-(3methanesulfonylphenyl)-2-(4-pyridyl)acetylene (29), 1-(4-methanesulfonylphenyl)-2-(2-pyridyl)acetylene (30), and 1-(4-methanesulfonylphenyl)2-(3-pyridyl)acetylene (31), exhibit potent (IC50 = 0.04-0.33 mu M range) and selective (SI = 18 to > 312 range) COX-2 inhibitory activities, that compare favorably with the reference drug celecoxib (COX-2 IC50 = 0.07 mu M; COX-2 SI = 473). The sulfonamide (22), and methylsulfonyl (27 and 31), compounds exhibited anti-inflammatory activities (ID50 = 59.9-76.6 mg/kg range) that were intermediate in potency between the reference drugs aspirin (ID50 = 128.7 mg/kg) and celecoxib (ID50 = 10.8 mg/kg). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.003

文献信息

• Synthesis of 3‐Arylselanyl Benzothiophenes through Visible‐Light‐Mediated Radical Cyclization
  作者：Sujith K P、Anna Lee

  DOI：10.1002/ejoc.202300257

  日期：2023.6.21

  The direct synthesis of 3-arylselanyl benzothiophenes was developed. The formation of arylselanyl radicals from diselenides in the presence of visible light enabled the direct synthesis of 3-arylselanyl benzothiophenes through intramolecular radical cyclization. The reaction does not require any catalysts or additives. This direct method provides a simple preparation route for benzothiophene derivatives

  开发了3-芳基硒基苯并噻吩的直接合成方法。在可见光存在下，二硒化物形成芳基硒基自由基，使得能够通过分子内自由基环化直接合成3-芳基硒基苯并噻吩。该反应不需要任何催化剂或添加剂。这种直接方法为苯并噻吩衍生物提供了一条简单的制备路线，苯并噻吩衍生物是有机合成中的重要支架。
• Three‐Component Synthesis of 3‐(Arylsulfonyl)benzothiophenes Using Acetic Acid as a Quencher for Methyl Radical‐Mediated Side Reactions
  作者：Vighneshwar Shridhar Bhat、Anna Lee

  DOI：10.1002/adsc.202300099

  日期：——

  one-pot, three-component synthesis of 3-(arylsulfonyl)benzothiophenes was developed. The reaction did not require any catalysts or additives. The desired products were obtained via an intramolecular radical cyclization. Acetic acid was employed as the solvent and a quencher for side reactions involving methyl radicals. Moreover, inexpensive potassium metabisulfite was used as a sulfur dioxide surrogate

  开发了 3-(芳基磺酰基) 苯并噻吩的一锅法、三组分合成法。该反应不需要任何催化剂或添加剂。通过分子内自由基环化获得所需产物。乙酸用作溶剂和涉及甲基自由基的副反应的猝灭剂。此外，廉价的焦亚硫酸钾被用作二氧化硫的替代物。该过程为合成苯并噻吩衍生物提供了更多机会，苯并噻吩衍生物存在于许多生物活性化合物中。