(4-phenyl-1H-pyrrol-3-yl)(thiophen-2-yl)methanone | 286956-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (4-phenyl-1H-pyrrol-3-yl)(thiophen-2-yl)methanone
• 英文别名: (4-phenyl-1H-pyrrol-3-yl)(2-thienyl)methanone；(4-phenyl-1H-pyrrol-3-yl)-thiophen-2-ylmethanone
• CAS: 286956-22-7
• 化学式: C₁₅H₁₁NOS
• 分子量: 253.324
• InChiKey: MZFMFMYTUJBQOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-phenyl-1H-pyrrol-3-yl)(thiophen-2-yl)methanone 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 33.5h， 生成 1-[(1-Methyl-4-phenyl-1H-pyrrol-3-yl)-thiophen-2-yl-methyl]-1H-imidazole
  参考文献：
  名称：

  Massa; Di Santo; Costi, Il Farmaco, 1993, vol. 48, # 6, p. 725 - 736

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙酰基噻吩 在 potassium tert-butylate 、 sodium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 (4-phenyl-1H-pyrrol-3-yl)(thiophen-2-yl)methanone
  参考文献：
  名称：

  多磷酸介导的酰基迁移在邻域特异性合成由查尔酮组成的2-酰基吡咯中的应用

  摘要：

  本文报道了一种无金属合成2-酰基吡咯的方法。目标分子的合成从查耳酮开始，分两个步骤进行。第一步涉及通过与TosMIC反应将查尔酮转化为相应的4-取代3-酰基吡咯。在随后的步骤中，通过多磷酸介导的3酰基吡咯的酰基重排为其2酰基同类物，以中等至高收率获得了目标分子。至关重要的最后一步是在吡咯环上进行各种取代。初步的机制确定实验表明了lium离子的参与。

  DOI：

  10.1002/jhet.3494

文献信息

• Pyrrolo[1,2-a]quinoxalines from chalcones: An alternate route
  作者：Uday Kumar Togiti、Adarash Kumar Shukla、Anupam Bhattacharya

  DOI：10.1016/j.tetlet.2021.153008

  日期：2021.4

  The synthesis of 2,4-disubstituted pyrrolo[1,2-a]quinoxalines from chalcones is reported. The key steps used are polyphosphoric acid (PPA) assisted acyl rearrangement of the pyrrole ring and Fe catalyzed reduction-cyclization leading to 2,4-disubstituted pyrrolo[1,2-a]quinoxalines. Despite the utilization of comparatively unreactive aromatic ketones, modest to good yields were obtained.

  据报道，从查耳酮合成 2,4-二取代吡咯并[1,2-a]喹啉。使用的关键步骤是多磷酸 （PPA） 辅助吡咯环的酰基重排和 Fe 催化的还原环化，导致 2,4-二取代吡咯并[1,2-a]喹啉。尽管使用了相对不反应性的芳香酮，但还是获得了中等到良好的产量。
• The pyrrole moiety as a template for COX-1/COX-2 inhibitors
  作者：Gerd Dannhardt、Werner Kiefer、Godehard Krämer、Sabine Maehrlein、Ulrike Nowe、Bernd Fiebich

  DOI：10.1016/s0223-5234(00)00150-1

  日期：2000.5

  Aroyl- and thiophene-substituted pyrrole derivatives have been synthesized as a new class of COX-1/COX-2 inhibitors. The inhibition of COX-1 was evaluated in a biological system using bovine PMNLs as the enzyme source, whereas LPS-stimulated human monocytes served as the enzyme source for inducible COX-2. The determination of the concentration of arachidonic acid metabolites was performed by HPLC for COX-1 and RIA for COX-2. Variation of the substitution pattern led to a series of active compounds which showed inhibition for COX-1 and COX-2. Structural requirements for the development of COX-1/COX-2 inhibitors are discussed, (C) 2000 Editions scientifiques et medicales Elsevier SAS.
• Modulators of sperm hypermotility and uses thereof
  申请人：Chong A. Jayhong

  公开号：US20070004785A1

  公开（公告）日：2007-01-04

  The invention provides novel compositions and compounds that inhibit CatSper channel activity, that preferentially inhibits sperm hyperactivity over sperm motility, or both. The compounds of the invention are useful as contraceptive agents that may be adminstered to males, females, or concurrently to both sexual partners. The invention further provides methods of conducting drug discovery business and of conducting a reproductive medicine business. The invention also provides methods of identifying compounds that modulate sperm hypermotility.
• MODULATORS OF SPERM HYPERMOBILITY AND USES THEREOF
  申请人：Hydra Biosciences, Inc.

  公开号：US20130123310A1

  公开（公告）日：2013-05-16

  The invention provides novel compositions and compounds that inhibit CatSper channel activity, that preferentially inhibits sperm hyperactivity over sperm motility, or both. The compounds of the invention are useful as contraceptive agents that may be adminstered to males, females, or concurrently to both sexual partners. The invention further provides methods of conducting drug discovery business and of conducting a reproductive medicine business. The invention also provides methods of identifying compounds that modulate sperm hypermotility.
• US8394840B2
  申请人：——

  公开号：US8394840B2

  公开（公告）日：2013-03-12