2,5-dimethyl-1-[4-(methylthio)phenyl]-1H-pyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,5-dimethyl-1-[4-(methylthio)phenyl]-1H-pyrrole
• 英文别名: 2,5-dimethyl-1-(4-methylsulfanyl-phenyl)-pyrrole；2,5-Dimethyl-1-(4-methylmercapto-phenyl)-pyrrol；2,5-Dimethyl-1-(4-methylsulfanylphenyl)pyrrole
• 化学式: C₁₃H₁₅NS
• mdl: MFCD12187261
• 分子量: 217.335
• InChiKey: UMENFUSIIJTXFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,5-dimethyl-1-[4-(methylthio)phenyl]-1H-pyrrole 在 potassium hydrogensulfate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 6.25h， 生成 ethyl (5E)-5-[[2,5-dimethyl-1-(4-methylsulfanylphenyl)pyrrol-3-yl]methylidene]-2-methyl-4-oxo-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Discovery and Structure–Activity Relationships of Pyrrolone Antimalarials

  摘要：

  In the pursuit of new antimalarial leads, a phenotypic screening of various commercially sourced compound libraries was undertaken by the World Health Organisation Programme for Research and Training in Tropical Diseases (WHO-TDR). We report here the detailed characterization of one of the hits from this process, TDR32750 (8a), which showed potent activity against Plasmodium falciparum K1 (EC50 similar to 9 nM), good selectivity (>2000-fold) compared to a mammalian cell line (L6), and significant activity against a rodent model of malaria when administered intraperitoneally. Structure-activity relationship studies have indicated ways in which the molecule could be optimized. This compound represents an exciting start point for a drug discovery program for the development of a novel antimalarial.

  DOI：

  10.1021/jm400009c
• 作为产物：
  描述：

  2,5-己二酮 、 4-氨基茴香硫醚 在 silica gel 、 对甲苯磺酸 作用下， 以 neat (no solvent) 为溶剂， 以84%的产率得到2,5-dimethyl-1-[4-(methylthio)phenyl]-1H-pyrrole
  参考文献：
  名称：

  Discovery and Structure–Activity Relationships of Pyrrolone Antimalarials

  摘要：

  In the pursuit of new antimalarial leads, a phenotypic screening of various commercially sourced compound libraries was undertaken by the World Health Organisation Programme for Research and Training in Tropical Diseases (WHO-TDR). We report here the detailed characterization of one of the hits from this process, TDR32750 (8a), which showed potent activity against Plasmodium falciparum K1 (EC50 similar to 9 nM), good selectivity (>2000-fold) compared to a mammalian cell line (L6), and significant activity against a rodent model of malaria when administered intraperitoneally. Structure-activity relationship studies have indicated ways in which the molecule could be optimized. This compound represents an exciting start point for a drug discovery program for the development of a novel antimalarial.

  DOI：

  10.1021/jm400009c

文献信息

• Applying green chemistry principles to iron catalysis: mild and selective domino synthesis of pyrroles from nitroarenes
  作者：Johannes Fessler、Kathrin Junge、Matthias Beller

  DOI：10.1039/d3sc02879h

  日期：——

  An efficient and general cascade synthesis of pyrroles from nitroarenes using an acid-tolerant homogeneous iron catalyst is presented. Initial (transfer) hydrogenation using the commercially available iron–Tetraphos catalyst is followed by acid catalysed Paal–Knorr condensation. Both formic acid and molecular hydrogen can be used as green reductants in this process. Particularly, under transfer hydrogenation

  提出了一种使用耐酸均相铁催化剂从硝基芳烃高效且通用地级联合成吡咯的方法。使用市售的铁-Tetraphos 催化剂进行初始（转移）氢化，然后进行酸催化的 Paal-Knorr 缩合。甲酸和分子氢均可用作该过程中的绿色还原剂。特别是在转移氢化条件下，均相催化剂在低温下表现出显着的反应活性、高官能团耐受性和优异的化学选择性，可转化多种底物。与经典的多相催化剂相比，该体系具有互补的反应活性，不存在脱卤、脱苄基、芳烃或烯烃加氢等典型副反应。因此，它在正交反应性方面增强了化学工具箱。该方法已成功应用于多功能类药物分子的后期修饰以及生物活性剂BM-635的一锅法合成。
• Buu-Hoi et al., Bulletin de la Societe Chimique de France, 1947, p. 128,135
  作者：Buu-Hoi et al.

  DOI：——

  日期：——
• Discovery and Structure–Activity Relationships of Pyrrolone Antimalarials
  作者：Dinakaran Murugesan、Alka Mital、Marcel Kaiser、David M. Shackleford、Julia Morizzi、Kasiram Katneni、Michael Campbell、Alan Hudson、Susan A. Charman、Clive Yeates、Ian H. Gilbert

  DOI：10.1021/jm400009c

  日期：2013.4.11

  In the pursuit of new antimalarial leads, a phenotypic screening of various commercially sourced compound libraries was undertaken by the World Health Organisation Programme for Research and Training in Tropical Diseases (WHO-TDR). We report here the detailed characterization of one of the hits from this process, TDR32750 (8a), which showed potent activity against Plasmodium falciparum K1 (EC50 similar to 9 nM), good selectivity (>2000-fold) compared to a mammalian cell line (L6), and significant activity against a rodent model of malaria when administered intraperitoneally. Structure-activity relationship studies have indicated ways in which the molecule could be optimized. This compound represents an exciting start point for a drug discovery program for the development of a novel antimalarial.