2,5-dimethyl-1-(2-(trifluoromethyl)phenyl)-1H-pyrrole | 571-66-4

• 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-(2-(trifluoromethyl)phenyl)-1H-pyrrole
• 英文别名: 2,5-dimethyl-1-[2-(trifluoromethyl)phenyl]-1H-pyrrole；2,5-dimethyl-1-[2-(trifluoromethyl)phenyl]pyrrole
• CAS: 571-66-4
• 化学式: C₁₃H₁₂F₃N
• mdl: MFCD03449181
• 分子量: 239.24
• InChiKey: RXYYBCWWVVOBNE-UHFFFAOYSA-N

物化性质

• 沸点：
  130 °C
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-dimethyl-1-(2-(trifluoromethyl)phenyl)-1H-pyrrole 在 盐酸 、 potassium hydrogensulfate 、 N,N'-羰基二咪唑 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 9.75h， 生成 (5E)-5-[[2,5-dimethyl-1-[2-(trifluoromethyl)phenyl]pyrrol-3-yl]methylidene]-N,2-dimethyl-4-oxo-1H-pyrrole-3-carboxamide
  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 、 邻氨基三氟甲苯 以 neat (no solvent) 为溶剂， 反应 16.0h， 以55%的产率得到2,5-dimethyl-1-(2-(trifluoromethyl)phenyl)-1H-pyrrole
  参考文献：
  名称：

  Synthesis, Structure and In Vitro Anti-Trypanosomal Activity of Non-Toxic Arylpyrrole-Based Chalcone Derivatives

  摘要：

  为了确定具有抗原虫活性的蒲公英素衍生物，合成了一系列相对未被探索的基于芳基吡咯烯的蒲公英素衍生物，产率在中等到良好之间。所得化合物在体外评估其对培养的布鲁氏锥虫427株的潜在活性。几种化合物显示出主要是适度的体外抗锥虫活性，其中化合物10e和10h 显示出活性，IC50值分别为4.09和5.11微摩尔。更重要的是，对它们在人宫颈腺癌（HeLa）细胞系中的活性进行同时评估表明这些化合物无毒。

  DOI：

  10.3390/molecules25071668

文献信息

• Discovery and optimisation studies of antimalarial phenotypic hits
  作者：Alka Mital、Dinakaran Murugesan、Marcel Kaiser、Clive Yeates、Ian H. Gilbert

  DOI：10.1016/j.ejmech.2015.08.044

  日期：2015.10

  There is an urgent need for the development of new antimalarial compounds. As a result of a phenotypic screen, several compounds with potent activity against the parasite Plasmodium falciparum were identified. Characterization of these compounds is discussed, along with approaches to optimise the physicochemical properties. The in vitro antimalarial activity of these compounds against P. falciparum K1 had EC50 values in the range of 0.09-29 mu M, and generally good selectivity (typically >100-fold) compared to a mammalian cell line (L6). One example showed no significant activity against a rodent model of malaria, and more work is needed to optimise these compounds. (C) 2015 The Authors. Published by Elsevier Masson SAS.
• Improving the Potency of <i>N</i>-Aryl-2,5-dimethylpyrroles against Multidrug-Resistant and Intracellular Mycobacteria
  作者：Meir Touitou、Fabrizio Manetti、Camila Maringolo Ribeiro、Fernando Rogerio Pavan、Nicolò Scalacci、Katarina Zrebna、Neelu Begum、Dorothy Semenya、Antima Gupta、Sanjib Bhakta、Timothy D. McHugh、Hanoch Senderowitz、Melina Kyriazi、Daniele Castagnolo

  DOI：10.1021/acsmedchemlett.9b00515

  日期：2020.5.14

  A series of N-phenyl-2,5-dimethylpyrrole derivatives, designed as hybrids of the antitubercular agents BM212 and SQ109, have been synthesized and evaluated against susceptible and drug-resistant mycobacteria strains. Compound 5d, bearing a cyclohexylmethylene side chain, showed high potency against M. tuberculosis including MDR-TB strains at submicromolar concentrations. The new compound shows bacteriostatic activity and low toxicity and proved to be effective against intracellular mycobacteria too, showing an activity profile similar to isoniazid.
• Multidisciplinary approaches to reducing error and risk in a patient care setting
  作者：Maureen Connor、Patricia Reid Ponte、James Conway

  DOI：10.1016/s0899-5885(02)00017-5

  日期：2002.12

  In 1995, a medication error at Boston's Dana-Farber Cancer Institute (DFCI) that received intense media scrutiny, transformed the Institute in many ways. Primarily, patient safety became a major priority that led to Institute-wide organizational learning. As a result, DFCI emerged as a national leader in the patient safety movement. A key factor believed to have contributed to this effort was the use of a multidisciplinary team approach to identifying and preventing errors, with the patient and family members as an integral part of the team. In addition to teamwork, other activities included implementing a new chemotherapy order entry system, transforming the culture to a non-punitive one where staff are encouraged to openly discuss errors and safety issues, and introducing a root cause analysis process for error/near miss investigations. Several guiding principles served as the foundation for the efforts including: 1) systems, not individuals, must be the focus of safety initiatives; 2) organizations must create a non-punitive culture; 3) changes must be hard-wired into systems; and 4) multidisciplinary participation, including patients and families, is critical to success.
• HETEROCYCLIC CARBOXAMIDE COMPOUNDS AS STEROID NUCLEAR RECEPTOR LIGANDS
  申请人：Exelixis, Inc.

  公开号：EP1844020A1

  公开（公告）日：2007-10-17
• [EN] HETEROCYCLIC CARBOXAMIDE COMPOUNDS AS STEROID NUCLEAR RECEPTORS LIGANDS<br/>[FR] COMPOSES CARBOXAMIDES HETEROCYCLIQUES UTILISES ENT ANT QU'AGENTS PHARMACEUTIQUES
  申请人：EXELIXIS INC

  公开号：WO2006076202A1

  公开（公告）日：2006-07-20

  [EN] Heterocyclic carboxamide compounds are described herein as being useful in modulating the activity of steroid nuclear receptors. Pharmaceutical compositions containing the compounds, methods of using the compounds and processes for making the compounds are also described.
  [FR] L'invention concerne des composés carboxamides hétérocycliques utiles dans la modulation de l'activité des récepteurs nucléaires des hormones stéroïdes. Des compositions pharmaceutiques contenant lesdits composés, des méthodes d'utilisation desdits composés et leurs procédés de fabrication sont également décrits.