1-[2-(三氟甲基)苯基]-1H-吡咯-3-甲醛 | 864548-01-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-[2-(三氟甲基)苯基]-1H-吡咯-3-甲醛
• 英文名称: 1-(2-(trifluoromethyl)phenyl)-1H-pyrrole-3-carbaldehyde
• 英文别名: 1-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carbaldehyde；1-[2-(trifluoromethyl)phenyl]pyrrole-3-carbaldehyde
• CAS: 864548-01-6
• 化学式: C₁₂H₈F₃NO
• 分子量: 239.197
• InChiKey: RUGAAPBKNGMDJR-UHFFFAOYSA-N

物化性质

• 沸点：
  320.9±42.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-methyl-3-oxo-1,2-dihydropyrrole-4-carboxylate 、 1-[2-(三氟甲基)苯基]-1H-吡咯-3-甲醛 在 potassium hydrogensulfate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以52%的产率得到ethyl (5E)-2-methyl-4-oxo-5-[[1-[2-(trifluoromethyl)phenyl]pyrrol-3-yl]methylidene]-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：

  邻氨基三氟甲苯 在 溶剂黄146 、 三氯氧磷 作用下， 反应 3.0h， 生成 1-[2-(三氟甲基)苯基]-1H-吡咯-3-甲醛
  参考文献：
  名称：

  Phenylpyrroles, a new chemolibrary virtual screening class of 5-HT7 receptor ligands

  摘要：

  Virtual screening studies have identified a series of phenylpyrroles as novel 5-HT7 receptor ligands. The synthesis and the affinity for the 5-HT7 receptor of these phenylpyrroles are described. Some of these compounds exhibited high affinity for the 5-HT7 receptors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.059

文献信息

• [EN] IMIDAZOLE-BASED ANTIMICROBIAL AGENTS<br/>[FR] AGENTS ANTIMICROBIENS À BASE D'IMIDAZOLE
  申请人：PROCOMCURE BIOTECH GMBH

  公开号：WO2016087618A1

  公开（公告）日：2016-06-09

  The present invention relates to novel therapeutic agents suitable for use in the treatment of mammalian disease and in particular to novel therapeutic agents suitable for use in the treatment of microbial infection in mammals. The present invention further relates to the use of pharmaceutical compositions comprising said agents in the treatment of medical conditions in mammals, in particular in the treatment of microbial infection. The agents and pharmaceutical compositions of the invention are of particular relevance in the treatment of diseases associated with antibiotic-resistant microbes.

  本发明涉及新型治疗剂，适用于治疗哺乳动物疾病，特别是适用于治疗哺乳动物微生物感染的新型治疗剂。本发明还涉及包含上述剂的药物组合物在治疗哺乳动物的医疗状况中的使用，特别是在治疗微生物感染中的使用。本发明的剂和药物组合物在治疗与抗生素耐药微生物相关的疾病方面具有特殊意义。
• [EN] NOVEL IMIDAZOLE-BASED HETEROCYCLIC COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS HÉTÉROCYCLIQUES À BASE D'IMIDAZOLE
  申请人：PROCOMCURE BIOTECH GMBH

  公开号：WO2016087615A1

  公开（公告）日：2016-06-09

  The present invention relates to novel compounds of formula (I) suitable e.g. as therapeutic agents for use in the treatment of mammalian disease and in particular to novel therapeutic agents suitable for use in the treatment of microbial infection in mammals. The present invention further relates to the use of pharmaceutical compositions comprising said agents in the treatment of medical conditions in mammals, in particular in the treatment of microbial infection. The agents and pharmaceutical compositions of the invention are of particular relevance in the treatment of diseases associated with antibiotic-resistant microbes. The present invention also relates to processes for making said agents.

  本发明涉及一种新型化合物，其化学式为(I)，适用于作为治疗剂用于治疗哺乳动物疾病，特别是适用于治疗哺乳动物微生物感染的新型治疗剂。本发明还涉及包含所述治疗剂的药物组合物在治疗哺乳动物的医疗状况中的使用，特别是在治疗微生物感染方面的使用。本发明的治疗剂和药物组合物在治疗与抗生素耐药微生物相关的疾病方面具有特殊的相关性。本发明还涉及制备所述治疗剂的方法。
• Imidazole-based heterocyclic compounds
  申请人：Procomcure Biotech GmbH

  公开号：US10314820B2

  公开（公告）日：2019-06-11

  The present invention relates to novel compounds of formula (I) suitable e.g. as therapeutic agents for use in the treatment of mammalian disease and in particular to novel therapeutic agents suitable for use in the treatment of microbial infection in mammals. The present invention further relates to the use of pharmaceutical compositions comprising said agents in the treatment of medical conditions in mammals, in particular in the treatment of microbial infection. The agents and pharmaceutical compositions of the invention are of particular relevance in the treatment of diseases associated with antibiotic-resistant microbes. The present invention also relates to processes for making said agents.

  本发明涉及适用于治疗哺乳动物疾病的新型式（I）化合物，特别是适用于治疗哺乳动物微生物感染的新型治疗剂。本发明还涉及包含上述制剂的药物组合物在治疗哺乳动物疾病中的用途，特别是在治疗微生物感染中的用途。本发明的制剂和药物组合物在治疗与抗生素耐药微生物相关的疾病方面具有特别重要的意义。本发明还涉及上述制剂的制造工艺。
• Imidazole-based antimicrobial agents
  申请人：Procomcure Biotech GmbH

  公开号：US10322110B2

  公开（公告）日：2019-06-18

  The present invention relates to therapeutic agents suitable for use in the treatment of microbial infection in mammals. The present invention further relates to the use of pharmaceutical compositions comprising said agents in the treatment of medical conditions in mammals, in particular in the treatment of microbial infection. The agents and pharmaceutical compositions of the invention are of particular relevance in the treatment of diseases associated with antibiotic-resistant microbes. In one particular embodiment, the pharmaceutical composition can have the structural moiety of formula (I) or a pharmaceutically-acceptable salt of said compound: wherein group A is selected from the formulae Group B is aryl, R1 is an optionally substituted aryl ring, an optionally substituted benzyl ring, CH3, or C2 to 6 alkyl, and R2 is hydrogen, an alkyl group, a halogen, or —(CH2)nN(CH3)2 where n is an integer from 1 to 3.

  本发明涉及适用于治疗哺乳动物微生物感染的治疗剂。本发明还涉及包含上述制剂的药物组合物在治疗哺乳动物的病症，特别是治疗微生物感染中的用途。本发明的制剂和药物组合物在治疗与抗生素耐药微生物相关的疾病方面具有特殊意义。在一个特定的实施方案中，药物组合物可以具有式（I）的结构分子或所述化合物的药学上可接受的盐： 其中 A 组选自式 B 组为芳基，R1 为任选取代的芳基环、任选取代的苄基环、CH3 或 C2 至 6 烷基，R2 为氢、烷基、卤素或-(CH2)nN(CH3)2，其中 n 为 1 至 3 的整数。
• 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.