5-(4-trifluoromethylphenyl)-5-methylhydantoin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-(4-trifluoromethylphenyl)-5-methylhydantoin
• 英文别名: 5-methyl-5-(4-(trifluoromethyl)phenyl)imidazolidine-2,4-dione；(RS)-5-methyl-5-(4-trifluoromethylphenyl)imidazolidine-2,4-dione；5-Methyl-5-[4-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
• 化学式: C₁₁H₉F₃N₂O₂
• mdl: MFCD09943776
• 分子量: 258.2
• InChiKey: SMZCVKDMQDNCQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-trifluoromethylphenyl)-5-methylhydantoin 在 sodium hydroxide 作用下， 以 水 为溶剂， 以9%的产率得到2-(4-trifluoromethylphenyl)-2-methylglycine
  参考文献：
  名称：

  Hydrophobic and electronic factors in the design of dialkylglycine decarboxylase mimics

  摘要：

  The first functional catalytic mimic of the enzyme dialkylglycine decarboxylase is described. This system utilizes a hydrophobically modified polyethylenimine polymer, a pyridoxamine cofactor, and a 2-aryl-2-alkylglycine sacrificial amine source to convert alpha-keto acids to alpha-amino acids at biologically relevant temperatures with multiple turnovers of the pyridoxamine catalyst. The effects of hydrophobic and electronic factors in the 2,2-disubstituted sacrificial amine source and the pyridoxamine catalyst on turnover frequency and turnover number are explored. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.019
• 作为产物：
  描述：

  三氟甲苯 在 aluminum (III) chloride 、 碳酸二甲酯 作用下， 以 乙醇 、 水 为溶剂， 生成 5-(4-trifluoromethylphenyl)-5-methylhydantoin
  参考文献：
  名称：

  1,1-双三氟甲基甲醇衍生物作为肝X受体β选择性激动剂的设计、合成和药理学

  摘要：

  发现了一系列作为肝 X 受体 (LXR) β-选择性激动剂的新型 1,3-双三氟甲基甲醇衍生物。结构-活性关系研究导致分子62的鉴定，它比 T0901317 和 GW3965 对 LXRβ更有效 ( E max ) 和选择性。此外，在 Bio F 1中， 62降低了 LDL-C 而没有提高血浆 TG 水平，并显着抑制了主动脉弓中的脂质积聚区域B 仓鼠喂食高脂肪和高胆固醇的饮食。我们证明了我们的 LXRβ 激动剂可能用作降血脂和抗动脉粥样硬化剂。在这份手稿中，我们报告了 1,3-双三氟甲基甲醇衍生物的设计、合成和药理学。

  DOI：

  10.1016/j.bmcl.2015.04.080

文献信息

• Design and discovery of 2-oxochromene derivatives as liver X receptor β-selective agonists
  作者：Takayuki Matsuda、Ayumu Okuda、Yuichiro Watanabe、Tohru Miura、Hidefumi Ozawa、Ayako Tosaka、Koichi Yamazaki、Yuki Yamaguchi、Sayaka Kurobuchi、Minoru Koura、Kimiyuki Shibuya

  DOI：10.1016/j.bmcl.2015.01.047

  日期：2015.3

  an attempt to molecularly design liver X receptor (LXR) β-selective agonists, we discovered that the combination of the 2-oxochromene moiety (head) and the imidazoline-2,4-dione moiety (tail) plays an important role in the expression potency and selectivity toward LXRβ. We synthesized a series of 2-oxochromene derivatives and identified 43 as a LXRβ-selective agonist that increased the HDL-C level without

  在分子设计肝X受体（LXR）β-选择性激动剂的尝试中，我们发现2-氧代色烯部分（头部）和咪唑啉-2,4-二酮部分（尾巴）的组合在表达能力和对LXRβ的选择性。我们合成了一系列2-oxochromene衍生物，并确定了43种LXRβ选择性激动剂，可在不显着升高TG水平的情况下增加HDL-C水平，并导致高脂饮食中主动脉弓内脂质蓄积面积减少。和胆固醇喂养的Bio F 1 B仓鼠。在这份手稿中，我们报告了这些2-氧代苯并二氢吡喃衍生物的设计，合成和药理作用。
• 2-Aminooxazolines as TAAR1 ligands
  申请人：Galley Guido

  公开号：US20080261920A1

  公开（公告）日：2008-10-23

  The invention relates to compounds of formula I wherein X, Y, R 1 , R 2 , and n are as defined herein or to a pharmaceutically suitable acid addition salt thereof. The invention also relates to pharmaceutical compositions containing such compounds and methods for the treatment of diseases related to the biological function of the trace amine associated receptors, which diseases include depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder, stress-related disorders, psychotic disorders, schizophrenia, neurological diseases, Parkinson's disease, neurodegenerative disorders, Alzheimer's disease, epilepsy, migraine, substance abuse and metabolic disorders, eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  本发明涉及化合物I的公式，其中X，Y，R1，R2和n如本文所定义，或其药学上适宜的酸加盐。本发明还涉及含有这种化合物的制药组合物和治疗与微量胺相关受体的生物学功能相关的疾病的方法，这些疾病包括抑郁症、焦虑症、双相情感障碍、注意力缺陷多动障碍、压力相关障碍、精神障碍、精神分裂症、神经系统疾病、帕金森病、神经退行性疾病、阿尔茨海默病、癫痫、偏头痛、物质滥用和代谢性疾病、进食障碍、糖尿病、糖尿病并发症、肥胖症、血脂异常、能量消耗和吸收障碍、体温稳态障碍和功能障碍、睡眠和昼夜节律障碍以及心血管疾病。
• 2-AMINOOXAZOLINES AS TAAR1 LIGANDS
  申请人：Galley Guido

  公开号：US20100120864A1

  公开（公告）日：2010-05-13

  The invention relates to compounds of formula I wherein X, Y, R 1 , R 2 , and n are as defined herein or to a pharmaceutically suitable acid addition salt thereof. The invention also relates to pharmaceutical compositions containing such compounds and methods for the treatment of diseases related to the biological function of the trace amine associated receptors, which diseases include depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder, stress-related disorders, psychotic disorders, schizophrenia, neurological diseases, Parkinson's disease, neurodegenerative disorders, Alzheimer's disease, epilepsy, migraine, substance abuse and metabolic disorders, eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  本发明涉及式I的化合物，其中X，Y，R1，R2和n如本文所定义，或其药学适宜的酸加盐。本发明还涉及含有此类化合物的制药组合物，以及用于治疗与微量胺相关受体的生物学功能相关的疾病的方法，这些疾病包括抑郁症，焦虑症，双相情感障碍，注意力缺陷多动障碍，应激相关障碍，精神疾病，精神分裂症，神经疾病，帕金森病，神经退行性疾病，阿尔茨海默病，癫痫，偏头痛，物质滥用和代谢性疾病，进食障碍，糖尿病，糖尿病并发症，肥胖症，血脂异常，能量消耗和吸收障碍，体温稳态障碍和功能障碍，睡眠和生物钟节律障碍以及心血管疾病。
• SUBSTITUTED CARBINOL COMPOUND
  申请人：Kowa Company, Ltd.

  公开号：EP2098515B1

  公开（公告）日：2012-02-08
• Identification and Profiling of Hydantoins—A Novel Class of Potent Antimycobacterial DprE1 Inhibitors
  作者：Maciej K. Rogacki、Eleni Pitta、Olga Balabon、Sophie Huss、Eva Maria Lopez-Roman、Argyrides Argyrou、Delia Blanco-Ruano、Monica Cacho、Christophe M. L. Vande Velde、Koen Augustyns、Lluis Ballell、David Barros、Robert H. Bates、Fraser Cunningham、Pieter Van der Veken

  DOI：10.1021/acs.jmedchem.8b01356

  日期：2018.12.27

  Tuberculosis is the leading cause of death worldwide from infectious diseases. With the development of drug-resistant strains of Mycobacterium tuberculosis, there is an acute need for new medicines with novel modes of action. Herein, we report the discovery and profiling of a novel hydantoin-based family of antimycobacterial inhibitors of the decaprenylphospho-beta-D-ribofuranose 2-oxidase (DprE1). In this study, we have prepared a library of more than a 100 compounds and evaluated them for their biological and physicochemical properties. The series is characterized by high enzymatic and whole-cell activity, low cytotoxicity, and a good overall physicochemical profile. In addition, we show that the series acts via reversible inhibition of the DprE1 enzyme. Overall, the novel compound family forms an attractive base for progression to further stages of optimization and may provide a promising drug candidate in the future.