2-氨基-1-(3-三氟甲基苯基)乙酮盐酸盐 | 61062-56-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-氨基-1-(3-三氟甲基苯基)乙酮盐酸盐
• 中文别名: 2-氨基-3'-三氟甲基苯乙酮盐酸盐
• 英文名称: 2-amino-1-(3-trifluoromethylphenyl)ethanone hydrochloride
• 英文别名: 2-Amino-1-(3-(trifluoromethyl)phenyl)ethanone hydrochloride；2-amino-1-[3-(trifluoromethyl)phenyl]ethanone;hydrochloride
• CAS: 61062-56-4
• 化学式: C₉H₈F₃NO*ClH
• mdl: MFCD11974307
• 分子量: 239.625
• InChiKey: HEPPSEJUYWXQJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  43.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氨基-1-(3-三氟甲基苯基)乙酮盐酸盐 在 palladium on activated charcoal ammonium acetate 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~80.0 ℃ 、379.21 kPa 条件下， 反应 18.0h， 生成 N-{4-[4-(3-Trifluoromethyl-phenyl)-1H-imidazol-2-yl]-cyclohexylmethyl}-benzenesulfonamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Substituted 2-Cyclohexyl-4-phenyl-1H-imidazoles:  Potent and Selective Neuropeptide Y Y5-Receptor Antagonists

  摘要：

  Antagonizing the robust stimulation of food intake by neuropeptide Y represents a new potential therapeutic approach for the treatment of obesity. Earlier pharmacological studies have pointed to the Y1 and Y5 receptors as the most likely mediators of the NPY orexigenic response. In this paper, we describe a new series of small molecule Y5 antagonists derived from a 2,4diaryl-1H-imidazole lead. The main objectives of our structural optimization efforts were to produce novel and potent Y5 antagonists with an improved oral pharmacokinetic profile and less affinity for the hERG potassium channel compared to the lead 2,4-diarylimidazole structures. These goals were accomplished by replacement of the 2-aryl ring with a cyclohexyl ring and subsequent elaboration of the 4-position of the cyclohexyl ring with a variety of hydrophilic functionalities. The resulting compound, N-(2-hydroxy-tert-butyl)(4-{4-[3-(trifluoro-methyl)phenyl]imidazol-2-yl}cyclohexyl)carboxamide (20), displayed good potency at the Y5 receptor (K-i = 3 nM), while interactions at the hERG channel were essentially eliminated (6% inhibition at a concentration of 3 muM). Importantly, the pharmacokinetic properties of 20 (F = 36%) represented a marked improvement over that of the initial 2,4-diarylimidazole structures.

  DOI：

  10.1021/jm030490g
• 作为产物：
  描述：

  间三氟甲基苯乙酮 在 二甲酰氨基钠 、 溴 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成 2-氨基-1-(3-三氟甲基苯基)乙酮盐酸盐
  参考文献：
  名称：

  [EN] N-(1-CYANO-PYRROLIDIN-3-YL)-5-(3-(TRIFLUOROMETHYL)PHENYL)OXAZOLE-2-CARBOXAMIDE DERIVATIVES AND THE CORRESPONDING OXADIAZOLE DERIVATIVES AS USP30 INHIBITORS FOR THE TREATMENT OF MITOCHONDRIAL DYSFUNCTION
  [FR] N-(1-CYANO-PYRROLIDIN-3-YL)-5-(3- (TRIFLUOROMÉTHYL)PHÉNYL)OXAZOLE-2-CARBOXAMIDE ET DÉRIVÉS D'OXADIAZOLE CORRESPONDANTS UTILISÉS EN TANT QU'INHIBITEURS D'USP30 POUR LE TRAITEMENT D'UN DYSFONCTIONNEMENT MITOCHONDRIAL

  摘要：

  本发明涉及一类具有作为去泛素化酶USP30抑制剂活性的N-氰基吡咯烷衍生物，可用于包括涉及线粒体功能障碍、癌症和纤维化等多种治疗领域：公式（I），公式（II）..

  公开号：

  WO2021239863A1

文献信息

• Substituted 2-cyclohexyl-4-phenyl-1H-imidazole derivatives
  申请人：NEUROGEN CORPORATION

  公开号：US20030144290A1

  公开（公告）日：2003-07-31

  Substituted 2-cyclohexyl-4-phenyl-1H-imidazole derivatives capable of modulating NPY5 receptor activity, are provided. Such compounds may be used to modulate NPY binding to NPY5 receptors in vivo or in vitro, and are particularly useful in the treatment of a variety of disorders (e.g., eating disorders such as obesity or bulimia, psychiatric disorders, diabetes and cardiovascular disorders such as hypertension) in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and methods for treating such disorders are provided, as are methods for using such compounds for detecting NPY5 receptors.

  提供了一种能够调节NPY5受体活性的取代2-环己基-4-苯基-1H-咪唑衍生物。这类化合物可用于体内或体外调节NPY与NPY5受体的结合，特别适用于治疗多种疾病（例如，肥胖或贪食症等饮食障碍、精神障碍、糖尿病以及高血压等心血管疾病）在人类、家养伴侣动物和家畜动物中的应用。还提供了用于治疗这些疾病的药物组合物和方法，以及使用这些化合物检测NPY5受体的方法。
• New Insights into the Bacterial RNA Polymerase Inhibitor CBR703 as a Starting Point for Optimization as an Anti-Infective Agent
  作者：Weixing Zhu、Jörg Haupenthal、Matthias Groh、Michelle Fountain、Rolf W. Hartmann

  DOI：10.1128/aac.02600-14

  日期：2014.7

  CBR703 was reported to inhibit bacterial RNA polymerase (RNAP) and biofilm formation, considering it to be a good candidate for further optimization. While synthesized derivatives of CBR703 did not result in more-active RNAP inhibitors, we observed promising antibacterial activities. These again correlated with a significant cytotoxicity toward mammalian cells. Furthermore, we suspect the promising effects on biofilm formation to be artifacts. Consequently, this class of compounds can be considered unattractive as antibacterial agents.

  摘要 据报道，CBR703 可抑制细菌 RNA 聚合酶（RNAP）和生物膜的形成，因此被认为是进一步优化的良好候选物。虽然合成的 CBR703 衍生物没有产生活性更强的 RNAP 抑制剂，但我们观察到其具有良好的抗菌活性。这些活性再次与对哺乳动物细胞的显著细胞毒性相关联。此外，我们怀疑对生物膜形成的良好效果是伪造的。因此，这类化合物作为抗菌剂并不具有吸引力。
• [EN] OXAZOLE AND OXADIAZOLE DERIVATIVES USEFUL AS AGONISTS OF FREE FATTY ACID RECEPTOR 1<br/>[FR] DÉRIVÉS D'OXAZOLE ET D'OXADIAZOLE UTILES EN TANT QU'AGONISTES DU RÉCEPTEUR 1 D'ACIDES GRAS LIBRES
  申请人：GBIOTECH S A R L

  公开号：WO2020211956A1

  公开（公告）日：2020-10-22

  The present invention relates to novel free fatty acid receptor (FFAR) agonists of general formula (I), in particular agonists of FFAR1, and to the use of said FFAR agonists as medicaments, in particular for treatment and/or prevention of type 2 diabetes mellitus (T2DM), R1-S-CH2-OXA-R2 (l) wherein OXA is selected from the group consisting of 1,3-oxazolyl 1,2,4-oxadiazolyl or 1,3,4-oxadiazolyl, R1 is selected from 1,3,5- triazinyl and pyrimidinyl and R2 is phenyl.

  本发明涉及一种新型自由脂肪酸受体（FFAR）激动剂，其一般式为（I），特别是FFAR1的激动剂，并将所述FFAR激动剂用作药物，特别用于治疗和/或预防2型糖尿病（T2DM），其中OXA选自1,3-噁唑基1,2,4-噁二唑基或1,3,4-噁二唑基的群，R1选自1,3,5-三嗪基和嘧啶基，R2为苯基。
• 1-[[[5-(Substituted phenyl)-2-oxazolyl]methylene]amino]-2,4-imidazolidinediones, a new class of skeletal muscle relaxants
  作者：R. L. White、F. L. Wessels、T. J. Schwan、K. O. Ellis

  DOI：10.1021/jm00385a006

  日期：1987.2

  A series of 1-[[[5-(substituted phenyl)-2-oxazolyl]methylene]amino]- 2,4-imidazolidinediones (6a-t) was synthesized, and the compounds were evaluated for direct skeletal muscle inhibition in the pithed rat gastrocnemius muscle preparation. The correctness of structural assignment of the new series was verified by alternate, unequivocal synthesis of one representative structure (6f). The phenyloxazoles

  合成了一系列的1-[[[[5-（取代的苯基）-2-恶唑基]亚甲基]氨基] -2,4-咪唑烷二酮（6a-t），并评价了这些化合物对骨骼肌的直接抑制作用。大鼠腓肠肌的制备。新序列结构分配的正确性通过一个代表性结构的交替，明确合成得到了验证（6f）。当静脉和口服给药时，苯恶唑6d，6g，6j，6k和6l表现出显着的骨骼肌松弛活性。这五种化合物的骨骼肌松弛剂作用与其他直接作用的骨骼肌松弛剂相似。由于恶唑系列的生物活性得以保留，因此恶唑部分被证明是呋喃的等规替代物。描述了这类新化合物的合成，并提供药理评价数据。还讨论了结构-活动关系。
• [EN] AGONISTS OF FREE FATTY ACID RECEPTOR 1 AND THEIR USE IN DISEASES ASSOCIATED WITH SAID RECEPTOR<br/>[FR] AGONISTES DU RÉCEPTEUR 1 D'ACIDE GRAS LIBRE ET LEUR UTILISATION DANS DES MALADIES ASSOCIÉES AUDIT RÉCEPTEUR
  申请人：GBIOTECH S A R L

  公开号：WO2022083853A1

  公开（公告）日：2022-04-28

  The present invention relates to novel free fatty acid receptor (FFAR) agonists (I), in particular agonists of FFAR1, and to the use of said FFAR agonists as medicaments, in particular for treatment and/or prevention of conditions or diseases amenable to enhanced activity of FFAR1 such as of conditions or diseases involving impaired control of glucose blood levels, metabolic syndrome, obesity, dyslipidemia, kidney diseases, fibrotic and sclerotic diseases as well as hepatic and biliary diseases. R1-S-CH2-OXA-R2(I).

  本发明涉及一种新型游离脂肪酸受体（FFAR）激动剂（I），特别是FFAR1的激动剂，以及将所述FFAR激动剂用作药物的用途，特别是用于治疗和/或预防适于增强FFAR1活性的情况或疾病，例如涉及糖血平衡受损、代谢综合征、肥胖症、血脂异常、肾脏疾病、纤维化和硬化疾病以及肝胆疾病的情况或疾病。其中，R1-S-CH2-OXA-R2（I）。