pyridin-3-yl(4-(trifluoromethyl)phenyl)methanone | 21221-92-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pyridin-3-yl(4-(trifluoromethyl)phenyl)methanone
• 英文别名: pyridin-3-yl-[4-(trifluoromethyl)phenyl]methanone
• CAS: 21221-92-1
• 化学式: C₁₃H₈F₃NO
• mdl: MFCD13152905
• 分子量: 251.208
• InChiKey: KUCXNAXAAXKXGV-UHFFFAOYSA-N

物化性质

• 沸点：
  330.2±42.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  pyridin-3-yl(4-(trifluoromethyl)phenyl)methanone 在 sodium tetrahydroborate 、 氯化亚砜 、 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 60.0h， 生成 C₂₂H₂₆F₃N₃O₂
  参考文献：
  名称：

  Design, structure–activity relationship and in vivo efficacy of piperazine analogues of fenarimol as inhibitors of Trypanosoma cruzi

  摘要：

  A scaffold hopping exercise undertaken to expand the structural diversity of the fenarimol series of anti-Trypanosoma cruzi (T. cruzi) compounds led to preparation of simple 1-[phenyl(pyridin-3-yl)methyl]piperazinyl. analogues of fenarimol which were investigated for their ability to inhibit T. cruzi in vitro in a whole organism assay. A range of compounds bearing amide, sulfonamide, carbamate/carbonate and aryl moieties exhibited low nM activities and two analogues were further studied for in vivo efficacy in a mouse model of T. cruzi infection. One compound, the citrate salt of 37, was efficacious in a mouse model of acute T. cruzi infection after once daily oral dosing at 20, 50 and 100 mg/kg for 5 days. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.050
• 作为产物：
  描述：

  4-三氟甲基苯甲酰氯 在 正丁基锂 、 三乙胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 pyridin-3-yl(4-(trifluoromethyl)phenyl)methanone
  参考文献：
  名称：

  Analogues of Fenarimol Are Potent Inhibitors of Trypanosoma cruzi and Are Efficacious in a Murine Model of Chagas Disease

  摘要：

  We report the discovery of nontoxic fungicide fenarimol (1) as an inhibitor of Trypanosoma cruzi (T. cruzi), the causative agent of Chagas disease, and the results of structure-activity investigations leading to potent analogues with low nM IC(50)s in a T. cruzi whole cell in vitro assay. Lead compounds suppressed blood parasitemia to virtually undetectable levels after once daily oral dosing in mouse models of T. cruzi infection. Compounds are chemically tractable, allowing rapid optimization of target biological activity and drug characteristics. Chemical and biological studies undertaken in the development of the fenarimol series toward the goal of delivering a new drug candidate for Chagas disease are reported.

  DOI：

  10.1021/jm2015809

文献信息

• METHYLENE LINKED QUINOLINYL MODULATORS OF RORyt
  申请人：Janssen Pharmaceutica NV

  公开号：US20150105366A1

  公开（公告）日：2015-04-16

  The present invention comprises compounds of Formula I. wherein: R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are defined in the specification. The invention also comprises a method of treating or ameliorating a syndrome, disorder or disease, wherein said syndrome, disorder or disease is rheumatoid arthritis or psoriasis. The invention also comprises a method of modulating RORγt activity in a mammal by administration of a therapeutically effective amount of at least one compound of claim 1.

  本发明包括式I的化合物。 其中： R1、R2、R3、R4、R5、R6、R7、R8和R9在说明书中定义。 本发明还包括治疗或改善综合征、紊乱或疾病的方法，其中所述综合征、紊乱或疾病为类风湿性关节炎或银屑病。本发明还包括通过给予治疗有效量的至少一个权利要求1的化合物，来调节哺乳动物中RORγt活性的方法。
• [EN] METHYLENE LINKED QUINOLINYL MODULATORS OF ROR-GAMMA-T<br/>[FR] MODULATEURS QUINOLINYLE À LIAISON MÉTHYLÈNE DE ROR-GAMMA-T
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2015057205A1

  公开（公告）日：2015-04-23

  The present invention comprises compounds of Formula (I). wherein: R1, R2, R3, R4, R5, R6, R7, R8, and R9 are defined in the specification. The invention also comprises a method of treating or ameliorating a syndrome, disorder or disease, wherein said syndrome, disorder or disease is rheumatoid arthritis or psoriasis. The invention also comprises a method of modulating RORγt activity in a mammal by administration of a therapeutically effective amount of at least one compound of claim 1.

  本发明包括公式(I)的化合物。其中：R1、R2、R3、R4、R5、R6、R7、R8和R9在说明书中定义。本发明还包括治疗或改善综合症、障碍或疾病的方法，其中所述综合症、障碍或疾病为类风湿性关节炎或银屑病。本发明还包括通过管理一个治疗有效量的至少一个权利要求1的化合物来调节哺乳动物中的RORγt活性的方法。
• Practical one-pot preparation of ketones from aryl and alkyl bromides with aldehydes and DIH via Grignard reagents
  作者：Souya Dohi、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1016/j.tet.2012.05.059

  日期：2012.8

  groups, such as ester, nitrile, ketone, and nitro groups with i-PrMgCl·LiCl or PhMgCl instead of Mg, also provided the corresponding diaryl and alkyl aryl ketones in good yields. The above methods are simple and practical transition-metal-free methods for the preparation of various diaryl ketones and alkyl aryl ketones bearing electron-rich aromatic groups and electron-deficient aromatic groups, as well

  通过衍生自芳基或烷基溴化物的格利雅试剂的反应，然后与芳族或脂族醛的反应以及随后用1,3-二碘的处理，可以有效地以高收率高效地制备各种二芳基酮，烷基芳基酮和二烷基酮。一锅法中的-5,5-二甲基乙内酰脲和K 2 CO 3。相同的处理的芳族溴化物轴承吸电子基团，如酯，腈，酮和硝基与我-PrMgCl·LiCl或PhMgCl代替Mg，也以良好的收率提供了相应的二芳基和烷基芳基酮。以上方法是用于制备各种带有富电子芳族基团和缺电子芳族基团的二芳基酮和烷基芳基酮以及二烷基酮的简单且实用的无过渡金属的方法。
• Synthesis of pyridylallylamines related to zimelidine and their inhibition of neuronal monoamine uptake
  作者：Thomas Hoegberg、Bengt Ulff、Anna L. Renyi、Svante B. Ross

  DOI：10.1021/jm00144a025

  日期：1981.12

  aim of obtaining compounds having a cis configuration (with respect to pyridyl and allylamine). Two methods utilized suitably substituted benzoylpyridines as starting materials. In two other routes, the bromine in 6 was either directly displaced (CN) or converted via the corresponding lithio derivative to H, Cl, I, Me, SiMe3, and SMe. The configurations were determined by UV, 1H NMR, and lanthanide-induced

  抗抑郁药齐美碱[6，（Z）-3-（4-溴苯基）-N，N-二甲基-3-（3-吡啶基）烯丙胺]的类似物是神经元5-羟色胺再摄取的选择性抑制剂，其合成方法如下：为了获得具有顺式构型（相对于吡啶基和烯丙胺）的化合物的几种途径。两种方法利用适当取代的苯甲酰基吡啶作为起始原料。在另外两个途径中，将6中的溴直接置换（CN）或通过相应的硫代衍生物转化为H，Cl，I，Me，SiMe3和SMe。通过UV，1H NMR和镧系元素引起的1H NMR位移确定构型。通过测量小鼠脑切片（体外和体内）中的[3H]去甲肾上腺素和5-羟基[14C]色胺的积累，将这些化合物评估为摄取抑制剂。在顺式系列中，对位取代有利于5-羟基色胺活性，而邻位取代有利于NA活性。对5-羟色胺的体外作用对对位取代基的变化不敏感，而仅用Cl，Br（6）和I观察到明显的体内作用。
• Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet-Spengler Reaction of Indolyl Dihydropyridines
  作者：Shou-Guo Wang、Zi-Lei Xia、Ren-Qi Xu、Xi-Jia Liu、Chao Zheng、Shu-Li You

  DOI：10.1002/anie.201703178

  日期：2017.6.19

  A highly efficient synthesis of the enantioenriched tetrahydro-β-carbolines was developed by using a chiral phosphoric acid catalyzed Pictet–Spengler reaction of indolyl dihydropyridines. The reaction proceeds under mild reaction conditions to afford the desired chiral tetrahydro-β-carbolines in good to excellent yields (up to 96 %) and high enantioselectivities (up to 99 % ee). With this method, a

  通过使用手性磷酸催化吲哚基二氢吡啶的Pictet-Spengler反应，开发了对映体富集的四氢-β-咔啉的高效合成方法。反应在温和的反应条件下进行，以良好的产率（高达96％）和高的对映选择性（高达99％ee）提供所需的手性四氢-β-咔啉。用这种方法，可以高效地完成橘皮苷的正式合成和十氢萘烷的全部合成。