4-(indolizin-2-yl)-N-methylbenzeneamine | 497848-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(indolizin-2-yl)-N-methylbenzeneamine
• 英文别名: 2-(4'-N-methylamino)phenylimidazo[1,2-a]pyridine；4-(Imidazo[1,2-a]pyridin-2-yl)-N-methylaniline；4-imidazo[1,2-a]pyridin-2-yl-N-methylaniline
• CAS: 497848-13-2
• 化学式: C₁₄H₁₃N₃
• 分子量: 223.277
• InChiKey: POPKEMGAZDABEZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(indolizin-2-yl)-N-methylbenzeneamine 在 sodium tetrahydroborate 、 碘 、 三氟乙酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 1.0h， 生成 [4-(3-Iodo-imidazo[1,2-a]pyridin-2-yl)-phenyl]-dimethyl-amine
  参考文献：
  名称：

  Structure−Activity Relationship of Imidazo[1,2-a]pyridines as Ligands for Detecting β-Amyloid Plaques in the Brain

  摘要：

  A series of novel beta-amyloid (Abeta) aggregate-specific ligands, 2-(4'-dimethylaminophenyl)-6-iodoimidazo[1,2-alpha]pyridine, (IMPY), and its related derivatives were prepared. An in vitro binding study with preformed Abeta aggregates showed that 16(IMPY) and its bromo derivative competed with binding of 2-(4'-dimethylaminophenyl)-6-iodobenzothiazole, [I-125]7(TZDM), a known ligand for Abeta aggregates, with high binding affinities (K-i = 15 and 10 nM, respectively). In vitro autoradiography of brain sections of a transgenic mouse (Tg2576) with [I-125]16(IMPY) displayed high selective binding to amyloid-like structures, comparable to that observed by staining with thioflavin-S visualized under fluorescence. In vivo biodistribution after an intravenous injection of [I-125]16(IMPY) in normal mice showed a high initial brain uptake and fast washout, indicating a low background activity associated with this iodinated ligand. Taken together, the data suggests that [I-123]16(IMPY) may be useful for imaging Abeta aggregates in patients with Alzheimer's disease.

  DOI：

  10.1021/jm020351j
• 作为产物：
  描述：

  N-(4-(imidazo[1,2-a]pyridin-2-yl)-phenyl)-2,2,2-trifluoroacetamide 在 水 、 sodium hydride 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(indolizin-2-yl)-N-methylbenzeneamine
  参考文献：
  名称：

  Discovery of BI 99179, a potent and selective inhibitor of type I fatty acid synthase with central exposure

  摘要：

  Based on a high-throughput screen, cyclopentanecarboxanilides were identified as a new chemotype of non-covalent inhibitors of type I fatty acid synthase (FAS). Starting from initial hits we aimed at generating a tool compound suitable for the in vivo validation of FAS as a therapeutic target. Optimisation yielded BI 99179 which is characterised by high potency, remarkably high selectivity and significant exposure (both peripheral and central) upon oral administration in rats. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.083

文献信息

• [EN] CYCLOPENTANECARBOXAMIDE DERIVATIVES, MEDICAMENTS CONTAINING SUCH COMPOUNDS AND THEIR USE<br/>[FR] DÉRIVÉS DE CYCLOPENTANECARBOXAMIDE, MÉDICAMENTS CONTENANT CES COMPOSÉS ET LEUR UTILISATION
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2011048018A1

  公开（公告）日：2011-04-28

  The invention relates to cyclopentanecarboxamide derivatives of formula 1, to their use as Fatty Acid Synthase inhibitors, to methods for their therapeutic use and to pharmaceutical compositions containing them, wherein R1, R2, R3, LO, W, AR1, n are as defined in claim 1.

  这项发明涉及公式1的环戊烷羧酰胺衍生物，它们的用途是作为脂肪酸合成酶抑制剂，用于它们的治疗用途的方法，以及含有它们的药物组合物，其中R1、R2、R3、LO、W、AR1、n如权利要求1中所定义。
• [EN] METHODS FOR THE TREATMENT OF NEUROLOGICAL DISORDERS<br/>[FR] MÉTHODES DE TRAITEMENT DE TROUBLES NEUROLOGIQUES
  申请人：YUMANITY THERAPEUTICS INC

  公开号：WO2020150423A1

  公开（公告）日：2020-07-23

  The present disclosure provides compounds and methods useful in the treatment of neurological disorders. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders.

  本公开提供了在治疗神经系统疾病中有用的化合物和方法。本发明的化合物可以单独或与其他药用活性剂结合使用，用于治疗或预防神经系统疾病。
• Cyclopentanecarboxamide derivatives, medicaments containing such compounds and their use
  申请人：Kley Joerg

  公开号：US20130053412A1

  公开（公告）日：2013-02-28

  The invention relates to cyclopentanecarboxamide derivatives of formula 1, to their use as Fatty Acid Synthase inhibitors, to methods for their therapeutic use and to pharmaceutical compositions containing them, wherein R 1 , R 2 , R 3 , LO, W, AR 1 , n are as defined in claim 1 .

  本发明涉及公式1的环戊烷羧酰胺衍生物，以及它们作为脂肪酸合成酶抑制剂的用途，它们的治疗应用方法以及含有它们的制药组合物，其中R1，R2，R3，LO，W，AR1，n如权利要求1所定义。
• WO2007/124345
  申请人：——

  公开号：——

  公开（公告）日：——
• Rapid palladium-catalyzed cross-coupling in the synthesis of aryl thioethers under microwave conditions
  作者：Lisheng Cai、Jessica Cuevas、Yi-Yuan Peng、Victor W. Pike

  DOI：10.1016/j.tetlet.2006.04.049

  日期：2006.6

  A Pd-catalyzed coupling of aromatic iodides or bromides and tin-thiolates under microwave conditions was developed to synthesize aromatic thioethers without concomitant formation of the reduced products. Ligand screening revealed DiPPF and BINAP-Tol as the most generally useful ligands for this transformation. A variety of iodides or bromides were coupled to give the thioethers rapidly (10 min) in 60-95% isolated yield. (c) 2006 Elsevier Ltd. All rights reserved.