2-(2-fluorophenylamino)ethanol | 73339-01-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(2-fluorophenylamino)ethanol
• 英文别名: N-hydroxyethyl-2-fluoroaniline；N-(2-Hydroxyethyl)-2-fluoranilin；2-(2-fluoranilino)ethanol；2-fluoro-phenylglycinol；2-Fluorophenylglycinol；2-(2-fluoroanilino)ethanol
• CAS: 73339-01-2
• 化学式: C₈H₁₀FNO
• 分子量: 155.172
• InChiKey: ZVJMODXGJDPCIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-fluorophenylamino)ethanol 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 1-(2-fluorophenyl)-1-(2-hydroxyethyl)-3-(4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)urea
  参考文献：
  名称：

  Bis-aryl Urea Derivatives as Potent and Selective LIM Kinase (Limk) Inhibitors

  摘要：

  The discovery/optimization of bis-aryl ureas as Limk inhibitors to obtain high potency and selectivity and appropriate pharmacokinetic properties through systematic SAR studies is reported. Docking studies supported the observed SAR. Optimized Limk inhibitors had high biochemical potency (IC50 < 25 nM), excellent selectivity against ROCK and JNK kinases (>400-fold), potent inhibition of cofilin phosphorylation in A7r5, PC-3, and CEM-SS T cells (IC50 < 1 mu M), and good in vitro and in vivo pharmacokinetic properties. In the profiling against a panel of 61 kinases, compound 18b at 1 mu M inhibited only Limk1 and STK16 with >= 80% inhibition. Compounds 18b and 18f were highly efficient in inhibiting cell-invasion/migration in PC-3 cells. In addition, compound 18w was demonstrated to be effective on reducing intraocular pressure (IOP) on rat eyes. Taken together, these data demonstrated that we had developed a novel class of bis-aryl urea derived potent and selective Limk inhibitors.

  DOI：

  10.1021/jm501680m
• 作为产物：
  描述：

  2-氟苯胺 在 吡啶 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-(2-fluorophenylamino)ethanol
  参考文献：
  名称：

  Bis-aryl Urea Derivatives as Potent and Selective LIM Kinase (Limk) Inhibitors

  摘要：

  The discovery/optimization of bis-aryl ureas as Limk inhibitors to obtain high potency and selectivity and appropriate pharmacokinetic properties through systematic SAR studies is reported. Docking studies supported the observed SAR. Optimized Limk inhibitors had high biochemical potency (IC50 < 25 nM), excellent selectivity against ROCK and JNK kinases (>400-fold), potent inhibition of cofilin phosphorylation in A7r5, PC-3, and CEM-SS T cells (IC50 < 1 mu M), and good in vitro and in vivo pharmacokinetic properties. In the profiling against a panel of 61 kinases, compound 18b at 1 mu M inhibited only Limk1 and STK16 with >= 80% inhibition. Compounds 18b and 18f were highly efficient in inhibiting cell-invasion/migration in PC-3 cells. In addition, compound 18w was demonstrated to be effective on reducing intraocular pressure (IOP) on rat eyes. Taken together, these data demonstrated that we had developed a novel class of bis-aryl urea derived potent and selective Limk inhibitors.

  DOI：

  10.1021/jm501680m

文献信息

• β-Amino alcohols from anilines and ethylene glycol through heterogeneous Borrowing Hydrogen reaction
  作者：Pedro J. Llabres-Campaner、Rafael Ballesteros-Garrido、Rafael Ballesteros、Belén Abarca

  DOI：10.1016/j.tet.2017.08.006

  日期：2017.9

  Borrowing Hydrogen (BH), also called Hydrogen Autotransfer (HA), reaction with neat ethylene glycol represents a key step in the preparation of β-amino alcohols. However, due to the stability of ethylene glycol, mono-activation has rarely been achieved. Herein, a combination of Pd/C and ZnO is reported as heterogeneous catalyst for this BH/HA reaction. This system results in an extremely air and moisture

  与纯乙二醇的借入氢（BH）也称为氢自动转移（HA），是制备β-氨基醇的关键步骤。然而，由于乙二醇的稳定性，很少实现单活化。在此，据报道Pd / C和ZnO的组合作为该BH / HA反应的非均相催化剂。该系统产生了极好的空气和湿气稳定性，并且经济的催化剂能够将水中的乙二醇单官能化，而无需进一步活化二醇。在这项工作中，已经探索了不同的二醇和芳族胺，为氨基醇的开发提供了一种新方法。这项研究揭示了两种固体物质的组合如何在异相中提供有趣的催化性能。ZnO激活乙二醇，而Pd / C则负责BH / HA循环。重新芳香化之前的原位BH / HA循环，代表串联异质过程。
• Thiazolinone unsubstituted quinolines
  申请人：Chen Li

  公开号：US20060004045A1

  公开（公告）日：2006-01-05

  Thiazolinone quinoline derivatives having no substitution on the quinoline ring active as CDK1 inhibitors which are useful as anti-proliferation agents such as for treating solid tumors.

  噻唑酮喹啉衍生物在喹啉环上没有取代基，作为CDK1抑制剂活性，可用作抗增殖剂，例如用于治疗实体肿瘤。
• Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
  申请人：Neurocrine Biosciences, Inc.

  公开号：US20030109535A1

  公开（公告）日：2003-06-12

  GnRH receptor antagonists are disclosed which have utility in the treatment of a variety of sex-hormone related conditions in both men and women. The compounds of this invention have the structure: 1 wherein A, R 1 , R 2 , R 3a , R 3b , R 4 , R 5 , R 6 , and n are as defined herein, including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof. Also disclosed are compositions containing a compound of this invention in combination with a pharmaceutically acceptable carrier, as well as methods relating to the use thereof for antagonizing gonadotropin-releasing hormone in a subject in need thereof.

  GnRH受体拮抗剂已被披露，对男性和女性的各种与性激素有关的疾病具有治疗作用。本发明的化合物具有以下结构：其中A、R1、R2、R3a、R3b、R4、R5、R6和n的定义如本文所述，包括立体异构体、前药和其药用可接受的盐。还披露了含有本发明化合物的组合物与药用可接受载体，以及与使用该化合物在需要的受试者中拮抗促性腺激素释放激素相关的方法。
• [EN] FACTOR XA INHIBITORS<br/>[FR] INHIBITEURS DE FACTEUR XA
  申请人：LILLY CO ELI

  公开号：WO2004060872A1

  公开（公告）日：2004-07-22

  Compounds of formula (I) in which R1, n, Z, R3 and R4 have any of the meanings given in the specification, are inhibitors of the serine protease Factor Xa and are useful in the treatment of thrombotic disorders.

  式(I)化合物中，R1、n、Z、R3和R4具有说明书中给出的任何含义，是丝氨酸蛋白酶因子Xa的抑制剂，并可用于治疗血栓性疾病。
• Pyridinium derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd

  公开号：US04962113A1

  公开（公告）日：1990-10-09

  Novel pyridinium derivatives represented by the formula (I): ##STR1## wherein ##STR2## is an optionally substituted pyridinium ring; R.sup.1 is a lower alkyl group or aralkyl group; R.sup.7 and R.sup.10 are independently hydrogen, a lower alkyl group, aryl group or aralkyl group; l is 0 or 1; R.sup.5 is a phenylene group or an alkylene group which may be substituted; R.sup.11 is an alkyl group or aryl group; X is a group of the formula: --CH.sub.2 OCH.sub.2 -- or a group of the formula: ##STR3## wherein R.sup.6 is hydrogen, a lower alkyl or a lower alkoxy, and m is an integer of 0 to 3; U is a group of the formula: ##STR4## wherein R.sup.4 is hydrogen, a lower alkyl group, aryl group or aralkyl group; Y and Z are independently a divalent chain group consisting of one to six members which is selected from the class consisting of groups of the formulae: ##STR5## wherein R is hydrogen, a lower alkyl group, acyl group or aryl group and at least one of which is a group of the formula: ##STR6## with the proviso that R may be the same or different from each other, or may form a ring together when two or more groups of the formula: ##STR7## are present, that R may be bonded to R.sup.4 when Y contains a group of the formula: ##STR8## and that R may be bonded to R.sup.11 when Z contains a group of the formula: ##STR9## and W.sup..crclbar. is a counter anion; are useful as a platelet activating factor antagonist.

  新型吡啶盐衍生物的结构如下（I）：##STR1##其中##STR2##是一个可选择取代的吡啶环；R.sup.1是一个低碳烷基或芳基烷基；R.sup.7和R.sup.10独立地是氢、低碳烷基、芳基或芳基烷基；l为0或1；R.sup.5是一个苯基或可能被取代的烷基；R.sup.11是一个烷基或芳基；X是一个式子：--CH.sub.2 OCH.sub.2 --或一个式子：##STR3##其中R.sup.6是氢、低碳烷基或低烷氧基，m是0到3的整数；U是一个式子：##STR4##其中R.sup.4是氢、低碳烷基、芳基或芳基烷基；Y和Z独立地是由1到6个成员组成的二价链状基团，选自下列式：##STR5##其中R是氢、低碳烷基、酰基或芳基，至少有一个是下列式之一：##STR6##但要求R可以相同也可以不同，或者当存在两个或更多的下列式之一：##STR7##时，R可以一起形成环；当Y包含一个下列式之一：##STR8##时，R可以与R.sup.4结合；当Z包含一个下列式之一：##STR9##时，R可以与R.sup.11结合；W.sup..crclbar.是一个反离子；这些化合物可用作血小板活化因子拮抗剂。