2-hydroxy-5-phenylpentanenitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxy-5-phenylpentanenitrile
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: ZNFNNFAXUNFARZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氨基-3-羟基吡啶 、 2-hydroxy-5-phenylpentanenitrile 在 乙酰氯 、 吡啶 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 10.5h， 以18%的产率得到1-(oxazolo[4,5-b]pyridin-2-yl)-4-phenylbutan-1-ol
  参考文献：
  名称：

  Comprehensive Analysis of Structure–Activity Relationships of α-Ketoheterocycles as sn-1-Diacylglycerol Lipase α Inhibitors

  摘要：

  Diacylglycerol lipase alpha (DAGL alpha) is responsible for the formation of the endocannabinoid 2-arachidonoylglycerol (2-AG) in the central nervous system. DAGL alpha inhibitors are required to study the physiological mile of 2-AG. Previously, we identified the alpha-ketoheterocycles as potent and highly selective DAGL alpha inhibitors. Here, we present the first comprehensive structure activity relationship study Of alpha-ketohetero cycles as DAGL alpha inhibitors. Our findings indicate that the active site, of DAGL alpha is remarkably sensitive to the type of heterocyclic scaffold with oxazolo-4N-pridines as the most active framework We uncovered a fundamental substituent effect in which electron-withdrawing meta-oxazole substituents increased inhibitor potency. (C-6-C-9)-iacyl chains with a distal phenyl group proved to be the most potent inhibitors. The integrated SAR data was consistent with the proposed binding pose in a DAGL alpha homology model. Altogether, our results may guide the design of future DAGL alpha inhibitors as leads for molecular therapies to treat neuroinflammation, obesity, and related metabolic disorders.

  DOI：

  10.1021/acs.jmedchem.5b01627
• 作为产物：
  描述：

  4-苯丁酸甲酯 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 lithium aluminium tetrahydride 、 溶剂黄146 、 sodium bromide 作用下， 以 四氢呋喃 、 乙酸乙酯 、 甲苯 为溶剂， 生成 2-hydroxy-5-phenylpentanenitrile
  参考文献：
  名称：

  Almond oxynitrilase-catalyzed transformation of aldehydes is strongly influenced by naphthyl and alkoxy substituents

  摘要：

  Different alpha- and beta-substituted aldehydes have been submitted to the catalytic action of almond oxynitrilase (PaHNL), in order to explore the influence of a stereocenter already present in the substrate on the selectivity of this enzyme.(1) The results indicate that naphthyl and alkoxy substituents in the alpha- and also in the beta-position to the aldehyde group significantly influence the stereochemical outcome of the PaHNL-catalyzed transformation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00427-9

文献信息

• Method of producing optically active alpha-hydroxy acid or alpha-hydroxyamide
  申请人：NITTO CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0711836A1

  公开（公告）日：1996-05-15

  A reaction system, wherein a cyanohydrin is converted into an optically active α-hydroxy acid or α-hydroxyamide via a treatment in a reaction tank (f) with a microorganism, is provided with an automatic cyanohydrin controller (h) comprising a cyano ion detector (a), a regulator (b) and a cyanohydrin supplier (i) and (j) linked thereto. The reaction is performed while automatically controlling the cyanohydrin concentration. Thus cyanohydrin can be supplied under automatic control at a relatively low and constant concentration on the basis of its consumption ratio. The reaction rate of the catalyst can be continuously regarded as the rate-limiting factor. As a result, a decrease in the enzymatic activity during the reaction can be suppressed and an optically active α-hydroxy acid or α-hydroxyamide can be efficiently obtained at a high yield.

  一种反应系统，通过在反应罐（f）中用微生物处理氰醇，将其转化为具有光学活性的 α-羟基酸或α-羟基酰胺，该系统配有氰醇自动控制器（h），该控制器由氰基离子检测器 （a）、调节器（b）以及与之相连的氰醇供应商（i）和（j）组成。反应在自动控制氰醇浓度的同时进行。 因此，氰醇可以在自动控制下，根据其消耗比，以相对较低且恒定的浓度供应。催化剂的反应速率可持续视为限速因素。因此，可抑制反应过程中酶活性的降低，并以高产率有效地获得具有光学活性的 α- 羟基酸或α- 羟基酰胺。
• Synthesis of Polyfluoro Ketones for Selective Inhibition of Human Phospholipase A₂ Enzymes
  作者：Constantinos Baskakis、Victoria Magrioti、Naomi Cotton、Daren Stephens、Violetta Constantinou-Kokotou、Edward A. Dennis、George Kokotos

  DOI：10.1021/jm800649q

  日期：2008.12.25

  The development of selective inhibitors for individual PLA(2) enzymes is necessary in order to target PLA(2)-specific signaling pathways, but it is challenging due to the observed promiscuity of known PLA(2) inhibitors. In the current work, we present the development and application of a variety of synthetic routes to produce pentafluoro, tetrafluoro, and trifluoro derivatives of activated carbonyl groups in order to screen for selective inhibitors and characterize the chemical properties that can lead to selective inhibition. Our results demonstrate that the pentafluoroethyl ketone functionality favors selective inhibition of the GVIA iPLA(2), a very important enzyme for which specific, potent, reversible inhibitors are needed. We find that 1,1,1,2,2-pentafluoro-7-phenyl-heptan-3-one (FKGK11) is a selective inhibitor of GVIA iPLA(2) (X-1(50) = 0.0073). Furthermore, we conclude that the introduction of an additional fluorine atom at the alpha' position of a trifluoromethyl ketone constitutes an important strategy for the development of new potent GVIA iPLA(2) inhibitors.
• PHARMACEUTICALLY ACTIVE COMPOUNDS AS DAG-LIPASE INHIBITORS
  申请人：Universiteit Leiden

  公开号：EP3145935A1

  公开（公告）日：2017-03-29
• US5736385A
  申请人：——

  公开号：US5736385A

  公开（公告）日：1998-04-07
• US7223784B2
  申请人：——

  公开号：US7223784B2

  公开（公告）日：2007-05-29