6-(hydroxymethyl)-2-naphthonitrile | 219873-03-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(hydroxymethyl)-2-naphthonitrile
• 英文别名: 6-(hydroxymethyl)naphthalene-2-carbonitrile
• CAS: 219873-03-7
• 化学式: C₁₂H₉NO
• 分子量: 183.21
• InChiKey: PCURJZMHSLMVLL-UHFFFAOYSA-N

物化性质

• 沸点：
  401.6±20.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  6-(hydroxymethyl)-2-naphthonitrile 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 6-styryl-naphthalene-2-carbonitrile
  参考文献：
  名称：

  Naphthamidine urokinase plasminogen activator inhibitors with improved pharmacokinetic properties

  摘要：

  A series of non-amide-linked 6-substituted-2-naphthamidine urokinase plasminogen activator (uPA) inhibitors are described. These compounds possess excellent binding activities and selectivities with significantly improved pharmacokinetic profiles versus previously described amide-linked inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.026
• 作为产物：
  描述：

  2,6-萘二羧酸二甲酯 在 吡啶 、 锂硼氢 、 氯化亚砜 、 氨 、 三氟乙酸酐 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 6-(hydroxymethyl)-2-naphthonitrile
  参考文献：
  名称：

  Substrate profiling of Finegoldia magna SufA protease, inhibitor screening and application to prevent human fibrinogen degradation and bacteria growth in vitro

  摘要：

  SufA, which belongs to the subtilisin-like serine protease family, contains a non-canonical Asp-His-Ser catalytic triad. Under in vitro conditions, SufA is capable of human fibrinogen hydrolysis leading to inhibition of fibrin network formation, thus suggesting its important role in the development and progression of Finegoldia magna infections. In addition, it has been demonstrated that SufA can hydrolyze antibacterial peptides such as LL-37 and the chemokine MIG/CXCL 9, hence evading host defence mechanisms. Although the SufA protease from E magna was discovered several years ago, its optimal substrate preference has not yet been identified. Considering the role of SufA, we have focused on the profiling of its substrate sequence preference spanning S1-S3 binding pockets using the FRET (fluorescence resonance energy transfer) approach. Next, based on the structure of the P1 residue of the developed substrate, we narrowed the inhibitor screening to the phosphonic analogues of amino acids containing an arginine-like side chain. Among all the compounds tested, only Cbz-6-AmNphth(P)(OPh)(2) showed any inhibitory activity against SufA displaying k(2)/K-i value of 10 800 M-1 s(-1). In addition, it prevented SufA-mediated human fibrinogen hydrolysis in vitro and exhibited potent antibacterial activity against E magna, Staphylococcus aureus and Escherichia coli.Herein, we report on the substrate specificity, synthesis and kinetic evaluation of phosphonic inhibitors of SufA protease from E magna which could help to establish its function in pathogenesis development and may lead to the elaboration of new antibacterial drugs. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2014.05.006

文献信息

• Naphthamidine urokinase inhibitors
  申请人：Abbott Laboratories

  公开号：US06495562B1

  公开（公告）日：2002-12-17

  Compounds having the formula are inhibitors of urokinase and are useful in the treatment of diseases in which urokinase plays a role. Also disclosed are urokinase-inhibiting compositions, methods for the preparation of urokinase-inhibitors, and a method of inhibiting urokinase in a mammal.

  具有以下化学式的化合物是尿激酶的抑制剂，对于尿激酶在某些疾病中发挥作用的治疗是有用的。还公开了抑制尿激酶的组合物、制备尿激酶抑制剂的方法，以及在哺乳动物中抑制尿激酶的方法。
• Deoxygenation of Ethers To Form Carbon–Carbon Bonds via Nickel Catalysis
  作者：Zhi-Chao Cao、Zhang-Jie Shi

  DOI：10.1021/jacs.7b02326

  日期：2017.5.17

  In this article a successful protocol was developed to construct carbon-carbon bonds by the extrusion of the O atom of ethers via nickel catalysis in the presence of reductants. This methodology is featured as a highly economic route to construct sp3-sp3 C-C bonds through dual C-O activation of ethers with good functional group tolerance.

  在这篇文章中，开发了一个成功的协议，通过在还原剂的存在下通过镍催化挤出醚的 O 原子来构建碳 - 碳键。该方法是通过具有良好官能团耐受性的醚的双 CO 活化来构建 sp3-sp3 CC 键的高度经济途径。
• Enantioselective α-Benzylation of Acyclic Esters Using π-Extended Electrophiles
  作者：Kevin J. Schwarz、Chao Yang、James W. B. Fyfe、Thomas N. Snaddon

  DOI：10.1002/anie.201806742

  日期：2018.9.10

  esters is reported. This reaction proceeds via stereodefined C1‐ammonium enolate nucleophiles. Critical to its success was the identification of benzylic phosphate electrophiles, which were uniquely reactive. Alkylated products were obtained with very high levels of enantioselectivity, and this method has been applied toward the synthesis of the thrombin inhibitor DX‐9065a.

  报道了无环酯的第一次不对称协作路易斯碱/钯催化的苄基烷基化。该反应通过立体定义的C1-烯醇铵盐亲核试剂进行。成功的关键是鉴定具有独特反应性的磷酸苄基亲电试剂。获得的烷基化产物具有很高的对映选择性，该方法已应用于凝血酶抑制剂DX‐9065a的合成。
• [EN] NAPHTHAMIDINE UROKINASE INHIBITORS<br/>[FR] INHIBITEUR DE NAPHTHAMIDINE UROKINASE
  申请人：ABBOTT LAB

  公开号：WO2001081314A1

  公开（公告）日：2001-11-01

  Compounds having formula (I) are inhibitors of urokinase and are useful in the treatment of diseases in which urokinase plays a role. Also disclosed are urokinase-inhibiting compositions, methods for the preparation of urokinase-inhibitors, and a method of inhibiting urokinase in a mammal.

  式(I)的化合物是尿激酶抑制剂，并可用于治疗与尿激酶有关的疾病。还公开了抑制尿激酶的组合物、制备尿激酶抑制剂的方法以及抑制哺乳动物体内尿激酶的方法。
• Urokinase inhibitors
  申请人：——

  公开号：US20010049374A1

  公开（公告）日：2001-12-06

  Compounds having the formula 1 are inhibitors of urokinase and are useful in the treatment of diseases in which urokinase plays a role. Also disclosed are urokinase-inhibiting compositions and a method of inhibiting urokinase in a mammal.

  化合物的化学式为1，它们是尿激酶抑制剂，在尿激酶发挥作用的疾病治疗中有用。还披露了抑制尿激酶的组合物和一种在哺乳动物中抑制尿激酶的方法。