methyl 4-amino-6-cyano-2-naphthoate | 220300-02-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 4-amino-6-cyano-2-naphthoate
• 英文别名: Methyl 4-amino-6-cyanonaphthalene-2-carboxylate
• CAS: 220300-02-7
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: UTWBQMZSBJPZGG-UHFFFAOYSA-N

物化性质

• 沸点：
  460.0±30.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-amino-6-cyano-2-naphthoate 在 lithium hydroxide 、 tris(dibenzylideneacetone)dipalladium (0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 6-Cyano-4-(pyrimidin-2-ylamino)-naphthalene-2-carboxylic acid
  参考文献：
  名称：

  Interaction with the S1β-pocket of urokinase: 8-heterocycle substituted and 6,8-disubstituted 2-naphthamidine urokinase inhibitors

  摘要：

  Several 8-substituted 2-naphthamidine-based inhibitors of the serine protease urokinase plasminogen activator (uPA) are described. Direct attachment of five-membered saturated or unsaturated rings improved inhibitor performance; substitution with sulfones further improved binding profiles. Combination of these substituents or of previously described NH-linked heteroaromatic rings with 6-phenyl amide substituents provided further enhancements to potency and selectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.030
• 作为产物：
  描述：

  6-cyano-naphthalene-2-carboxylic acid methyl ester 在 palladium on activated charcoal 硫酸 、 氢气 、 potassium nitrate 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 methyl 4-amino-6-cyano-2-naphthoate
  参考文献：
  名称：

  Interaction with the S1β-pocket of urokinase: 8-heterocycle substituted and 6,8-disubstituted 2-naphthamidine urokinase inhibitors

  摘要：

  Several 8-substituted 2-naphthamidine-based inhibitors of the serine protease urokinase plasminogen activator (uPA) are described. Direct attachment of five-membered saturated or unsaturated rings improved inhibitor performance; substitution with sulfones further improved binding profiles. Combination of these substituents or of previously described NH-linked heteroaromatic rings with 6-phenyl amide substituents provided further enhancements to potency and selectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.030

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。
• [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。
• Naphthamidine urokinase plasminogen activator inhibitors with improved pharmacokinetic properties
  作者：Milan Bruncko、William J. McClellan、Michael D. Wendt、Daryl R. Sauer、Andrew Geyer、Christopher R. Dalton、Michele A. Kaminski、Moshe Weitzberg、Jane Gong、Joseph F. Dellaria、Robert Mantei、Xumiao Zhao、Vicki L. Nienaber、Kent Stewart、Vered Klinghofer、Jennifer Bouska、Todd W. Rockway、Vincent L. Giranda

  DOI：10.1016/j.bmcl.2004.10.026

  日期：2005.1

  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.
• NAPHTHAMIDINE UROKINASE INHIBITORS
  申请人：ABBOTT LABORATORIES

  公开号：EP1276722B1

  公开（公告）日：2006-03-08
• US6495562B1
  申请人：——

  公开号：US6495562B1

  公开（公告）日：2002-12-17