o-difluoromethoxy-5-nitrobenzaldehyde | 145742-63-8

• 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: o-difluoromethoxy-5-nitrobenzaldehyde
• 英文别名: 2-(Difluoromethoxy)-5-nitrobenzaldehyde
• CAS: 145742-63-8
• 化学式: C₈H₅F₂NO₄
• mdl: MFCD00521794
• 分子量: 217.129
• InChiKey: YERTUMJMWKSDIU-UHFFFAOYSA-N

物化性质

• 熔点：
  43-44°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  o-difluoromethoxy-5-nitrobenzaldehyde 在 氢气 、 镍 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 2,6-dimethyl-3,5-dicarboethoxy-4-(2-difluoromethoxy-5-isothiocyanatophenyl)-1,4-dihydropyridine
  参考文献：
  名称：

  Vasorelaxation by New Hybrid Compounds Containing Dihydropyridine and Pinacidil-Like Moieties

  摘要：

  The synthesis and pharmacological properties of a novel type of vasorelaxant hybrid compounds are described. The investigated compounds originate from fluorinated 4-aryl-1,4-dihydropyridines, which are known calcium channel blockers, and/or from fluorinated analogues of pinacidil, which is an opener of ATP-sensitive potassium channels. In particular, we studied the most potent hybrid, 2,6-dimethyl-3,5-dicarbomethoxy-4-(2-difluoromethoxy-5-N-(N "-cyano-N'-1,2,2-trimethyl-propylguanidyl)-phenyl)-1,4-dihydropyridine (4a), together with its parent compounds, the dihydropyridine 1b and the pinacidil analogue 3. In isolated rat mesenteric arteries, micromolar concentrations of 4a relaxed contractions exerted by K+-depolarization or by norepinephrine. The latter effect was sensitive to the potassium channel blocker glibenclamide. Micromolar 4a also inhibited [H-3](+)-isradipine and [H-3]P1075 binding to rat cardiac membranes, and it blocked L-type calcium. channels expressed in a mammalian cell line. The respective parent compounds 1b and 3 were always more potent and more selective regarding calcium channel or potassium channel interaction, respectively. In contrast, 4a combined both effects within the same concentration range, indicating that it may represent a lead structure for a novel class of pharmacological hybrid compounds.

  DOI：

  10.1021/jm990443h
• 作为产物：
  描述：

  (二氟甲氧基)苯甲醛 在 硫酸 、 硝酸 作用下， 反应 1.0h， 以90%的产率得到o-difluoromethoxy-5-nitrobenzaldehyde
  参考文献：
  名称：

  Vasorelaxation by New Hybrid Compounds Containing Dihydropyridine and Pinacidil-Like Moieties

  摘要：

  The synthesis and pharmacological properties of a novel type of vasorelaxant hybrid compounds are described. The investigated compounds originate from fluorinated 4-aryl-1,4-dihydropyridines, which are known calcium channel blockers, and/or from fluorinated analogues of pinacidil, which is an opener of ATP-sensitive potassium channels. In particular, we studied the most potent hybrid, 2,6-dimethyl-3,5-dicarbomethoxy-4-(2-difluoromethoxy-5-N-(N "-cyano-N'-1,2,2-trimethyl-propylguanidyl)-phenyl)-1,4-dihydropyridine (4a), together with its parent compounds, the dihydropyridine 1b and the pinacidil analogue 3. In isolated rat mesenteric arteries, micromolar concentrations of 4a relaxed contractions exerted by K+-depolarization or by norepinephrine. The latter effect was sensitive to the potassium channel blocker glibenclamide. Micromolar 4a also inhibited [H-3](+)-isradipine and [H-3]P1075 binding to rat cardiac membranes, and it blocked L-type calcium. channels expressed in a mammalian cell line. The respective parent compounds 1b and 3 were always more potent and more selective regarding calcium channel or potassium channel interaction, respectively. In contrast, 4a combined both effects within the same concentration range, indicating that it may represent a lead structure for a novel class of pharmacological hybrid compounds.

  DOI：

  10.1021/jm990443h

文献信息

• Cyanamide: a convenient building block to synthesize 4-aryl-2-cyanoimino-3,4-dihydro-1H-pyrimidine systems via a multicomponent reaction
  作者：R. Hulme、O.D.P. Zamora、E.J. Mota、M.A. Pastén、R. Contreras-Rojas、R. Miranda、I. Valencia-Hernández、J. Correa-Basurto、J. Trujillo-Ferrara、F. Delgado

  DOI：10.1016/j.tet.2008.01.087

  日期：2008.4

  4-Aryl-2-cyanoimino-3,4-dihydro-1H-pyrimidine derivatives were prepared using a multicomponent reaction by reacting a mixture of arene or heteroarenecarbaldehyde, 1,3-dicarbonyl compounds, and cyanamide under acidic conditions. The novelty of this approach derives from its use of cyanamide as a building block in a four-component Biginelli-type reaction. Varying the reaction conditions led to the formation of

  使用芳烃或杂亚芳基甲醛，1，3-二羰基化合物和氰胺的混合物在酸性条件下反应，使用多组分反应制备4-芳基-2-氰基氨基-3,4-二氢-1 H-嘧啶衍生物。这种方法的新颖性源于其在四组分Biginelli型反应中使用氰胺作为基本组成部分。改变反应条件导致形成N-（2-亚氨基-6-苯基-1,3,5-氧二叠氮基-4-亚烷基）氰酰胺或3,4-二氢嘧啶-2（1 H）-。合成的杂环骨架的类型取决于酸催化剂的性质以及所采用的反应条件。
• [EN] MACROCYCLIC FACTOR VIIA INHIBITORS USEFUL AS ANTICOAGULANTS<br/>[FR] INHIBITEURS MACROCYCLIQUES DU FACTEUR VIIA UTILES EN TANT QU'ANTICOAGULANTS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2008079836A4

  公开（公告）日：2009-03-12
• MACROCYCLIC FACTOR VIIA INHIBITORS USEFUL AS ANTICOAGULANTS
  申请人：Wurtz Nicholas Ronald

  公开号：US20100113488A1

  公开（公告）日：2010-05-06

  The present invention relates generally to novel macrocycles of Formula (I): or stereoisomers, tautomers, pharmaceutically acceptable salts, solvates, or prodrugs thereof, wherein the variables A, B, C, D, L, M, W, Z 1 , Z 2 , Z 3 , Z 4 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are as defined herein. These compounds are selective inhibitors of factor VIIa which can be used as medicaments.
• US8420830B2
  申请人：——

  公开号：US8420830B2

  公开（公告）日：2013-04-16
• Vasorelaxation by New Hybrid Compounds Containing Dihydropyridine and Pinacidil-Like Moieties
  作者：Lev M. Yagupolskii、Wolfram Antepohl、Ferruh Artunc、Renate Handrock、Boris M. Klebanov、Irina I. Maletina、Bent Marxen、Kirill I. Petko、Ulrich Quast、Anna Vogt、Carolin Weiss、Jutta Zibold、Stefan Herzig

  DOI：10.1021/jm990443h

  日期：1999.12.1

  The synthesis and pharmacological properties of a novel type of vasorelaxant hybrid compounds are described. The investigated compounds originate from fluorinated 4-aryl-1,4-dihydropyridines, which are known calcium channel blockers, and/or from fluorinated analogues of pinacidil, which is an opener of ATP-sensitive potassium channels. In particular, we studied the most potent hybrid, 2,6-dimethyl-3,5-dicarbomethoxy-4-(2-difluoromethoxy-5-N-(N "-cyano-N'-1,2,2-trimethyl-propylguanidyl)-phenyl)-1,4-dihydropyridine (4a), together with its parent compounds, the dihydropyridine 1b and the pinacidil analogue 3. In isolated rat mesenteric arteries, micromolar concentrations of 4a relaxed contractions exerted by K+-depolarization or by norepinephrine. The latter effect was sensitive to the potassium channel blocker glibenclamide. Micromolar 4a also inhibited [H-3](+)-isradipine and [H-3]P1075 binding to rat cardiac membranes, and it blocked L-type calcium. channels expressed in a mammalian cell line. The respective parent compounds 1b and 3 were always more potent and more selective regarding calcium channel or potassium channel interaction, respectively. In contrast, 4a combined both effects within the same concentration range, indicating that it may represent a lead structure for a novel class of pharmacological hybrid compounds.