4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzaldehyde | 1444001-64-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzaldehyde
• 英文别名: 4-(5-Oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzaldehyde；4-(5-oxo-4H-1,2,4-oxadiazol-3-yl)benzaldehyde
• CAS: 1444001-64-2
• 化学式: C₉H₆N₂O₃
• 分子量: 190.158
• InChiKey: XBMSUNCPVYPPTH-UHFFFAOYSA-N

物化性质

• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzaldehyde 在 palladium 10% on activated carbon 、 水 、 氢气 、 三乙酰氧基硼氢化钠 、 lithium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 生成 (S)-1-(4-(5-(((4-carbamimidoylbenzyl)amino)methyl)-2-oxooxazolidin-3-yl)phenyl)piperidine-4-carboxylic acid acetate
  参考文献：
  名称：

  Low molecular weight dual inhibitors of factor Xa and fibrinogen binding to GPIIb/IIIa with highly overlapped pharmacophores

  摘要：

  Dual antithrombotic agents acting as anticoagulants and aggregation inhibitors could have substantial advantages over currently prescribed combinations of antithrombotic drugs. Herein, we report compounds with moderate inhibitory activity for factor Xa and fibrinogen GPIIb/IIIa binding (both in the micromolar range). These compounds resulted from our efforts to merge the pharmacophores of selective factor Xa inhibitor rivaroxaban with a mimic of the Arg-Gly-Asp (RGD) sequence of fibrinogen to obtain designed multiple ligands with potential antithrombotic activity. Resulting from this study, a structurally novel class of submicromolar fibrinogen GPIIb/IIIa binding inhibitor bearing 1,2,4-oxadiazol-5(4H)-one moiety is also described. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.056
• 作为产物：
  描述：

  4-(1,3-dioxolan-2-yl)-N'-((ethoxycarbonyl)oxy)benzimidamide 在 4-甲基苯磺酸吡啶 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 6.25h， 生成 4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzaldehyde
  参考文献：
  名称：

  Low molecular weight dual inhibitors of factor Xa and fibrinogen binding to GPIIb/IIIa with highly overlapped pharmacophores

  摘要：

  Dual antithrombotic agents acting as anticoagulants and aggregation inhibitors could have substantial advantages over currently prescribed combinations of antithrombotic drugs. Herein, we report compounds with moderate inhibitory activity for factor Xa and fibrinogen GPIIb/IIIa binding (both in the micromolar range). These compounds resulted from our efforts to merge the pharmacophores of selective factor Xa inhibitor rivaroxaban with a mimic of the Arg-Gly-Asp (RGD) sequence of fibrinogen to obtain designed multiple ligands with potential antithrombotic activity. Resulting from this study, a structurally novel class of submicromolar fibrinogen GPIIb/IIIa binding inhibitor bearing 1,2,4-oxadiazol-5(4H)-one moiety is also described. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.056

文献信息

• [EN] SUBSTITUTED OXADIAZOLE DERIVATIVES AS S1P AGONISTS IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISEASES<br/>[FR] DÉRIVÉS D'OXADIAZOLE SUBSTITUÉS COMME AGONISTES DE S1P DANS LE TRAITEMENT DE MALADIES AUTO-IMMUNES ET INFLAMMATOIRES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2010085582A1

  公开（公告）日：2010-07-29

  [00180] Disclosed are compounds of Formula (I) or pharmaceutically acceptable salts thereof, wherein Q is or R1 is cycloalkyl, heteroaryl, or heterocyclyl, each optionally substituted with one to five substituents independently selected from C1 to C6 alkyl, C1 to C4 haloalkyl, -OR4, and/or halogen; and R2, R3, R4, and n are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as vascular disease and autoimmune diseases.

  [00180] 公开了公式(I)的化合物或其药用可接受的盐，其中Q是或R1是环烷基、杂芳基或杂环烷基，每个环烷基、杂芳基或杂环烷基可选地被一个到五个独立选自C1至C6烷基、C1至C4卤代烷基、-OR4和/或卤素的取代基所取代；R2、R3、R4和n的定义如本文中所述。还公开了使用这些化合物作为G蛋白偶联受体S1P1的选择性激动剂的方法，以及包含这些化合物的药物组合物。这些化合物在治疗、预防或减缓多种治疗领域，如血管疾病和自身免疫疾病的疾病或障碍的进展方面是有用的。
• [EN] PYRAZOLE-I, 2, 4 -OXAD IAZOLE DERIVATIVES AS S.PHING0SINE-1-PH0SPHATE AGONISTS<br/>[FR] DÉRIVÉS DE PYRAZOLE-1,2,4-OXADIAZOLE EN TANT QU'AGONISTES DE SPHINGOSINE-1-PHOSPHATE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2010085584A1

  公开（公告）日：2010-07-29

  Disclosed are compounds of Formula (I) or a pharmaceutically acceptable salt thereof, wherein: n is zero or an integer selected from 1 through 4; R1 is cycloalkyl, aryl, heteroaryl, or heterocyclyl, each optionally substituted with one to five substituents independently selected from C1 to C6 alkyl, C1 to C4 haloalkyl, benzyl, OR4, and/or halogen; and R2, R3, R4, and n are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

  公开的是Formula (I)或其药学上可接受的盐的化合物，其中：n为零或选自1至4的整数；R1为环烷基、芳基、杂芳基或杂环烷基，每个可选地用从C1到C6烷基、C1到C4卤代烷基、苄基、OR4和/或卤素中独立选择的一个到五个取代基取代；R2、R3、R4和n在此处有定义。还公开了将这些化合物用作G蛋白偶联受体S1P1的选择性激动剂的方法，以及包含这些化合物的药物组合物。这些化合物在治疗、预防或减缓多种治疗领域的疾病或疾病的进展方面是有用的，例如自身免疫疾病和血管疾病。
• PYRAZOLE-I, 2, 4 -OXAD IAZOLE DERIVATIVES AS S.PHING0SINE-1-PH0SPHATE AGONISTS
  申请人：Bristol-Myers Squibb Company

  公开号：EP2382211B1

  公开（公告）日：2012-12-19
• Rh(iii)-catalyzed C(sp2)–H functionalization/[4+2] annulation of oxadiazolones with iodonium ylides to access diverse fused-isoquinolines and fused-pyridines
  作者：Wang-Liang Chen、Jia-Lin Song、Sheng Fang、Jiong-Bang Li、Shang-Shi Zhang、Bing Shu

  DOI：10.1039/d4cc02046d

  日期：——

  A Rh(iii)-catalyzed C–H/N–H [4+2] annulation of oxadiazolones with iodonium ylides was developed, which afforded a series of fused-isoquinolines and fused-pyridines.