2-(Phenoxymethyl)-5-[6-[5-(phenoxymethyl)-1,3,4-oxadiazol-2-yl]hexyl]-1,3,4-oxadiazole | 858538-33-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(Phenoxymethyl)-5-[6-[5-(phenoxymethyl)-1,3,4-oxadiazol-2-yl]hexyl]-1,3,4-oxadiazole
• CAS: 858538-33-7
• 化学式: C₂₄H₂₆N₄O₄
• 分子量: 434.495
• InChiKey: OBFXTUSSRDHANK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  96.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(Phenoxymethyl)-5-[6-[5-(phenoxymethyl)-1,3,4-oxadiazol-2-yl]hexyl]-1,3,4-oxadiazole 、 苄胺 反应 30.0h， 以27%的产率得到4-Benzyl-3-[6-[4-benzyl-5-(phenoxymethyl)-1,2,4-triazol-3-yl]hexyl]-5-(phenoxymethyl)-1,2,4-triazole
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Three-Dimensional Quantitative Structure−Activity Relationship Study of Small-Molecule Positive Modulators of Adrenomedullin

  摘要：

  Adrenomedullin (AM) is a peptide hormone implicated in blood pressure regulation and in the pathophysiology of several diseases such as hypertension, cancer, diabetes, and renal disorders, becoming an interesting new target for the development of drugs. In a recent high-throughput screening study, a positive modulator with a bistriazole structure has been identified.(1) In this work, a new series of structurally related compounds has been synthesized by reaction of phenoxyacetic acid with the corresponding dihydrazide, followed by treatment of the formed bisoxadiazoles with benzylamine. The affinity toward AM of the lead compound, and a structurally related family obtained from the small-molecule NCI library together with the synthesized series, has been determined. A three-dimensional quantitative structure-activity relationship (3D-QSAR) study and conformational and molecular dynamics simulations have shown that the presence of a free NH and a phenyl group is essential for the interaction of these compounds with AM.

  DOI：

  10.1021/jm050021+
• 作为产物：
  描述：

  辛二酰肼 在 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 2-(Phenoxymethyl)-5-[6-[5-(phenoxymethyl)-1,3,4-oxadiazol-2-yl]hexyl]-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Three-Dimensional Quantitative Structure−Activity Relationship Study of Small-Molecule Positive Modulators of Adrenomedullin

  摘要：

  Adrenomedullin (AM) is a peptide hormone implicated in blood pressure regulation and in the pathophysiology of several diseases such as hypertension, cancer, diabetes, and renal disorders, becoming an interesting new target for the development of drugs. In a recent high-throughput screening study, a positive modulator with a bistriazole structure has been identified.(1) In this work, a new series of structurally related compounds has been synthesized by reaction of phenoxyacetic acid with the corresponding dihydrazide, followed by treatment of the formed bisoxadiazoles with benzylamine. The affinity toward AM of the lead compound, and a structurally related family obtained from the small-molecule NCI library together with the synthesized series, has been determined. A three-dimensional quantitative structure-activity relationship (3D-QSAR) study and conformational and molecular dynamics simulations have shown that the presence of a free NH and a phenyl group is essential for the interaction of these compounds with AM.

  DOI：

  10.1021/jm050021+

文献信息

• Synthesis, Biological Evaluation, and Three-Dimensional Quantitative Structure−Activity Relationship Study of Small-Molecule Positive Modulators of Adrenomedullin
  作者：Mario A. García、Sonsoles Martín-Santamaría、Mónica Cacho、Fernando Moreno de la Llave、Miguel Julián、Alfredo Martínez、Beatriz de Pascual-Teresa、Ana Ramos

  DOI：10.1021/jm050021+

  日期：2005.6.1

  Adrenomedullin (AM) is a peptide hormone implicated in blood pressure regulation and in the pathophysiology of several diseases such as hypertension, cancer, diabetes, and renal disorders, becoming an interesting new target for the development of drugs. In a recent high-throughput screening study, a positive modulator with a bistriazole structure has been identified.(1) In this work, a new series of structurally related compounds has been synthesized by reaction of phenoxyacetic acid with the corresponding dihydrazide, followed by treatment of the formed bisoxadiazoles with benzylamine. The affinity toward AM of the lead compound, and a structurally related family obtained from the small-molecule NCI library together with the synthesized series, has been determined. A three-dimensional quantitative structure-activity relationship (3D-QSAR) study and conformational and molecular dynamics simulations have shown that the presence of a free NH and a phenyl group is essential for the interaction of these compounds with AM.