3-(2,3-dihydroxylphenoxy)propanenitrile | 934391-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(2,3-dihydroxylphenoxy)propanenitrile
• 英文别名: 3-(2,3-Dihydroxyphenoxy)propanenitrile
• CAS: 934391-20-5
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: COTHVWHPZGZDHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  73.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2,3-dihydroxylphenoxy)propanenitrile 在 硫酸 作用下， 反应 3.0h， 以54%的产率得到7,8-dihydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis, structural revision, and antioxidant activities of antimutagenic homoisoflavonoids from Hoffmanosseggia intricata

  摘要：

  Intricatinol and intricatin, the two homoisoflavonoids isolated from Hoffmanosseggia intricata, and two analogs have been synthesized from pyrogallol in three steps. The spectral data of synthetic intricatinol are in good agreement with those of natural metabolite, but the spectral data of intricatin are not corroborative with those of the natural product. The structure of intricatin has been thus revised to 8-methoxybonducellin, a compound isolated from Caesalpinia pulcherrima. The antioxidant activity of all the four homoisoflavonoids was determined by superoxide (NBT) and DPPH free radical scavenging methods. The synthetic analog 7,8-dihydroxy-3-[(3,4-dihydroxyphenyl)methylene]chroman-4-one displayed excellent activity in both methods.

  DOI：

  10.1016/j.bmcl.2006.12.008
• 作为产物：
  描述：

  丙烯腈 、 邻苯三酚 在 sodium methylate 作用下， 反应 7.0h， 以22%的产率得到3-(2,3-dihydroxylphenoxy)propanenitrile
  参考文献：
  名称：

  Evaluation of the pharmacophoric motif of the caged Garcinia xanthones

  摘要：

  几种带有独特结构和强效生物活性的囊状（caged）Garciniaxanthone家族成员的结合，促使我们评估它们的药效团（pharmacophore）。我们开发了一种Pd(0)催化的方法，用于酚类化合物的反向普雷尼尔化（reverse prenylation），结合Claissen/Diels–Alder反应级联，实现了对各种囊状类似物的快速和高效获取。这些化合物的生长抑制活性评估得出结论，完整的ABC环系统及其C环囊状结构对生物活性至关重要。与克鲁文酮（cluvenone，每个7号的化合物）进行的研究还表明，这些化合物能够诱导细胞凋亡，并在多药耐药性白血病细胞中表现出显著的细胞毒性。因此，囊状Garciniaxanthone结构代表了一种新的强效药效团。

  DOI：

  10.1039/b913496d

文献信息

• Evaluation of the pharmacophoric motif of the caged Garcinia xanthones
  作者：Oraphin Chantarasriwong、Woo Cheal Cho、Ayse Batova、Warinthorn Chavasiri、Curtis Moore、Arnold L. Rheingold、Emmanuel A. Theodorakis

  DOI：10.1039/b913496d

  日期：——

  The combination of unique structure and potent bioactivity exhibited by several family members of the caged Garciniaxanthones, led us to evaluate their pharmacophore. We have developed a Pd(0)-catalyzed method for the reverse prenylation of catechols that, together with a Claisen/Diels–Alder reaction cascade, provides rapid and efficient access to various caged analogues. Evaluation of the growth inhibitory activity of these compounds leads to the conclusion that the intact ABC ring system containing the C-ring caged structure is essential to the bioactivity. Studies with cluvenone (7) also showed that these compounds induce apoptosis and exhibit significant cytotoxicity in multidrug-resistant leukemia cells. As such, the caged Garciniaxanthone motif represents a new and potent pharmacophore.

  几种带有独特结构和强效生物活性的囊状（caged）Garciniaxanthone家族成员的结合，促使我们评估它们的药效团（pharmacophore）。我们开发了一种Pd(0)催化的方法，用于酚类化合物的反向普雷尼尔化（reverse prenylation），结合Claissen/Diels–Alder反应级联，实现了对各种囊状类似物的快速和高效获取。这些化合物的生长抑制活性评估得出结论，完整的ABC环系统及其C环囊状结构对生物活性至关重要。与克鲁文酮（cluvenone，每个7号的化合物）进行的研究还表明，这些化合物能够诱导细胞凋亡，并在多药耐药性白血病细胞中表现出显著的细胞毒性。因此，囊状Garciniaxanthone结构代表了一种新的强效药效团。
• Synthesis, structural revision, and antioxidant activities of antimutagenic homoisoflavonoids from Hoffmanosseggia intricata
  作者：Vidavalur Siddaiah、Muchchintala Maheswara、Chunduri Venkata Rao、Somepalli Venkateswarlu、Gottumukkala V. Subbaraju

  DOI：10.1016/j.bmcl.2006.12.008

  日期：2007.3

  Intricatinol and intricatin, the two homoisoflavonoids isolated from Hoffmanosseggia intricata, and two analogs have been synthesized from pyrogallol in three steps. The spectral data of synthetic intricatinol are in good agreement with those of natural metabolite, but the spectral data of intricatin are not corroborative with those of the natural product. The structure of intricatin has been thus revised to 8-methoxybonducellin, a compound isolated from Caesalpinia pulcherrima. The antioxidant activity of all the four homoisoflavonoids was determined by superoxide (NBT) and DPPH free radical scavenging methods. The synthetic analog 7,8-dihydroxy-3-[(3,4-dihydroxyphenyl)methylene]chroman-4-one displayed excellent activity in both methods.