3-methoxy-1-(3-phenylpropyl)-2(1H)-pyridinethione | 1225601-87-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methoxy-1-(3-phenylpropyl)-2(1H)-pyridinethione
• CAS: 1225601-87-5
• 化学式: C₁₅H₁₇NOS
• 分子量: 259.372
• InChiKey: FSQDEDIYYHYJRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  14.16
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-methoxy-1-(3-phenylpropyl)-2(1H)-pyridinethione 在 三溴化硼 、 甲醇 、 水 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到3-hydroxy-1-(3-phenylpropyl)-2(1H)-pyridinethione
  参考文献：
  名称：

  Synthesis of Metal Complexes with 1-Substituted 3-Hydroxy-2(1H)-pyridinethiones and Their Insulin-Mimetic Activities

  摘要：

  Eight kinds of 1-alky1-3-hydroxy-2(1H)-pyridinethiones were synthesized from a commercially available 3-methoxy-2(1H)-pyridinone via 3 steps. Zn(II) and vanadyl complexes were synthesized by treatment with Zn(OAc)(2) or ZnSO(4), and VOSO(4), respectively. Vanadyl complexes were found to exist in VO(S(2)O(2)) coordination mode by means of ESR spectroscopy. From in vitro evaluation of the inhibitory effect on FFA release from rat adipocytes treated with epinephrine, it was found that IC(50) values of Zn(II) complexes with 1-alky1-3-hydroxy-2(1H)-pyridinethiones, regardless of the methylene-chain length at N-1 position, were in micromolar levels. In other words, these Zn(II) complexes showed higher insulin-mimetic activities than those synthesized previously. On the other hand, the insulin-mimetic activity of vanadyl complexes unfortunately could not be measured owing to their insolubility in KRB buffer which is used in vitro assay.

  DOI：

  10.3987/com-09-11862
• 作为产物：
  描述：

  3-methoxy-1-(3-phenylpropyl)-2(1H)-pyridinone 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 5.5h， 以88%的产率得到3-methoxy-1-(3-phenylpropyl)-2(1H)-pyridinethione
  参考文献：
  名称：

  Synthesis of Metal Complexes with 1-Substituted 3-Hydroxy-2(1H)-pyridinethiones and Their Insulin-Mimetic Activities

  摘要：

  Eight kinds of 1-alky1-3-hydroxy-2(1H)-pyridinethiones were synthesized from a commercially available 3-methoxy-2(1H)-pyridinone via 3 steps. Zn(II) and vanadyl complexes were synthesized by treatment with Zn(OAc)(2) or ZnSO(4), and VOSO(4), respectively. Vanadyl complexes were found to exist in VO(S(2)O(2)) coordination mode by means of ESR spectroscopy. From in vitro evaluation of the inhibitory effect on FFA release from rat adipocytes treated with epinephrine, it was found that IC(50) values of Zn(II) complexes with 1-alky1-3-hydroxy-2(1H)-pyridinethiones, regardless of the methylene-chain length at N-1 position, were in micromolar levels. In other words, these Zn(II) complexes showed higher insulin-mimetic activities than those synthesized previously. On the other hand, the insulin-mimetic activity of vanadyl complexes unfortunately could not be measured owing to their insolubility in KRB buffer which is used in vitro assay.

  DOI：

  10.3987/com-09-11862