1-苄基-2-甲基-1,2-二氢吲唑-3-酮 | 4454-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 1-苄基-2-甲基-1,2-二氢吲唑-3-酮
• 英文名称: 1-Benzyl-2-methyl-indazolin-3-on
• 英文别名: 1-benzyl-2-methyl-1,2-dihydro-indazol-3-one；1-Benzyl-2-methyl-1,2-dihydro-indazol-3-on；1-Benzyl-2-methylindazol-3-one
• CAS: 4454-32-4
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: NFORNYYKGJATQW-UHFFFAOYSA-N

物化性质

• 熔点：
  84 °C
• 沸点：
  389.4±35.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苄基-2-甲基-1,2-二氢吲唑-3-酮 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 50.25h， 生成 3-methyl-2-phenyl-4(3H)-quinazolinone
  参考文献：
  名称：

  On the isomerization of dialkyl indazolones to dihydro quinazolinones

  摘要：

  DOI：

  10.1016/s0040-4039(00)85183-7
• 作为产物：
  描述：

  硫酸二甲酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 1-苄基-2-甲基-1,2-二氢吲唑-3-酮
  参考文献：
  名称：

  Milrath, Monatshefte fur Chemie, 1908, vol. 29, p. 915

  摘要：

  DOI：

文献信息

• Indazolinones, a new series of redox-active 5-lipoxygenase inhibitors with built-in selectivity and oral activity
  作者：P. Bruneau、C. Delvare、M. P. Edwards、R. M. McMillan

  DOI：10.1021/jm00107a023

  日期：1991.3

  Since the hypothetical mechanisms of hydroperoxydation of arachidonic acid by, respectively, 5-lipoxygenase (5-LPO) and cyclooxygenase (CO) involve a redox cycle, a compound which reduces 5-LPO and CO to their inactive state would give a nonselective inhibitor of both enzymes. Structural modifications of such a compound could be expected to give improved potency and selectivity for 5-LPO and oral activity. Such an approach has led to the discovery of 1,2-dihydroindazol-3-ones which are potent 5-LPO inhibitors with various degrees of selectivity. Structure-activity relationship studies indicated that while N-1,N-2-unsubstituted and N-1-substituted derivatives are orally inactive, N-2-alkyl derivatives are orally active and inhibit both 5-LPO and CO. In contrast, N-2-benzyl derivatives are selective for 5-LPO but possess only weak oral activity. Further structural modifications have identified ICI 207968 [1,2-dihydro-2-(3-pyridylmethyl)-3H-indazol-3-one, 21a] which combines potent oral activity and high selectivity. Methemoglobin (MHb) induction by 21a in dog blood precluded its development for clinical use. Attempts at dissociating 5-LPO inhibitory properties and MHb formation showed that MHb formation in vitro seemed to be related to the redox potential of the compounds whereas 5-LPO inhibition was not. This study led to a series of 4-(N-n-pentylcarbamoyl)indazolinones which maintained in vitro 5-LPO potency but did not induce MHb.
• BRUNEAU, P.;DELVARE, C.;EDWARDS, M. P.;MCMILLAN, R. M., J. MED. CHEM. , 34,(1991) N, C. 1028-1036
  作者：BRUNEAU, P.、DELVARE, C.、EDWARDS, M. P.、MCMILLAN, R. M.

  DOI：——

  日期：——
• BAIOCCHI L.; PICCONI G., TETRAHEDRON LETT., 27,(1986) N 43, 5255-5256
  作者：BAIOCCHI L.、 PICCONI G.

  DOI：——

  日期：——
• On the isomerization of dialkyl indazolones to dihydro quinazolinones
  作者：Leandro Baiocchi、Giuseppe Picccni

  DOI：10.1016/s0040-4039(00)85183-7

  日期：1986.1
• Milrath, Monatshefte fur Chemie, 1908, vol. 29, p. 915
  作者：Milrath

  DOI：——

  日期：——