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ethyl 2-[(5-methylpyridin-3-yl)methyl]-3-oxoindazole-1-carboxylate | 120276-38-2

中文名称
——
中文别名
——
英文名称
ethyl 2-[(5-methylpyridin-3-yl)methyl]-3-oxoindazole-1-carboxylate
英文别名
——
ethyl 2-[(5-methylpyridin-3-yl)methyl]-3-oxoindazole-1-carboxylate化学式
CAS
120276-38-2
化学式
C17H17N3O3
mdl
——
分子量
311.34
InChiKey
JWFMDQSKIPKZAN-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.56
  • 重原子数:
    23.0
  • 可旋转键数:
    3.0
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.24
  • 拓扑面积:
    66.12
  • 氢给体数:
    0.0
  • 氢受体数:
    6.0

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    ethyl 2-[(5-methylpyridin-3-yl)methyl]-3-oxoindazole-1-carboxylate氢氧化钾 作用下, 以 乙醇 为溶剂, 反应 0.17h, 以83%的产率得到1,2-dihydro-2-[3-(5-methylpyridyl)methyl]-3H-indazol-3-one
    参考文献:
    名称:
    Indazolinones, a new series of redox-active 5-lipoxygenase inhibitors with built-in selectivity and oral activity
    摘要:
    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.
    DOI:
    10.1021/jm00107a023
  • 作为产物:
    参考文献:
    名称:
    Indazolinones, a new series of redox-active 5-lipoxygenase inhibitors with built-in selectivity and oral activity
    摘要:
    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.
    DOI:
    10.1021/jm00107a023
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文献信息

  • 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:——
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