1-羟基-4-甲基-1,3-二氢-2H-苯并咪唑-2-酮 | 71468-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1-羟基-4-甲基-1,3-二氢-2H-苯并咪唑-2-酮
• 英文名称: 1-hydroxy-4-methyl-1H-benzo[d]imidazol-2(3H)-one
• 英文别名: 1-hydroxy-4-methyl-1H-benzimidazol-2(3H)-one；1-hydroxy-4-methyl-1,3-dihydro-benzoimidazol-2-one；1-Hydroxy-4-methylbenzimidazolon；3-hydroxy-7-methyl-1H-benzimidazol-2-one
• CAS: 71468-11-6
• 化学式: C₈H₈N₂O₂
• 分子量: 164.164
• InChiKey: VNDSIERCDSIXQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-羟基-4-甲基-1,3-二氢-2H-苯并咪唑-2-酮 、 乙酸酐 以25%的产率得到
  参考文献：
  名称：

  MACHIN J.; SMITH D. M., J. CHEM. SOC. PERKIN TRANS., PART 1, 1979, NO 5, 1371-1378

  摘要：

  DOI：
• 作为产物：
  描述：

  邻甲苯异氰酸酯 在 palladium 10% on activated carbon 、 氢气 、 lead(IV) tetraacetate 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 20.0 ℃ 、206.85 kPa 条件下， 反应 0.58h， 生成 1-羟基-4-甲基-1,3-二氢-2H-苯并咪唑-2-酮
  参考文献：
  名称：

  Synthesis and SAR of 1-Hydroxy-1H-benzo[d]imidazol-2(3H)-ones as Inhibitors of d-Amino Acid Oxidase

  摘要：

  A series of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones were synthesized and evaluated for their ability to inhibit human and porcine forms of D-amino acid oxidase (DAAO). The inhibitory potency is largely dependent on the size and position of substituents on the benzene ring with IC50 values of the compounds ranging from 70 nM to greater than 100 mu M. Structure-activity relationships of this new class of DAAO inhibitors will be presented in detail along with comparisons to previously published SAR data from other classes of DAAO inhibitors. Two of these compounds were given to mice orally together with D-serine to assess their effects on plasma D-serine pharmacokinetics.

  DOI：

  10.1021/ml300212a

文献信息

• o-Nitroaniline derivatives. Part 14.1,2 Cyclisations leading to benzimidazole N-oxides, N-hydroxybenzimidazolones and N-hydroxyquinoxaline-2,3-diones: a mechanistic borderline
  作者：Pamela A. Collins Cafiero、Colin S. French、Michael D. McFarlane、Raymond K. Mackie、David M. Smith

  DOI：10.1039/a607378f

  日期：——

  The base-induced cyclisations of N-(o-nitrophenyl)glycine derivatives (nitriles 9 or esters 13) bearing additional substituents at the other ortho-position are anomalous, resembling those involving N-(o-nitrophenyl)sarcosine analogues. The nitriles are converted into N-hydroxybenzimidazolones 10 and the esters into 1-hydroxyquinoxaline-2,3(1H,4H )diones 14 and 2,2′-diaminoazoxybenzene derivatives 15, instead of, or in addition to, the expected 2-substituted 1H-benzimidazole 3-oxides 11 and 16 or the 2-unsubstituted analogues, 17. The possibility that all these reactions proceed through a common 2,1,4-benzoxadiazine intermediate, 18, is explored.

  基诱导的 N-(o-硝基苯)甘氨酸衍生物（含有额外取代基的腈 9 或酯 13）环化反应表现出异常，类似于 N-(o-硝基苯)天冬氨酸类似物所涉及的反应。这些腈被转化为 N-羟基苯并咪唑酮 10，而酯被转化为 1-羟基喹咯啉-2,3(1H,4H)二酮 14 和 2,2′-二氨基偶氮苯衍生物 15，而不是预期的 2-取代 1H-苯并咪唑 3-氧化物 11 和 16，或 2-未取代的类似物 17。探索了所有这些反应通过一个共同的 2,1,4-苯并噁二嗪中间体 18 进行的可能性。
• A new route to -hydroxyquinoxaline-2,3-diones and some aza-analogues
  作者：Michael D. McFarlane、David M. Smith

  DOI：10.1016/s0040-4039(01)91374-7

  日期：1987.1

  Reactions of -(-nitroaryl)sarcosine esters with bases give 1-hydroxy-4-methyl-quinoxaline-2,3-diones as the principal products; the corresponding reactions of -(3-nitro-2-pyridyl)sarcosine esters give 1-hydroxy-4-methylpyrido[2,3-]pyrazine-2,3-diones. The significance of these results, in relation to a general mechanism for nitro-group condensations, is discussed.

  的反应- （-nitroaryl）肌氨酸酯与碱得到1-羟基-4-甲基-喹喔啉-2,3-二酮作为主产品; -（3-硝基-2-吡啶基）肌氨酸酯的相应反应得到1-羟基-4-甲基吡啶并[2，3- ]吡嗪-2，3-二酮。讨论了这些结果与硝基缩合的一般机理有关的意义。
• Synthesis and SAR of 1-Hydroxy-1<i>H</i>-benzo[<i>d</i>]imidazol-2(3<i>H</i>)-ones as Inhibitors of <scp>d</scp>-Amino Acid Oxidase
  作者：James F. Berry、Dana V. Ferraris、Bridget Duvall、Niyada Hin、Rana Rais、Jesse Alt、Ajit G. Thomas、Camilo Rojas、Kenji Hashimoto、Barbara S. Slusher、Takashi Tsukamoto

  DOI：10.1021/ml300212a

  日期：2012.10.11

  A series of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones were synthesized and evaluated for their ability to inhibit human and porcine forms of D-amino acid oxidase (DAAO). The inhibitory potency is largely dependent on the size and position of substituents on the benzene ring with IC50 values of the compounds ranging from 70 nM to greater than 100 mu M. Structure-activity relationships of this new class of DAAO inhibitors will be presented in detail along with comparisons to previously published SAR data from other classes of DAAO inhibitors. Two of these compounds were given to mice orally together with D-serine to assess their effects on plasma D-serine pharmacokinetics.
• MACHIN J.; SMITH D. M., J. CHEM. SOC. PERKIN TRANS., PART 1, 1979, NO 5, 1371-1378
  作者：MACHIN J.、 SMITH D. M.

  DOI：——

  日期：——