1-hydroxy-3-methyl-1H-benzo[d]imidazol-2(3H)-one | 19808-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-hydroxy-3-methyl-1H-benzo[d]imidazol-2(3H)-one
• 英文别名: 1-hydroxy-3-methyl-1H-benzimidazol-2(3H)-one；1-hydroxy-3-methyl-1,3-dihydro-benzoimidazol-2-one；1-Hydroxy-3-methyl-benzimidazol-2-on；1-Hydroxy-3-methylbenzimidazol-2-one
• CAS: 19808-72-1
• 化学式: C₈H₈N₂O₂
• 分子量: 164.164
• InChiKey: KDJGHPUGSYIWDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 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：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基-2-硝基苯胺 在 potassium carbonate 、 zinc(II) chloride 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 3.5h， 生成 1-hydroxy-3-methyl-1H-benzo[d]imidazol-2(3H)-one
  参考文献：
  名称：

  o-Nitroaniline derivatives. Part 14.1,2 Cyclisations leading to benzimidazole N-oxides, N-hydroxybenzimidazolones and N-hydroxyquinoxaline-2,3-diones: a mechanistic borderline

  摘要：

  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。

  DOI：

  10.1039/a607378f

文献信息

• 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。
• IDO Inhibitors
  申请人：Mautino Mario

  公开号：US20110053941A1

  公开（公告）日：2011-03-03

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

  目前提供以下方法：(a) 通过接触本文中描述的化合物的调节有效量与吲哚胺2,3-二氧化酶相互作用，从而调节吲哚胺2,3-二氧化酶的活性；(b) 治疗需要吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制的患者，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(c) 治疗需要抑制吲哚胺-2,3-二氧化酶酶活性的医疗状况，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(d) 增强抗癌治疗的有效性，包括给予抗癌剂和本文中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(f) 治疗与传染病相关的免疫抑制，例如HIV-1感染，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量。
• Selective inhibitors of clinically important mutants of the EGFR tyrosine kinase
  申请人：CS PHARMATECH LIMITED

  公开号：US10435388B2

  公开（公告）日：2019-10-08

  The present invention provides compounds of Formula (I) or a subgeneric structure or species thereof or a pharmaceutically acceptable salt, ester, solvate, and/or prodrug thereof and methods and compositions for treating or ameliorating abnormal cell proliferative disorders, such as cancer, wherein A, R2, R3, R10, E1, E2, E3, Y, and Z are as defined herein.

  本发明提供了式(I)化合物或其亚属结构或种类或其药学上可接受的盐、酯、溶液剂和/或原药，以及用于治疗或改善异常细胞增殖性疾病（如癌症）的方法和组合物，其中A、R2、R3、R10、E1、E2、E3、Y和Z如本文所定义。
• 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.
• SELECTIVE INHIBITORS OF CLINICALLY IMPORTANT MUTANTS OF THE EGFR TYROSINE KINASE
  申请人：CS Pharmatech Limited

  公开号：EP3399968B1

  公开（公告）日：2021-10-20