3-甲基-1H-吡咯并[2,1-c][1,4]恶嗪-1-酮 | 116212-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 3-甲基-1H-吡咯并[2,1-c][1,4]恶嗪-1-酮
• 英文名称: 3-methyl-1H-pyrrolo[2,1-c][1,4]oxazin-1-one
• 英文别名: 3-methylpyrrolo[2,1-c][1,4]oxazin-1-one
• CAS: 116212-48-7
• 化学式: C₈H₇NO₂
• 分子量: 149.149
• InChiKey: KXSQOAJHQJAJRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  92-94 °C
• 沸点：
  138.2±40.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 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：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-甲基-1H-吡咯并[2,1-c][1,4]恶嗪-1-酮 在 肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 N-(3-methyl-1-oxopyrrolo[1,2-a]pyrazin-2(1H)-yl)acetamide
  参考文献：
  名称：

  Synthesis and biological evaluation of new pyrrolopyrazinone compounds as potential antitumor agents

  摘要：

  A series of pyrrolo[1,2-a]pyrazinone compounds (5a-9f) were synthesized, and their cytotoxic activity against SKOV-3, A549, HeLa cells in vitro were evaluated by the MU method. Some of the compounds showed potential antitumor activity against three tumor cell lines. Among them, compounds 9c and 9d showed the most potent cytotoxic activity. The preliminary mechanism of action was discussed. (C) 2013 Hong-Rui Song and Wei Shi. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.04.020
• 作为产物：
  描述：

  1-(2-oxopropyl)-1H-pyrrole-2-carbaldehyde 在 caesium carbonate 、 4-甲氧基-3-硝基三氟甲苯 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以54%的产率得到3-甲基-1H-吡咯并[2,1-c][1,4]恶嗪-1-酮
  参考文献：
  名称：

  氧化 N-杂环卡宾 (NHC) 催化快速获得功能化的吡咯并恶嗪酮

  摘要：

  报道了N-杂环卡宾 (NHC) 催化的N-取代吡咯 2-甲醛在氧化条件下的分子内环化，从而可以轻松合成吡咯并恶嗪酮衍生物。该策略成功的关键是使用 NHC 生成酰基唑以及碱介导的烯醇化物形成。随后将烯醇化物与酰基唑鎓进行分子内酰化，得到所需产物。反应条件温和，官能团相容性好，产物收率高是本发明的优点。

  DOI：

  10.1016/j.tet.2021.132330

文献信息

• CXCR7 ANTAGONISTS
  申请人：ChemoCentryx, Inc.

  公开号：US20140154179A1

  公开（公告）日：2014-06-05

  Compounds having formula I, or pharmaceutically acceptable salts, hydrates or N-oxides thereof are provided and are useful for binding to CXCR7, and treating diseases that are dependent, at least in part, on CXCR7 activity. Accordingly, the present invention provides in further aspects, compositions containing one or more of the above-noted compounds in admixture with a pharmaceutically acceptable excipient.

  提供具有化学式I的化合物，或其药用可接受的盐、水合物或N-氧化物，并且这些化合物可用于与CXCR7结合，治疗部分或完全依赖于CXCR7活性的疾病。因此，根据本发明的进一步方面，提供含有上述化合物之一或多个的组合物与药用可接受的赋形剂混合物。
• Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products
  作者：Sultan Taskaya、Nurettin Menges、Metin Balci

  DOI：10.3762/bjoc.11.101

  日期：——

  efficiently converted into 3,4-dihydropyrrolo- and indolo-oxazin-1-one derivatives by a gold(III)-catalyzed cyclization reaction. Some of the products underwent TFA-catalyzed double bond isomerization and some did not. Cyclization reactions in the presence of alcohol catalyzed by Au(I) resulted in the formation of hemiacetals after cascade reactions.

  通过金（III）催化的环化反应，将各种N-炔丙基吡咯和吲哚羧酸有效地转化为3，4-二氢吡咯并-和吲哚-恶嗪-1-酮衍生物。一些产物进行了TFA催化的双键异构化，而另一些则没有。在由Au（I）催化的醇存在下的环化反应导致级联反应后半缩醛的形成。
• Development of 4-Heteroarylamino-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octanes] as α7 Nicotinic Receptor Agonists
  作者：Matthew D. Hill、Haiquan Fang、H. Dalton King、Christiana I. Iwuagwu、Ivar M. McDonald、James Cook、F. Christopher Zusi、Robert A. Mate、Ronald J. Knox、Debra Post-Munson、Amy Easton、Regina Miller、Kimberley Lentz、Wendy Clarke、Yulia Benitex、Nicholas Lodge、Robert Zaczek、Rex Denton、Daniel Morgan、Linda Bristow、John E. Macor、Richard Olson

  DOI：10.1021/acsmedchemlett.6b00471

  日期：2017.1.12

  [oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (20) and (1′S,3′R,4′S)-N-(7-chloropyrrolo[2,1-f][1,2,4]triazin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (21), were identified. Both agonists improved cognition in a preclinical rodent model of learning and memory. Additionally, 5-HT3A receptor SAR suggested the presence of a steric site that when engaged led to significant loss of affinity

  我们描述了含奎尼丁的螺氨基甲酸酯的合成及其作为α7烟碱乙酰胆碱受体（nAChR）部分激动剂的效用。融合的合成路线可用于快速SAR调查，并提供了多种多样的融合6,5-杂芳基类似物。两个有效的和选择性α7nAChR的部分激动剂，（1'小号，3' - [R，4'小号） - ñ - （7-溴吡咯并[2,1- ˚F ] [1,2,4]三嗪-4-基） - 4H-1'-氮杂螺[恶唑恶唑-5,3'-二环[2.2.2]辛] -2-胺（20）和（1'小号，3' - [R，4'小号） - ñ - （7-氯吡咯[2,1- f鉴定了[[1,2,4]三嗪-4-基）-4H-1'-氮杂螺并[恶唑-5,3'-双环[2.2.2]正辛] -2-胺（21）。两种激动剂在临床前啮齿动物学习和记忆模型中均提高了认知度。此外，5-HT 3A受体SAR提示存在一个空间位点，该位点在接合时会导致该受体的亲和力明显下降。
• CXCR7 antagonists
  申请人：CHEMOCENTRYX, INC.

  公开号：US10287292B2

  公开（公告）日：2019-05-14

  Compounds having formula I, or pharmaceutically acceptable salts, hydrates or N-oxides thereof are provided and are useful for binding to CXCR7, and treating diseases that are dependent, at least in part, on CXCR7 activity. Accordingly, the present invention provides in further aspects, compositions containing one or more of the above-noted compounds in admixture with a pharmaceutically acceptable excipient.

  具有式 I 的化合物、 本发明提供了具有式 I 的化合物或其药学上可接受的盐、水合物或 N-氧化物，可用于与 CXCR7 结合，治疗至少部分依赖于 CXCR7 活性的疾病。因此，本发明在进一步的方面提供了含有一种或多种上述化合物与药学上可接受的赋形剂混合的组合物。
• Phenylethynyl-pyrrolo[1,2-a]pyrazine: A new potent and selective tool in the mGluR5 antagonists arena
  作者：Fabrizio Micheli、Barbara Bertani、Andrea Bozzoli、Luca Crippa、Paolo Cavanni、Romano Di Fabio、Daniele Donati、Paola Marzorati、Giancarlo Merlo、Alfredo Paio、Lorenzo Perugini、Paola Zarantonello

  DOI：10.1016/j.bmcl.2008.02.024

  日期：2008.3

  The synthesis and the structure activity of a new series of pyrrolo[1,2- a] pyrazine is reported. These molecules are potent and selective non-competitive mGluR5 antagonists and may shed new light on the pattern of substitution tolerated by this receptor. (C) 2008 Elsevier Ltd. All rights reserved.