3-(1-甲基-1H-咪唑-2-基)-3-氧代丙酸乙酯 | 1229426-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(1-甲基-1H-咪唑-2-基)-3-氧代丙酸乙酯
• 英文名称: ethyl 3-(1-methyl-1H-imidazol-2-yl)-3-oxopropanoate
• 英文别名: ethyl 3-(1-methylimidazol-2-yl)-3-oxopropanoate
• CAS: 1229426-30-5
• 化学式: C₉H₁₂N₂O₃
• mdl: MFCD24147690
• 分子量: 196.206
• InChiKey: ZMMLBTOFERWSQO-UHFFFAOYSA-N

物化性质

• 沸点：
  333.8±44.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1-甲基-1H-咪唑-2-基)-3-氧代丙酸乙酯 在 N-碘代丁二酰亚胺 、 亚硝酸特丁酯 、 三乙胺 、 copper dichloride 、 lithium hydroxide 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 5.0h， 生成 2-[(3S,4R)-4-[(3,4-dichloro-5-methyl-1H-pyrrole-2-carbonyl)amino]-3-methoxy-1-piperidyl]-4-(1-methylimidazol-2-yl)thiazole-5-carboxylic acid
  参考文献：
  名称：

  Optimization of Pyrrolamide Topoisomerase II Inhibitors Toward Identification of an Antibacterial Clinical Candidate (AZD5099)

  摘要：

  AZD5099 (compound 63) is an antibacterial agent that entered phase 1 clinical trials targeting infections caused by Gram-positive and fastidious Gram-negative bacteria. It was derived from previously reported pyrrolamide antibacterials and a fragment-based approach targeting the ATP binding site of bacterial type II topoisomerases. The program described herein varied a 3-piperidine substituent and incorporated 4-thiazole substituents that form a seven-membered ring intramolecular hydrogen bond with a 5-position carboxylic acid. Improved antibacterial activity and lower in vivo clearances were achieved. The lower clearances were attributed, in part, to reduced recognition by the multidrug resistant transporter Mrp2. Compound 63 showed notable efficacy in a mouse neutropenic Staphylococcus aureus infection model. Resistance frequency versus the drug was low, and reports of clinical resistance due to alteration of the target are few. Hence, 63 could offer a novel treatment for serious issues of resistance to currently used antibacterials.

  DOI：

  10.1021/jm500462x
• 作为产物：
  描述：

  1-甲基-1H-咪唑-2-甲酸乙酯 、 ethyl potassium malonate 在 水 、 sodium hydroxide 、 N,N'-羰基二咪唑 、 三乙胺 、 magnesium chloride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 10.0h， 以38%的产率得到3-(1-甲基-1H-咪唑-2-基)-3-氧代丙酸乙酯
  参考文献：
  名称：

  CYCLIC AMINE DERIVATIVE AS AGENT FOR PROMOTING ADVILLIN FUNCTION, AND NOVEL CYCLIC AMINE DERIVATIVE AND PHARMACEUTICAL USE THEREOF

  摘要：

  本发明的目的是提供一种促进advillin功能的制剂，包括低分子量化合物，并可用于治疗轴突损伤。本发明提供了一种促进advillin功能的制剂，包括一种通常由以下化学式表示的环状胺衍生物或其药学上可接受的盐作为活性成分。

  公开号：

  US20220081431A1

文献信息

• Enantioselective Conjugate Addition of 2-Acylimidazoles with Nitroalkenes Promoted by Chiral-at-Metal Rhodium(III) Complexes
  作者：Ganesh Kumar Thota、Gui-Jun Sun、Tao Deng、Yi Li、Qiang Kang

  DOI：10.1002/adsc.201701377

  日期：2018.3.20

  An enantioselective conjugate addition of 2‐acylimidazoles with nitroalkenes catalyzed by chiral‐at‐metal rhodium(III) complex under mild reaction conditions was developed, affording versatile γ‐nitro ketone skeletons in good yields with excellent enantioselectivities (up to >99% ee).

  开发了在温和的反应条件下手性金属铑（III）配合物催化的2-酰基咪唑与硝基烯烃的对映选择性共轭加成反应，提供了具有良好对映选择性（高达> 99％ee）的高产率的通用γ-硝基酮骨架。
• [EN] 2- (PIPERIDIN-1-YL) -4-AZOLYL-THIAZOLE-5-CARBOXYLIC ACID DERIVATIVES AGAINST BACTERIAL INFECTIONS<br/>[FR] DÉRIVÉS D'ACIDE 2-(PIPÉRIDIN-1-YL)-4-AZOLYL-THIAZOLE-5-CARBOXYLIQUE CONTRE LES INFECTIONS BACTÉRIENNES
  申请人：ASTRAZENECA AB

  公开号：WO2010067125A1

  公开（公告）日：2010-06-17

  Compounds of formula (I) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.

  公式（I）的化合物及其药用盐已被描述。还描述了它们的制备过程、含有它们的药物组合物、它们作为药物的用途以及它们在治疗细菌感染中的用途。
• 2-(PIPERIDIN-1-YL)-4-AZOLYL-THIAZOLE-5-CARBOXYLIC ACID DERIVATIVES AGAINST BACTERIAL INFECTIONS
  申请人：Peer Mohamed Shahul Hameed

  公开号：US20120022107A1

  公开（公告）日：2012-01-26

  Compounds of formula (I) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.

  描述了式(I)的化合物及其药学上可接受的盐。还描述了它们的制备过程，包含它们的制药组合物，以及它们作为药物治疗细菌感染的用途。
• CYCLIC AMINE DERIVATIVE AS ADVILLIN FUNCTION PROMOTER AND NOVEL CYCLIC AMINE DERIVATIVE AND PHARMACEUTICAL USE THEREOF
  申请人：Toray Industries, Inc.

  公开号：EP3903784A1

  公开（公告）日：2021-11-03

  An object of the present invention is to provide an agent for promoting advillin function that comprises a low molecular weight compound, and is useful for treatment of axonal injury. The present invention provides an agent for promoting advillin function, comprising a cyclic amine derivative typically represented by the following chemical formula, or a pharmacologically acceptable salt thereof as an active ingredient.

  本发明的目的是提供一种促进豚草素功能的制剂，该制剂由低分子量化合物组成，可用于治疗轴突损伤。本发明提供了一种促进 advillin 功能的制剂，其活性成分包括通常由以下化学式表示的环胺衍生物或其药理学上可接受的盐。
• Cyclic amine derivative and pharmaceutical use thereof
  申请人：Toray Industries, Inc.

  公开号：US10173999B2

  公开（公告）日：2019-01-08

  A compound exerts an analgesic effect against pain, in particular, neuropathic pain and/or fibromyalgia syndrome. A cyclic amine derivative represented by the following general formula, or a pharmacologically acceptable salt thereof: Methods using the compound including the cyclic amine derivative or a pharmacologically acceptable salt thereof to treat pain, neuropathic pain and fibromyalgia syndrome.

  一种化合物对疼痛，尤其是神经性疼痛和/或纤维肌痛综合征具有镇痛效果。由以下通式代表的环胺衍生物，或其药理学上可接受的盐： 使用包括环胺衍生物或其药理学上可接受的盐的化合物治疗疼痛、神经性疼痛和纤维肌痛综合征的方法。