3-氧代-N-吡啶-3-基丁酰胺 | 1657-34-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3-氧代-N-吡啶-3-基丁酰胺
• 英文名称: N-(3-pyridyl)-3-oxobutanamide
• 英文别名: 3-(3-oxobutyrylamido)pyridine；3-oxo-N-(pyridin-3-yl)butanamide；3-oxo-N-3-pyridinylbutanamide；3-oxo-N-(3-pyridyl)butanamide；3-oxo-N-pyridin-3-yl-butyramide；N-[3]pyridyl-acetoacetamide；N-[3]Pyridyl-acetoacetamid；N-(3-Pyridyl)-2-oxo-butyramid；3-Acetoacetamino-pyridin；3-oxo-N-pyridin-3-ylbutanamide
• CAS: 1657-34-7
• 化学式: C₉H₁₀N₂O₂
• mdl: MFCD01102497
• 分子量: 178.191
• InChiKey: FAIPYLBFPQYODX-UHFFFAOYSA-N

物化性质

• 熔点：
  134-135 °C(Solv: benzene (71-43-2))
• 沸点：
  393.2±22.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氧代-N-吡啶-3-基丁酰胺 、 1-苄基-2-甲基磺酰-咪唑-5-甲醛 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以55%的产率得到4-(1-benzyl-2-(methylthio)-1H-imidazol-5-yl)-2,6-dimethyl-N3,N5-bis(pyridin-3-yl)-1,4-dihydropyridine-3,5-dicarboxamide
  参考文献：
  名称：

  Synthesis and antitubercular activity of novel 4-substituted imidazolyl-2,6-dimethyl-N3,N5-bisaryl-1,4-dihydropyridine-3,5-dicarboxamides

  摘要：

  A series of 4-substituted imidazolyl-2,6-dimethyl-N-3,N-5-bisaryl-1,4-dihydropyridine-3,5-dicarboxamides were prepared. They were screened as antitubercular agents against Mycobacterium tuberculosis H(37)Rv. Minimum inhibitory concentrations (MICs) were determined using agar proportion method. Compound 3i with 1-benzyl-2-methylthio-1H-imidazole-5-yl substituent at C-4 position and 4'-chloromophenyl group at C-3 and C-5 positions of the 1,4-dihydropyridine ring was the most potent one among the tested compounds. It was as potent as rifampicin against M. tuberculosis H37RV. Compound 31 also was an active antitubercular agent with the same substituent as compound 3i at the C-4 position and 31-pyridyl group at C-3 and C-5 positions of the 1,4-dihydropyridine ring. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.03.027
• 作为产物：
  描述：

  3-(3-oxobutylamido)picolinic acid 以 甲苯 、 均三甲苯 为溶剂， 反应 17.0h， 生成 3-氧代-N-吡啶-3-基丁酰胺
  参考文献：
  名称：

  Bohn, Bernhard; Heinrich, Nicolaus; Vorbrueggen, Helmut, Heterocycles, 1994, vol. 37, # 3, p. 1731 - 1746

  摘要：

  DOI：

文献信息

• <p>Virtual Screening and Optimization of Novel mTOR Inhibitors for Radiosensitization of Hepatocellular Carcinoma</p>
  作者：Ying-Qi Feng、Shuang-Xi Gu、Yong-Shou Chen、Xu-Dong Gao、Yi-Xin Ren、Jian-Chao Chen、Yin-Ying Lu、Heng Zhang、Shuang Cao

  DOI：10.2147/dddt.s249156

  日期：——

  thus, mTOR inhibitors have potential as novel radiosensitizers to enhance the efficacy of radiotherapy for HCC. Methods: A lead compound was found based on pharmacophore modeling and molecular docking, and optimized according to the differences between the ATP-binding pockets of mTOR and PI3K. The radiosensitizing effect of the optimized compound ( 2a) was confirmed by colony formation assays and DNA

  背景：放疗对多种肿瘤都有改善作用，但肝细胞癌 (HCC) 对这种治疗不敏感。过活化的哺乳动物雷帕霉素靶蛋白（mTOR）在肝癌对放疗的抵抗中起重要作用；因此，mTOR 抑制剂具有作为新型放射增敏剂的潜力，可增强 HCC 放射治疗的疗效。 方法：基于药效团建模和分子对接发现先导化合物，并根据mTOR和PI3K的ATP结合口袋之间的差异进行优化。优化后化合物的放射增敏作用( 2a) 通过体外集落形成试验和 DNA 双链断裂试验得到证实。描述了该化合物的发现和临床前特征。 结果：鉴定出mTOR中的关键氨基酸残基，构建了精准的虚拟筛选模型。具有 4,7-二氢-[1,2,4]三唑并[1,5-a]嘧啶支架的化合物2a对 mTOR (mTOR IC 50 =7.1 nmol/L (nM)) 具有良好的 126-选择性超过 PI3Kα。此外，2a以剂量依赖性方式显着增强了HCC对体外放射治疗的敏感性。 结论：开发了一类新的选择性
• Copper-Catalysed (Diacetoxyiodo)benzene-Promoted Aerobic Esterification Reaction: Synthesis of Oxamates from Acetoacetamides
  作者：Zhiguo Zhang、Xiaolong Gao、Haifeng Yu、Guisheng Zhang、Jianming Liu

  DOI：10.1002/adsc.201800616

  日期：2018.9.3

  A copper‐catalysed (diacetoxyiodo)benzene‐promoted aerobic esterification reaction of acetoacetamides was developed for the synthesis of oxamates, which are useful precursors in synthetic organic chemistry. This practical and mild synthetic approach proceeded at 25 °C under open‐air conditions and afforded methyl 2‐oxo‐2‐(phenylamino)acetates in good to excellent yields combined with C−C σ‐bond cleavage

  开发了铜催化（二乙酰氧基碘）苯促进的乙酰乙酰胺需氧酯化反应，以合成草酸盐，草酸盐在合成有机化学中是有用的前体。这种实用且温和的合成方法在露天条件下于25°C进行，提供了具有良好或优异收率的2-氧代-2-（苯基氨基）乙酸甲酯，并带有C-Cσ-键裂解和正式的C-H氧化键功能化。提出了一种机制。
• Activated Anilide in Heterocyclic Synthesis: Synthesis of New Dihydropyridines, Dihydropyridazines and Thiourea Derivatives
  作者：Ibrahim S. A. Hafiz、Mahmoud M. M. Ramiz、Ahmed A. M. Sarhan

  DOI：10.1002/cjoc.201190216

  日期：2011.6

  A series of new dihydropyridines, butanamide, dihydropyridazines and thiourea derivatives have been prepared through the reactions of 3‐aminopyridine (1) and N‐(pyridin‐3‐yl)‐3‐(pyridin‐3‐ylimino)butanamide 3 with some electrophilic reagents, aryl diazonium salts and isothiocyanates. Elementary analysis, MS, IR, and 1H NMR spectra confirmed the identity of the products.

  通过3-氨基吡啶（1）和N-（吡啶-3-基）-3-（吡啶-3-氨基）丁酰胺3与一些亲电子的反应，制备了一系列新的二氢吡啶，丁酰胺，二氢哒嗪和硫脲衍生物。试剂，芳基重氮盐和异硫氰酸盐。元素分析，MS，IR和1 H NMR光谱证实了产物的身份。
• Use of Cinnamoyl Compound
  申请人：Shiraki Hiroaki

  公开号：US20090143368A1

  公开（公告）日：2009-06-04

  A composition for inhibiting the extracellular matrix gene transcription comprising a cinnamoyl compound represented by the formula (I): and an inert carrier, or the like.

  一种用于抑制细胞外基质基因转录的组合物，包括由式（I）表示的肉桂酰化合物和惰性载体等。
• Discovery of tetrasubstituted thiophenes as Cisd2 activators: A potential novel therapeutic option in nonalcoholic fatty liver disease
  作者：Chun-Hsu Yao、Zhao-Qing Shen、Yesudoss Christu Rajan、Yu-Wen Huang、Chin-Yu Lin、Jen-Shin Song、Hui-Yi Shiao、Yi-Yu Ke、Yu-Shiou Fan、Chi-Hui Tsai、Teng-Kuang Yeh、Ting-Fen Tsai、Jinq-Chyi Lee

  DOI：10.1016/j.ejmech.2023.115583

  日期：2023.10

  evaluation of a series of Cisd2 activators, all thiophene analogs, based on a hit obtained using two-stage screening and prepared via either the Gewald reaction or by intramolecular aldol-type condensation of an N,S-acetal. Metabolic stability studies of the resulting potent Cisd2 activators suggest that thiophenes 4q and 6 are suitable for in vivo studies. The results from studies on 4q-treated and

  肝脏中 Cisd2 的下调与非酒精性脂肪性肝病 (NAFLD) 的发展有关，因此增加 Cisd2 的水平是此类疾病的潜在治疗方法。在此，我们描述了一系列 Cisd2 激活剂（所有噻吩类似物）的设计、合成和生物学评价，基于使用两阶段筛选获得的命中，并通过 Gewald 反应或 N 的分子内羟醛型缩合制备。，S-缩醛。对所得有效 Cisd2 激活剂的代谢稳定性研究表明，噻吩4q和6适用于体内研究。对4q处理和6处理的 Cisd2hKO-het 小鼠（携带杂合肝细胞特异性 Cisd2 敲除）的研究结果证实（1）Cisd2 水平与 NAFLD 之间存在相关性，（2）这些化合物具有在没有可检测到的毒性的情况下预防 NAFLD 的发生和进展。