N-(5-bromopyridin-2-yl)-3-oxobutanamide | 64500-14-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(5-bromopyridin-2-yl)-3-oxobutanamide
• CAS: 64500-14-7
• 化学式: C₉H₉BrN₂O₂
• 分子量: 257.087
• InChiKey: AVNQQIFGMLNEEN-UHFFFAOYSA-N

物化性质

• 熔点：
  164-165 °C(Solv: methanol (67-56-1))
• 沸点：
  433.5±40.0 °C(Predicted)
• 密度：
  1.586±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  N-(5-bromopyridin-2-yl)-3-oxobutanamide 在 硫酸 作用下， 生成 7-溴-2-甲基吡啶并[1,2-a]嘧啶-4-酮
  参考文献：
  名称：

  Kutscherow, Zhurnal Obshchei Khimii, 1950, vol. 20, p. 1890,1892, 1896; engl. Ausg. S. 1957, 1959,1963

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-5-溴吡啶 、 乙酰乙酸乙酯 在 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 以0.13 kg的产率得到N-(5-bromopyridin-2-yl)-3-oxobutanamide
  参考文献：
  名称：

  WO2023/58645

  摘要：

  公开号：

文献信息

• Antiproliferative effect, alteration of cancer cell cycle progression and potential MET kinase inhibition induced by 3,4-dihydropyrimidin-2(1H)-one C5 amide derivatives
  作者：Fatemeh Moosavi、Ahmad Ebadi、Maryam Mohabbati、Tahereh Damghani、Motahareh Mortazavi、Ramin Miri、Omidreza Firuzi

  DOI：10.1016/j.ejphar.2021.173850

  日期：2021.3

  4-dihydropyrimidin-2(1H)-one C5 amide derivatives were synthesized and their cancer cell growth inhibitory activity was examined against MCF-7, HT-29 and MOLT-4 cells and also NIH/3T3 non-cancer cells by MTT assay. The antiproliferative effect of the most potent derivatives were tested against MET-dependent EBC-1 and MKN-45, lung and gastric cancer cell lines, respectively. MET kinase inhibition was measured by a

  癌症仍然是全球第二大死亡原因。发现新型治疗剂对于改善我们的医疗管理能力至关重要。MET受体酪氨酸激酶途径的失调在癌症进展中起重要作用，使该受体成为抗癌药物发现的有吸引力的分子靶标。在这项研究中，27，3,4-dihydropyrimidin-2（1 H）合成一种C5酰胺衍生物，并通过MTT分析检测其对MCF-7，HT-29和MOLT-4细胞以及NIH / 3T3非癌细胞的癌细胞生长抑制活性。测试了最有效衍生物的抗增殖作用，分别针对MET依赖的EBC-1和MKN-45，肺癌和胃癌细胞系。通过均相时间分辨荧光（HTRF）测定法测量MET激酶抑制。通过RNase / PI流式细胞术检测受试化合物对细胞周期的影响。许多化合物对乳腺癌和结肠癌以及白血病细胞系表现出相当大的抗增殖作用，相对而言保留非癌细胞。一些衍生物轴承苯并噻唑基甲酰胺部分在C5位（15，21，23，31，和37）显示出最高的活性与IC
• 3,4-Dihydropyrimidin-2(1H)-one C5 Amides as Inhibitors of T NFα Production: Synthesis, Biological Evaluation and Molecular Modeling
  作者：Ahmad Ebadi、Mehdi Khoshneviszadeh、Katayoun Javidnia、Mohammad Hossein Ghahremani、Omidreza Firuzi、Ramin Miri

  DOI：10.2174/1570180814666170306120235

  日期：2017.7.20

  arthritis. Objective: In the present contribution, 16 derivatives of 3,4-dihydropyrimidin-2(1H)-one(thione) C5 amide were synthesized and their anti-inflammatory activities were investigated. Methods: We synthesized 3,4-dihydropyrimidin-2(1H)-one(thione) C5 amide derivatives according to Biginelli method. Inhibitory effect of newly synthesized derivatives was evaluated on TNF-α production in lipopolysaccharide-stimulated

  背景：调节促炎细胞因子尤其是 TNFα 可以在炎症性疾病中发挥治疗作用，这种方法在类风湿性关节炎等疾病的药物开发中备受关注。目的：在目前的贡献中，合成了 16 种 3,4-二氢嘧啶-2(1H)-酮 (硫酮) C5 酰胺的衍生物并研究了它们的抗炎活性。方法：我们根据 Biginelli 方法合成了 3,4-二氢嘧啶-2（1H）-酮（硫酮）C5 酰胺衍生物。评估了新合成衍生物对脂多糖刺激的外周血单核细胞 (PBMC) 中 TNF-α 产生的抑制作用。结果：这些化合物中的大多数都表现出对脂多糖刺激的外周血单核细胞 (PBMC) 中 TNF-α 的良好抑制。化合物 6k 和 6c 显示出最高水平的 TNFα 抑制（在 50 μM 时分别为 74.9 和 72.2）。分子模型研究表明，化合物 6k 与 p38α MAPK 的活性位点形成稳定的复合物。结论：两种最有效化合物的共同结构特征是在 DHPM
• Microwave Assisted Synthesis of Pyrimidines in Ionic Liquid and Their Potency as Non-Classical Malarial Antifolates
  作者：Jaimin D. Bhatt、Chaitanya J. Chudasama、Kanuprasad D. Patel

  DOI：10.1002/ardp.201600148

  日期：2016.10

  Synthesis of pyrazole‐linked triazolo‐pyrimidine hybrids was achieved by employing Biginelli‐type reaction methodology in an ionic liquid (triethylammonium acetate) under microwave irradiation. This method proved to be highly efficient and the ionic liquid employed was found recyclable for up to five consecutive cycles. The synthesized molecules were further screened for their antimalarial efficacy

  在微波辐射下，通过在离子液体（醋酸三乙铵）中采用 Biginelli 型反应方法合成吡唑连接的三唑并嘧啶杂化物。该方法被证明是高效的，并且发现所使用的离子液体最多可连续循环五个循环。进一步筛选合成分子的抗疟功效，筛选出活性支架 J15、J18、J21、J24、J27 和 J30。在针对活性恶性疟原虫二氢叶酸还原酶 (Pf-DHFR) 的酶抑制研究中，通过计算和体外评估了活性分子，证明了它们作为 DHFR 抑制剂的效力。还通过在计算机中预测 ADME 特性来研究活性实体的口服生物利用度，表明其具有良好的生物利用度。
• Diarylpyrazole Ligated Dihydropyrimidine Hybrids as Potent Non-Classical Antifolates and Their Efficacy Against <i>Plasmodium falciparum</i>
  作者：Jaimin D. Bhatt、Chaitanya J. Chudasama、Kanuprasad D. Patel

  DOI：10.1002/ardp.201700088

  日期：2017.9

  of diarylpyrazole clubbed dihydropyrimidine derivatives (J1–J30) was synthesized under microwave‐assisted heating conditions by employing Biginelli reaction methodology and utilizing triethylammonium acetate both as a catalyst and as reaction medium, leading towards a greener reaction pathway. The synthesized entities were screened for their antimalarial efficacy against a Plasmodium falciparum strain

  在微波辅助加热条件下，采用 Biginelli 反应方法，利用三乙基乙酸铵作为催化剂和反应介质，合成了一系列二芳基吡唑棒状二氢嘧啶衍生物（J1-J30），从而实现了更绿色的反应途径。合成的实体在体外针对恶性疟原虫菌株的抗疟功效进行了筛选。从体外筛选中获得的活性实体（J9、J15、J21、J25 和 J27）在体外和计算机中使用 Glide 进一步评估了它们对 Pf-DHFR 酶的酶抑制效力。此外，测试了活性支架对 Vero 细胞的细胞毒性，证明了它们的无毒行为和选择性。ADME 参数也在计算机中进行了评估和预测，
• Pyrazole clubbed triazolo[1,5-a]pyrimidine hybrids as an anti-tubercular agents: Synthesis, in vitro screening and molecular docking study
  作者：Jaimin D. Bhatt、Chaitanya J. Chudasama、Kanuprasad D. Patel

  DOI：10.1016/j.bmc.2015.11.018

  日期：2015.12

  A series of novel pyrazole linked triazolo-pyrimidine hybrids were synthesized and evaluated for their anti-tuberculosis activity against M.tb H37Rv strain. Some of the screened entities rendered promising anti-tb activity (MIC: 0.39 mu g/mL) and were found non toxic against Vero cells (IC50: >= 20 mu g/mL). Further, the docking study against wild type InhA enzyme of Mycobacterium tuberculosis using Glide reproduced the most active inhibitors (J21 and J27) with lowest binding energies and highest Glide XP scores demonstrating efficient binding to the active pocket. Additionally, the enzyme inhibition assay and ADME prediction of the active proved to be an attest to the possibility of developing compound J27 as a potent anti-tubercular lead. (c) 2015 Elsevier Ltd. All rights reserved.