N-(5-methylpyrid-2-yl)amide of acetoacetic acid | 16867-46-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(5-methylpyrid-2-yl)amide of acetoacetic acid
• 英文别名: N-(5-methyl-2-pyridyl)-3-oxobutanamide；N-(5-methyl-pyridin-2-yl)-3-oxo-butyramide；N-(5-methyl-[2]pyridyl)-acetoacetamide；N-(5-Methyl-[2]pyridyl)-acetoacetamid；Acetessigsaeure-2-amido-5-methylpyridin；2-(Acetoacetamido)-5-methyl-pyridin；N-(5-Methyl-2-pyridyl)acetoacetamide；N-(5-methylpyridin-2-yl)-3-oxobutanamide
• CAS: 16867-46-2
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: HOVYZMGQZFHEHY-UHFFFAOYSA-N

物化性质

• 熔点：
  162.0-163.0 °C
• 沸点：
  408.8±35.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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-methylpyrid-2-yl)amide of acetoacetic acid 在 PPA 作用下， 反应 9.0h， 以69%的产率得到4,7-dimethyl-2-oxo-(2H)-pyrido[1,2-a]pyrimidine
  参考文献：
  名称：

  4-甲基-2-氧代-(2H)-吡啶基-[1,2-a]嘧啶的独特合成1*

  摘要：

  摘要 从 N-(1,3-二氧丁基)-2-氨基吡啶/甲基吡啶/喹啉合成 4-甲基-2-氧代-(2H)-吡啶并[1,2-a]嘧啶，正在报道。*RRL 通讯第 2336 号

  DOI：

  10.1081/scc-120002513
• 作为产物：
  描述：

  2-氨基-5-甲基吡啶 、 乙酰乙酸乙酯 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 1.0h， 以57%的产率得到N-(5-methylpyrid-2-yl)amide of acetoacetic acid
  参考文献：
  名称：

  New α-Amido-α-aminonitrones As Building Blocks for Constructing ­Heterocyclic Systems

  摘要：

  新、稳定的α-酰胺-α-氨基亚硝胺以良好的产率从3-氧代丁酸N-吡啶-2-基酰胺和亚硝基苯获得。然后，α-酰胺-α-氨基亚硝胺被用作新的、多功能的构建块，利用双电亲和体和双核亲和体试剂获得各种杂环化合物。使用二碘甲烷作为试剂，形成了1,2,5-噁二嗪衍生物，而与芳香性1,2、1,3和1,4-二胺的反应分别产生了喹喔啉、喹唑啉、苯并咪唑和二苯并[d,f][1,3]二氮杂萘衍生物。

  DOI：

  10.1055/s-2008-1067236

文献信息

• 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，
• Microwave Induced Acetoacetylation of Hetaryl and Aryl Amines
  作者：O. P. Suri、N. K. Satti、K. A. Suri

  DOI：10.1080/00397910008086998

  日期：2000.10

  Acetoacetylation of hetaryl and aryl amines by interaction with ethyl acetoacetate under microwave irradiation, without any catalyst and/or solvent, is reported.
• Derivatives of the N-(pyrid-2-yl)amides of 3-aminocrotonic acid as chelating ligands
  作者：V. A. Dorokhov、S. V. Baranin、A. Dib、K. L. Cherkasova、M. N. Bochkareva、V. S. Bogdanov

  DOI：10.1007/bf01150906

  日期：1992.4

  New chelating ligands, N-(pyrid-2-yl)amides of 4,4,4-trichloro-3-amino-2-cyanocrotonic acid have been synthesized from N-(pyrid-2-yl)amides of cyanoacetic acid and CCl3CN. It has been demonstrated that by the action of butylthiodibutylborane they form binuclear boron chelate complexes. Analogous chelates have also been obtained from the N-(pyrid-2-yl)amides of acetoacetic and 4,4,4-trichloro-3-aminocrotonic acids.
• 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.