1-(5-methyl-1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethanone | 351068-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(5-methyl-1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethanone
• 英文别名: 1-[5-Methyl-1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl]ethanone；1-[5-methyl-1-(3-nitrophenyl)triazol-4-yl]ethanone
• CAS: 351068-65-0
• 化学式: C₁₁H₁₀N₄O₃
• mdl: MFCD02157501
• 分子量: 246.225
• InChiKey: URKVIRSKBUWXFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  93.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(5-methyl-1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethanone 在 ammonium acetate 、 一水合肼 、 sodium nitrite 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 、 溶剂黄146 、 苯 为溶剂， 反应 17.0h， 生成 phenyl 2-methyl-6-(5-methyl-1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)pyridin-3-yl-carbamate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Some New Pyridines, Isoxazoles and Isoxazolopyridazines Bearing 1,2,3-Triazole Moiety

  摘要：

  Some new isoxazole derivatives 3a-d were synthesized via the reaction of 3-(dimethylamino)-1-(5-methyl-1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)prop-2-en-1-one (1) with different hydroximoyl chlorides derivatives 2a-d. From these new isoxazoles 3a-d a new series of isoxazolopyridazines 4a-d was derived using hydrazine hydrate. In addition, enaminone 1 was reacted with ethyl acetoacetate to afford the corresponding ester derivative 6, the latter was submitted to react with different chemical reagents to obtain a variety of bioactive substituted pyridine derivatives. The azido derivative 14, was used as the key molecule for the synthesis of new urea and aryl carbamate derivatives upon its reaction with different amines and phenol through Curtius rearrangement. The chemical compositions of all the new compounds were investigated from their spectral and microanalytical data. The synthesized compounds were tested for their pharmacological potency as, anti-hepatic cancer and anti-microbial agents. Most of the tested compounds showed good anti-hepatic cancer results comparing with the standard drug doxorubicin especially when their toxic effects on the normal cell lines were studied. Referring to the anti-microbial test most of the compounds showed strong effects.

  DOI：

  10.32383/appdr/103101
• 作为产物：
  描述：

  间硝基苯胺 在 盐酸 、 sodium azide 、 三乙胺 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 1-(5-methyl-1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethanone
  参考文献：
  名称：

  Synthesis, In Vitro and In Silico Biological Studies of 1, 2, 3-Triazole-Furan Chalcone Hybrids

  摘要：

  在本研究中，我们重点开发了 1、2、3-三唑呋喃查尔酮混合物及其生物特性。目标分子的合成涉及一系列反应，即重氮化反应、亲核取代反应、环加成反应以及最后的无溶剂克莱森-施密特缩合反应。通过预测物质的活性光谱，对合成化合物的生物特性进行了研究，结果表明合成化合物可作为温和的抗菌剂。

  DOI：

  10.59467/ijhc.2023.33.369

文献信息

• A combined experimental and theoretical study of the thermal cycloaddition of aryl azides with activated alkenes
  作者：Sarah Zeghada、Ghenia Bentabed-Ababsa、Aïcha Derdour、Safer Abdelmounim、Luis R. Domingo、José A. Sáez、Thierry Roisnel、Ekhlass Nassar、Florence Mongin

  DOI：10.1039/c1ob05176h

  日期：——

  β-dicarbonyl compounds with their enol forms, a 1,3-dipolar cycloaddition of the enol forms with the aryl azides (high activation energy), and a dehydration process (lower activation energy). The effect of non-conventional activation methods on the degradation of 1,2,3-triazolines was next studied experimentally. Finally, some of the 1,2,3-triazoles such synthesized were evaluated for their bactericidal and

  一方面是由芳基叠氮化物进行反应，另一方面是由β-二羰基化合物或丙二腈衍生的活化烯烃，通过常规加热或微波活化，得到1-芳基-1 H-1,2,3-三唑 理论上已经使用DFT方法在B3LYP / 6-31G *水平上研究了涉及β-二羰基化合物的反应机理和区域选择性：它们是包含β-二羰基化合物及其烯醇形式的互变异构平衡的多米诺过程。烯醇的1，3-偶极环加成与芳基叠氮化物（高活化能）和脱水过程（较低活化能）形成。接下来通过实验研究非常规活化方法对1,2,3-三唑啉降解的影响。最后，评估了这样合成的一些1,2,3-三唑的杀菌和细胞毒性活性。
• Synthesis and antibacterial evaluation of pyrazolines carrying (benzyloxy)benzaldehyde moiety
  作者：C. H. Aminath Rajeena、Vinuta Kamat、Veerabhadragouda B. Patil、Suresh P. Nayak、Sheela Khanapure、Delicia A. Barretto、Shyam K. Vootla

  DOI：10.1007/s13738-021-02403-9

  日期：2022.5

  were prepared by the reaction of 3-(4-(benzyloxy)phenyl)-1-(1-(arylphenyl)-5-methyl-1H-1,2,3-triazol-4-yl)prop-2-en-1-one with hydrazine hydrate in the presence of glacial acetic acid medium. The structures of the newly synthesized pyrazoline derivatives were established by elemental analysis, FT-IR, 1H NMR, 13C1H} NMR, and mass spectral analysis. In addition, synthesized compounds DFT calculations

  由3-(4-(苄氧基)苯基)-1-(1-(芳基苯基)-5-甲基-1 H -1反应制备了一系列新型1,2,3-三唑连接的吡唑啉类似物， 2,3-triazol-4-yl)prop-2-en-1-one 与水合肼在冰醋酸介质存在下。通过元素分析、FT-IR、1 H NMR、13 C 1确定了新合成的吡唑啉衍生物的结构H}核磁共振和质谱分析。此外，合成化合物的DFT计算和合成化合物的3D结构使用Gaussian 09软件进行，混合模型和MM2力技术用于获得能量最小化结构。测定合成的吡唑啉对革兰氏阳性和革兰氏阴性菌株的抗菌活性。其中，吡唑啉苯环上的间氯取代化合物对铜绿假单胞菌的抑制程度最高，苯环对位溴取代的化合物对金黄色葡萄球菌的抑制程度最高。 图形摘要
• Synthesis, In Vitro and In Silico Biological Studies of 1, 2, 3-Triazole-Furan Chalcone Hybrids
  作者：T. M. Somanatha、G. Krishnaswamy、R. Bhavana、K. Radhakrishna、G. Shivaraj、S. Sreenivasa、M. Shet Prakash

  DOI：10.59467/ijhc.2023.33.369

  日期：2023.9.30

  In the present investigation, we focused our interest to develop 1, 2, 3-triazolefuran chalcone hybrids along with their biological profile. The synthesis of target molecules involves sequence of reactions, namely diazotization, nucleophilic substitution, cycloaddition and finally, solvent-free Claisen–Schmidt condensation reaction. The biological profile of the synthesized compounds was carried out using prediction of activity spectra for substances and results revealed that the synthesized compounds may act as mild antimicrobial agents.

  在本研究中，我们重点开发了 1、2、3-三唑呋喃查尔酮混合物及其生物特性。目标分子的合成涉及一系列反应，即重氮化反应、亲核取代反应、环加成反应以及最后的无溶剂克莱森-施密特缩合反应。通过预测物质的活性光谱，对合成化合物的生物特性进行了研究，结果表明合成化合物可作为温和的抗菌剂。
• Synthesis and Biological Evaluation of Some New Pyridines, Isoxazoles and Isoxazolopyridazines Bearing 1,2,3-Triazole Moiety
  作者：anhar hassan、Huda Rashdan、sara nabil、dina elnagar

  DOI：10.32383/appdr/103101

  日期：2019.6.28

  Some new isoxazole derivatives 3a-d were synthesized via the reaction of 3-(dimethylamino)-1-(5-methyl-1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)prop-2-en-1-one (1) with different hydroximoyl chlorides derivatives 2a-d. From these new isoxazoles 3a-d a new series of isoxazolopyridazines 4a-d was derived using hydrazine hydrate. In addition, enaminone 1 was reacted with ethyl acetoacetate to afford the corresponding ester derivative 6, the latter was submitted to react with different chemical reagents to obtain a variety of bioactive substituted pyridine derivatives. The azido derivative 14, was used as the key molecule for the synthesis of new urea and aryl carbamate derivatives upon its reaction with different amines and phenol through Curtius rearrangement. The chemical compositions of all the new compounds were investigated from their spectral and microanalytical data. The synthesized compounds were tested for their pharmacological potency as, anti-hepatic cancer and anti-microbial agents. Most of the tested compounds showed good anti-hepatic cancer results comparing with the standard drug doxorubicin especially when their toxic effects on the normal cell lines were studied. Referring to the anti-microbial test most of the compounds showed strong effects.
• 1,2,3‐Triazole‐based esters and carboxylic acids as nonclassical carbonic anhydrase inhibitors capable of cathepsin B inhibition
  作者：Kiran Siwach、Manishita Rani、Lalit Vats、Simone Giovannuzzi、Avijit Kumar Paul、Mettle Brahma、Neetu Kumari、Mulaka Maruthi、Neera Raghav、Claudiu T. Supuran、Pawan K. Sharma

  DOI：10.1002/ardp.202300372

  日期：2024.3

  carboxylic acid derivative 6c was found to be the most potent inhibitor of hCA IX and hCA XII with a KI value of 0.7 μM for both the isoforms. The newly synthesised compounds showed dual inhibition towards CA as well as cathepsin B. The ester derivatives exhibited higher % inhibition at 10−7 M concentration as compared with the corresponding carboxylic acid derivatives against cathepsin B. The results

  在此，我们报告了 28 种新的 1,2,3-三唑衍生物库的设计和合成，这些衍生物带有羧酸和酯部分，作为碳酸酐酶 (CA) 和组织蛋白酶 B 酶的双重抑制剂。体外测定了合成化合物对四种人 CA (hCA) 亚型 I、II、IX 和 XII 的抑制潜力。与酯衍生物相比，羧酸衍生物对 hCA II、IX 和 XII 显示出低微摩尔抑制。大多数目标化合物对 hCA I 亚型的抑制作用较差。发现 4-氟苯基附加的羧酸衍生物6c是 hCA IX 和 hCA XII 最有效的抑制剂，两种亚型的K I值为 0.7 μM。新合成的化合物对 CA 和组织蛋白酶 B 表现出双重抑制作用。与相应的羧酸衍生物相比，酯衍生物在 10 -7 M 浓度下对组织蛋白酶 B 表现出更高的抑制百分比。目标化合物的计算机研究结果发现与组织蛋白酶B的活性位点与体外结果有良好的相关性。此外，两种化合物5i和6c对A549肺癌细胞表现出细胞毒活性，IC