2-cyano-N-(2-nitrophenyl)acetamide | 65372-22-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-cyano-N-(2-nitrophenyl)acetamide
• 英文别名: Cyanessigsaeure-(2-nitro-anilid)
• CAS: 65372-22-7
• 化学式: C₉H₇N₃O₃
• mdl: MFCD01910047
• 分子量: 205.173
• InChiKey: KOSHCVNYQCNGAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  98.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-cyano-N-(2-nitrophenyl)acetamide 在 palladium on activated charcoal sodium hydroxide 、 tetraphosphorus decasulfide 、 氢气 、 sodium acetate 、 一氯化碘 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 、 sodium iodide 、 肼 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 盐酸 、 甲醇 、 乙醇 、 二乙二醇二甲醚 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 25.0~105.0 ℃ 、101.33 kPa 条件下， 反应 16.75h， 生成 (4-Iodo-5-thia-7,10,17-triazatetracyclo[8.7.0.02,6.011,16]heptadeca-1(17),2(6),3,7,11,13,15-heptaen-8-yl)hydrazine
  参考文献：
  名称：

  五环三唑并二氮杂as类化合物作为PAF拮抗剂

  摘要：

  噻吩[3,2- f ] [1,2,4]三唑并[4,3- a ] [1,4]二氮杂ino- [4,5- a ]苯并咪唑和噻吩并[ n ]描述了吲唑并[2，3- d ] [1,2,4]三唑并[4,3- a ] [1,4]苯并二氮杂pine 。炔丙基连接的喹啉酮的附接产生化合物6和16，其通过在豚鼠中的静脉内施用途径表现出PAF-拮抗剂活性。更有效的化合物16在支气管收缩试验中还表现出良好的口服活性，ID 50为0.2 mg / kg。

  DOI：

  10.1002/jhet.5570280448
• 作为产物：
  描述：

  2-硝基苯胺 、 氰乙酸 在 dicyclohexyldiimide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以74%的产率得到2-cyano-N-(2-nitrophenyl)acetamide
  参考文献：
  名称：

  五环三唑并二氮杂as类化合物作为PAF拮抗剂

  摘要：

  噻吩[3,2- f ] [1,2,4]三唑并[4,3- a ] [1,4]二氮杂ino- [4,5- a ]苯并咪唑和噻吩并[ n ]描述了吲唑并[2，3- d ] [1,2,4]三唑并[4,3- a ] [1,4]苯并二氮杂pine 。炔丙基连接的喹啉酮的附接产生化合物6和16，其通过在豚鼠中的静脉内施用途径表现出PAF-拮抗剂活性。更有效的化合物16在支气管收缩试验中还表现出良好的口服活性，ID 50为0.2 mg / kg。

  DOI：

  10.1002/jhet.5570280448

文献信息

• Synthesis and Antioxidant Evaluation of Some New Pyridopyrazolotriazine Derivatives
  作者：Moustafa A. Gouda

  DOI：10.1002/jhet.2045

  日期：2015.7

  hydrazone derivatives 4a,4b, 9, 10, 11, 18a, 18b, 19a,19b, 20, and 25, respectively. The previous synthesized compounds underwent cyclization in acetic acid to give the corresponding pyridopyrazolotriazines 5a,5b, 12, 13, 14, 21a,21b, 22a, 22b, 22c, 23, and 26, respectively. The newly synthesized compounds were characterized by elemental analysis and spectral data and screened for their antioxidant activities

  吡唑并Diazodization [3,4 b ]吡啶1，得到重氮盐2即加上活性亚甲基化合物如3a中，图3b，6，7，8，图15A，15B，16A，16B，17，和24在吡啶，得到芳基腙衍生物4A，4B，9，10，11，18A，18B，19A，19B，20和25。在乙酸先前合成的化合物环化后行，得到相应的pyridopyrazolotriazines图5a，5b中，12，13，14，21A，21B，22A，22B，22C，23和26，分别。通过元素分析和光谱数据对新合成的化合物进行表征，并筛选其抗氧化活性。ABTS方法的结果清楚地表明，化合物1，图4b，图5b，11，20，25，和26中显示有希望的体外抗氧化活性。化合物1和4a对由博来霉素铁络合物诱导的DNA损伤表现出高度的保护作用。
• Competing transformations of 2-cyanoacetanilides in the reactions with derivatives of ethoxymethylenemalonic acid
  作者：Valeriya P. Tkachova、Nikolay Yu. Gorobets、Roman P. Tkachov、Vladimir I. Musatov、Vladimir D. Dyachenko

  DOI：10.3998/ark.5550190.0013.635

  日期：——

  ile 1B and ethyl ethoxymethylenecyanoacetate 1C in cyclocondensations with 2-cyanoacetanilides 2 behave as a three-carbon fragment transfer reagent to afford the corresponding 5-cyano- and 5-ethoxycarbonyl-6-amino-1-aryl-3cyanopyridin-2(1H)-one derivatives 7B and 8C. One carbon transfer described earlier for such reactions with a use of diethyl 2-(ethoxymethylene)malonate 1A was observed only as a

  乙氧基亚甲基丙二腈 1B 和乙氧基亚甲基氰基乙酸乙酯 1C 在与 2-氰基乙酰苯胺 2 的环缩合反应中充当三碳片段转移试剂，得到相应的 5-氰基-和 5-乙氧基羰基-6-氨基-1-芳基-3氰基吡啶-2(1H)-一种衍生物 7B 和 8C。早先描述的使用 2-(乙氧基亚甲基)丙二酸二乙酯 1A 的此类反应的碳转移仅作为 1C 的副过程观察到，导致 2-氨基-5-氰基-6-氧代-N,1-二芳基-1,6-二氢吡啶-3甲酰胺。
• 10.1007/s10593-024-03312-4
  作者：Osipov, Dmitry V.、Krasnikov, Pavel E.、Artemenko, Alina A.

  DOI：10.1007/s10593-024-03312-4

  日期：——

  A reaction of 2-trifluoroacetyl-1H-benzo[f]chromenes with N-arylamides of cyanoacetic acid led to the synthesis of a series of 2-oxo-6-trifluoromethylpyridine-3-carboxamides as products of a cascade of the carbo-Michael reaction, Thorpe–Ziegler cyclization, and Dimroth rearrangement. In the case of 1H-benzo[f]chromene-2-carbaldehydes, the corresponding Knoevenagel adducts were isolated.

  2-三氟乙酰基-1H-苯并[f]色烯与氰基乙酸的N-芳基酰胺反应，合成了一系列2-氧代-6-三氟甲基吡啶-3-甲酰胺，作为碳迈克尔级联的产物反应、Thorpe-Ziegler 环化和 Dimroth 重排。对于1H-苯并[f]色烯-2-甲醛，分离出相应的Knoevenagel 加合物。
• Fusco,R.; Rossi,S., Gazzetta Chimica Italiana, 1964, vol. 94, p. 3 - 30
  作者：Fusco,R.、Rossi,S.

  DOI：——

  日期：——
• Synthesis, pharmacological assessment, molecular modeling and in silico studies of fused tricyclic coumarin derivatives as a new family of multifunctional anti-Alzheimer agents
  作者：Jeelan Basha Shaik、Bhagath Kumar Palaka、Mohan Penumala、Kasi Viswanath Kotapati、Subba Rao Devineni、Siddhartha Eadlapalli、M. Manidhar Darla、Dinakara Rao Ampasala、Ramakrishna Vadde、G. Damu Amooru

  DOI：10.1016/j.ejmech.2015.10.046

  日期：2016.1

  A series of fused tricyclic coumarin derivatives bearing iminopyran ring connected to various amido moieties were developed as potential multifunctional anti-Alzheimer agents for their cholinesterase inhibitory and radical scavenging activities. In vitro studies revealed that most of these compounds exhibited high inhibitory activity on acetylcholinesterase (AChE), with IC50 values ranging from 0.003 to 0.357 mu M which is 2-220 folds more potent than the positive control, galantamine. Their inhibition selectivity against AChE over butyrylcholinesterase (BuChE) has increased about 194 fold compared with galantamine. The developed compounds also showed potent ABTS radical scavenging activity (IC50 7.98 -15.99 mu M). Specifically, the most potent AChE inhibitor 6n (IC50 0.003 +/- 0.0007 mu M) has an excellent antioxidant profile as determined by the ABTS method (IC50 7.98 0.77 mu M). Moreover, cell viability studies in SK N SH cells showed that the compounds 6m-q have significant neuroprotective effects against H2O2-induced cell death, and are not neurotoxic at all concentrations except 6n and 6q. The kinetic analysis of compound 6n proved that it is a mixed-type inhibitor for EeAChE (K-i1 0.0103 mu M and K-i2 0.0193 mu M). Accordingly, the molecular modeling study demonstrated that 6m-q with substituted benzyl amido moiety possessed an optimal docking pose with interactions at catalytic active site (CAS) and peripheral anionic site (PAS) of AChE simultaneously and thereby they might prevent aggregation of A beta induced by AChE. Furthermore, in silico ADMET prediction studies indicated that these compounds satisfied all the characteristics of CNS acting drugs. Most active inhibitor 6n is permeable to BBB as determined in the in vivo brain AChE activity. To sum up, the multipotent therapuetic profile of these novel tricyclic coumarins makes them promising leads for developing anti-Alzheimer agents. (C) 2015 Elsevier Masson SAS. All rights reserved.