N`-[(3,4-dimethoxyphenyl)-methylidene]-2-cyanoacetohydrazide | 88614-67-9

• 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: N`-[(3,4-dimethoxyphenyl)-methylidene]-2-cyanoacetohydrazide
• 英文别名: cyanoacetic acid (3,4-dimethoxybenzylidene)-hydrazide；N'-(3,4-dimethoxybenzylidene)-2-cyanoacetohydrazide；2-cyano-N-[(3,4-dimethoxyphenyl)methylideneamino]acetamide
• CAS: 88614-67-9
• 化学式: C₁₂H₁₃N₃O₃
• 分子量: 247.254
• InChiKey: MSTGEGLMWQNHML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N`-[(3,4-dimethoxyphenyl)-methylidene]-2-cyanoacetohydrazide 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-(3,4-dimethoxyphenyl)-7-[(4-methoxy-benzylidene) amino]-5-oxo-1,5-dihydro-[1,2,4]triazolo[1,5-a] pyridine-6-carbonitrile
  参考文献：
  名称：

  Synthesis of Some New 7-(arylidene/heteroylidene imino)-2-(3,4-dimethoxy-phenyl)-5-oxo- 1,5-dihydro-[1,2,4]triazolo[1,5-α]pyridine-6-carbonitrile Derivatives as Potent Antibacterial and Anti-inflammatory Agents

  摘要：

  由 7-氨基-2-(3,4-二甲氧基苯基)-5-氧代-1,5-二氢-[1,2,4]三唑并[1,5-α]吡啶-6-甲腈衍生物，即、希夫碱（4a-4j）是由 7-氨基-2-(3,4-二甲氧基苯基)-5-氧代-1,5-二氢-[1,2,4]三唑并[1,5-α]吡啶-6-甲腈（3）与取代的苯甲醛或庚醛在冰醋酸存在下反应合成的。对化合物 3、4a-4j 的抗菌和抗炎特性进行了研究，结果表明一些合成化合物的活性优于标准参考药物。化合物 4b、4c、4f、4g 和 4i 的最小抑菌浓度为 10 μg/mL，低于环丙沙星。此外，还对这些化合物的抗炎特性进行了体外测试，发现与标准参考药物布洛芬相比，化合物 4a 和 4f 在 100 μg/mL 的浓度下具有更强的抗炎作用。

  DOI：

  10.59467/ijhc.2023.33.278
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 在 哌啶 、 己酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 N`-[(3,4-dimethoxyphenyl)-methylidene]-2-cyanoacetohydrazide
  参考文献：
  名称：

  Alonso, Paloma; Martin-Leon, Nazario; Quinteiro, Margarita, Liebigs Annalen der Chemie, 1990, # 9, p. 841 - 846

  摘要：

  DOI：

文献信息

• Novel Polyfunctional Pyridines as Anticancer and Antioxidant Agents. Synthesis, Biological Evaluation and <i>in Silico</i> ADME-T Study
  作者：Mona Hany Badr、Sherif Ahmed Fawzi Rostom、Mohammed Fouad Radwan

  DOI：10.1248/cpb.c16-00761

  日期：——

  Two series of novel alkoxylated 2-oxo(imino)-3-pyridinecarbonitriles (structurally-relevant to some reported anticancer pyridines with phosphodiesterase 3A (PDE3A) inhibitory activity) were synthesized and evaluated for their in vitro differential tumor cell growth inhibitory potential against the breast MCF7, hepatocellular Hep-G2, colon CACO-2 cell lines, and a normal human foreskin fibroblast Hs27

  合成了两个系列的新型烷氧基化2-氧代（亚氨基）-3-吡啶甲腈（与一些报道的具有磷酸二酯酶3A（PDE3A）抑制活性的抗癌吡啶结构相关），并评估了它们对乳腺的体外差异性肿瘤细胞生长抑制潜力MCF7，肝细胞Hep-G2，结肠CACO-2细胞系和正常人包皮成纤维细胞Hs27细胞系。与阿霉素（LC50 3.94 µM）相比，化合物8、16和19表现出对乳腺MCF7的可识别的生长抑制能力和选择性（分别为LC50 19.15、17.34和14.70 µM）。同时，化合物8、15、16和19在2,2-二苯基-1-picylhydrazyl（DPPH）分析中具有独特的抗氧化潜力，对正常人包皮成纤维细胞Hs27细胞系的生长显示出微弱的抑制作用。进一步评估了这四种化合物对PDE3A（当前的抗肿瘤治疗靶标）的体外抑制作用，与​​阳性对照米力农相比，其中16和19对PDE3A的抑制作用中等至弱。不能推断出抗癌潜力
• Facile isocyanide-based one-pot three-component regioselective synthesis of highly substituted pyridin-2(1H)-one derivatives at ambient temperature
  作者：Ming Li、Wei Kong、Li-Rong Wen、Fang-Hui Liu

  DOI：10.1016/j.tet.2012.03.124

  日期：2012.6

  A novel one-pot three-component regioselective synthesis of highly substituted pyridin-2-one derivatives starting from simple and readily available starting materials is described. The reactive zwitterionic intermediate generated by the addition of an isocyanide to dimethyl acetylenedicarboxylate (DMAD) was trapped with N-arylidene-2-cyanoacetohydrazides to afford the title compounds in moderate to

  描述了一种从简单易得的起始原料开始的高度取代的吡啶-2-酮衍生物的新颖的一锅三组分区域选择性合成。通过在N-亚芳基-2-氰基乙酰肼中捕获N，亚芳基-2-氰基乙酰肼，将通过向乙炔基二羧酸二甲酯（DMAD）中添加异氰化物而生成的反应性两性离子中间体，在不使用任何催化剂和其他添加剂的情况下以中等至良好的收率得到标题化合物。
• 7‐Amino‐2‐aryl/hetero‐aryl‐5‐oxo‐5,8‐dihydro[1,2,4]triazolo[1,5‐<i>a</i>]pyridine‐6‐carbonitriles: Synthesis and adenosine receptor binding studies
  作者：Khasim Shaik、Pran Kishore Deb、Raghu Prasad Mailavaram、Balakumar Chandrasekaran、Sonja Kachler、Karl‐Norbert Klotz、Abdul Muttaleb Yousef Jaber

  DOI：10.1111/cbdd.13528

  日期：——

  A series of novel 7‐amino‐5‐oxo‐2‐substituted‐aryl/hetero‐aryl‐5,8‐dihydro[1,2,4]triazolo[1,5‐a]pyridine‐6‐carbonitriles (4a–4t) was synthesized, characterized and evaluated for their binding affinity and selectivity towards hA1, hA2A, hA2B and hA3 adenosine receptors (ARs). Compound 4a with a phenyl ring at 2‐position of the triazolo moiety of the scaffold showed high affinity and selectivity for

  一系列新颖的7-氨基-5-氧代-2-取代的芳基/杂芳基-5,8-二氢[1,2,4]三唑[1,5 - a ]吡啶-6-腈（4a– 4吨）合成，其特征在于，评价向HA的结合亲和力和选择性1，HA 2A，HA 2B和HA 3腺苷受体（ARS）。在支架的三唑部分的2位带有苯环的化合物4a对hA 1 AR（K i hA 1  = 0.076μM，hA 2A  = 25.6μM和hA 3）具有高亲和力和选择性 > 100μM）。在苯环的不同位置引入各种给电子和吸电子基团，导致对所有AR的亲和力和选择性大大降低，除了在2位带有4-羟基苯基的化合物4b。有趣的是，用较小的杂环噻吩环取代苯环（π过量的体系）导致对化合物4t的hA 1 AR的亲和力进一步提高（K i hA 1  = 0.051μM，hA 2A  = 9.01μM和hA 3  > 13.9μM），同时保留了对所有其他类似于化合物4a的AR亚型的
• Microwave Assisted Synthesis and Evaluation of N-Cinnamoyl Aryl Hydrazones for Cytotoxic and Antioxidant Activities
  作者：T.Sarala Devi

  DOI：10.13005/ojc/320350

  日期：2016.6.28

  A series of N-cinnamoyl aryl hydrazones 2a-2i were synthesized in good yields by microwave irradiation technique. The title compounds were formed by nucleophilic condensation of various N-1-substituted benzylidene-2-cyano aceto hydrazides with N,N-dimethyl amino benzaldehyde. The intermediate N-1-substituted benzylidene-2-cyano aceto hydrazide was obtained by condensing various substituted benzaldehydes with cyanoacetohydrazide. The structures of the compounds were characterized by IR, H-1 NMR and Mass spectra. The antioxidant activity was studied by reduction of DPPH, scavenging of nitric oxide and hydrogen peroxide methods with ascorbic acid as the standard drug. The compounds were evaluated for cytotoxic activity by BSLT method and their ED50 values were compared the standard podophyllotoxin. Among the compounds evaluated, N-1-benzylidene-2-cyano-3-(4-dimethylamino) phenyl acrylo hydrazide (2a) and N-1-(4-methoxy-benzylidene)-2-cyano3-(4-dimethylamino) phenyl acrylohydrazide (2e) showed good antioxidant activity towards all the three models. The compounds 2a and 2e showed ED50 values 3.07 mu g/ml and 3.7 mu g/ml respectively which were compared against the standard podophyllotoxin (1.64 mu g/ml).
• Reactivity of 6-Methylchromone-3-carbonitrile Towards Some Nitrogen Nucleophilic Reagents
  作者：Magdy A. Ibrahim、Nasser M. El-Gohary、Sara Said

  DOI：10.3987/com-18-13874

  日期：——

  The chemical reactivity of 6-methylchromone-3-carbonitrile (1) was studied towards a variety of nitrogen nucleophiles. A variety of products was obtained from the reaction of carbonitrile 1 with hydrazine hydrate, S-benzyl dithiocarbazate, isonicotinic acid hydrazide and cyanoacetohydrazide. A diversity of Schiff bases bearing 2-amino-6-methylchromone linked variable heterocyclic systems was efficiently synthesized. Reaction of carbonitrile 1 with guanidine and cyanoguanidine resulted in ring conversion producing chromeno[4,3-d]pyrimidines. Reaction of carbonitrile 1 was also studied towards some 1,4-binucleophiles.