2-氰基-N-(2-乙基苯基)乙酰胺 | 87165-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氰基-N-(2-乙基苯基)乙酰胺
• 英文名称: 2-cyano-N-(2-ethylphenyl) acetamide
• 英文别名: 2-cyano-N-(2-ethylphenyl)acetamide
• CAS: 87165-08-0
• 化学式: C₁₁H₁₂N₂O
• mdl: MFCD01355333
• 分子量: 188.229
• InChiKey: PSOHSBHEQKJRIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  130-133 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  404.8±38.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氰基-N-(2-乙基苯基)乙酰胺 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.33h， 生成 2-N-[4-(6-methyl-1,3-benzothiazol-2-yl)phenyl]-imino-5-hydroxymethyl-8-methyl-2H-pyrano[3,2-c]pyridin-3-[N-(2-ethylphenyl)]carboxamide
  参考文献：
  名称：

  Synthesis and antimicrobial activity of 5-hydroxymethyl- 8-methyl-2-(N-arylimino)-pyrano[2,3-c]pyridine-3-(N-aryl)-carboxamides

  摘要：

  Several novel 2-imino-5-hydroxymethyl-8-methyl-2H-pyrano[2,3-c]pyridine-3-(N-aryl)carboxamides were prepared by reaction of pyridoxal hydrochloride with various N-arylcyanoacetamides. Reaction of these compounds with aromatic amines furnished a wide series of 2-(N-R-phenyl) imino-5-hydroxymethyl-8-methyl-2H-pyrano[2,3-c]pyridine-3-carboxamides. Antibacterial and antifungal activities of the synthesized compounds were studied. Most of the obtained compounds demonstrated significant activity against bacterial or fungal strains (MIC in the range of 12.5-25 mu g/mL), displaying comparable or even better efficacy than the standard drugs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.081
• 作为产物：
  描述：

  2-乙基苯胺 、 氰乙酸乙酯 反应 2.0h， 以80%的产率得到2-氰基-N-(2-乙基苯基)乙酰胺
  参考文献：
  名称：

  新型吡非尼酮类似物作为抗纤维化剂：2-吡啶酮和熔融吡啶酮的合成和抗纤维化评估

  摘要：

  合成了一系列新的取代的1-（2-乙基苯基）-2-氧代-1,2-二氢吡啶-3-腈。此外，已经制备并评估了取代的双环衍生物， 如 噻吩并[3,4- c ]吡啶酮，吡啶并[3,4- c ]吡啶酮，苯并[ c ]吡啶酮和三环衍生物铬诺[3,4- c ]吡啶酮。具有抗纤维化作用 在测试的化合物中，化合物 4d 和 5a 表现出强大的抗纤维化活性，而对肝和肾功能无有害副作用。报告了详细的合成，光谱和生物学数据。

  DOI：

  10.1007/s00044-006-0146-2

文献信息

• Identification of Novel Fused Heteroaromatics-Based MALT1 Inhibitors by High-Throughput Screening to Treat B Cell Lymphoma
  作者：Xuewu Liang、Chenxia Sun、Chunpu Li、Haolan Yu、Xiaohui Wei、Xuyi Liu、Wei Bao、Yuqiang Shi、Xiaochen Sun、Mirzadavlat Khamrakulov、Chenghua Yang、Hong Liu

  DOI：10.1021/acs.jmedchem.1c00466

  日期：2021.7.8

  lymphoid tissue lymphoma translocation protein 1 (MALT1) inhibitors is of great value and significance in the treatment of neoplastic disorders and inflammatory and autoimmune diseases. However, there is a lack of effective MALT1 inhibitors in clinic. Herein, a novel class of potent 5-oxo-1-thioxo-4,5-dihydro-1H-thiazolo[3,4-a]quinazoline-based MALT1 inhibitors and their covalent derivatives were first identified

  黏膜相关淋巴组织淋巴瘤易位蛋白 1 (MALT1) 抑制剂的开发在肿瘤性疾病、炎症和自身免疫性疾病的治疗中具有重要价值和意义。然而，临床上缺乏有效的MALT1抑制剂。在此，首次通过高通量鉴定和设计了一类新型有效的 5-oxo-1-thioxo-4,5-dihydro-1 H - thiazolo[3,4- a ]quinazoline 抑制剂及其共价衍生物。筛选。我们证明了化合物15c、15e和20c有效抑制 MALT1 蛋白酶并对活化的 B 细胞样弥漫性大 B 细胞淋巴瘤具有低个位数微摩尔效力显示出选择性细胞毒性。此外，化合物20c以剂量依赖性方式特异性抑制 MALT1 依赖性 TMD8 细胞中的 NF-κB 信号传导并诱导细胞凋亡。更重要的是，20c在 TMD8 异种移植肿瘤模型中显示出良好的药代动力学特性和抗肿瘤功效，且无显着毒性。总的来说，这项研究为 MALT1 抑制剂的进一步结构
• Development of Novel AKR1C3 Inhibitors as New Potential Treatment for Castration-Resistant Prostate Cancer
  作者：Satoshi Endo、Hiroaki Oguri、Jin Segawa、Mina Kawai、Dawei Hu、Shuang Xia、Takuya Okada、Katsumasa Irie、Shinya Fujii、Hiroaki Gouda、Kazuhiro Iguchi、Takuo Matsukawa、Naohiro Fujimoto、Toshiyuki Nakayama、Naoki Toyooka、Toshiyuki Matsunaga、Akira Ikari

  DOI：10.1021/acs.jmedchem.0c00939

  日期：2020.9.24

  crystallographic study of AKR1C3 complexes with 2j and 2l. The inhibitors suppressed proliferation of prostate cancer 22Rv1 and PC3 cells through both androgen-dependent and androgen-independent mechanisms. Additionally, 2j and 2l prevented prostate tumor growth in a xenograft mouse model. Furthermore, the inhibitors significantly augmented apoptotic cell death induced by anti-CRPC drugs (abiraterone or enzalutamide)

  醛基酮还原酶（AKR）1C3催化活性雄激素的合成，从而促进前列腺癌的发展。AKR1C3还通过前列腺素和反应性醛的代谢促进非雄激素依赖性细胞增殖和存活。由于其在去势抵抗性前列腺癌（CRPC）组织中的升高，AKR1C3是CRPC的有希望的治疗靶标。在这项研究中，我们发现了一种新型的强效AKR1C3抑制剂N-（4-氟苯基）-8-羟基-2-亚氨基-2 H-色烯-3-羧酰胺（2d），并用IC 50合成了其衍生物值比其他AKR（1C1、1C2和1C4）高25-56 nM，选择性> 220倍。通过结晶研究AKR1C3与2j和2l的复合物阐明了抑制效力的结构因素。所述抑制剂通过雄激素依赖性和雄激素依赖性机制抑制前列腺癌22Rv1和PC3细胞的增殖。另外，2j和2l阻止了异种移植小鼠模型中前列腺肿瘤的生长。此外，这些抑制剂显着增加了由抗CRPC药物（阿比特龙或enzalutamide）诱导的凋亡细胞死亡。
• Reactions of diethyl 2-(ethoxymethylene)malonate with 2-cyanoacetanilides: unexpected transfer of the ethoxymethylene moiety
  作者：Nikolay Yu. Gorobets、Valeriya P. Tkachova、Roman P. Tkachov、Oleksandr D. Dyachenko、Eduard B. Rusanov、Vladimir D. Dyachenko

  DOI：10.3998/ark.5550190.0011.b21

  日期：——

  A sodium ethoxide catalyzed reaction of N-substituted cyanoacetanilides 1a-f with diethyl 2-(ethoxymethylene)malonate 2 unexpectedly leads to the corresponding 2-amino-5-cyano-6oxo-N,1-diaryl-1,6-dihydropyridine-3-carboxamides 3a-f, while the expected 5-cyano-2hydroxy-6-oxo-1-aryl-1,6-dihydropyridine-3-carboxylates 4a-f were observed only as minor products.

  N-取代的氰基乙酰苯胺 1a-f 与 2-(乙氧基亚甲基)丙二酸二乙酯 2 的乙醇钠催化反应出人意料地生成了相应的 2-amino-5-cyano-6oxo-N,1-diaryl-1,6-dihydropyridine-3 -carboxamides 3a-f，而预期的 5-cyano-2hydroxy-6-oxo-1-aryl-1,6-dihydropyridine-3-carboxylates 4a-f 仅作为次要产物被观察到。
• Synthesis, Antibacterial and Cytotoxic Activities of Cyanoenonebenzenesulfonamide, Acetamide and Pyridine-3-carbonitrile Derivatives
  作者：Mansour S. Alsaid、Mostafa M. Ghorab、Victor Kuete、Abdelaaty A. Shahat、Thomas Efferth

  DOI：10.14233/ajchem.2014.18085

  日期：——

  A series of sulfonamides having biologically active acrylamides moieties (2, 3, 5), penta-2,4-dienamide (4), chromene-2-carboxamide (6), acetamide derivatives (7, 8) and pyridone derivative (9) were prepared. The structure of the synthesized compounds was verified by elemental analyses, IR, 1H NMR and 13C NMR spectra. In addition, the structure compound 9 was confirmed through X-ray crystallography. The antibacterial activities of all the synthesized compounds were evaluated against a panel of multi-drug resistant (MDR) Gram-negative strains of Escherichia coli, Enterobactera erogenes, Klebsie-llapneumoniae and Pseudomonas aeruginosa whilst their cytotoxic effects were tested against the leukemia CCRF-CEM and its adriamycin resistant subline CEM/ADR5000 cell lines. Compounds 1-5, 7 and 8 displayed or weak activities on at least one of the ten tested bacterial strains. The best MIC value of 64 μg/mL was obtained with 3 against E. aerogenes ATCC 13048. None of the compounds displayed significant cytotoxic effect against the two studied leukemia cell line. Nevertheless, the activity of compounds 4, 5, 8 and 9 were better than that of doxorubicin towards the resistant CEM/ADR5000 cell line.

  制备了一系列具有生物活性的丙烯酰胺基团的磺酰胺化合物（2、3、5），戊-2,4-二烯酰胺（4），香豆素-2-羧酰胺（6），乙酰酰胺衍生物（7、8）和吡啶酮衍生物（9）。通过元素分析、红外光谱（IR）、¹H NMR和¹³C NMR光谱确认了合成化合物的结构。此外，化合物9的结构通过晶体学确认。评估了所有合成化合物对一系列多药耐药（MDR）阴性革兰氏菌株，包括大肠杆菌、嗜热变形杆菌、克雷伯氏肺炎菌和铜绿假单胞菌的抗菌活性，同时还测试了它们对白血病CCRF-CEM及其阿霉素耐药亚系CEM/ADR5000细胞系的细胞毒性。化合物1-5、7和8在至少一种测试的十种细菌株上表现出或微弱的活性。在对E. aerogenes ATCC 13048的测试中，化合物3的最佳最低抑菌浓度（MIC）值为64 µg/mL。所有化合物对研究的两种白血病细胞系均未显示显著的细胞毒性。然而，化合物4、5、8和9的活性比多柔比星对耐药CEM/ADR5000细胞系的活性更好。
• Substituted phenyl-5-aminopyrazoles
  申请人：American Cyanamid Company

  公开号：US04393217A1

  公开（公告）日：1983-07-12

  This disclosure describes novel substituted phenyl-5-aminopyrazoles useful as anxiolytic and/or anti-depressant agents.

  这份披露描述了新型的取代苯基-5-氨基吡唑类化合物，可用作抗焦虑和/或抗抑郁药物。