2-((2-methoxynaphthalen-1-yl)methylene)malononitrile | 351897-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((2-methoxynaphthalen-1-yl)methylene)malononitrile
• 英文别名: 2-[(2-Methoxynaphthalen-1-yl)methylidene]propanedinitrile
• CAS: 351897-09-1
• 化学式: C₁₅H₁₀N₂O
• mdl: MFCD00582539
• 分子量: 234.257
• InChiKey: IGOKMWRNDCSMGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氰乙酰肼 、 2-((2-methoxynaphthalen-1-yl)methylene)malononitrile 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以75%的产率得到1,6-diamino-4-(2-methoxynaphthalen-1-yl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  Synthesis and Antimicrobial Evaluation of Some New Dihydropyridine, Pyrazole, Chromene, Pyrrole, Thiazole and Thiophene Derivatives

  摘要：

  Synthesis of 2-cyano-N((2-methoxynaphthalen-1-yl)methylene)acetohydrazide (3) and its use as a key intermediate for the synthesis of some new heterocyclic compounds such as dihydropyridines (4, 6 and 8), pyrazoles (9 and 10), chromene (11), pyrroles (12 and 13), thiazoles (14 and 17) and thiophene (18-20) derivatives were described. The structures of newly synthesized compounds have been established on the basis of their IR, H-1-NMR, C-13-NMR and mass spectral data and have been screened for their antimicrobial activity.

  DOI：

  10.3987/com-14-13072
• 作为产物：
  描述：

  2-甲氧基-1-萘醛 、 丙二腈 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以89.8%的产率得到2-((2-methoxynaphthalen-1-yl)methylene)malononitrile
  参考文献：
  名称：

  Synthesis and Antimicrobial Evaluation of Some New Dihydropyridine, Pyrazole, Chromene, Pyrrole, Thiazole and Thiophene Derivatives

  摘要：

  Synthesis of 2-cyano-N((2-methoxynaphthalen-1-yl)methylene)acetohydrazide (3) and its use as a key intermediate for the synthesis of some new heterocyclic compounds such as dihydropyridines (4, 6 and 8), pyrazoles (9 and 10), chromene (11), pyrroles (12 and 13), thiazoles (14 and 17) and thiophene (18-20) derivatives were described. The structures of newly synthesized compounds have been established on the basis of their IR, H-1-NMR, C-13-NMR and mass spectral data and have been screened for their antimicrobial activity.

  DOI：

  10.3987/com-14-13072

文献信息

• Rapid access to novel 2-alkylthiopyrimidine derivatives and attempt of their Tacrine analogs synthesis
  作者：Chamseddine Derabli、Raouf Boulcina、Gilbert Kirsch、Abdelmadjid Debache

  DOI：10.1080/00397911.2018.1557687

  日期：2019.2.1

  Abstract A variety of novel 2-alkylthiopyrimidines were synthesized through simple condensation of arylidenemalononitriles with different 2-alkylthiouronium halide derivatives catalyzed by anhydrous potassium carbonate (K2CO3). The reactions have been carried out under mild conditions in i-PrOH, and the products were obtained in moderate to good yields with a simple work-up method. Subsequently, some

  摘要 通过亚芳基丙二腈与不同的 2-烷基硫脲卤化物衍生物在无水碳酸钾 (K2CO3) 的催化下进行简单缩合，合成了多种新型 2-烷基硫代嘧啶类化合物。反应在温和条件下在 i-PrOH 中进行，并通过简单的后处理方法以中等至良好的产率获得产物。随后，通过应用 Friedländer 反应将这些化合物的一些实例转化为他克林类似物。
• Synthesis and antitumor activity of some novel hydrazide, 1,2-dihydropyridine, chromene, and benzochromene derivatives
  作者：Mostafa M. Ghorab、Mansour S. Al-Said

  DOI：10.1002/jhet.829

  日期：2012.3

  ydrazide 2a, 2b, 2c were obtained via reaction of acetophenone derivatives 1a, 1b, 1c with cyanoacetic acid hydrazide. The hydrazidehydrazone derivative 2a underwent a novel series of heterocyclization reactions via its reaction with aromatic aldehydes and/or arylidenemalononitriles to produce arylidene and dihydropyridine derivatives 3 5l, respectively. Structures of the newly synthesized compounds

  通过苯乙酮衍生物1a，1b，1c与氰基乙酸酰肼反应制得2-氰基-N'-[1-（取代苯基）亚乙基]乙酰肼2a，2b，2c。酰肼hydr衍生物2a通过与芳族醛和/或芳基丙二腈反应分别进行芳环和二氢吡啶衍生物3 5l的反应，进行了一系列新的杂环化反应。新合成化合物的结构通过元素分析，IR，13 C-NMR，1确证。 H-NMR和质谱数据。评估了所有新合成的化合物对艾氏腹水癌（EAC）细胞的体外抗肿瘤活性。与作为参考药物的阿霉素（CAS 23214‐92‐8）相比，其中一些具有有趣的细胞毒性活性。J.杂环化​​学。（2011）。
• Synthesis and biological evaluation of 2-amino-7,7-dimethyl 4-substituted-5-oxo-1-(3,4,5-trimethoxy)-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile derivatives as potential cytotoxic agents
  作者：Saleh I. Alqasoumi、Areej M. Al-Taweel、Ahmed M. Alafeefy、Mostafa M. Hamed、Eman Noaman、Mostafa M. Ghorab

  DOI：10.1016/j.bmcl.2009.10.065

  日期：2009.12

  The present work reports the synthesis of some novel quinoline derivatives bearing a trimethoxyphenyl moiety. The trimethoxybenzene moiety has been reported to be crucial to obtain relevant cytotoxic and antitubulin responses. All the newly synthesized compounds were evaluated for their in vitro anticancer activity. Several compounds showed interesting cytotoxic activities compared to the used reference

  已鉴定出大量源自自然来源或化学合成的抗有丝分裂药物，并显示出它们干扰微管蛋白系统的作用。抑制微管蛋白聚合是可用于癌症治疗的重要靶标之一。 本工作报道了一些带有三甲氧基苯基部分的新型喹啉衍生物的合成。据报道，三甲氧基苯部分对于获得相关的细胞毒性和抗微管蛋白反应至关重要。评价所有新合成的化合物的体外抗癌活性。与使用的参考药物相比，几种化合物表现出令人感兴趣的细胞毒性活性。
• Discovering some novel tetrahydroquinoline derivatives bearing the biologically active sulfonamide moiety as a new class of antitumor agents
  作者：Saleh I. Alqasoumi、Areej M. Al-Taweel、Ahmed M. Alafeefy、Mostafa M. Ghorab、Eman Noaman

  DOI：10.1016/j.ejmech.2010.01.022

  日期：2010.5

  5 μg/mL) are more potent and efficacious than Doxorubicin (CAS-23214-92-8) as reference drug with (IC50 value = 37.5 μg/mL). Also, compounds 28, 30, 31, and 34 (with IC50 values = 25 μg/mL) are nearly as active as Doxorubicin.

  本文介绍了一些新型的4-（2-氨基-3-氰基-4-（取代的芳基）-5-氧代-5,6,7,8-四氢喹啉-1（4H）-基）苯磺酰胺的合成（23 - 41）开始与4-（3-氧代-环己-1-烯基氨基）苯磺酰胺（3）。评价所有新合成的化合物的体外抗肿瘤活性。化合物32，25，41，35，33，和37与IC 50个值（2.5，3，5，10，12，和12.5微克/毫升）是更有效的和多柔比星相比（CAS-23214-92-8）有效作为参考药物与（IC 50值= 37.5μg/ mL）。另外，化合物28，30，31，和34（用IC 50个值= 25微克/毫升）几乎作为活性如多柔比星。
• Anticancer activity of novel indenopyridine derivatives
  作者：Mostafa M. Ghorab、Mansour S. Al-Said

  DOI：10.1007/s12272-012-0605-x

  日期：2012.6

  Eighteen new 4-[2-amino-3-cyano-5-oxo-4-substitutedaryl-4H-indeno[1,2-b]pyridin-1-(5H)-yl]benzenesulfonamide derivatives 6a–q were synthesized via a reaction of aromatic aldehydes, enaminone 3 and malononitrile in one-pot reaction. Also, compounds 6a–q were obtained, via another route by reaction of enaminone 3 with arylidenemalononitriles 4a–q. The structure of the synthesized compounds was characterized by microanalysis, IR, 1H-NMR, 13C-NMR and mass spectral data. All the target compounds were subjected to in vitro anticancer activity against breast cancer cell line (MCF7). Compound 6d showed a higher potency with IC50 value (4.34 μM) than that of the Doxorubicin (5.40 μM), as the reference drug, while compound 6n with IC50 value (6.84 μM) is nearly as active as Doxorubicin. Also, compounds 6a–c, 6e, 6f, 6h and 6p exhibited a moderate activity, while compounds 3, 6g, 6i–m, 6o and 6q showed weak activity.

  通过芳香醛、烯胺酮 3 和丙二腈的一锅反应，合成了 18 种新的 4-[2-氨基-3-氰基-5-氧代-4-取代芳基-4H-茚并[1,2-b]吡啶-1-(5H)-基]苯磺酰胺衍生物 6a-q。此外，还通过另一条途径，即烯胺酮 3 与芳基亚甲基丙二腈 4a-q 反应，得到了化合物 6a-q。通过微量分析、红外光谱、1H-NMR、13C-NMR 和质谱数据对合成化合物的结构进行了表征。所有目标化合物都对乳腺癌细胞株（MCF7）具有体外抗癌活性。化合物 6d 的 IC50 值（4.34 μM）比参考药物多柔比星的 IC50 值（5.40 μM）更高，而化合物 6n 的 IC50 值（6.84 μM）几乎与多柔比星的活性相同。此外，化合物 6a-c、6e、6f、6h 和 6p 表现出中等活性，而化合物 3、6g、6i-m、6o 和 6q 则表现出弱活性。