4-(2-naphthyl)semicarbazide | 99844-04-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(2-naphthyl)semicarbazide
• 英文别名: 4-[2]naphthyl semicarbazide；4-[2]Naphthyl-semicarbazid；(β-Naphthylaminoformyl)-hydrazin；4-β-Naphthyl-semicarbazid；1-Amino-3-naphthalen-2-ylurea
• CAS: 99844-04-9
• 化学式: C₁₁H₁₁N₃O
• 分子量: 201.228
• InChiKey: HKNBPWYTSDIJTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-naphthyl)semicarbazide 、 4-phenylfuroxan-3-carboxaldehyde 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以54%的产率得到1-naphthalen-2-yl-3-[(E)-(2-oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methylideneamino]urea
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 1,2,5-OxadiazoleN-Oxide Derivatives as Potential Hypoxic Cytotoxins and DNA-Binders

  摘要：

  Several new 1,2,5-oxadiazole N-oxide derivatives were synthesized to be tested both as potential selective hypoxic cell cytotoxins and as DNA-binding agents. The compounds prepared included bis(1,2,5-oxadiazole N-oxide) derivatives and oxadiazole rings linked to naphthyl residues. The compounds were tested for their cytotoxicity in oxia and hypoxia and they proved to be non-selective and less active than the parent compounds 3-formyl-4-phenyl-1,2,5-oxadiazole N2-oxide (3) and 3-chloromethyl-4-phenyl-1,2,5-oxadiazole N2-oxide (4). The DNA-affinity assays showed that the compounds tested have poor affinity for this biomolecule.

  DOI：

  10.1002/1521-4184(200011)333:11<387::aid-ardp387>3.0.co;2-n
• 作为产物：
  描述：

  N-(2-萘基)脲 在 乙醇 、 肼 作用下， 生成 4-(2-naphthyl)semicarbazide
  参考文献：
  名称：

  Sah; Tao, Journal of the Chinese Chemical Society (Peking), 1936, vol. 4, p. 501,503

  摘要：

  DOI：

文献信息

• Preparation of substituted semicarbazides from corresponding amines and hydrazines via phenyl carbamates
  作者：Rebecca Hron、Branko S. Jursic

  DOI：10.1016/j.tetlet.2014.01.052

  日期：2014.2

  A simple synthetic procedure for the conversion of amines and hydrazines into substituted semicarbazides was developed. The initial condensation between the desired amine and phenyl chloroformate into phenyl carbamate is followed by the addition of hydrazine under basic conditions. The reaction is tolerable to a variety of functional groups, with mild conditions and high percent yields.

  开发了一种简单的合成方法，用于将胺和肼转化为取代的氨基脲。所需的胺和氯甲酸苯酯之间最初的缩合成氨基甲酸苯酯，然后在碱性条件下加入肼。该反应可耐受各种官能团，条件温和，收率高。
• Synthesis, Biological Activities, and Quantitative Structure–Activity Relationship (QSAR) Study of Novel Camptothecin Analogues
  作者：Dan Wu、Shao-Yong Zhang、Ying-Qian Liu、Xiao-Bing Wu、Gao-Xiang Zhu、Yan Zhang、Wei Wei、Huan-Xiang Liu、An-Liang Chen

  DOI：10.3390/molecules20058634

  日期：——

  mmol/L and 0.00942 mmol/L, respectively) compared with CPT (LC50 0.19719 mmol/L) against T. Cinnabarinus. Based on the observed bioactivities, preliminary structure–activity relationship (SAR) correlations were also discussed. Furthermore, a three-dimensional quantitative structure–activity relationship (3D-QSAR) model using comparative molecular field analysis (CoMFA) was built. The model gave statistically

  为了继续我们旨在开发基于天然产物的杀虫剂的计划，设计、合成了三个系列的新型喜树碱衍生物，并评估了它们对朱砂、甘蓝和松材线虫的生物活性。所有衍生物对三种测试的昆虫物种均表现出良好至极好的活性，LC50 值范围为 0.00761 至 0.35496 mmol/L。值得注意的是，所有化合物都比 CPT 更有效地对抗朱砂，化合物 4d 和 4c 显示出优于 CPT（LC50 0.19719 mmol/L）的活性（分别为 0.00761 mmol/L 和 0.00942 mmol/L） . 朱砂。基于观察到的生物活性，还讨论了初步的构效关系 (SAR) 相关性。此外，建立了使用比较分子场分析（CoMFA）的三维定量构效关系（3D-QSAR）模型。该模型给出了具有统计学意义的结果，交叉验证的 q2 值为 0.580，相关系数 r2 为 0.991，rpred2 为 0.993。QSAR分析表明取代基的
• New Vanadium( <scp>V</scp> ) Complexes with Salicylaldehyde Semicarbazone Derivatives: Synthesis, Characterization, and in vitro Insulin‐Mimetic Activity − Crystal Structure of [V ^v O ₂ (salicylaldehyde semicarbazone)]
  作者：Pabla Noblía、Enrique J. Baran、Lucía Otero、Patricia Draper、Hugo Cerecetto、Mercedes González、Oscar E. Piro、Eduardo E. Castellano、Toshifumi Inohara、Yusuke Adachi、Hiromu Sakurai、Dinorah Gambino

  DOI：10.1002/ejic.200300421

  日期：2004.1

  The new dioxo(semicarbazone)vanadium(V) complexes cis-VO2L, where L = salicylaldehyde semicarbazone (L1), salicylaldehyde 4-n-butylsemicarbazone (L2), or salicylaldehyde 4-(2-naphthyl)semicarbazone (L3), have been synthesized, characterized by 1H and 13C NMR and FTIR spectroscopy and tested for bioactivity as potential insulin-mimetic agents. All dioxovanadium(V) complexes exhibited essentially no

  新的二氧（缩氨基脲）钒（V）配合物顺式-VO2L，其中 L = 水杨醛缩氨基脲 (L1)、水杨醛 4-n-丁基缩氨基脲 (L2) 或水杨醛 4-(2-萘基)缩氨基脲 (L3)，合成，通过 1H 和 13C NMR 和 FTIR 光谱表征并测试作为潜在胰岛素模拟剂的生物活性。所有二氧钒 (V) 复合物在体外基本上没有模拟胰岛素活性，但 VO2L2 复合物在抗坏血酸存在下表现出活性，类似于硫酸氧钒的活性。新型复合物 VO2L1 的分子结构已通过 X 射线衍射方法解决。它在四方空间群 P42/n 中结晶，a = 12.7674(7)，c = 11.5308(5) A，Z = 8。钒原子处于扭曲的方形锥体配位中，L1通过其偶氮甲炔氮原子、羰基氧原子和去质子化苯酚氧原子作为三齿配体。配位球由顺式位置的两个氧代配体完成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451
• Highly selective c-Jun N-terminal kinase (JNK) 2 and 3 inhibitors with in vitro CNS-like pharmacokinetic properties prevent neurodegeneration
  作者：Gary D. Probst、Simeon Bowers、Jennifer M. Sealy、Anh P. Truong、Roy K. Hom、Robert A. Galemmo、Andrei W. Konradi、Hing L. Sham、David A. Quincy、Hu Pan、Nanhua Yao、May Lin、Gergley Tóth、Dean R. Artis、Wes Zmolek、Karina Wong、Ann Qin、Colin Lorentzen、David F. Nakamura、Kevin P. Quinn、John-Michael Sauer、Kyle Powell、Lany Ruslim、Sarah Wright、David Chereau、Zhao Ren、John P. Anderson、Frédérique Bard、Ted A. Yednock、Irene Griswold-Prenner

  DOI：10.1016/j.bmcl.2010.11.010

  日期：2011.1

  In this Letter, we describe the discovery of selective JNK2 and JNK3 inhibitors, such as 10, that routinely exhibit >10-fold selectivity over JNK1 and >1000-fold selectivity over related MAPKs, p38α and ERK2. Substitution of the naphthalene ring affords an isoform selective JNK3 inhibitor, 30, with approximately 10-fold selectivity over both JNK1 and JNK2. A naphthalene ring penetrates deep into the selectivity pocket accounting for the differentiation amongst the kinases. Interestingly, the gatekeeper Met146 sulfide interacts with the naphthalene ring in a sulfur-π stacking interaction. Compound 38 ameliorates neurotoxicity induced by amyloid-β in human cortical neurons. Lastly, we demonstrate how to install propitious in vitro CNS-like properties into these selective inhibitors.
• Borsche, Chemische Berichte, 1901, vol. 34, p. 4301
  作者：Borsche

  DOI：——

  日期：——