1-氨基-3-丁基脲 | 20605-19-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1-氨基-3-丁基脲
• 英文名称: 4-butyl-3-semicarbazide
• 英文别名: 4-butyl semicarbazide；4-n-butyl-semicarbazide；3-Amino-1-butylurea；1-amino-3-butylurea
• CAS: 20605-19-0
• 化学式: C₅H₁₃N₃O
• mdl: MFCD00047818
• 分子量: 131.178
• InChiKey: OQGXXDLQVFZTAD-UHFFFAOYSA-N

物化性质

• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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-phenylfuroxan-3-carboxaldehyde 、 1-氨基-3-丁基脲 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以49%的产率得到4-butyl-1-<(4-phenyl-1,2,5-oxadiazol-3-yl N₂-oxide)methylidene>semicarbazide
  参考文献：
  名称：

  1,2,5-Oxadiazole N-Oxide Derivatives and Related Compounds as Potential Antitrypanosomal Drugs:  Structure−Activity Relationships

  摘要：

  The syntheses of a new series of derivatives of 1,2,5-oxadiazole N-oxide, benzo[1,2-c]1,2,5-oxadiazole N-oxide, and quinoxaline di-hr-oxide are described. In vitro antitrypanosomal activity of these compounds was tested against epimastigote forms of Trypanosoma cruzi. For the most effective drugs, derivatives IIIe and IIIf, the 50% inhibitory dose (ID50) was determined as well as their cytotoxicity against mammalian fibroblasts. Electrochemical studies and ESR spectroscopy show that the highest activities observed are associated with the facile mono-electronation of the N-oxide moiety. Lipophilic-hydrophilic balance of the compounds could also play an important role in their effectiveness as antichagasic drugs.

  DOI：

  10.1021/jm9805790
• 作为产物：
  描述：

  异氰酸正丁酯 在 肼 作用下， 生成 1-氨基-3-丁基脲
  参考文献：
  名称：

  Collard-Charon,C.; Renson,M., Bulletin des Societes Chimiques Belges, 1963, vol. 72, p. 291 - 303

  摘要：

  DOI：

文献信息

• Copper-Catalyzed Oxidative Carbamoylation of <i>N</i> -Arylacrylamides with Hydrazinecarboxamides Leading to 2-(Oxindol-3-yl)acetamide<b>s</b>
  作者：Zeng-Yang He、Jing-Yu Guo、Shi-Kai Tian

  DOI：10.1002/adsc.201800012

  日期：2018.4.3

  radical carbamoylation/cyclization reaction of N‐arylacrylamides with hydrazinecarboxamides has been developed for facile access to 2‐(oxindol‐3‐yl)acetamides, which had been utilized as precursors in the synthesis of natural bioactive pyrrolidinoindolines. In the presence of 1 mol% of copper(II) carbonate and 4 equiv. of tert‐butyl hydroperoxide, a wide range of N‐arylacrylamides underwent highly regioselective

  已开发出N-芳基丙烯酰胺与肼甲酰胺的串联氨基甲酰化/环化反应，可轻松获得2-（oxindol-3-yl）乙酰胺，后者已被用作天然生物活性吡咯烷二氢吲哚的合成前体。在1摩尔％的碳酸铜（II）和4当量的存在下。在叔丁基过氧化氢中，广泛的N-芳基丙烯酰胺与肼甲酰胺进行了高度区域选择性的氨基甲酰基化反应，然后进行5-exo-trig环化反应，从而以中等至优异的收率得到结构多样的2-（oxindol-3-yl）乙酰胺。
• Synthesis, cytotoxicity, and in vivo antitumor activity study of parthenolide semicarbazones and thiosemicarbazones
  作者：Xinxin Jia、Qi Liu、Shiyi Wang、Binglin Zeng、Guohua Du、Chen Zhang、Yan Li

  DOI：10.1016/j.bmc.2020.115557

  日期：2020.7

  anticancer activities. In order to further improve its biological activity, a series of parthenolide semicarbazone or thiosemicarbazone derivatives was synthesized and evaluated for their anticancer activity. Derivatives were tested in vitro against 5 human tumor cell lines, and many of these showed higher cytotoxicity than parthenolide. Five compounds were further studied for their antitumor activity in mice

  偏苯二酚是一种重要的倍半萜内酯，具有有效的抗癌活性。为了进一步提高其生物活性，合成了一系列的小白菊内酯半卡巴or或硫代半卡巴zone衍生物，并对其抗癌活性进行了评估。衍生物在体外针对5种人类肿瘤细胞系进行了测试，其中许多都显示出比单杀氰菊酯更高的细胞毒性。进一步研究了五种化合物在小鼠中的抗肿瘤活性。该体内结果表明，化合物4D既表现出有前途的抗小鼠结肠肿瘤和免疫系统副作用小的抗肿瘤活性。化合物4d的细胞凋亡和细胞周期分布还进行了研究。分子对接研究揭示之间的多重相互作用4D和NF- κ B.我们的研究结果表明缩氨基脲作为具有抗癌活性的有前途的类型的化合物的潜力。
• Facile one-pot synthesis of 4-substituted semicarbazides
  作者：Andrey V. Bogolubsky、Yurii S. Moroz、Pavel K. Mykhailiuk、Yurii V. Dmytriv、Sergey E. Pipko、Liudmyla N. Babichenko、Anzhelika I. Konovets、Andrey Tolmachev

  DOI：10.1039/c4ra12425a

  日期：——

  and disubstituted semicarbazides was prepared in a one-pot two-step approach. The method includes formation of a carbamate from bis(2,2,2-trifluoroethyl)carbonate or 2,2,2-trifluoroethylchloroformate and a primary or secondary amine and subsequent interaction of the carbamate with hydrazine to result in a semicarbazide. The approach allowed to obtain 4-substituted semicarbazides on a large scale in

  用一锅两步法制备了25种4-一元和二取代的氨基脲的多样化文库。该方法包括由碳酸双（2,2,2-三氟乙基）酯或氯甲酸2,2,2-三氟乙基酯与伯胺或仲胺形成氨基甲酸酯，以及随后使氨基甲酸酯与肼相互作用以生成氨基脲。该方法允许以高收率和高纯度大规模获得4-取代的氨基脲。
• Benzo[1, 2-c]1, 2, 5-oxadiazole N-Oxide Derivatives as Potential Antitrypanosomal Drugs. Structure-Activity Relationships. Part II
  作者：Gabriela Aguirre、Hugo Cerecetto、Rossanna Di Maio、Mercedes González、Williams Porcal、Gustavo Seoane、Miguel A. Ortega、Ignacio Aldana、Antonio Monge、Ana Denicola

  DOI：10.1002/1521-4184(200201)335:1<15::aid-ardp15>3.0.co;2-8

  日期：2002.1

  The preparation of new derivatives of benzo[1, 2‐c]1, 2, 5‐oxadiazole N‐oxide is described. These derivatives were chosen in order to investigate and confirmprevious structural features found necessary to display an adequate antitrypanosomal activity. The compounds synthesized were tested in vitro against epimastigote forms of Trypanosoma cruzi.The presence of a bromine atom in the benzo system produced

  描述了苯并 [1, 2-c]1, 2, 5-恶二唑 N-氧化物的新衍生物的制备。选择这些衍生物是为了研究和确认先前发现的表现出足够的抗锥虫活性所必需的结构特征。合成的化合物在体外针对克氏锥虫的上鞭毛体形式进行了测试。苯并系统中溴原子的存在产生的化合物活性低于相应的脱卤类似物。然而，5-(溴甲基)-7-溴苯并 [1, 2-c] 恶二唑 N-氧化物 (23) 是对 T. cruzi 最具细胞毒性的化合物。为此，确定了 50% 抑制剂量 (ID50)，它与 ​​Nifurtimox 的数量级相同。
• 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