N-(3,5-dimethylphenyl)hydrazinecarbamide

• 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-(3,5-dimethylphenyl)hydrazinecarbamide
• 英文别名: 1-Amino-3-(3,5-dimethylphenyl)urea
• 化学式: C₉H₁₃N₃O
• 分子量: 179.222
• InChiKey: NLEKPKRMXAAESN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  N-(3,5-dimethylphenyl)hydrazinecarbamide 在 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 28.0h， 生成 7-chloro-2-(3,5-dimethyl-phenylamino)-4,4-dioxo-4H-4λ⁶,9-dithia-1,3,3a-triaza-cyclopenta[b]naphthalene-6-carbonitrile
  参考文献：
  名称：

  Synthesis and anticancer activity of 2-amino-8-chloro-5,5-dioxo[1,2,4]triazolo[2,3- b ][1,4,2]benzodithiazine derivatives

  摘要：

  A new series of 1-(6-chloro- 1, 1 -dioxo- 1,4,2-benzodithiazin-3-yl)-4-arylsemicarbazides (4-16) were obtained. Intramolecular ring closure in semicarbazides 4-16 upon treatment with phosphorus oxychloride resulted in the formation of 2-amino-8-chloro-5,5-dioxo[1,2,4]triazolo[2,3-b][1,4,2]benzodithiazines 17-29 with potential antitumor activity. The structures of these compounds were confirmed on the basis of elemental analysis, spectral data and X-ray analysis. Compounds 17-29 were screened at the US National Cancer Institute (NCI) for their activities against a panel of 59 tumor cell lines, and relationships between structure and antitumor activity in vitro are discussed. The benzodithiazines 18, 19, 23, 28 and 29 were inactive, whereas the other compounds exhibited reasonable activity against numerous human tumor cell lines. The prominent compound 17 showed significant activity against the leukemia SR cell line (log GI(50)= -7.67, log TGI= -6.90 and log LC50=-4.77). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00638-7
• 作为产物：
  描述：

  1-氨基-3,5-二甲苯 在 hydrazine hydrate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 3.08h， 生成 N-(3,5-dimethylphenyl)hydrazinecarbamide
  参考文献：
  名称：

  通过氨基甲酸苯酯由相应的胺和肼制备取代的氨基脲

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2014.01.052

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 and Antimalarial Activity of Novel Dihydro-Artemisinin Derivatives
  作者：Yang Liu、Kunqiang Cui、Weiqiang Lu、Wei Luo、Jian Wang、Jin Huang、Chun Guo

  DOI：10.3390/molecules16064527

  日期：——

  The Plasmodium falciparum cysteine protease falcipain-2, one of the most promising targets for antimalarial drug design, plays a key role in parasite survival as a major peptide hydrolase within the hemoglobin degradation pathway. In this work, a series of novel dihydroartemisinin derivatives based on (thio)semicarbazone scaffold were designed and synthesized as potential falcipain-2 inhibitors. The

  恶性疟原虫半胱氨酸蛋白酶 falcipain-2 是抗疟药物设计中最有希望的靶点之一，作为血红蛋白降解途径中的主要肽水解酶，在寄生虫存活中起着关键作用。在这项工作中，设计并合成了一系列基于（硫代）缩氨基脲支架的新型双氢青蒿素衍生物作为潜在的 falcipain-2 抑制剂。体外生物测定表明，大多数目标化合物对 P. falciparum falcipain-2 显示出优异的抑制活性，IC(50) 值在 0.29-10.63 μM 范围内。进行分子对接研究以研究抑制剂的结合亲和力和相互作用模式。总结了初步的SARs，可以作为进一步研究抗疟药物开发的基础。
• Synthesis of 3-(tri/difluoromethyl)-1<i>H</i>-1,2,4-triazol-5(4<i>H</i>)-ones <i>via</i> the cyclization of hydrazinecarboxamides with tri/difluoroacetic anhydride
  作者：Yi You、Yueji Chen、Chenhui You、Junwen Wang、Zhiqiang Weng

  DOI：10.1039/c9ob01865d

  日期：——

  An efficient method for the synthesis of structurally diverse 4-aryl-3-(tri/difluoromethyl)-1H-1,2,4-triazol-5(4H)-ones through the cyclization of hydrazinecarboxamides with tri/difluoroacetic anhydride is presented. The method is simple and environmentally benign, providing tri/difluoromethylated 1,2,4-triazol-5(4H)-ones in moderate-to-good yields. A mechanism is proposed to proceed via a tandem reaction

  提出了一种通过肼羧酰胺与三/二氟乙酸酐环化合成结构多样的4-芳基-3-（三/二氟甲基）-1H-1,2,4-三唑-5（4H）-的有效方法。该方法简单且对环境无害，可以以中等至良好的产率提供三/二氟甲基化的1,2,4-三唑-5（4H）-一。提出了通过三/二氟乙酰化，亲核加成和水消除的串联反应进行的机制。这些化合物中的一些表现出有希望的杀虫活性。
• 3-三氟(二氟)甲基-1,2,4-三氮唑-5-酮类化合物的合成方法
  申请人：福州大学

  公开号：CN110194749B

  公开（公告）日：2022-04-26

  本发明公开了一种3‑三氟(二氟)甲基‑1,2,4‑三氮唑‑5‑酮类化合物及其合成方法和应用。以氨基脲作为底物，三氟(二氟)乙酸酐作为多氟烷基源，在无任何催化剂条件下，一步合成3‑三氟(二氟)甲基‑1,2,4‑三氮唑‑5‑酮类化合物。该合成方法具有操作简便、条件温和、原料廉价易得、产物多样化等优点。该类含氟化合物对粘虫、桃蚜等具有很好活性，在600 mg/L剂量下，对害虫的死亡率高达100%，可作为一种潜在的含氟杀虫剂。
• Design and synthesis of novel triazole antifungal derivatives by structure-based bioisosterism
  作者：Chunquan Sheng、Xiaoying Che、Wenya Wang、Shengzheng Wang、Yongbing Cao、Zhenyuan Miao、Jianzhong Yao、Wannian Zhang

  DOI：10.1016/j.ejmech.2011.03.019

  日期：2011.11

  The incidence of life-threatening fungal infections is increasing dramatically. In an attempt to develop novel antifungal agents, our previously synthesized phenoxyalkylpiperazine triazole derivatives were used as lead structures for further optimization. By means of structure-based bioisosterism, triazolone was used as a new bioisostere of oxygen atom. This type of bioisosteric replacement can improve the water solubility without loss of hydrogen-bonding interaction with the target enzyme. A series of triazolone-containing triazoles were rationally designed and synthesized. As compared with fluconazole, several compounds showed higher antifungal activity with broader spectrum, suggesting their potential for further evaluations. (C) 2011 Elsevier Masson SAS. All rights reserved.