2-(2-fluorophenylmethylene)hydrazine carboxamide

• 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: 2-(2-fluorophenylmethylene)hydrazine carboxamide
• 英文别名: [(2-fluorophenyl)methylideneamino]urea
• 化学式: C₈H₈FN₃O
• mdl: MFCD00743766
• 分子量: 181.169
• InChiKey: HWCTVJBBBDHFEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-fluorophenylmethylene)hydrazine carboxamide 在 正丁基锂 、 溴 、 sodium acetate 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 7.0h， 生成 2-[2-(2-fluorophenyl)-1,3,4-oxodiazol-5-yl]benzisoselenazol-3(2H)-one
  参考文献：
  名称：

  Synthesis and <i>in Vitro</i> Antitumor Activity of 1,3,4-Oxadiazole Derivatives Based on Benzisoselenazolone

  摘要：

  一系列基于苯并亚硒氮烯的 novel 1,3,4-噁二唑衍生物已被合成，并在体外测试了其对人癌细胞系的抗增殖活性：SSMC-7721（人肝癌细胞）、MCF-7（人乳腺癌细胞）和 A549（人肺癌细胞）。所有合成的化合物均表现出抗增殖活性，并对不同癌细胞表现出选择性细胞毒性。化合物 7d 和 7i 对 MCF-7 细胞表现出显著的抗增殖活性，其 IC50 值分别为 1.07 和 1.76 µM。化合物 7d 被发现是对 SSMC-7721 细胞最有效的化合物，其 IC50 值为 4.46 µM。

  DOI：

  10.1248/cpb.c12-00250
• 作为产物：
  描述：

  盐酸氨基脲 、 2-氟苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 生成 2-(2-fluorophenylmethylene)hydrazine carboxamide
  参考文献：
  名称：

  Synthesis and <i>in Vitro</i> Antitumor Activity of 1,3,4-Oxadiazole Derivatives Based on Benzisoselenazolone

  摘要：

  一系列基于苯并亚硒氮烯的 novel 1,3,4-噁二唑衍生物已被合成，并在体外测试了其对人癌细胞系的抗增殖活性：SSMC-7721（人肝癌细胞）、MCF-7（人乳腺癌细胞）和 A549（人肺癌细胞）。所有合成的化合物均表现出抗增殖活性，并对不同癌细胞表现出选择性细胞毒性。化合物 7d 和 7i 对 MCF-7 细胞表现出显著的抗增殖活性，其 IC50 值分别为 1.07 和 1.76 µM。化合物 7d 被发现是对 SSMC-7721 细胞最有效的化合物，其 IC50 值为 4.46 µM。

  DOI：

  10.1248/cpb.c12-00250

文献信息

• Spectroscopic Characterization and Biological Potential of Palladium(II) Complexes of Benzylidenehydrazinecarboxamide or -carbothioamide
  作者：Nighat Fahmi、Chitra Saxena、Ranvir V. Singh

  DOI：10.1246/bcsj.69.963

  日期：1996.4

  the synthesis, stereochemistry, and biochemical behavior of palladium(II) complexes of benzylidenehydrazinecarboxamide or -carbothioamide is presented. The bimolar addition and substitution products have been characterized by elemental analyses, conductance measurements, molecular-weight determinations, magnetic susceptibilities, and spectral studies viz., IR, 1H NMR, 19F NMR, and UV. The data support

  在本文中，简要介绍了苄叉肼甲酰胺或 -碳硫酰胺的钯 (II) 配合物的合成、立体化学和生化行为。双摩尔加成和取代产物已通过元素分析、电导测量、分子量测定、磁化率和光谱研究（即 IR、1H NMR、19F NMR 和 UV）进行表征。数据支持硫或氧和氮与钯的结合（X 是 O 或 S）类型的配合物。已经提出了方形平面几何。代表性的游离配体 () 及其各自的金属配合物在体外针对多种微生物进行了测试，以评估它们的抗菌性能，并在体内测试了它们的杀菌潜力。结果确实是积极的。
• Synthesis of 2-Amino-1,3,4-oxadiazoles and 2-Amino-1,3,4-thiadiazoles via Sequential Condensation and I₂-Mediated Oxidative C–O/C–S Bond Formation
  作者：Pengfei Niu、Jinfeng Kang、Xianhai Tian、Lina Song、Hongxu Liu、Jie Wu、Wenquan Yu、Junbiao Chang

  DOI：10.1021/jo502518c

  日期：2015.1.16

  2-Amino-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles were synthesized via condensation of semicarbazide/thiosemicarbazide and the corresponding aldehydes followed by I-2-mediated oxidative C-O/C-S bond formation. This transition-metal-free sequential synthesis process is compatible with aromatic, aliphatic, and cinnamic aldehydes, providing facile access to a variety of diazole derivatives bearing a 2-amino substituent in an efficient and scalable fashion.
• Saxena, Chitra; Singh, R. V., Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 97, # 1-4, p. 17 - 26
  作者：Saxena, Chitra、Singh, R. V.

  DOI：——

  日期：——
• Some aryl semicarbazones possessing anticonvulsant activitie
  作者：JR Dimmock、KK Sidhu、SD Tumber、SK Basran、M Chen、JW Quail、J Yang、I Rozas、DF Weaver

  DOI：10.1016/0223-5234(96)88237-7

  日期：——

  A number of aryl semicarbazones displayed anticonvulsant activity in the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) screens when administered intraperitoneally to mice. When given by the oral route to rats, protection was afforded in the MES but not scPTZ tests. Correlations were noted between the sigma and sigma* values of the aryl substituents, the interplanar angles made by the aryl rings with the adjacent carbimino groups and the shapes of certain semicarbazones determined by X-ray crystallography, and the activities in the rat oral MES screen. Molecular modeling studies revealed a number of statistically significant descriptors which contributed to anticonvulsant activity.
• Ultrapotent Inhibitor of <i>Clostridioides difficile</i> Growth, Which Suppresses Recurrence <i>In Vivo</i>
  作者：George A. Naclerio、Nader S. Abutaleb、Daoyi Li、Mohamed N. Seleem、Herman O. Sintim

  DOI：10.1021/acs.jmedchem.0c01198

  日期：2020.10.22

  Clostridioides difficile is the leading cause of healthcare-associated infection in the U.S. and considered an urgent threat by the Centers for Disease Control and Prevention (CDC). Only two antibiotics, vancomycin and fidaxomicin, are FDA-approved for the treatment of C. difficile infection (CDI), but these therapies still suffer from high treatment failure and recurrence. Therefore, new chemical entities to treat CDI are needed. Trifluoromethylthio-containing N-(1,3,4-oxadiazol-2-yl)benzamides displayed very potent activities [sub-μg/mL minimum inhibitory concentration (MIC) values] against Gram-positive bacteria. Here, we report remarkable antibacterial activity enhancement via halogen substitutions, which afforded new anti-C. difficile agents with ultrapotent activities [MICs as low as 0.003 μg/mL (0.007 μM)] that surpassed the activity of vancomycin against C. difficile clinical isolates. The most promising compound in the series, HSGN-218, is nontoxic to mammalian colon cells and is gut-restrictive. In addition, HSGN-218 protected mice from CDI recurrence. Not only does this work provide a potential clinical lead for the development of C. difficile therapeutics but also highlights dramatic drug potency enhancement via halogen substitution.