5-bromo-2-hydroxy-3-methoxybenzaldehyde semicarbazone | 215459-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-bromo-2-hydroxy-3-methoxybenzaldehyde semicarbazone
• 英文别名: [(5-Bromo-2-hydroxy-3-methoxyphenyl)methylideneamino]urea
• CAS: 215459-02-2
• 化学式: C₉H₁₀BrN₃O₃
• 分子量: 288.101
• InChiKey: OAYQKIUURFKUPS-UHFFFAOYSA-N

物化性质

• 熔点：
  263-264 °C
• 密度：
  1.71±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  五羰基溴铼(I) 、 5-bromo-2-hydroxy-3-methoxybenzaldehyde semicarbazone 以 甲苯 为溶剂， 反应 24.0h， 以32%的产率得到[Re^I(CO)₃Br(5-bromo-2-hydroxy-3-methoxybenzaldehyde semicarbazone)]
  参考文献：
  名称：

  Newfac-三羰基铼 (I) 氨基脲配合物：合成、表征和生物学评价

  摘要：

  扩展我们之前关于水杨醛缩氨基脲金属配合物作为前瞻性抗锥虫剂的工作，合成并表征了五种新的含有 fac-Rel(CO)3 的配合物和这种缩氨基脲系列的配体。红外光谱证明了这些潜在的三齿配体仅通过羰基氧和偶氮甲碱氮（所谓的 N，O 方式）的非典型配位模式，并得到了理论计算的支持。其中三种化合物显示出中等的体外抗克氏锥虫活性，并且相对于相应的游离配体具有增加的活性。溴化配体 5-溴-2-羟基苯甲醛缩氨基脲 (L2) 和 5-溴-2-羟基-3-甲氧基苯甲醛缩氨基脲 (L5) 导致最活跃的铼 (I) 配合物。这些化合物是少数报道的对 T. cruzi 具有体外活性的铼络合物实例之一。图形摘要 在克氏锥虫上合成、表征和评估了五种新的 fac-Rel(CO)3-三齿缩氨基脲复合物。DFT 计算支持观察到的非典型双齿协调模式。

  DOI：

  10.1080/00958972.2014.926008

文献信息

• Expanding the family of heteroleptic oxidovanadium(IV) compounds with salicylaldehyde semicarbazones and polypyridyl ligands showing anti-Trypanosoma cruzi activity
  作者：Gonzalo Scalese、Julio Benítez、Santiago Rostán、Isabel Correia、Lara Bradford、Marisol Vieites、Lucía Minini、Alicia Merlino、E. Laura Coitiño、Estefania Birriel、Javier Varela、Hugo Cerecetto、Mercedes González、João Costa Pessoa、Dinorah Gambino

  DOI：10.1016/j.jinorgbio.2015.03.002

  日期：2015.6

  Searching for prospective vanadium-based drugs for the treatment of Chagas disease, a new series of heteroleptic [VIVO(L-2H)(NN)] compounds was developed by including the lipophilic 3,4,7,8-tetramethyl-1,10-phenanthroline (tmp) NN ligand and seven tridentate salicylaldehyde semicarbazone derivatives (L1–L7). The compounds were characterized in the solid state and in solution. EPR spectroscopy suggests

  为寻找可用于治疗恰加斯病的钒基药物，开发了一系列新的杂合[V IV O（L-2H）（NN）]化合物，其中包括亲脂性的3,4,7,8-四甲基-1 ，10-菲咯啉（tmp）NN配体和七个三齿水杨醛半卡巴zone衍生物（L1-L7）。在固态和溶液中对化合物进行表征。EPR光谱表明，NN配体以轴向-赤道模式通过两个氮供体原子结合成双齿。室温下充气溶液的EPR和51 V-NMR光谱表明，该化合物对水解稳定，并且没有明显的V IV氧化为V V至少在24小时内发生。与参考药物Nifurtimox相比，该复合物在体外对负责查加斯病的寄生虫克氏锥虫的活性更高，并且大多数比其他NN先前报道的[V IV O（L-2H）（NN）]复合物更具活性。配体。使用J-774鼠巨噬细胞作为哺乳动物细胞模型分析了对寄生虫的选择性。由于高活性和高选择性，L2，L4，L5和L7复合物可被视为进一步药物开发的新选择。亲脂性可能在新化合物的生物活性中起重要作用。[V
• A new series of heteroleptic oxidovanadium(iv) compounds with phenanthroline-derived co-ligands: selective Trypanosoma cruzi growth inhibitors
  作者：Mariana Fernández、Javier Varela、Isabel Correia、Estefanía Birriel、Jorge Castiglioni、Virtudes Moreno、Joao Costa Pessoa、Hugo Cerecetto、Mercedes González、Dinorah Gambino

  DOI：10.1039/c3dt50512j

  日期：——

  Searching for prospective metal-based drugs for the treatment of Chagas disease, a new series of ten mixed-ligand oxidovanadium(IV) complexes, [VIVO(L-2H)(NN)], where L is a tridentate salicylaldehyde semicarbazone derivative (L1–L5) and NN is either 5-amine-1,10-phenanthroline (aminophen) or 5,6-epoxy-5,6-dihydro-1,10-phenanthroline (epoxyphen), were synthesized. The compounds were characterized in

  寻找用于治疗恰加斯病的潜在金属基药物，这是一系列新的十种混合配体氧化钒（IV）配合物，[V IV O（L-2H）（NN）]，其中L是三齿水杨醛半卡巴zone衍生物（L1-L5）和NN是5-amine-1,10-phenothroline（氨基酚） 或者 5,6-环氧-5,6-二氢-1,10-菲咯啉（环氧），被合成。在固态和溶液中对化合物进行表征。EPR光谱表明，NN配体在轴向-赤道模式下通过两个氮供体原子充当双齿。通过EPR和51 V核磁共振波谱研究了溶液中配合物的稳定性。复合物进行了评价体外它们对活动克氏锥虫（克氏锥虫），疟原虫引起该疾病，以及使用J-774小鼠巨噬细胞分析了它们的选择性，作为哺乳动物模型。所有复合物的活性均高于参考药物Nifurtimox和先前报道的[V IVO（L-2H）（NN）]配合物。通常，它们比相应的游离NN配体更具活性。络合导致对寄生虫的选择性大大提高。此外，
• Searching for gallium bioactive compounds: Gallium(III) complexes of tridentate salicylaldehyde semicarbazone derivatives
  作者：Dinorah Gambino、Mariana Fernández、Diego Santos、Gustavo A. Etcheverría、Oscar E. Piro、Fernando R. Pavan、Clarice Q.F. Leite、Isabel Tomaz、Fernanda Marques

  DOI：10.1016/j.poly.2011.02.037

  日期：2011.4

  methods. The gallium(III) ion is in a distorted octahedral environment, coordinated to two nearly planar and mutually perpendicular 3-ethoxysalicylaldehyde semicarbazonato anions acting as tridentate ligands through their phenol and carbonyl oxygen atoms and their azomethine nitrogen atom. Their biological potential has been explored by evaluating their activity on Mycobacterium tuberculosis, causative

  在寻找镓生物活性化合物时，已合成了五种Ga（III）配合物[Ga III（L–H）2 ]（NO 3），其中三齿水杨醛半卡巴zone衍生物为配体（L），并在固态和通过不同的技术解决。[Ga III（L4-H）2 ]（NO 3）·2H 2的晶体结构通过X射线衍射法解决了其中L4为3-乙氧基水杨醛半脲的O。镓（III）离子处于扭曲的八面体环境中，通过其苯酚和羰基氧原子以及它们的偶氮甲碱氮原子与两个接近平面且相互垂直的3-乙氧基水杨醛半咔唑阴离子配位为三齿配体。通过评估其对结核分枝杆菌的活性来探索其生物学潜力。，结核病的病原体及其对肿瘤细胞系的细胞毒性。选择了三种不同的人类肿瘤细胞系，它们显示出对金属药物的不同程度的抵抗力：卵巢A2780（低抵抗力），乳腺癌MCF7（中等抵抗力）和前列腺PC3（高抵抗力）细胞。尽管复合物未显示对结核分枝杆菌有活性，但与镓的复合作用已导致有机化合物的细胞毒性增强。在
• Oxidovanadium(IV) and dioxidovanadium(V) complexes of tridentate salicylaldehyde semicarbazones: Searching for prospective antitrypanosomal agents
  作者：Mariana Fernández、Lorena Becco、Isabel Correia、Julio Benítez、Oscar E. Piro、Gustavo A. Echeverria、Andrea Medeiros、Marcelo Comini、María Laura Lavaggi、Mercedes González、Hugo Cerecetto、Virtudes Moreno、Joao Costa Pessoa、Beatriz Garat、Dinorah Gambino

  DOI：10.1016/j.jinorgbio.2013.02.010

  日期：2013.10

  As a contribution to the identification of the relevant species for biological activity and the understanding of structure-activity relationships of [(VO)-O-IV(L-2H)(NN)] antitrypanosomal complexes (NN is a bidentate polypyridyl DNA intercalator; L is a tridentate salicylaldehyde semicarbazone derivative), new [(VO2)-O-V(L-2H)] complexes and [(VO)-O-IV(L-2H)(NN)] complexes including bipy or dppz (dipyrido[3,2-a: 2',3'-c]phenazine) co-ligands are prepared and characterized in the solid state and in solution. Their activity is evaluated on Trypanosoma cruzi. The lipophilicity, as structural descriptor related to bioactivity, of the whole [(VO)-O-IV(L-2H)(NN)] series is determined. Furthermore, the antiproliferative effect of those new compounds showing activity against T. cruzi is evaluated on the genetically related parasite T. brucei with the aim to develop broad spectrum agents. The new [WO (L-2H)(dppz)] complexes are about ten to fifteen times more toxic to T. cruzi than the bipy analogues and show quite good in vitro activity on T. brucei brucei. They are shown to interact with DNA, suggesting that this biomolecule may be the parasite target. The stability of the (VO)-O-IV-complexes in solution is accessed by several techniques. Globally the data suggest that the relevant species for biological activity are the [(VO)-O-IV(L-2H)(NN)] compounds, their order of activity being dependent on the NN nature, but not much on the substitution on the salicylaldehyde semicarbazone moiety. A parabolic relationship between biological response and lipophilicity (determined as R-M = log [(1 / R-f) -1] by a TLC method) is obtained. From this correlation an optimum R-M value, close to 1.44, was found, which may be used as design guide for future development of antitrypanosomal compounds. (C) 2013 Elsevier Inc. All rights reserved.