3-maleimidobenzaldehyde | 76620-02-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3-maleimidobenzaldehyde
• 英文别名: 3-(2,5-dioxopyrrol-1-yl)benzaldehyde
• CAS: 76620-02-5
• 化学式: C₁₁H₇NO₃
• 分子量: 201.181
• InChiKey: HEWIMBSYHHCGKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-maleimidobenzaldehyde 、 4-phenylbutyric acid hydrazide trifluoroacetate 以 四氢呋喃 为溶剂， 反应 24.0h， 以72%的产率得到4-Phenyl-butyric acid [1-[3-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl]-meth-(E)-ylidene]-hydrazide
  参考文献：
  名称：

  抗癌药物氯霉素的白蛋白结合物：合成、表征和体外功效

  摘要：

  在我们努力提高抗肿瘤剂的选择性和毒性特征的过程中，苯丁酸氮芥 (1-4) 的四种马来酰亚胺衍生物与硫醇化人血清白蛋白结合，它们在药物和间隔物之间​​的化学连接的稳定性方面有所不同。1 是苯丁酸氮芥的脂肪族马来酰亚胺酯衍生物，而 2-4 是乙醛、苯乙酮和苯甲醛羧腙衍生物。使用相关模型化合物 5、7、8 和 9（苯丁酸氮芥被 4-苯基丁酸取代）在 pH 5.0 下进行的 HPLC 稳定性研究表明，羧腙衍生物具有酸敏感性；7 的酸不稳定性特别突出，半衰期只有几个小时。借助 4-（4-硝基苄基）-吡啶（NBP）测定白蛋白结合苯丁酸氮芥的烷基化活性，证明平均三个等价物是蛋白质结合的。使用碘化丙啶荧光测定法评估游离苯丁酸氮芥和相应白蛋白偶联物在 MCF7 乳腺癌和 MOLT4 白血病细胞系中的细胞毒性，表明苯丁酸氮芥通过酯键与白蛋白结合的偶联物不如苯丁酸氮芥活性。相比之下，苯丁酸氮芥通过羧腙键与白蛋白

  DOI：

  10.1002/(sici)1521-4184(199802)331:2<47::aid-ardp47>3.0.co;2-r
• 作为产物：
  描述：

  m-N-马来酰亚氨基苯甲酸 在 氯化亚砜 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 48.0h， 生成 3-maleimidobenzaldehyde
  参考文献：
  名称：

  Synthese von neuen bifunktionellen Maleinimidverbindungen zur Herstellung von Chemoimmunokonjugaten

  摘要：

  Bifunctional maleimide compounds are suitable for binding small molecules to carrier proteins in that they bind to the sulfhydryl group of proteins through the double bond of the maleimide group and to molecules of low molecular weight (e.g. anticancer drugs) through a functional group X. 18 maleimide compounds of the general formula Maleimid-R-X (R = phenylene, benzyl-, methylene-, ethylene, or a m-benzoylethylamide group and X = hydroxp-, amino-, hydrazino-, carboxylic acid-, carboxylic anhydride-, carboxylic acid chloride-, carboxylic acid hydrazide-, oxycarbonylchloride-, aldehyde, keto-, or p-toluenesulfonate-group) were synthesized and characterized through H-1- and C-13-NMR-spectroscopy, elemental analysis, and mass spectrometry.

  DOI：

  10.1007/bf00807643

文献信息

• CURATIVES FOR EPOXY ADHESIVE COMPOSITIONS
  申请人：Dershem Stephen M.

  公开号：US20100113643A1

  公开（公告）日：2010-05-06

  The invention provides epoxy and oxetane compositions including the novel acyloxy and N-acyl curing agents described herein. Use of invention curing agents result in cured adhesive compositions with remarkably increased adhesion and reduced hydrophilicity when compared to resins cured with other types of curing agents. Furthermore, the curatives of this invention do not interfere with free-radical cure and are thus suited for use in hybrid cure thermoset compositions.

  该发明提供了包括新型酰氧基和N-酰基固化剂的环氧树脂和氧环烷组合物。使用该发明的固化剂可使胶粘剂组合物固化后的粘附性大大增加，并且与用其他类型的固化剂固化的树脂相比，其亲水性减少。此外，该发明的固化剂不会干扰自由基固化，因此适用于混合固化热固性组合物的使用。
• CURATIVES FOR EPOXY COMPOSITIONS
  申请人：Dershem Stephen M.

  公开号：US20100249276A1

  公开（公告）日：2010-09-30

  The invention provides epoxy and oxetane compositions including the novel acyloxy and N-acyl curing agents described herein. Use of invention curing agents result in cured adhesive compositions with remarkably increased adhesion and reduced hydrophilicity when compared to resins cured with other types of curing agents. Furthermore, the curatives of this invention do not interfere with free-radical cure and are thus suited for use in hybrid cure thermoset compositions.

  本发明提供了环氧和氧杂环烷组分，包括本文所述的新型酰氧基和N-酰基固化剂。使用本发明的固化剂可使固化的粘合剂组分具有显著增强的粘附性和降低的亲水性，与使用其他类型固化剂固化的树脂相比。此外，本发明的固化剂不干扰自由基固化，因此适用于混合固化热固性组分的使用。
• PYRAZOLE-TYPE CYANINE DYE
  申请人：Wako Pure Chemical Industries, Ltd.

  公开号：EP2006289B1

  公开（公告）日：2011-11-30
• Synthesis and in Vitro Efficacy of Transferrin Conjugates of the Anticancer Drug Chlorambucil
  作者：Ulrich Beyer、Thomas Roth、Peter Schumacher、Gerhard Maier、Anuschka Unold、August W. Frahm、Heinz H. Fiebig、Clemens Unger、Felix Kratz

  DOI：10.1021/jm9704661

  日期：1998.7.1

  One strategy for improving the selectivity and toxicity profile of antitumor agents is to design drug carrier systems employing soluble macromolecules or carrier proteins. Thus, five maleimide derivatives of chlorambucil were bound to thiolated human serum transferrin which differ in the stability of the chemical link between drug and spacer. The maleimide ester derivatives 1 and 2 were prepared by reacting 2-hydroxyethylmaleimide or 3-maleimidophenol with the carboxyl group of chlorambucil, and the carboxylic hydrazone derivatives 5-7 were obtained through reaction of 2-maleimidoacetaldehyde, 3-maleimidoacetophenone, or 3-maleimidobenzaldehyde with the carboxylic acid hydrazide derivative of chlorambucil. The alkylating activity of transferrin-bound chlorambucil was determined with the aid of 4-(4-nitrobenzyl)pyridine (NBP) demonstrating that on average 3 equivalents were protein-bound. Evaluation of the cytotoxicity of free chlorambucil and the respective transferrin conjugates in the MCF7 mammary carcinoma and MOLT4 leukemia cell line employing a propidium iodide fluorescence assay demonstrated that the conjugates in which chlorambucil was bound to transferrin through non-acid-sensitive linkers, i.e., an ester or benzaldehyde carboxylic hydrazone bond, were not, on the whole, as active as chlorambucil. In contrast, the two conjugates in which chlorambucil was bound to transferrin through acid-sensitive carboxylic hydrazone bonds were as active as or more active than chlorambucil in both cell lines. Especially, the conjugate in which chlorambucil was bound to transferrin through an acetaldehyde carboxylic hydrazone bond exhibited IC50 values which were approximately 3-18-fold lower than those of chlorambucil. Preliminary toxicity studies in mice showed that this conjugate can be administered at higher doses in comparison to unbound chlorambucil. The structure-activity relationships of the transferrin conjugates are discussed with respect to their pH-dependent acid sensitivity, their serum stability, and their cytotoxicity.
• EP0766689B1
  申请人：——

  公开号：EP0766689B1

  公开（公告）日：1999-10-20

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