beta-alanine hydroxamate | 36212-73-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: beta-alanine hydroxamate
• 英文别名: β-alaninehydroxamic acid；3-aminopropionohydroxamic acid；3-Amino-propionylhydroxamsaeure；3-amino-N-hydroxypropanamide
• CAS: 36212-73-4
• 化学式: C₃H₈N₂O₂
• 分子量: 104.109
• InChiKey: YDHOAQXHVQTASS-UHFFFAOYSA-N

物化性质

• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1Z)-N-甲基-1-苯基乙烷亚胺 、 beta-alanine hydroxamate 以 甲醇 为溶剂， 反应 4.0h， 以32%的产率得到3-Hydroxy-2-methyl-2-phenyl-1,3-diazinan-4-one
  参考文献：
  名称：

  Reaction of β-aminopropionohydroxamic acid with aldehydes and ketones

  摘要：

  beta-Aminopropionohydroxamic acid reacts with aliphatic aldehydes or ketones to give 2-substituted 1-hydroxytetrahydropyrimidin-6-ones, while its reaction with aromatic carbonyl compounds leads to either the same products or Schiff's bases, which can exist in tautomeric equilibrium in solution.

  DOI：

  10.1007/bf02495976
• 作为产物：
  描述：

  beta-丙氨酸乙酯盐酸盐 在 羟胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以240 mg的产率得到beta-alanine hydroxamate
  参考文献：
  名称：

  Reactivity and mechanism of α-nucleophile scaffolds as catalytic organophosphate scavengers

  摘要：

  设计和体外验证极性α-亲核试剂支架，提供强大的催化活性和实际用于有机磷去污的效用。

  DOI：

  10.1039/c9ob00503j

文献信息

• Cysteine derivatives as acetyl lysine mimics to inhibit zinc-dependent histone deacetylases for treating cancer
  作者：Jie Wang、Zhuoxian Cao、Fang Wang、Pan Wang、Jianxiong An、Xiaozhong Fu、Ting Liu、Yan Li、Yongjun Li、Yonglong Zhao、Hening Lin、Bin He

  DOI：10.1016/j.ejmech.2021.113799

  日期：2021.12

  potent inhibitors. Here we describe the rational design, synthesis, biological evaluation, molecular docking and in vivo efficacy study of a class of HDAC inhibitors using Nε-acetyl lysine mimics that are derived from cysteine. As a result, compounds 7a, 9b and 13d demonstrated pan-HDAC inhibition and broad cytotoxicity against several cancer cell lines, comparable to the approved HDAC inhibitor SAHA

  锌依赖性组蛋白脱乙酰酶 (HDACs) 是重要的表观遗传调节因子，已成为治疗癌症的重要药物靶点。尽管有五种 HDAC 抑制剂已被批准用于治疗多种癌症，但仍需要发现新的 HDAC 抑制剂以探索治疗实体瘤癌症的治疗潜力。底物模拟物是一种强大的合理设计方法，用于开发有效的抑制剂。在这里，我们描述了使用衍生自半胱氨酸的N ε -乙酰赖氨酸模拟物对一类 HDAC 抑制剂的合理设计、合成、生物学评估、分子对接和体内功效研究。结果，化合物7a、9b和13d证明了对几种癌细胞系的泛HDAC抑制和广泛的细胞毒性，与批准的HDAC抑制剂SAHA相当。此外，13d在 A549 异种移植小鼠模型中显着抑制肿瘤生长而没有任何明显的体重减轻，这支持了半胱氨酸衍生的乙酰赖氨酸模拟物是具有治疗癌症潜力的有前景的 HDAC 抑制剂。
• Half-sandwich type rhodium(<scp>iii</scp>)–aminohydroxamate complexes: the role of the position of the amino group in metal ion binding
  作者：Péter László Parajdi-Losonczi、Péter Buglyó、Hana Skakalova、Jana Kasparkova、Norbert Lihi、Etelka Farkas

  DOI：10.1039/c7nj04711h

  日期：——

  with β-alaha− in a wide pH-range, very stable dinuclear cluster ions exist. With γ-abha−, in the most stable complexes, two ligands (in reverse variation) link two half-sandwich cations, coordinating each ligand via the hydroxamate chelate to one metal centre, while via the amino-N to the other one. This arrangement seems to be further stabilized by a hydrogen bond as DFT calculations support the extra

  [（η之间的复合物形成平衡5 -Cp *）的Rh III（H 2 O）3 ] 2+和aminohydroxamic酸（L-2-氨基- Ñ羟基乙酰胺（α-alahaH），3-氨基- Ñ -hydroxypropanamide（使用pH电位法，1 H NMR和ESI-MS方法研究了相对于异羟肟酸酯功能具有不同螯合位置的伯氨基的β-alahaH）和4-氨基-N-羟基丁酰胺（GABAha，γ-abhaH））以及报告了水溶液中存在的配合物的形成常数。（O，O）和（N氨基，N发现异羟肟酸酯螯合物在很大程度上决定了所形成的单核和多种双核物种中的配位模式。同时用α-alaha - ，五元（N，N）螯合的单核络合物占优势，与β-alaha -在宽pH范围内，存在非常稳定的双核簇离子。与γ-艾卜哈- ，在最稳定的复合物，两种配体（在反向变化）连接两个半夹心阳离子，协调各个配体通过所述异羟肟酸盐螯合物在1个金属
• Reactions of 3-hydroxytetrahydropyrimidin-4-ones with electrophilic reagents
  作者：O. A. Luk'yanov、P. B. Gordeev

  DOI：10.1007/bf02498277

  日期：1999.12

  The reactions of nonsubstituted or 2-aryl-substituted 3-hydroxytetrahydropyrimidin-4-ones (HTHP) with carboxylic acid chlorides, tosyl chloride, or aryl isocyanates afford mainlyN,O-diacylated,N,O-ditosylated, orN,O-diarylcarbamoylated HTHP, respectively.N,O-Diacylated HTHP are also formed in the reactions of acid chlorides with Schiff's bases based on β-aminopropionohydroxamic acid.N-Acylated HTHP

  未取代或 2-芳基取代的 3-羟基四氢嘧啶-4-酮 (HTHP) 与羧酸氯化物、甲苯磺酰氯或异氰酸芳基酯的反应主要提供 N,O-二酰化、N,O-二甲苯基化或 N,O-二芳基氨基甲酰化 HTHP N,O-二酰化HTHP 也可在酰氯与基于β-氨基丙异羟肟酸的席夫碱反应中形成。N-酰化HTHP 可以通过用氨处理N,O-二酰化HTHP 来获得。2,2-二烷基（亚烷基）取代的 HTHP 与酰基氯或异氰酸苯酯的反应分别生成 N,O-二酰化或 N,O-二苯基氨基甲酰化 β-氨基丙异羟肟酸。
• Stoichiometric diversity of Ni(ii) metallacrowns with β-alaninehydroxamic acid in aqueous solution
  作者：Maurizio Remelli、Dimitri Bacco、Francesco Dallavalle、Eddy Lazzari、Nicola Marchetti、Matteo Tegoni

  DOI：10.1039/c3dt50370d

  日期：——

  The complex-formation equilibria of the system Ni(II)/β-alaninehydroxamic acid (β-AlaHA, LH) have been studied in solution by using potentiometry, calorimetry, ESI mass spectrometry and UV-Visible spectrophotometry. A series of mononuclear and polynuclear species have been identified at different pH and for different Ni(II)/ligand ratios. Among the polymetallic species, we have identified the 12-metallacrown-4 (12-MC-4) species [Ni5(LH−1)4]2+, which is analogous to the previously characterized [Cu5(LH−1)4]2+ 12-MC-4 complex, and which corresponds to the metallacrown complex predicted by the Metallacrown Structural Paradigm. Besides this species, we have very unexpectedly identified in solution three other polynuclear species, corresponding to the stoichiometries [Ni4(LH−1)4], [Ni5(LH−1)5] and [Ni6(LH−1)6]. A metallacrown with the same stoichiometry as [Ni5(LH−1)5] containing α-AlaHA as the ligand has been previously reported, while the other two species are new for the speciation systems of Cu(II) or Ni(II) aminohydroxamic acids. Intriguingly, all the three latter stoichiometries correspond to those of vacant 12-MC-4, 15-MC-5 or 18-MC-6 species. The thermodynamic parameters related to their formation in solution are discussed, together with the speciation of the mononuclear complexes, on the basis of the structural and thermodynamic information available on metallacrowns.

  通过电位法、热量法、电喷雾质谱法和紫外可见分光光度法，对Ni(II)/β-丙氨酸羟肟酸（β-AlaHA，LH）系统的复杂平衡进行了研究。在不同pH值和不同Ni(II)/配体比下，确定了一系列单核和多核物种。在多金属物种中，我们确定了12-金属冠-4（12-MC-4）物种[Ni5(LH≠1)4]2+，它与之前鉴定的[Cu5(LH≠1)4]2+ 12-MC-4复合物类似，与金属冠结构范式预测的金属冠复合物相对应。除了这个物种，我们还意外地在溶液中发现了其他三个多核物种，它们与化学计量比[Ni4(LH≠1)4]、[Ni5(LH≠1)5]和[Ni6(LH≠1)6]相对应。之前有报道过一种与[Ni5(LH≠1)5]具有相同化学计量比的金属冠，其中包含作为配体的β-丙氨酸羟肟酸，而其他两种物种对于Cu(II)或Ni(II)氨基羟肟酸的物种系统来说是新的。有趣的是，后三种化学计量比都与空12
• FEATURES OF DICYANAMIDE BINDING TO A POLYNUCLEAR METALLAMACROCYCLIC COPPER COMPLEX
  作者：R. V. Rumyantsev、M. A. Katkova、G. S. Zabrodina、S. Y. Ketkov

  DOI：10.1134/s002247662309007x

  日期：2023.9

  intermolecular O–H…N interactions, the neighboring molecules form infinite 1D chains linked together by π…π interactions of two cyano groups. An analysis of the electron density topology in Cu5(β-alaha)4(DCA)2(H2O)2 and the molecular electrostatic potential, performed on the basis of DFT calculations, shows that the coordination of dicyanamide leads to the formation of intramolecular non-covalent interactions

  摘要 SC-XRD测定了铜与二氰胺(DCA) Cu 5 (β-alaha) 4 (DCA) 2 (H 2 O) 2 ·H 2 O ( I )多核金属大环β-丙氨酸羟化物的晶体结构。由于分子间 O-H…N 相互作用，相邻分子形成通过两个氰基的 π…π 相互作用连接在一起的无限一维链。Cu 5 (β-alaha) 4 (DCA) 2 (H 2 O) 2电子密度拓扑分析基于DFT计算的分子静电势表明，二氰胺的配位导致DCA与金属冠的铜原子和Cu3上配位的水分子形成分子内非共价相互作用。