glutarodihydroxamic acid | 7068-55-5

• 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: glutarodihydroxamic acid
• 英文别名: Glutarohydroxamic acid；Glutarodihydroxamsaeure；N,N'-dihydroxypentanediamide
• CAS: 7068-55-5
• 化学式: C₅H₁₀N₂O₄
• mdl: MFCD25966438
• 分子量: 162.145
• InChiKey: VGLJEIRGKRANJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [Zn2(μ-CF3COO)2(CF3COO)2(μ-H2O)(N,N,N',N'-tetramethylethylenediamine)2] 、 glutarodihydroxamic acid 以 甲醇 为溶剂， 以47%的产率得到[Zn4(CF3COO)3(N,N,N',N'-tetramethylethylenediamine)4(glutarodihydroxamate)]
  参考文献：
  名称：

  二，三和四核异羟肟酸锌络合物作为异羟肟酸抑制锌水解酶的结构模型。

  摘要：

  尝试生产结构模型配合物[M2（mu-O2CR）2（O2CR）2（mu-H2O）（tmen）2]的Zn类似物（M = Ni，Co，Mn； R = CH（3），C（ CH3）3，CF3）通过一系列羧酸锌与N，N，N'，N'-四甲基乙二胺（tmen）的反应生成单核络合物[Zn（OAc）（2）（tmen）]（1 ）和[Zn（crot）2（tmen）]。对于R = CH3和（CH）2CH3，分别为（0.5）H2O（2）和双核络合物[Zn（2）（mu-piv）（2）（ piv）（2）（mu-H2O）（tmen）2]（3）和[Zn2（mu-OAc（F））2（OAc（F））2（mu-H2O）（tmen）2]（4）对于R分别为C（CH 3）3和CF 3。与类似的咪唑系列相反，即[M2（mu-O2CR）2（O2CR）2（mu-H2O）（Im）4]（M = Ni，Co，Mn; R = CH3，C（CH3）3 ，

  DOI：

  10.1021/ic050849m
• 作为产物：
  描述：

  戊二酸二乙酯 在 羟胺 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 生成 glutarodihydroxamic acid
  参考文献：
  名称：

  Hydroxamic Acids As a Novel Family of Serine Racemase Inhibitors: Mechanistic Analysis Reveals Different Modes of Interaction with the Pyridoxal-5′-phosphate Cofactor

  摘要：

  Mammalian serine racemase (SR) is a pyridoxal-5-phosphate (PLP) dependent enzyme responsible for the biosynthesis of the neurotransmitter D-Scrine, which activates N-methyl-D-aspartate (NMDA) receptors in the CNS. Aberrant regulation of NMDA receptor signaling has been implicated in a variety of neuropathologies, and inhibitors of SR would therefore be a worthwhile too] for further investigation or treatment of such conditions. Here, we identify a series of small aliphatic hydroxamic acids (HAS) that act as potent SR inhibitors. However, specificity studies showed that some of these HAS can act as nonspecific inhibitors of PLP-dependent enzymes. We employed NMR, MS, and UV/vis spectroscopic techniques to reveal that the nonspecific effect is likely due to irreversible interaction of the HA moiety with PLP to form aldoxime species. We also characterize L-aspartic acid beta-hydroxamate as a competitive and selective SR inhibitor that could be used as a scaffold for further inhibitor development.

  DOI：

  10.1021/jm900775q

文献信息

• Novel elimination of hydroxylamine and formation of a nickel tetramer on reactions of glutarodihydroxamic acid with model dinickel hydrolases‡
  作者：David A. Brown、Laurence P. Cuffe、Noel J. Fitzpatrick、William K. Glass、Kara Herlihy、Hassan Nimir、Oliver Deeg、William Errington、Terence J. Kemp

  DOI：10.1039/a806911e

  日期：——

  Reactions of glutarodihydroxamic acid with the hydrolase enzyme urease models, [Ni2(µ-H2O)(OAc)4(tmen)2] and [Ni2(OAc)3(urea)(tmen)2][OTf], lead to novel hydroxylamine elimination and formation of [Ni2(OAc)2µ-O(N)(OC)2(CH2)3}(tmen)2][OTf] and the tetramer [Ni4(OAc)2(gluA2)2(tmen)4][OTf]2, respectively, both of which are structurally characterised by X-ray crystallography.

  戊二羟肟酸与水解酶脲酶模型 [Ni2(µ-H2O)(OAc)4(tmen)2] 和 [Ni2(OAc)3(urea)(tmen)2][OTf] 的反应，产生新型羟胺消除和形成 [Ni2(OAc)2µ-O(N)(OC)2(CH2)3}(tmen)2][OTf] 和分别是四聚体[Ni4(OAc)2(gluA2)2(tmen)4][OTf]2，两者均通过X射线晶体学进行了结构表征。
• Structure determination of dihydroxamic acids and their trimethylsilyl derivatives by NMR spectroscopy
  作者：Jan Schraml、Magdalena Kv�?alov�、Vratislav Blechta、Ludmila Soukupov�、Otto Exner、Hans-Michael Boldhaus、Frank Erdt、Claus Bliefert

  DOI：10.1002/1097-458x(200009)38:9<795::aid-mrc732>3.0.co;2-a

  日期：2000.9

  and hydroximic structures, the most reliable parameter is the 15N chemical shift, which differs in the two classes of compounds by about 120 ppm. To differentiate E and Z hydroxamic conformers 13C chemical shifts of C O groups are preferable to 15N chemical shifts but for distinguishing E and Z isomers of the hydroximic structure both 15N and 13C NMR of the C N group are useful. 17O NMR data are of

  制备同源系列的二异羟肟酸 [HONHCO(CH2)nCONHOH，n = 0、1、2、3、4 和 6] 并进行三甲基甲硅烷基化 [1(n) 和 2(n)]。1(n) 的溶液 NMR 光谱 (1H, 13C, 15N) 表明异羟肟端基假定构象异构体的 Z-Z 和 Z-E 组合。一个例外是草酰二异羟肟酸，它假定只有一种组合。13C 交叉极化魔角旋转再现了该化合物的溶液化学位移，并表明了之前通过 X 射线衍射确定的 Z-Z 组合。三甲基甲硅烷基化生成两端均具有羟基结构的化合物，两个基团都被二甲硅烷基化。Z-Z、Z-E 和 E-E 异构体组合在光谱中可见，并且可以确定它们的比例。同样，草酰二羟肟酸衍生物是一个例外：只发现了一种硅烷化产物，无法确定其几何形状。选择性去耦实验（15N1H} 和 13C1H}）是用于识别 E 和 Z 构象异构体的 15N 富集的廉价替代方法。为了区分异羟肟和异羟肟结构，最可靠的参数是
• Conformational behaviour of hydroxamic acids: ab initio and structural studies
  作者：David A. Brown、Raymond A. Coogan、Noel J. Fitzpatrick、William K. Glass、Dau E. Abukshima、Loreto Shiels、Markku Ahlgrén、Kimmo Smolander、Tuula T. Pakkanen、Tapani A. Pakkanen、Mikael Peräkylä

  DOI：10.1039/p29960002673

  日期：——

  The conformational behaviour of a series of monohydroxamic acids, p-RC(6)H(4)CONR'OH (R = Me, R' = H, Me; R = MeO, R' = H, Me; R = NO2, R' = H), and a series of dihydroxamic acids, (CH2)(n)(CONR'OH)(2) (n = 3-8, 10, R' = H and n = 7, R' = Me), in methanol, DMSO and chloroform and in the solid state has been examined using IR and NMR spectroscopy, X-Ray crystal structure determinations of p-MeC(6)H(4)CONMeOH and the monohydrate of glutarodihydroxamic acid (n = 3) together with ab initio molecular orbital calculations for several hydrated and unhydrated hydroxamic acids have been performed. Hydrogen bonding effects are shown to be important in both the solid state and solution, The cis(Z) conformation of the hydroxamate group(s) (CONHOH) is preferentially stabilized by hydrogen bonding with water molecules.
• Hydroxylamine derivatives as potential antimalarial agents. 1. Hydroxamic acids
  作者：John B. Hynes

  DOI：10.1021/jm00300a056

  日期：1970.11
• Brown, D. A.; Geraty, R. A.; Glennon, J. D., Synthetic Communications, 1985, vol. 15, # 13, p. 1159 - 1164
  作者：Brown, D. A.、Geraty, R. A.、Glennon, J. D.、Choileain, N. Ni

  DOI：——

  日期：——