N-salicylidene-4-aminobutyric acid | 63399-98-4

• 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: N-salicylidene-4-aminobutyric acid
• 英文别名: DL-N-salicylidene-γ-amino-butyric acid；H2SGABA；4-{[(6-Oxocyclohexa-2,4-dien-1-ylidene)methyl]amino}butanoic acid；4-[(2-hydroxyphenyl)methylideneamino]butanoic acid
• CAS: 63399-98-4
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: ZNJRNOWSYOVYEB-UHFFFAOYSA-N

物化性质

• 沸点：
  406.5±30.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-salicylidene-4-aminobutyric acid 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 4-<<<2-hydroxyphenyl>methyl>amino>butanoic acid
  参考文献：
  名称：

  Transition-state analogues as inhibitors for GABA-aminotransferase

  摘要：

  Our previous calculations on the reaction catalysed by GABA-aminotransferase (GABA-T) have been utilized in this work in order to synthesize a series of reversible inhibitors of this enzyme. The synthesized transition-state analogues and their precursors inhibited GABA-T competitively in both the holoenzyme and apoenzyme at 10(-3) and 10(-5) M, respectively. In the case of the holoenzyme, the transition-state analogue series (the conformationally restricted series) gave a significant increase in inhibition values over the open (less conformationally restricted) series.

  DOI：

  10.1016/0223-5234(91)90022-f
• 作为产物：
  描述：

  水杨醛 、 4-氨基丁酸 以 乙醇 为溶剂， 生成 N-salicylidene-4-aminobutyric acid
  参考文献：
  名称：

  Ramanujam, V. V.; Sivasankar, B., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1981, vol. 20, # 7, p. 749 - 751

  摘要：

  DOI：

文献信息

• Synthesis, crystal structure and antiradical effect of copper(ii) Schiff base complexes containing five-, six- and unusual seven-membered rings
  作者：Zita Puterová、Jindra Valentová、Zuzana Bojková、Jozef Kožíšek、Ferdinand Devínsky

  DOI：10.1039/c0dt00901f

  日期：——

  The synthesis and solid-state structure of mononuclear copper(II) complexes [Cu(SAIB)(H2O)2] (1), [Cu(SBAIB)(H2O)2]·H2O (2) and [Cu(SGABA)(H2O)2] (3) are described. Schiff base ligands H2SAIB, H2SBAIB and H2SGABA chelate the copper(II) ion in an O,N,O tridentate fashion. The square-pyramidal geometry of the final complexes is completed by two water ligands. The formation of an unusual seven-membered

  单核铜（II）配合物[Cu（SAIB）（H 2 O）2 ]（1），[Cu（SBAIB）（H 2 O）2 ]·H 2 O（2）和描述了[Cu（SGABA）（H 2 O）2 ]（3）。席夫碱配体ħ 2 SAIB，H 2 SBAIB和H 2 SGABA螯合物的铜（II）离子在ø，Ñ，ö三齿方式。最终络合物的方锥几何由两个完成水配体。据报道，在一组铜（II）N-水杨基-氨基酸酸酯中形成了一个不寻常的七元环。通过抗自由基活性测定评估了化合物1-3。
• Lurie, E. Yu.; Mosina, E. M.; Efremova, A. A., Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 8, p. 520 - 523
  作者：Lurie, E. Yu.、Mosina, E. M.、Efremova, A. A.、Kaplun, A. P.、Shvets, V. I.

  DOI：——

  日期：——
• Lurie, E. Yu.; Kaplun, A. P.; Kulakov, V. N., Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 4, p. 264 - 268
  作者：Lurie, E. Yu.、Kaplun, A. P.、Kulakov, V. N.、Shvets, V. I.

  DOI：——

  日期：——
• Magnetism of novel Schiff-base copper(II) complexes derived from aminoacids
  作者：Z. Puterová-Tokárová、V. Mrázová、R. Boča

  DOI：10.1016/j.poly.2013.05.045

  日期：2013.9

  Magnetic properties of five copper(II) complexes of the formula [CuL3(H2O)(2)] or [CuL4(H2O)] were investigated. These contain a Schiff-base L derived from salicylaldehyde and aminoacids. The ligand L is represented by four bonding isomers (1 through 4) and it is either tridentate (L-3) or tetradentate (L-4). The fifth ligand contains sulfonato group instead of the carboxyl one. Structurally, two complexes are monomers (I and 4), one is a dimer (5), and two are polymers (2 and 3). Their magnetic behaviour is more complex: 1 behaves as an antiferromagnetic Heisenberg diad, 2 and 4 are ferromagnetic chains, 3 is a combined ferromagnetic/antiferromagnetic ladder (ribbon), and 5 exhibits a complex 3D-ordering with unusual temperature evolution of the effective magnetic moment. (C) 2013 Elsevier Ltd. All rights reserved.
• Functionalities of conjugated compounds of γ-aminobutyric acid with salicylaldehyde or cinnamaldehyde
  作者：Tai-Ti Liu、Yi-Wei Tseng、Tsung-Shi Yang

  DOI：10.1016/j.foodchem.2015.06.077

  日期：2016.1

  Aldehydes or ketones can react with amino compounds to form Schiff base adducts, which have been widely studied and shown to exhibit antimicrobial, antioxidant or antiviral activity. Salicylaldehyde (SA) and cinnamaldehyde (CA) are components of plant essential oils. gamma-Aminobutyric acid (GA) is an important substance in the mammalian central nervous system and responsible for many bioactivities. This study aimed to synthesize functional Schiff base adducts using GA and SA or CA; to study the antimicrobial activity, antioxidant activity and tyrosinase-inhibition activity of these adducts (SA-GA and CA-GA) and their metal complexes - SA-GA-Cu (or Zn) and CA-GA-Cu (or Zn); and to find their applications in food systems. SA-GA and CA-GA both exhibited good antibacterial effects, and so did their Cu complexes. As for antioxidant activity, SA-GA and CA-GA were superior to their metal complexes in most tests. Regarding inhibition of enzymatic browning of mushrooms, both SA-GA-Cu and CA-GA-Cu could inhibit tyrosinase activity effectively. (C) 2015 Published by Elsevier Ltd.