potassium (2S)-2-(2-hydroxybenzylideneamino)-3-phenylpropanoate

• 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: potassium (2S)-2-(2-hydroxybenzylideneamino)-3-phenylpropanoate
• 英文别名: potassium 2-(2-hydroxybenzylideneamino)-3-phenylpropanoate；potassium 2-([(E)-(2-hydroxyphenyl)methylidene]amino)phenylpropionate
• 化学式: C₁₆H₁₄NO₃*K
• 分子量: 307.39
• InChiKey: CCZZTXFAVSKDMA-VNKRLIBXSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.82
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.72
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  potassium (2S)-2-(2-hydroxybenzylideneamino)-3-phenylpropanoate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以87.04%的产率得到potassium 2-(2-hydroxybenzylamino)-3-phenylpropanoate
  参考文献：
  名称：

  还原氨基酸席夫碱的水溶性铂（II）配合物：合成，表征和抗肿瘤活性。

  摘要：

  摘要 合成了一系列具有还原性氨基酸席夫碱的水溶性铂（II）配合物作为潜在的抗癌剂，并通过1 H NMR，EA，MS，IR和摩尔电导率进行了表征。测试了这些化合物与鲑鱼精子DNA的DNA相互作用，并通过MTT分析验证了其对HL-60，KB，BGC-823和Bel-7402细胞系的体外抗癌活性。一种复合物（ 5g ）对BGC-823和HL-60细胞的杀伤作用优于顺铂，对Bel-7402细胞具有很强的杀伤作用。 图形概要

  DOI：

  10.1007/s11164-012-0593-y
• 作为产物：
  描述：

  L-苯丙氨酸 、 水杨醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以80.3%的产率得到potassium (2S)-2-(2-hydroxybenzylideneamino)-3-phenylpropanoate
  参考文献：
  名称：

  还原氨基酸席夫碱的水溶性铂（II）配合物：合成，表征和抗肿瘤活性。

  摘要：

  摘要 合成了一系列具有还原性氨基酸席夫碱的水溶性铂（II）配合物作为潜在的抗癌剂，并通过1 H NMR，EA，MS，IR和摩尔电导率进行了表征。测试了这些化合物与鲑鱼精子DNA的DNA相互作用，并通过MTT分析验证了其对HL-60，KB，BGC-823和Bel-7402细胞系的体外抗癌活性。一种复合物（ 5g ）对BGC-823和HL-60细胞的杀伤作用优于顺铂，对Bel-7402细胞具有很强的杀伤作用。 图形概要

  DOI：

  10.1007/s11164-012-0593-y

文献信息

• Water-Soluble Monochloroplatinum(II) Complexes with Amino Acid Derived Schiff Bases as Ligands: Synthesis, Characterisation and Antitumour Activity
  作者：Li-Jun Li、Chao Tian、Zheng Wang、Guang-Yuan Wang、Lian-Zeng Wang、Jian-Long Du

  DOI：10.3184/174751912x13270814162774

  日期：2012.2

  A series of water-soluble monochloroplatinum(II) complexes K[PtCl(L)] (L = amino acid derived schiff base) have been synthesised as potential anticancer agents and characterised by ¹H NMR, elemental analysis, IR spectroscopy and molar conductivity measurements. These compounds were tested for their DNA interaction ability with salmon sperm DNA and their in vitro anticancer activities have been validated against Hela and A549 cell lines by the CCK-8 assay. Whilst some complexes had better cytotoxic activities against the Hela cell line compared with cisplatin, all the complexes had little cytotoxicity against the A549 cell line compared with cisplatin.

  我们合成了一系列水溶性单氯铂（II）配合物 K[PtCl(L)]（L = 氨基酸衍生的希夫碱），作为潜在的抗癌剂，并通过 1H NMR、元素分析、红外光谱和摩尔电导率测量对其进行了表征。测试了这些化合物与鲑鱼精子 DNA 的 DNA 相互作用能力，并通过 CCK-8 试验验证了它们对 Hela 和 A549 细胞系的体外抗癌活性。与顺铂相比，一些复合物对 Hela 细胞系的细胞毒性更强，但与顺铂相比，所有复合物对 A549 细胞系的细胞毒性都很小。
• Synthesis, structure and cytotoxic activity of diethyltin<i>N</i>-[(2-oxyphenyl)methylene]phenylalaninates
  作者：Qingtao Liu、Hao Zhang、Xiaoliang Zheng、Wenqiang Wang、Laijin Tian

  DOI：10.1002/aoc.3480

  日期：2016.8

  trimeric [Sn3O6C3] core. Each tin atom is six‐coordinated in distorted [SnC2NO3] octahedral geometry. Compound 3 is a centrosymmetric weak dimer in which the two tin centers are linked by two asymmetric SnO⋅⋅⋅Sn bridges involving the phenolic oxygen of the ligand and two Sn⋅⋅⋅O interactions from ether oxygen of the adjacent ligand. The coordination geometry of the tin atom can be described as a distorted

  四个新diethyltin ñ - [（2-氧苯基）亚甲基] phenylalaninates，（CH 3 CH 2）2 Sn的[2-O-3-X-5-YC 6 ħ 2 CHNCH（CH 2 PH）COO]（X ，Y = H，H，1 ;是H，Br，2 ; H，OCH 3，3 ; BR，BR，4），已经合成和表征使用元素分析和红外和NMR（1个H，13 C和119 Sn的）光谱。的晶体结构1，2，3，4已被确定。化合物1和2具有带三聚[Sn 3 O 6 C 3 ]核的12元大环结构。每个锡原子在扭曲的[SnC 2 NO 3 ]八面体几何形状中六配位。化合物3是中心对称的弱二聚体，其中两个锡中心由两个不对称的Sn连接涉及配体，并从相邻的配体的醚氧2个Sn⋅⋅⋅O相互作用的酚氧O⋅⋅⋅Sn桥。锡原子的配位几何结构可以描述为在轴向位置带有两个乙基的扭曲的五边形双锥体。化合物4是一种新型的双核锡配
• Electronic and magnetic properties of iron (III) dinuclear complexes with carboxylate bridges
  作者：Verónica Paredes-Garcı́a、Ramón O. Latorre、Evgenia Spodine

  DOI：10.1016/j.poly.2004.03.024

  日期：2004.7

  series of dinuclear iron (III) complexes with carboxylate bridges, of the type [Fe2L2(H20)4](NO3)2(H2O)m (m=1–3), where L=Schiff base derived from L-α-amino acids and salicylaldehyde have been prepared and characterised by different spectroscopic techniques, magnetic susceptibility, conductivity, and electrochemical measurements. The dimeric iron complexes contain hexacoordinated iron (III), with the metal

  摘要[Fe2L2（H20）4]（NO3）2（H2O）m（m = 1–3）类型的一系列具有羧酸盐桥的双核铁（III）配合物，其中L =源自L-α的席夫碱已经制备了氨基酸和水杨醛，并通过不同的光谱技术，磁化率，电导率和电化学测量对其进行了表征。二聚铁配合物含有六配位的铁（III），金属离子被水分子，水杨亚胺配体和桥连的羧酸盐基团包围。铁原子的不等价通过Mossbauer光谱检测到，这反映为存在两个重叠的四极双峰（δ1-0.52-0.67mm s-1，δ2-0.64-0.80mm s-1，ΔEQ1-0.38-0.80mm s-1和ΔEQ2（〜0.68–1.01 mm s-1），所有复合物的强度比约为1：1。在5–300 K的温度区间内测定了配合物的磁化率，并显示出随着温度降低，有效磁矩降低了。摩尔磁化率与温度的倒数关系图表明，两个铁（III）离子反铁磁耦合非常弱（-J〜0.09-0.21 cm-
• Self-assembly of extended Schiff base amino acetate skeletons, 2-{[(2Z)-(3-hydroxy-1-methyl-2-butenylidene)]amino}phenylpropionate and 2-{[(E)-1-(2-hydroxyaryl)alkylidene]amino}phenylpropionate skeletons incorporating organotin(IV) moieties: Synthesis, spectroscopic characterization, crystal structures, and in vitro cytotoxic activity
  作者：Tushar S. Basu Baul、Cheerfulman Masharing、Giuseppe Ruisi、Robert Jirásko、Michal Holčapek、Dick de Vos、David Wolstenholme、Anthony Linden

  DOI：10.1016/j.jorganchem.2007.06.061

  日期：2007.10

  The organotin(IV) compounds, [(Ph3SnLH)-H-1](n) center dot nCCl(4) (1), [Me2SnL2(OH2)] (2), [(Bu2SnL2)-Bu-n] (3), [Ph2SnL2](n) (4), [(Ph3SnLH)-H-2](n) (5) and [(Ph3SnLH)-H-3](n) (7) (L-1=2-[(2Z)-(3-hydroxy-1-methyl-2-butenylidene)]amino}phenylpropionate and L2-3 = 2-[(E)-1-(2-hydroxyaryl)alkylidene]amino}phenylpropionate), were synthesized by treating the appropriate organotin(IV) chloride(s) with the potassium salt of the ligand in a suitable solvent, while [(Bu2SnL3)-Bu-n(OH2)] (6) was obtained by reacting the acid form of L-3 (generated in situ) with (Bu2SnO)-Bu-n. These complexes have been characterized by H-1, C-13, Sn-119 NMR, ESI-MS, IR and Sn-119m Mossbauer spectroscopic techniques in combination with elemental analyses. The crystal structures of 1 and 4-7 were determined. The crystal structures of complexes 1, 5 and 7 reveal that the complexes exist as polymeric chains in which the L-bridged Sn-atoms adopt a trans-R3SnO2 trigonal bipyramidal configuration with R groups in the equatorial positions and the axial locations occupied by a carboxylate oxygen from the carboxylate ligand and the alcoholic or phenolic oxygen of the next carboxylate ligand in the chain. The carboxylate ligands coordinate in the zwitterionic form with the alcoholic/phenolic proton moved to the nearby nitrogen atom. A polymeric zig-zag cis-bridged chain structure is observed for 4, without considering the weak Sn center dot center dot center dot O interaction, the Sn-atom having a slightly distorted trigonal bipyramidal coordination geometry with the two O atoms of the tridentate amino propionate ligand in axial positions. On the other hand, the structure of 6 reveals a monomeric molecule in which the Sn-atom has a distorted octahedral coordination geometry involving the tridentate carboxylate ligand, two n-butyl ligands occupying trans-positions and one water ligand. The in vitro cytotoxic activity of triphenyltin(IV) compounds, viz., 1, 5 and 7 against WIDR, M19 MEL, A498, IGROV, H226, MCF7 and EVSA-T human tumor cell lines are also reported. (C) 2007 Elsevier B.V. All rights reserved.
• Benzaldehyde Schiff bases regulation to the metabolism, hemolysis, and virulence genes expression in vitro and their structure–microbicidal activity relationship
  作者：Lei Xia、Yu-Fen Xia、Li-Rong Huang、Xiao Xiao、Hua-Yong Lou、Tang-Jingjun Liu、Wei-Dong Pan、Heng Luo

  DOI：10.1016/j.ejmech.2015.04.042

  日期：2015.6

  There is an urgent need to develop new antibacterial agents because of multidrug resistance by bacteria and fungi. Schiff bases (aldehyde or ketone-like compounds) exhibit intense antibacterial characteristics, and are therefore, promising candidates as antibacterial agents. To investigate the mechanism of action of newly designed benzaldehyde Schiff bases, a series of high-yielding benzaldehyde Schiff bases were synthesized, and their structures were determined by NMR and MS spectra data. The structure microbicidal activity relationship of derivatives was investigated, and the antibacterial mechanisms were investigated by gene assays for the expression of functional genes in vitro using Escherichia coli, Staphylococcus aureus, and Bacillus subtilis. The active compounds were selective for certain active groups. The polar substitution of the R-2 group of the amino acids in the Schiff bases, affected the antibacterial activity against E. coli and S. aureus; specific active group at the R-3 or R-4 groups of the acylhydrazone Schiff bases could improve their inhibitory activity against these three tested organisms. The antibacterial mechanism of the active benzaldehyde Schiff bases appeared to regulate the expression of metabolism-associated genes in E. coli, hemolysis-associated genes in B. subtilis, and key virulence genes in S. aureus. Some benzaldehyde Schiff bases were bactericidal to all the three strains and appeared to regulate gene expression associated with metabolism, hemolysis, and virulence, in vitro. The newly designed benzaldehyde Schiff bases possessed unique antibacterial activity and might be potentially useful for prophylactic or therapeutic intervention of bacterial infections. (C) 2015 Published by Elsevier Masson SAS.