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。
• Enhanced enantioselectivity in heterogeneous manganese-catalyzed asymmetric epoxidation with nanosheets modified amino acid Schiff bases as ligands by modulating the orientation and the arrangement order
  作者：Zhe An、Yuanzhong Tang、Yitao Jiang、Hongbo Han、Qi Ping、Wenlong Wang、Yanru Zhu、Hongyan Song、Xin Shu、Xu Xiang、Jing He

  DOI：10.1016/j.jcat.2021.08.015

  日期：2021.10

  work proposes an efficient strategy to promote the enantioselectivity of Mn(III)-catalyzed indene epoxidation, which simply utilizes the nanosheets of layered double hydroxides (LDHs) to modify α-amino acid derivatives as chiral ligands, achieving an enantioselectivity of more than 91.0%, much higher than that (<35%) in the previous reports using chiral ligands without any rotational-symmetry. By virtue

  烯烃的催化对映选择性环氧化在光学活性环氧树脂的生产中起着重要作用。过渡金属配合物通过使用具有旋转对称性和庞大取代基的特权手性配体证明对未官能化烯烃的催化环氧化是有效的，这通常需要复杂的多步合成并且通常非常昂贵。在这里，这项工作提出了一种有效的策略来促进 Mn(III) 催化的茚环氧化的对映选择性，它简单地利用层状双氢氧化物 (LDH) 的纳米片来修饰作为手性配体的 α-氨基酸衍生物，实现了更高的对映选择性。超过 91.0%，远高于之前使用没有任何旋转对称性的手性配体的报告中的 (<35%)。凭借 LDH 的“灵活”层间空间，叔-亮氨酸、L-缬氨酸、L-亮氨酸和L-苯丙氨酸阴离子已进一步原位衍生为L-叔-亮氨酸、L-缬氨酸、L-亮氨酸和L-苯丙氨酸席夫碱阴离子。在与 L-苯丙氨酸席夫碱阴离子嵌入的 LDH 配位的 Mn(III) 上，茚转化率为 81.0 ± 1.0%，化学选择性为 89.0
• 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.