(S)-1-{[(1-hydroxy-3-phenylpropan-2-yl)imino]methyl}naphthalen-2-ol | 1448002-82-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-{[(1-hydroxy-3-phenylpropan-2-yl)imino]methyl}naphthalen-2-ol
• 英文别名: (S)-[(1-hydroxymethyl-2-phenylethylimino)methyl]naphthalen-2-ol；2-((1-hydroxy-3-phenylpropan-2-ylimino)methyl)naphthalene-1-ol；(s)-1-{[(1-Hydroxy-3-phenylpropan-2-yl)imino]-methyl}naphthalen-2-ol；1-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]iminomethyl]naphthalen-2-ol
• CAS: 1448002-82-1
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: UQEOWLVGVJEKDP-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-{[(1-hydroxy-3-phenylpropan-2-yl)imino]methyl}naphthalen-2-ol 、 manganese (II) acetate tetrahydrate 以 甲醇 为溶剂， 反应 5.0h， 以57.7%的产率得到
  参考文献：
  名称：

  Chiral manganese (IV) complexes derived from Schiff base ligands: Synthesis, characterization, in vitro cytotoxicity and DNA/BSA interaction

  摘要：

  Two new couples of chiral manganese (IV) complexes with Schiff-base ligands, Lambda-[Mn(R-L-1)(2)]center dot 2(CH3OH) (Lambda-1) and Delta-[Mn(S-L-1)(2)]center dot 2(CH3OH) (Delta-1), Lambda-[Mn(R-L-2)(2)]center dot(H2O)(2) (Lambda-2) and Delta-[Mn(S-L-2)(2)]center dot(H2O)(2) (Delta-2), {H2L1 = (R/S)-(+/-)-1-[(1-hydroxymethyl-propylimino)-methyl]-naphthalen-2-ol, H2L2 = (R/S)-(+/-)-1-[(1-Hydroxymethyl-2-phenyl-ethylimino)-methyl]-naphthalen-2-ol} have been synthesized, and fully characterized by elemental analyses, UV-Vis spectrum, circular dichroism spectrum, FT-IR spectrum, mass spectrum, and single crystal X-ray diffraction (SXRD). The interaction of the four chiral Mn (IV) complexes with CT-DNA and BSA were also investigated by various spectroscopic techniques (UV-visible, fluorescence spectroscopic). The results show that the Delta-complexes exhibit more efficient CT-DNA interaction with respect to the Lambda-complexes. All the complexes could quench the intrinsic fluorescence of BSA by a static quenching process. In addition, the vitro cytotoxicity of these complexes toward four kinds of cancerous cell lines (A549, HeLa, HL-60, and Caco-2) was assayed by the MIT method, which exhibited to be selectively active against certain cell lines. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotobiol.2015.11.005
• 作为产物：
  描述：

  L-苯丙氨醇 、 2-羟基-1-萘甲醛 以 乙醇 为溶剂， 以83%的产率得到(S)-1-{[(1-hydroxy-3-phenylpropan-2-yl)imino]methyl}naphthalen-2-ol
  参考文献：
  名称：

  新型手性席夫碱钯(II)、镍(II)、铜(II)和铁(II)配合物：合成、表征、抗癌活性和分子对接研究

  摘要：

  本研究以( S )-2-氨基-3-苯基-1-丙醇与2-羟基苯甲醛和2-羟基-1-萘醛为金属缩合反应合成了两种手性席夫碱配体(L1和L2)。用于制备 Pd(II)、Fe(II)、Ni(II) 和 Cu(II) 过渡金属络合物的前体。使用 X 射线（L1-Pd(II)）、NMR、FT-IR、UV-Vis、磁化率、摩尔电导率和元素分析对化合物进行了表征。采用3- ( 4,5-二甲基噻唑-2-基)-2,5-二苯基溴化四唑 (MTT) 测定。在合成的化合物中，L1-Pd(II)特别被发现是该系列中最有效的抗癌候选药物，在 DLD-1 和 MDA-MB-231 细胞系中的IC 50值分别为 4.07 和 9.97 µM。此外，分子对接结果表明，Glu122、Asn103、Ala104、Lys126、Phe114、Leu123和Lys126氨基酸是结肠癌抗原蛋白的结合位点，其中活性最强的复合物L1-Pd(II)可以抑制当前的目标。

  DOI：

  10.1016/j.bioorg.2022.106176

文献信息

• Asymmetric henry reaction catalyzed by chiral schiff base
  作者：De-qiang Ran、Tian-hua Shen、Xiao-cong Zhou、Jun-qi Li、Fu-na Cui、Chun-an Ma、Qing-bao Song

  DOI：10.1134/s1070428013060080

  日期：2013.6

  Four chiral Schiff bases were synthesized conveniently from chiral amino alcohol and 2-hydroxynaphthalene-1-carbaldehyde. These ligands were used to catalyze the addition of nitroalkanes to aldehydes under ambient conditions in good yields with up to 91% ee.