Synthesis method and application of o-vanillin isonicotinoyl hydrazone iron and nickel complex

A technology of ortho-vanillin and nicotinyl hydrazone nickel ortho, which is applied in the field of bio-inorganic chemistry and achieves the effects of being convenient for industrialized production, readily available and cheap raw materials, and simple and feasible preparation method.

Active Publication Date: 2021-02-02
NANJING FORESTRY UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

The iron and nickel complexes of o-vanillin isonicotinoyl hydrazone and their biological activities have not been reported in the literature

Method used

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  • Synthesis method and application of o-vanillin isonicotinoyl hydrazone iron and nickel complex
  • Synthesis method and application of o-vanillin isonicotinoyl hydrazone iron and nickel complex
  • Synthesis method and application of o-vanillin isonicotinoyl hydrazone iron and nickel complex

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Embodiment 1

[0020] FeLCl 2 ·H 2 The specific steps of the synthesis method of O are as follows: dissolving o-vanillin isonicotidine hydrazone (27.1 mg, 0.1 mmol) in 10 mL of MeOH, heated and stirred, and FeCl 3 ·6H 2 O (27.0 mg, 0.1 mmol) was dissolved in 3 mL of MeCN and slowly added dropwise to the ligand solution to obtain an amber solution, which was allowed to reflux for 3 h and then cooled to room temperature, and slowly volatilized for two weeks to obtain a black flaky single crystal. Its crystal structure is shown in figure 1 .

Embodiment 2

[0022] The specific steps of the synthetic method of NiLphen are: dissolving o-vanillin isonicotidine hydrazone (27.1mg, 0.1mmol) in 12mLTHF / H 2 O mixed solution, and added 30 μL Et 3 N, stirring, Ni(OAc) 2 4H 2 O (24.8mg, 0.1mmol) dissolved in 12mL THF / H 2 The O mixed solution was then added dropwise to the ligand solution, and finally 18 mg of 1,10-phenanthroline was added to obtain an orange-yellow solution, which was sonicated until clear. After filtering, let it stand for slow volatilization for a week to obtain orange flaky single crystal. Its crystal structure is shown in figure 1 .

[0023] In vitro anti-tumor activity research was carried out for the above complexes, and the Cell Counting Kit-8 method was used to measure the inhibitory rates of complexes 1 and 2 on human lung cancer cells (A549) and human cervical cancer cells (HeLa), and the IC50 (μM) was calculated. The results are shown in Table 3.

[0024] The Cell Counting Kit-8 is called for short CCK-8 k...

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Abstract

The invention discloses two kinds of transition metal complexes of o-vanillin isonicotinoyl hydrazone iron and nickel and a preparation method thereof. The molecular formula and molecular weight of both are C 14 h 13 Cl 2 N 3 o 4 Fe(414.02g / mol) and C 52 h 38 N 10 Ni 2 o 6 (1016.34 g / mol). h 2 L is the analytically pure ortho-vanillin condensed isonicotinoid hydrazide Schiff base, and the metal salt is FeCl 3 ·6H 2 O and Ni(OAc) 2 4H 2 O. The synthesis method is to use o-vanillin isonicotinoyl hydrazone and ferric chloride hexahydrate or nickel acetate tetrahydrate as raw materials, in MeOH / MeCN or THF / H 2 React in the O mixed solution for 3 hours, filter, and place in the condition of no external interference to slowly volatilize for about a week to obtain bulk crystals suitable for single crystal X-ray diffraction. The invention has the advantages of simple process, low cost, easy control of chemical components, etc., belongs to the field of bioinorganic chemistry, or has potential application value in antitumor and antioxidative activities.

Description

technical field [0001] The invention relates to o-vanillin isonicotinoyl hydrazone iron and nickel complexes, a preparation method and application thereof, and belongs to the field of bioinorganic chemistry. Background technique [0002] Cisplatin is one of the commonly used chemical drugs for cancer treatment, but its application is limited by factors such as toxic side effects (nephrotoxicity, bone marrow toxicity, ototoxicity, neurotoxicity), drug resistance, and inability to take it orally. These shortcomings have prompted people to develop metal anticancer drugs with better pharmacological activity. Metallic anticancer drugs currently developed are mainly divided into two categories: one is platinum anticancer drugs, and the other is non-platinum anticancer drugs. Non-platinum anticancer drugs mainly focus on trace metal elements that are biologically active and essential to life, such as iron, nickel, copper, etc. These metals are cheap and easy to obtain, and have g...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/02C07F15/04A61P35/00A61P39/06
CPCA61P35/00A61P39/06C07B2200/13C07F15/025C07F15/045
Inventor 李月琴黎芸王娜娜杨志伟
Owner NANJING FORESTRY UNIV
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