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Piperazine derivatives containing oxadiazole and its preparation method and use
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A technology of oxadiazole and derivatives is applied in the field of piperazine derivatives containing oxadiazole and the preparation thereof, and achieves the effects of high yield, few reaction steps and inhibition of cancer cell growth
Inactive Publication Date: 2018-10-16
SHANDONG UNIV OF TECH
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[0003] Judging from the current state of the art, oxadiazoles and their derivatives have potential anticancer activity, and these compounds have nonselective and broad-spectrum anticancer activity against all cancer cells
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Embodiment 1
[0028] 5-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-3-((4-(4-methoxyphenyl)piperazine-1 Preparation of -yl)methyl)-1,3,4-oxadiazole-2(3H)-thione.
[0029]
[0030] Above-mentioned compound preparation method is as follows:
[0031] (1) reflux reaction of 3,4-dihydroxybenzoic acid, concentrated sulfuric acid, and methanol, and TLC detection until the disappearance of raw materials to obtain a solid product;
[0032] The dosage ratio of 3,4-dihydroxybenzoic acid, concentrated sulfuric acid and methanol is 1:0.1:5, wherein, 3,4-dihydroxybenzoic acid is measured in mmol, and concentrated sulfuric acid and methanol are measured in mL.
[0033] (2) the solid product obtained in step (1), acetone, dibromoethane, and potassium carbonate are refluxed to obtain a solid product;
[0034] The solid product that step (1) obtains, acetone, dibromoethane, the consumption ratio of salt of wormwood is 1:20:1:1.5, wherein, the solid product that step (1) obtains, dibromoethane, salt of wormwood...
Embodiment 2
[0043] 5-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-3-((4-(4-nitrophenyl)piperazine-1- Preparation of base)methyl)-1,3,4-oxadiazole-2(3H)-thione.
[0044]
[0045] The preparation method is the same as in Example 1. Substitute p-nitrophenylpiperazine for p-methoxyphenylpiperazine to obtain the target compound.
[0046] Yellow powder, the yield is 85%, Mp: 202.6-202.7 ° C. 1H NMR (400MHz, CDCl 3 ):3.035-3.061(m,4H),3.487-3.513(m,4H),4.352-4.380(m,4H),5.165(s,2H),6.832-6.856(d,J=9.6Hz,2H), 6.988-7.008 (d, J=8.0Hz, 1H), 7.454-7.480 (m, 2H), 8.139-8.162 (d, J=9.2Hz, 2H).
Embodiment 3
[0048] 5-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-3-((4-(2-methoxyphenyl)piperazine-1 Preparation of -yl)methyl)-1,3,4-oxadiazole-2(3H)-thione.
[0049]
[0050] The preparation method is the same as in Example 1. Substituting o-methoxyphenylpiperazine for p-methoxyphenylpiperazine to obtain the target compound.
[0051]White powder, the yield is 80%, Mp:181.0-181.7℃.1H NMR (400MHz, CDCl 3 ):3.120(s,8H),3.877(s,3H),4.348-4.388(m,4H),5.181(s,2H),6.879-6.899(d,J=8.0Hz,1H),6.942-7.071( m, 4H), 7.468-7.494 (m, 2H).
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Abstract
The invention belongs to the technical field of organic synthesis, and specifically relates to a piperazine derivative containing oxadiazole, a preparation method and application thereof. The piperazine derivatives containing oxadiazole according to the present invention have the following structural formula: wherein, R is o-chlorophenyl, benzyl, o-methoxyphenyl, p-methoxyphenyl, p-fluorophenyl, Pyridyl, o-fluorophenyl, p-nitrophenyl, p-chlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, m-methoxyphenyl, diphenylmethyl or A kind of m-trifluoromethylphenyl. The invention introduces the oxadiazole with good anticancer activity into the phenylpiperazine ring to prepare the piperazine derivative containing the oxadiazole. The piperazine derivatives containing oxadiazole have obvious inhibitory effect on the growth of cancer cells, and the raw materials used are cheap, easy to obtain, few reaction steps, high yield, suitable for industrial production, and used for preparing anticancer drugs.
Description
technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a piperazine derivative containing oxadiazole, a preparation method and application thereof. Background technique [0002] In recent years, the application of piperazine compounds in organic synthesis and medicine has attracted widespread attention in the fields of organic chemistry and pharmacy. The piperazine ring is a six-membered heterocyclic ring containing two nitrogen atoms in the molecule. It is an ideal structural unit of nitrogen-rich heterocyclic compounds, and has the characteristics of high formation enthalpy and good thermal stability. Most of the compounds containing phenylpiperazine ring have high pharmacological activity, and some have been developed into clinical drugs. [0003] Judging from the current prior art, oxadiazoles and their derivatives have potential anticancer activities, and these compounds have nonselective and broad-spectrum...
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