N-alkyl-1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H-2,4 alpha-methanonaphthalene-7-amine compound as well as synthetic method and application thereof

A technology of endomethylene naphthalene and amine compounds, which is applied in the field of organic compounds, can solve the problems of difficulty in widespread use, few sources of compounds, and low activity, and achieve good effects of inhibiting cancer cell proliferation and activity

Inactive Publication Date: 2014-07-30
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The search for new active leads from plants or the development of new drugs through analogy synthesis or biological rational design has become a hotspot in the research of pesticide and medicinal chemistry and toxicology. However, compounds with antibacterial and antitumor physiological activities are isolated from plant resources. There are many disadvantages such as few sources or low activity, high price and difficult to widely popularize and use.

Method used

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  • N-alkyl-1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H-2,4 alpha-methanonaphthalene-7-amine compound as well as synthetic method and application thereof
  • N-alkyl-1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H-2,4 alpha-methanonaphthalene-7-amine compound as well as synthetic method and application thereof
  • N-alkyl-1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H-2,4 alpha-methanonaphthalene-7-amine compound as well as synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 N-hydrocarbyl-1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H-2,4α-endomethylenenaphthalene-7-amine compounds preparation of

[0043] The precursor of N-hydrocarbyl-1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H-2,4α-methanonaphthalene-7-amines The number of carbon atoms in the skeleton is shown in the following formula.

[0044]

[0045] 1) N-methyl-1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H-2,4α-endomethylenenaphthalene-7-amine ( 1) Synthesis of

[0046] With 5.45g isolongifolenone, 15.5g30% (mass percent) methylamine-ethanol solution, 0.3g (accounting for 8% of the isolongifolenone molar number) BF 3 (C 2 h 5 ) 2 Add O and 30mL ethanol to a 100mL three-neck flask equipped with a stirrer, control the temperature at 30°C, and react for 24h under nitrogen protection. GC detects that the imine is about 85.0%, and add 2.72g NaBH in batches at 0°C 4 , react overnight at room temperature after the addition. After adding distilled water to destroy, add ethy...

Embodiment 2

[0075] Embodiment 2 antibacterial test

[0076] 1) The strains to be tested

[0077] Candida albicans (C.albicans), Aspergillus niger (A.niger), Candida tropicalis (G.tropicalis), Escherichia coli (E.coli), Staphylococcus aureus (S.aureus), Pseudomonas fluorescens (P.Fluorescens), Bacillus subtilis (B.subtilis), both provided by Microbiology Laboratory, School of Chemical Engineering, Nanjing Forestry University.

[0078] 2) Preparation of medium

[0079] Beef extract-peptone medium for bacterial culture is prepared as follows: Weigh 5g of beef extract, 10g of peptone, 1g of glucose, 18g of agar, and 1000mL of water, heat and melt, adjust the pH to 7.0-7.2 with 10% sodium hydroxide solution, and pack in Add a cotton plug to the Erlenmeyer flask, autoclave with damp heat (121°C, 20min), and set aside.

[0080] The potato dextrose agar medium (PDA medium) used for fungal culture was prepared as follows: 20 g of potatoes, 20 g of glucose, 18 g of agar, and 1000 mL of water. C...

Embodiment 3

[0090] Embodiment 3 antitumor test

[0091] 1. Cell scratch test

[0092] Tumor is a kind of disease characterized by uncontrolled cell growth and proliferation. Abnormal cell proliferation, differentiation and apoptosis are all involved in the occurrence and development of tumors. As the simplest detection method, cell scratch is used for cell migration research.

[0093] The inhibitory activity of compounds (1)-(10) on human breast cancer cell MCF-7 was evaluated by cell scratch test. The MCF-7 cells were provided by the Institute of Chinese Materia Medica, Chinese Academy of Chinese Medical Sciences. The specific method is as follows: draw a horizontal line at intervals of about 0.5 to 1 cm on the back of the 6-well plate to ensure that at least 5 lines pass through each well; add about 5×10 5 MCF-7 cells; after overnight, use a pipette tip to draw a horizontal line of "one" on the monolayer cells, wash the cells three times with PBS, remove the marked cells, add serum-f...

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Abstract

The invention discloses an N-alkyl-1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H-2,4 alpha-methanonaphthalene-7-amine compound as well as a synthetic method and an application thereof. Longifolene serving as a heavy oil main component is relatively rich terpenoid in numerous natural extracts. The synthetic method comprises the following steps: obtaining isolongifolene through longifolene isomerization, obtaining isolongifolenone through allylic oxidation of the isolongifolene, carrying out dehydration condensation on the isolongifolenone and primary amine so as to obtain imine and obtaining the chiral N-alkyl-1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H-2,4 alpha-methanonaphthalene-7-amine compound after reduction. The compound has vey good inhibition activity on candida albicans, aspergillus niger, candida tropicalis, escherichia coli, staphylococcus aureus, pseudomonas fluorescens, bacillus subtilis and the like, a part of compound has good cancer cell proliferation inhibition activity on human breast cancer cells MCF-7, human lung adenocarcinoma cells A549, hepatoma cells HepG2 and SMMC-7721, and the N-alkyl-1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H-2,4 alpha-methanonaphthalene-7-amine compound is a potential antibacterial and bactericidal and anti-tumor compound.

Description

technical field [0001] The invention belongs to the technical field of organic compounds, in particular to an N-hydrocarbyl-1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H-2,4α-bridge Methylene naphthalene-7-amine compounds and their synthesis methods and applications. Background technique [0002] A wide variety of nitrogen-containing compounds has received extensive attention in the research field of natural product chemistry. They widely exist in many organisms in nature, and most of them have special physiological, pharmacological and other biological activities. It includes not only common amines, alkaloids, antibiotics, vitamins, indoles, amides, guanidines and other compounds, but also amino acids and peptides that have an important impact on human metabolism. [0003] Scientific researchers have not only extracted some antibacterial and anticancer natural nitrogen-containing compounds from natural products, but also obtained a large number of nitrogen-containing drugs...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/41C07C211/45C07C209/00A61P35/00A61P31/04A61P31/10
CPCY02A50/30
Inventor 王石发彭晗杨益琴徐徐谷文吴君鲍名凯邢蓥滢
Owner NANJING FORESTRY UNIV
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