Application of terpenoid coumarins in the treatment of gastric cancer

Abstract

The invention relates to the application of a class of drugs with anti-gastric cancer effect. The drug is a monomer or composition of six terpenoid coumarin compounds obtained by chemical synthesis. Six monomeric compounds were obtained by various chemical reactions and separation and purification methods, and their chemical structures were identified by modern spectral techniques, and finally determined to be 4‑methyl‑8‑nitro‑Z‑hesperidolide (1) , 4‑Methyl‑5‑Hydroxy‑Z‑hesperidolide (2), 4‑methyl‑5‑O‑neroli‑Z‑hesperidolide (3), 4‑hydroxy‑5 ‑Methyl‑Z‑hesperidolide (4), 4‑hydroxy‑5‑methyl‑8‑hesperidyl‑Z‑hesperidolide (5), 4‑hydroxy‑5‑methyl‑ 6‑hesperidyl‑Z‑hesperidolide (6). Experimental studies have found that compounds 1-6 have better anti-proliferation effects on gastric cancer cells and higher selectivity.

Description

technical field

[0001] The invention belongs to the technical field of medicine, and specifically relates to the application of a series of terpene coumarin compounds in the preparation of drugs for treating gastric cancer. The series of compounds are six new terpene coumarin compounds chemically synthesized: 4-methyl-8 -Nitro-Z-hesperidolide (1), 4-methyl-5-hydroxy-Z-hesperidolide (2), 4-methyl-5-O-nerolyl-Z- Hesperidolide (3), 4-Hydroxy-5-methyl-Z-hesperidolide (4), 4-Hydroxy-5-methyl-8-hesperidyl-Z-hesperidin Esters (5), 4-Hydroxy-5-methyl-6-hesperidyl-Z-hesperidolide (6). Background technique

[0002] Terpenoid coumarins are an important class of natural products. About 140 compounds of this type have been reported so far, which are distributed in Rutaceae, Compositae and Umbelliferae plants in nature, among which Umbelliferae Ferulicum is the most widely distributed plant. Modern pharmacological research has found that terpene coumarins have various pharmacological a...

Examples

Embodiment example

[0011] 1. Invention compound 4-methyl-8-nitro-Z-hesperidolide (1), 4-methyl-5-hydroxyl-Z-hesperidolide (2), 4-methyl- 5-O-Neryl-Z-hesperidolide (3), 4-hydroxy-5-methyl-Z-hesperidolide (4), 4-hydroxy-5-methyl-8- Synthesis experiment of hesperidyl-Z-hesperidone (5), 4-hydroxy-5-methyl-6-hesperidyl-Z-hesperidolide (6).

[0012] (1) Experimental raw material: nerolidol

[0013] (2) Method Add a certain amount of nerol, catalytic amount of pyridine (Py), and anhydrous ether into a 150ml three-necked flask, and slowly add phosphorus tribromide dropwise under conditions of ice-water bath and nitrogen protection, with the temperature controlled at 0°C Anhydrous ether solution, keep 0 ℃ reaction, prepare neryl bromide; with phloroglucinol and ethyl acetoacetate, in POCl 3 Under catalysis, the intermediate 4-methyl-5,7-dihydroxycoumarin is generated by pechmann condensation reaction; with 3,5-dihydroxytoluene and dimethylformamide (DMF) in POCl 3 Under catalysis, the intermediate com...

technical field

[0001] The invention belongs to the technical field of medicine, and specifically relates to the application of a series of terpene coumarin compounds in the preparation of drugs for treating gastric cancer. The series of compounds are six new terpene coumarin compounds chemically synthesized: 4-methyl-8 -Nitro-Z-hesperidolide (1), 4-methyl-5-hydroxy-Z-hesperidolide (2), 4-methyl-5-O-nerolyl-Z- Hesperidolide (3), 4-Hydroxy-5-methyl-Z-hesperidolide (4), 4-Hydroxy-5-methyl-8-hesperidyl-Z-hesperidin Esters (5), 4-Hydroxy-5-methyl-6-hesperidyl-Z-hesperidolide (6). Background technique

[0002] Terpenoid coumarins are an important class of natural products. About 140 compounds of this type have been reported so far, which are distributed in Rutaceae, Compositae and Umbelliferae plants in nature, among which Umbelliferae Ferulicum is the most widely distributed plant. Modern pharmacological research has found that terpene coumarins have various pharmacological a...

Examples

Embodiment example

[0011] 1. Invention compound 4-methyl-8-nitro-Z-hesperidolide (1), 4-methyl-5-hydroxyl-Z-hesperidolide (2), 4-methyl- 5-O-Neryl-Z-hesperidolide (3), 4-hydroxy-5-methyl-Z-hesperidolide (4), 4-hydroxy-5-methyl-8- Synthesis experiment of hesperidyl-Z-hesperidone (5), 4-hydroxy-5-methyl-6-hesperidyl-Z-hesperidolide (6).

[0012] (1) Experimental raw material: nerolidol

[0013] (2) Method Add a certain amount of nerol, catalytic amount of pyridine (Py), and anhydrous ether into a 150ml three-necked flask, and slowly add phosphorus tribromide dropwise under conditions of ice-water bath and nitrogen protection, with the temperature controlled at 0°C Anhydrous ether solution, keep 0 ℃ reaction, prepare neryl bromide; with phloroglucinol and ethyl acetoacetate, in POCl 3 Under catalysis, the intermediate 4-methyl-5,7-dihydroxycoumarin is generated by pechmann condensation reaction; with 3,5-dihydroxytoluene and dimethylformamide (DMF) in POCl 3 Under catalysis, the intermediate com...

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