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Podophyllotoxin compounds containing 1,2,4-triazone structure and application thereof

A technology of podophyllotoxin and epipodophyllotoxin, which is applied to the pharmaceutical composition containing the compound and the field of application in medicine, and can solve the problems of easy drug resistance and large toxic and side effects

Active Publication Date: 2019-08-09
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, novel podophyllotoxin antineoplastic drugs such as etoposide and teniposide still have relatively large toxic and side effects and are prone to drug resistance, so people's research on podophyllotoxin has not stopped

Method used

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  • Podophyllotoxin compounds containing 1,2,4-triazone structure and application thereof
  • Podophyllotoxin compounds containing 1,2,4-triazone structure and application thereof
  • Podophyllotoxin compounds containing 1,2,4-triazone structure and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Example 1: 4β-(4-methyl-3,5-dioxo-2-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxamide )-4-deoxyepipodophyllotoxin (compound 1)

[0066]

[0067] IR(KBr,cm -1 ):3430,2923,1773,1725,1681,1587,1485,1432,1384,1327,1239,1127, 1037,1001,927,768; MS(ESI)m / z(%):643.7[M+H] + .

Embodiment 2

[0068] Example 2: 4β-(4-methyl-3,5-dioxo-2-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxamide )-4'-desmethyl-4-deoxyepipodophyllotoxin (Compound 2)

[0069]

[0070] MS(ESI) m / z(%): 629.6[M+H]+, 651.5[M+Na]+;

Embodiment 3

[0071] Example 3: 4β-[4-methyl-3,5-dioxo-2-(4-fluorophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine- 6-Carboxamido]-4-deoxyepipodophyllotoxin (compound 3)

[0072]

[0073] 1 H NMR (600MHz, DMSO-d 6)δ9.04(d, J=8.4Hz, 1H), 7.57(m, 2H), 7.37(t, J=9.0Hz, 2H), 6.84(s, 1H), 6.57(s, 1H), 6.30( s,2H),6.02(s,1H),6.00(s,1H),5.38(m,1H),4.59(d,J=5.4Hz,1H),4.38(t,J=7.8Hz,1H), 3.91(m,1H),3.66(s,6H),3.62(s,3H),3.24(s,3H),3.19(m,1H),3.06(m,1H); MS(ESI)m / z( %):661.3[M+H] + ,683.2[M+Na] + .

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Abstract

The invention discloses a podophyllotoxin compound containing a 1,2,4-triazone structure, and an application thereof. The compound has a structure represented by general formula (I). Podophyllotoxin derivatives containing 1,2,4-triazone, represented by the general formula (I), and pharmaceutically acceptable salts thereof have antitumor effects. In-vitro cell activity experiments prove that the podophyllotoxin derivatives containing 1,2,4-triazone have a good inhibition effect on a human chronic myelocytic leukemia cell K562, a human cervical carcinoma cell Hela and a human breast cancer cellMCF-7. The compounds have a good antitumor medicine exploitation and application prospect.

Description

technical field [0001] The present invention relates to novel podophyllotoxin derivatives containing 1,2,4-triazinone structure and pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, their preparation methods and compounds containing said compounds pharmaceutical composition. The present invention also relates to the use of the compounds and their pharmaceutically acceptable salts, hydrates, solvates or prodrugs in preparing medicines for treating and / or preventing cancer. Background technique [0002] Podophyllotoxin is a class of natural products with a 2,3-butylpropyl-4-aryltetrahydronaphthalene skeleton, which is mainly isolated from the roots and stems of plants of the genus Podophyllum in the family Berberaceae, and has significant antitumor activities . However, podophyllotoxin can cause more serious adverse reactions, such as damage to normal cells, and cause gastrointestinal discomfort, etc., so that its application as an anti-tumor drug ha...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04A61K31/53A61P35/00A61P35/02
CPCC07D493/04
Inventor 刘举陈烨王洋李军周子筠
Owner LIAONING UNIVERSITY
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