Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of isophthalimide compound with antitumor activity and application thereof

A technology of isophthalimide and anti-tumor activity, applied in the field of medicine, can solve problems such as poor selectivity, toxic and side effects, and achieve a good inhibitory effect

Inactive Publication Date: 2015-10-14
SHAANXI UNIV OF TECH
View PDF8 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing anti-tumor drugs have problems such as poor selectivity, toxic side effects, and drug resistance.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of isophthalimide compound with antitumor activity and application thereof
  • A kind of isophthalimide compound with antitumor activity and application thereof
  • A kind of isophthalimide compound with antitumor activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: the synthesis of compound (1)

[0040]

[0041] Dissolve 1.88g (18.43mmol, 2.00equiv) of diisopropylamine in 10mL tetrahydrofuran in a 100mL round-bottomed flask, then under nitrogen protection, add 7.4mL (2.00equiv) of n-butyllithium dropwise at -70oC, and the dropping time is about 10min, and continue stirring for 2h at -70 ～ 0oC, then add dropwise 3.0g (9.23mmol, 1.00equiv) of 1-(benzenesulfonyl)-6-(trifluoromethyl)-1H-indole dissolved in 10mL tetrahydrofuran, the dropwise addition time is about 20min, and continue stirring 1h, then added dropwise 2.19g (12.96mmol, 1.40equiv) of 5-fluoro-2-nitrobenzaldehyde dissolved in 10mL tetrahydrofuran, continued to stir for 1h, then naturally raised to room temperature and reacted overnight, then quenched by adding ammonium chloride aqueous solution, After the reaction is complete, wash with ethyl acetate 100mL×3, dry over anhydrous sodium sulfate, concentrate the organic phase under reduced pressure, and fina...

Embodiment 2

[0052] Embodiment 2: the synthesis of compound (2)

[0053] Using the same starting material as in Example 1, but using 5-chloro-2-nitrobenzaldehyde in the addition reaction of the second step, and then according to the synthetic method of Example 1, that is, synthetic route I, it can be obtained Compound (2), the specific structural formula is as follows:

[0054]

[0055] (ES,m / z):705.2[M+H] +1 , 707.2[M+H+2] +1 ; H NMR (300MHz, CDCl 3 )δ:8.31(d,J=9Hz,1H),7.97(d,J=3Hz,1H),7.84-7.90(m,2H),7.67-7.70(m,3H),7.33-7.44(m,3H ),7.19(s,1H),3.69(t,J=6.6Hz,2H),3.52-3.66(m,12H),3.46(t,J=6,6Hz,2H),2.71-2.76(m,3H ), 2.51(t, J=6Hz, 2H), 1.87-1.91(m, 2H), see figure 2 .

Embodiment 3

[0056] Embodiment 3: the synthesis of compound (3)

[0057] Using the same starting material as in Example 1, but using 5-(propylamino)-2-nitrobenzaldehyde in the addition reaction of the second step, and then according to the synthetic method of Example 1, i.e. synthetic route 1, The compound (3) can be obtained, and the specific structural formula is as follows:

[0058]

[0059] (ES,m / z):770.2[M+H] +1 , 772.2[M+H+2] +1 ; H NMR (300MHz, CDCl 3 )δ:12.28(s,1H),10.23(s,1H),7.90(d,J=8.8Hz,1H),7.77(s,1H),7.55(s,1H),7.49(s,1H), 7.34(d,J=10.4Hz,3H),7.11(s,1H),6.98(s,1H),3.59 - 3.30(m,20H),2.57(t,J=7.0Hz,2H),2.42(t,J=5.6Hz,2H),1.72(s,2H),1.57(m,4H),088(t,J =7.0Hz,6H), see image 3 .

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the technical field of medicines, and specifically relates to isophthalamide compounds having anti-tumor activity and an application thereof. The isophthalamide compounds include compounds as shown in a general formula (I) as shown in specification, isomers of the compounds of the general formula (I) or the salts of the compounds of the general formula (I), wherein R1, R2, R3 and R4 can be the same or different, and are selected from hydrogen, cyano group, hydroxyl, halogenated alkyl, alkoxy, alkoxyalkyl, alkylamido, alkylamidoalkyl or R5; X represents S, O, NH or N-alkyl; the R5 is substituted carbonyl. The pharmacological activity screening results of the compounds indicate that the compounds have a good inhibition effect on MCF-7 (human breast cancer cells) and HeLa (human cervical cancer cells) and also have a favorable development and application prospect in the aspect of anti-tumor.

Description

technical field [0001] The invention belongs to the technical field of medicine, in particular to an isophthalimide compound with antitumor activity and its application. Background technique [0002] Tumor is a major chronic disease that plagues the health of modern people. It has high morbidity, high mortality, high recurrence rate, and difficult treatment. About 7 million people die of cancer in the world every year, accounting for about a quarter of the total number of deaths. Among them, breast cancer and ovarian cancer are the main malignant tumors that endanger women's health. About 1.2 million women in the world develop breast cancer every year. At present, the mortality rate of cancer patients in our country exceeds 30%, which has become the second largest factor of death in our country. Drug therapy has become an effective and widely used treatment method for malignant tumors. In 2010, the global sales of antineoplastic drugs were about 60 billion US dollars. Th...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/14A61K31/404A61K31/5377A61K31/454A61P35/00A61P35/02
CPCC07D209/12
Inventor 卢久富
Owner SHAANXI UNIV OF TECH