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Compounds and preparation method thereof, application of compounds in preparing antineoplastic drugs and antineoplastic drugs prepared from compounds

A technology of anti-tumor drugs and compounds, applied in the direction of anti-tumor drugs, steroids, drug combinations, etc., can solve the problems of low biological activity and selectivity, high toxicity, etc., and achieve high biological activity and selectivity, low toxicity, and stability good sex effect

Inactive Publication Date: 2015-04-22
JIANGSU NAIQUE BIOLOGICAL ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the existing products still have disadvantages such as low biological activity and selectivity, and high toxicity.

Method used

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  • Compounds and preparation method thereof, application of compounds in preparing antineoplastic drugs and antineoplastic drugs prepared from compounds
  • Compounds and preparation method thereof, application of compounds in preparing antineoplastic drugs and antineoplastic drugs prepared from compounds
  • Compounds and preparation method thereof, application of compounds in preparing antineoplastic drugs and antineoplastic drugs prepared from compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] 4-(5-(1,3-Benzodioxane)-((3aR,4aS,8S,10aS,11S,12S,12aS)-(8,11,12-trihydroxy)-(10a,12a- Dimethyl)-(1,2-cyclopentyl)-1,10a-b-epoxy tetradecyl)-(4,5-dihydropyrazole))benzenesulfonamide (compound 46) preparation of

[0054]

[0055] Under stirring at -20°C, add the corresponding intermediate 34 (10.0 mmol) and dichloromethane (25 mL) obtained in step 5 to a 50 mL round-bottomed flask in sequence, and gradually add boron tribromide (5 mmol) dropwise to continue the reaction with stirring After 1 h, the reaction flask was transferred to room temperature, and the reaction was continued for 12 h. TLC tracking reaction (developing agent V AcOEt :V 正己烷 =1:2), after the reaction was completed, filtered, the solid was washed with distilled water, and finally dried in vacuo, and the obtained solid was dissolved in absolute ethanol for recrystallization and purification to obtain the crystalline target compound.

[0056] White crystals were obtained with a yield of 54.3%. m.p...

Embodiment 2

[0058] 4-(5-(4-methyl-1,3-benzodioxane)-((3aR,4aS,8S,10aS,11S,12S,12aS)-(8,11,12-trihydroxy)- (10a,12a-Dimethyl)-(1,2-cyclopentyl)-1,10a-b-epoxytetradecyl)-(4,5-dihydropyrazole))benzenesulfonate Preparation of Amide (Compound 47)

[0059]

[0060] The preparation method refers to Example 1. White crystals were obtained with a yield of 46.2%. m.p.219~220℃; 1 H NMR (DMSO-d 6 ,300MHz)δ:8.00(d,J=7.5Hz,2H,ArH),7.76(d,J=7.5Hz,2H,ArH),6.89(s,2H,NH 2 ), 5.91(d, J=4.7Hz, 1H, ArH), 5.82~5.67(m, 2H, ArH), 5.50(s, 1H, CH 2 ),5.40(dd,J 1 =11.3Hz,J 2 =11.1Hz,1H,CH 2 ), 5.39(s, 2H, OH), 4.48(s, 1H, OH), 4.15(d, J=10.1Hz, 1H, CH), 3.54~3.29(m, 5H, CH and CH 2 ),2.24~2.15(m,2H,CH 2 ), 2.01(t, J=4.5Hz, 1H, CH), 1.80~1.10(m, 18H, CH and CH 2 ),0.88(s,3H,CH 3 ),0.84(s,3H,CH 3 ).ESI-MS:682.9[M+H] + .Anal.Calcd for C 36 h 47 N 3 o 8 S: C, H, N.

Embodiment 3

[0062] 4-(5-(4,7-Dimethyl-1,3-benzodioxane)-((3aR,4aS,8S,10aS,11S,12S,12aS)-(8,11,12-tri Hydroxy)-(10a,12a-dimethyl)-(1,2-cyclopentyl)-1,10a-b-epoxytetradecyl)-(4,5-dihydropyrazole) ) Preparation of benzenesulfonamide (compound 48)

[0063]

[0064] The preparation method refers to Example 1. White crystals were obtained with a yield of 48.2%. m.p.199~200℃; 1 H NMR (DMSO-d 6 ,300MHz)δ:8.04(d,J=7.2Hz,2H,ArH),7.75(d,J=7.1Hz,2H,ArH),6.88(s,2H,NH 2 ), 5.92(d, J=4.7Hz, 1H, ArH), 5.80~5.67(m, 2H, ArH), 5.50(s, 1H, CH 2 ),5.40(dd,J 1 =11.2Hz,J 2 =11.4Hz,1H,CH 2 ), 5.37(s, 2H, OH), 4.49(s, 1H, OH), 4.12(d, J=9.5Hz, 1H, CH), 3.53~3.29(m, 5H, CH and CH 2 ),2.28~2.16(m,2H,CH 2 ), 2.01(t, J=4.2Hz, 1H, CH), 1.81~1.05(m, 20H, CH and CH 2 ),0.89(s,3H,CH 3 ),0.85(s,3H,CH 3 ).ESI-MS:696.9[M+H] + .Anal.Calcd for C 37 h 49 N 3 o 8 S: C, H, N.

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Abstract

The invention discloses compounds disclosed as Formula VIII and a preparation method thereof, application of the compounds in preparing antineoplastic drugs and antineoplastic drugs prepared from compounds. In the Formula VIII, R1 is selected from H, CH3 and CF3, R2 is selected from H, CH3 and Br, and n is 1 or 2. Compared with the prior art, the compounds have the advantages of high bioactivity, high selectivity and lower toxicity, and have obvious inhibiting actions on human mammary cancer cells, cervical carcinoma cells, lung cancer cells and liver cancer cells.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a compound, its preparation method, its application in the preparation of anti-tumor drugs and the prepared anti-tumor drugs. Background technique [0002] C 21 Steroidal saponin is a steroidal saponin component obtained by extraction, separation and purification from the traditional Chinese medicine Tongguanteng. Its aglycone is a unique steroidal saponin structure composed of 21 C atoms, so it is called C 21 steroidal saponins. have C 21 Steroidal saponin core compounds have pharmacological activities such as immunoregulation and anti-asthma, and have been widely used clinically as the index active ingredients of drugs. [0003] The applicant has found through repeated research: C 21 Steroidal saponins may have good antitumor activity. Currently for such C 21 The research content of steroidal saponins mainly includes: separation, purification, analysis and det...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14A61P35/00
CPCC07J71/001
Inventor 朱海亮严晓强俞海荣钟飞杨永安
Owner JIANGSU NAIQUE BIOLOGICAL ENG