Supercharge Your Innovation With Domain-Expert AI Agents!

Multi-sulfo gibberellic acid ester compound, as well as preparation method and anti-tumor application thereof

A technology for polythiogibberellic acid and ester compounds, which is applied in the fields of chemistry and medicine, and can solve problems such as toxic side effects and limitations

Active Publication Date: 2018-07-13
YUNNAN UNIV
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, most commonly used chemotherapeutic drugs have limited their application due to severe side effects. It is still an important and urgent task to find chemotherapeutic drugs with new targets, new structures, high activity and low toxicity.

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
  • Multi-sulfo gibberellic acid ester compound, as well as preparation method and anti-tumor application thereof
  • Multi-sulfo gibberellic acid ester compound, as well as preparation method and anti-tumor application thereof
  • Multi-sulfo gibberellic acid ester compound, as well as preparation method and anti-tumor application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Preparation and structural data of 13‐hydroxy‐3,15‐dioxo‐1,17‐dicarboxymethylthiomethyl gibberellic acid (DSG0101):

[0055]

[0056]13‐Hydroxy‐3,15‐dioxogibberellic acid methyl ester (372mg, 1.0mmol) was dissolved in chloroform (10mL), then thioglycolic acid (0.15mL, 1.33g / mL, 2.2mmol, 2.2eq. ) and diisopropylethylamine (0.050mL, 0.78g / mL, 0.3 mmol, 0.3eq.), heated at reflux at 70°C overnight. After the completion of the reaction was detected by TLC, the solvent was evaporated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (petroleum ether / ethyl acetate / acetic acid=2:3:0.005) to obtain 367 mg of white solid, yield: 66%.

[0057] 1 H‐NMR (300MHz, CD 3 OD): δ=3.79(1H,d,J=6.9Hz),3.61(3H,s),3.44(1H,d,J=9.6Hz), 3.35(2H,s),3.30(1H,q), 3.21(1H,d,J=9.6Hz), 3.00‐2.78(5H,m), 2.63(1H,t), 2.46(1H,d,J=11.4Hz), 2.12(1H,d,J=11.4Hz ),2.02‐1.95(1H,m),1.80(1H,q),1.14(3H,s);

[0058] 13 C‐NMR (75MHz, CD 3 OD): Δ = 216.62,200.00...

Embodiment 2

[0061] Preparation and structural data of 13‐hydroxy‐3,15‐dioxo‐1,17‐bis(2‐carboxyethylthio)gibberellic acid methyl ester (DSG0102):

[0062]

[0063] The preparation method is the same as in Example 1, the amount of mercaptopropionic acid is (0.19mL, 1.22g / mL, 2.2mmol, 2.2eq.), the amount and operation process of other reactants, catalysts, solvents are the same as in Example 1, and the silica gel column layer Analysis (petroleum ether / ethyl acetate=2:3) gave 467 mg of white solid, yield: 79.8%.

[0064] 1 H‐NMR (300MHz, CD 3 OD): δ=3.65(1H,d,J=6.6Hz),3.53(3H,s),3.17(1H,d,J=9.6Hz), 2.89(1H,d,J=9.6Hz),2.89‐ 2.70(5H,m),2.67(1H,d,J=9.0Hz),2.61‐2.49(7H,m),2.03(2H,d,J=11.7Hz),1.98‐1.65(4H,m),1.06 (3H,s);

[0065] 13 C‐NMR (75MHz, CD 3 OD): Δ = 216.87,200.11,175.84,174.97,172.64,96.76.70,65.41, 63.25,62.14,55.03,52.52,45.07, 42.23,35.48.7, 29.65,29.7,29.7,29.7,29.7,29.7,29.7,29.7. ,10.72;

[0066] HRMS(ESI):m / z[M‐H] ‐ calcd for C 26 h 32 o 11 S 2 :583.1313; found: 5...

Embodiment 3

[0068] Preparation and structural data of 13‐hydroxy‐3,15‐dioxo‐1,17‐bis((R)‐2‐methoxycarbonyl‐2‐acetylamino)ethylthiogibberellic acid methyl ester (DSG0103):

[0069]

[0070] 13‐Hydroxy‐3,15‐dioxogibberellic acid methyl ester (372mg, 1.0mmol) was dissolved in dichloromethane (10mL), and then N‐acetyl‐L‐cysteine ​​methyl ester (390mg, 2.2 mmol, 2.2eq.) and triethylamine (0.138mL, 0.73g / mL, 1.0mmol, 1.0eq.), reacted overnight at room temperature, after the reaction was detected by TLC, the solvent was evaporated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (petroleum ether / ethyl acetate=2:3) to obtain 656 mg of white solid, yield: 90.3%.

[0071] 1 H‐NMR (300MHz, CDCl 3 ): δ=6.66‐6.59(2H,m),4.86‐4.79(1H,m),4.75‐4.69(1H,m),3.76(3H,s),3.74(3H,s),3.60(3H,s ),3.50(1H,d,J=7.0Hz),3.50(1H,d,J=7.0Hz),3.32(1H,d,J=9.6Hz),3.17(2H,dd,J=13.6,4.3Hz ),3.12‐3.03(1H,m),3.03‐2.97(2H,m),2.93(1H,t), 2.90‐2.83(2H,m),2.79(2H,t),2.72(1H,t), ...

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 discloses a multi-sulfo gibberellic acid ester compound as shown in a general formula (I), a medicine composition adopting the multi-sulfo gibberellic acid ester compound as an active ingredient, a preparation method of the multi-sulfo gibberellic acid ester compound, and application of the multi-sulfo gibberellic acid ester compound to preparation of an antitumor drug. The multi-sulfo gibberellic acid ester compound is of a gibberellic acid basic skeleton structure; a 1-locus, a 13-locus and a 17-locus are connected with two or three same alkyl sulphanyl groups. The compound shows favorable inhibiting activity on multiple human tumor cell lines. The multi-sulfo gibberellic acid ester compound is prepared from a gibberellic acid derivative containing double alpha,beta-unsaturated ketone structure and a compound containing sulfydryl through reaction under different conditions.

Description

Technical field: [0001] The invention belongs to the fields of chemistry and medicine, and specifically relates to a class of polythiogibberellic acid ester compounds, a preparation method thereof and an antitumor application. Background technique: [0002] Malignant tumors seriously threaten human health and life. With the aging of China's population and the impact of environmental factors, the incidence and mortality of tumors are on the rise. At present, the main tumor treatment methods include surgical treatment, radiotherapy and drug treatment (ie chemotherapy). Malignant tumors are systemic rather than local diseases. Drug therapy acting on the whole body is currently the most important treatment method and occupies an irreplaceable important position in the treatment of tumors. Most commonly used chemotherapeutic drugs currently have severe side effects that limit their application. It is still an important and urgent task to find chemotherapeutic drugs with new targ...

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 Applications(China)
IPC IPC(8): C07D307/93C07D307/00A61K31/366A61P35/00A61P35/02
CPCC07D307/00C07D307/93
Inventor 张洪彬陈静波隋迎春赵玉祥飞鹏
Owner YUNNAN UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com