Supercharge Your Innovation With Domain-Expert AI Agents!

Preparation and application of sulfonamide compound

A technology of sulfenamides and compounds, applied in the field of sulfenamide compounds and their preparation

Inactive Publication Date: 2013-06-19
TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE
View PDF4 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] So far, there is no drug that can fundamentally inhibit or eliminate breast cancer stem cells and achieve a complete cure

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
  • Preparation and application of sulfonamide compound
  • Preparation and application of sulfonamide compound
  • Preparation and application of sulfonamide compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0042] The starting materials used in the preparation of the compounds of the present invention are known, can be prepared according to known methods, or are commercially available.

[0043] The invention also relates to novel intermediates and / or starting materials. Particular preference is given to reaction conditions and novel intermediates which are the same or similar to those mentioned in the examples.

[0044] Both intermediates and final products can be worked up and / or purified according to conventional methods, including pH adjustment, extraction, filtration, drying, concentration, chromatography, trituration, crystallization, and the like.

[0045] In addition, the compounds of the present invention can be prepared by various methods known in the art or variations on the methods described herein.

[0046] The following examples are only used to illustrate the present invention and do not limit the present invention in any way.

Embodiment 1

[0047]The preparation of embodiment 1 (S)-N-((R)-tert-butylsulfinamide)-2-(4-isobutylphenyl) propanamide

[0048]

[0049] step 1

[0050] Take a 50ml round bottom flask, add CDI (0.41g, 2.52mmol) into (S)-2-(4-isobutylphenyl)propionic acid (0.52g, 2.52mmol) in a dry dichloromethane solution, The mixed solution was stirred at 0-5°C for 2 hours. Add (R)-(+)-tert-butylsulfinamide (0.31g, 2.52mmol) and DBU (0.3ml) and stir at room temperature for about 6 hours, follow the reaction by TLC, after the reaction is over. NaH for organic phase 2 PO 4 (2*5ml), washed with saturated saline (2*5ml). After drying over anhydrous sodium sulfate, the solvent was removed. Separation by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) gave the target compound (0.62 g, yield 79%).

[0051] MS of the compound: [M+H] + 310.18; 1 H-NMR (400MHz CDCl 3 ): δδppm 7.16(q, 4H), 6.77(s, 1H CONH), 3.75(q, 1H), 2.46(d, 2H), 1.84(m, 1H), 1.56(d, 3H), 1.05(s , 9H), 0.89(d, ...

Embodiment 2

[0052] Preparation of Example 2 (R)-N-((R)-tert-butylsulfinamide)-2-(4-isobutylphenyl) propanamide

[0053]

[0054] step 1

[0055] Take a 50ml round bottom flask, add CDI (0.41g, 2.52mmol) into (R)-2-(4-isobutylphenyl)propionic acid (0.52g, 2.52mmol) in a dry dichloromethane solution, The mixed solution was stirred at 0-5°C for 2 hours. Add (R)-(+)-tert-butylsulfinamide (0.31g, 2.52mmol) and DBU (0.3ml) and stir at room temperature for about 6 hours, follow the reaction by TLC, after the reaction is over. NaH for organic phase 2 PO 4 (2*5ml), washed with saturated saline (2*5ml). After drying over anhydrous sodium sulfate, the solvent was removed. Separation by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) gave the target compound (0.62 g, yield 79%).

[0056] MS of the compound: [M+H] + 310.18; 1 H-NMR (400MHz, CDCl 3 ): δδppm 7.16(q, 4H), 6.774(s, 1H CONH), 3.75(q, 1H), 2.46(d, 2H), 1.84(m, 1H), 1.56(d, 3H), 1.05(s , 9H), 0.89(d, 6H)....

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 relates to preparation and application of a sulfonamide compound, and particularly provides the sulfonamide compound. According to the structure displayed in a general formula (I), the sulfonamide compound can restrain survival and growth of SUM-159, HCC-1954 and MCF-7 cells, wherein R is from a C1-C4 linear chain or a branched paraffin or three fluorinated alkyl or cyclohexyl or o-methylphenyl or 3- pyridyl or 2- pyridyl ethyl, and n=0, 1, 2, or 3.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to sulfenamide compounds and their preparation methods and uses. Background technique [0002] Breast cancer (mammary carcinoma) is the most common malignant tumor in humans and one of the main malignant tumors in women. The vast majority of malignant tumors of the breast originate from the epithelial tissue of the breast (breast cancer), and a few of them can originate from various non-epithelial tissues of the breast (various sarcomas). Mixed carcinosarcomas can occasionally be seen. The incidence of breast cancer is increasing year by year, and the incidence rate of the population is 23 / 100,000; it accounts for 7-10% of various malignant tumors in women's whole body. [0003] In 2010, Max S. Wicha, a researcher at the University of Michigan in the United States, identified a new role for a receptor, CXCR1, which is located on the surface of breast cancer stem cells and has the...

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): C07C313/06C07D295/26A61K31/145A61K31/5375A61P35/00
Inventor 陈悦饶子和杨诚白翠改金秉德戴东方张伟王颂
Owner TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE
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