Thiazole heterocyclic compounds, and preparation method and application thereof

A compound and heterocyclic technology, applied in the fields of thiazole heterocyclic compounds and their preparation and application, can solve the problems of poor curative effect of leukemia and the like

Inactive Publication Date: 2017-01-04
TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE
View PDF4 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The technical effects described are novel chemicals called Thiazolylheterocycles which have been discovered through various experimentations on different types of cancerous tissues such as blood vessels or lymphatic system. These molecules prevent certain forms of tumors from growing outwardly like other organs during their growth process. They may even help stop some kinds of brain damage caused by chemotherapy drugs.

Problems solved by technology

The technical problem addressed by this patented research relates to finding a chemical called histidylinleucimide (HDL-32) that could effectively prevent recurrence of relapsing forms of Acrocytoma Loss Grafts (AML)-associated lyrican syndrome (ALS)/myocardial infarbility/accelerated cutoff mutism (AFCI)).

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
  • Thiazole heterocyclic compounds, and preparation method and application thereof
  • Thiazole heterocyclic compounds, and preparation method and application thereof
  • Thiazole heterocyclic compounds, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Example 1 Chemical Synthesis and Structure Identification of Thiazole Heterocyclic Compounds with General Formula One

[0086]

[0087] In the above general formula one:

[0088]

[0089] The chemical synthesis experimental steps of the thiazole heterocyclic compounds with general formula one (the experimental steps of the example compounds included in general formula one) are as follows:

[0090] 1. General synthetic route

[0091]

[0092] 2. Specific synthesis steps:

[0093] 2.1: Compound 3: N-(2-chloro-6-methylphenyl)-2-((6-(4-(2-(1,3-dioxoisoindoline)ethyl)piperazine Synthesis of )-2-methylpyrimidine)amino)thiazole-5-carboxamide

[0094]

[0095] At 0°C, compound 1 (500mg, 1.02mmol), triphenylphosphine PPh 3 (349mg, 1.33mmol), phthalimide 2 (195.7mg, 1.33mg) was added to 10mL redistilled anhydrous tetrahydrofuran, and then added diisopropyl azodicarboxylate DIAD ( 226.4mg, 1.33mmol), stirred at low temperature for 10min and then moved to room temp...

example 1

[0096] Example 1 compound 4a: N-(2-chloro-(6-methylphenyl)-2-[[6-[4-(2-aminoethyl)-1-piperazinyl]-2-methyl- Synthesis of 4-pyrimidinyl]amino]-5-thiazolecarboxamide

[0097]

[0098] Add compound 3 (606 mg, 0.98 mmol) into a round bottom flask with 10 mL of ethanol, then add 5 mL of hydrazine hydrate, heat to 78 ° C and reflux for two hours to complete the reaction, concentrate under reduced pressure to remove the reaction solvent, and then add chlorinated The sodium-saturated solution was extracted three times with tetrahydrofuran, and the organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. Further purification by column chromatography yielded compound 4a (white solid). 1HNMR (400MHz, DMSO-d 6 )δppm 9.88 (br, 1H), 8.23 ​​(s, 1H), 7.40 (dd, J=7.2Hz, 1H), 7.24-7.30 (m, 2H), 6.06 (s, 1H), 3.52 (br, 4H ), 2.68(t, J=6.4Hz, 2H), 2.44(t, J=4.4Hz, 4H), 2.41(s, 3H), 2.36(t, J=6.4Hz, 2H), 2.24(s, 3H ); 13 CNMR (100MHz, DMSO-d 6 )δ165.61, 163.11, 1...

example 2

[0100] Example 2 Compound 4b: N-(2-chloro-(6-methylphenyl)-2-[[6-[4-(2-isothiocyanate)-1-piperazinyl]-2-form Synthesis of yl-4-pyrimidinyl]amino]-5-thiazolecarboxamide

[0101]

[0102] At 0°C, compound 4a (100mg, 0.21mmol) was added to a round bottom flask with 3mL of dichloromethane, then dicyclohexylcarbodiimide DCC (1.1eq) was added, and then carbon disulfide CS was slowly added dropwise under stirring. 2 (15eq), after the dropwise addition, stirred at low temperature for 5 minutes, removed the ice-water bath, and then stirred at room temperature until the reaction was complete. Concentrate under reduced pressure to remove the reaction solvent, and purify by silica gel column chromatography to obtain compound 4b (white solid). of the compound 1 HNMR (400MHz, DMSO-d 6 )δppm11.47(s, 1H), 9.88(s, 1H), 8.23(s, 1H), 7.40(dd, J=1.2, 7.2Hz, 1H), 7.24-7.30(m, 2H), 6.07(s , 1H), 3.80(t, J=6.0Hz, 2H), 3.54(br, 4H), 2.66(t, J=6.0Hz, 2H), 2.54(br, 4H), 2.42(s, 3H), 2.24 (s, 3H...

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 provides thiazole heterocyclic compounds, and a preparation method and application thereof. The thiazole heterocyclic compounds have a general structural formula as described in the specification. Results of cell-level experiments show that the thiazole heterocyclic compounds provided by the invention can inhibit proliferation of K562, HL60 and KGla cells. In particular, the compound (compound 4c) in an embodiment 3 can also inhibit proliferation of K562, HL60 and KGla cells under the condition that the concentration of the compound is lower than the concentration of a positive control drug dasatinib. Thus, the thiazole heterocyclic compounds provided by the invention can be used for treating leukemia.

Description

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

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
Owner TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap