Unlock instant, AI-driven research and patent intelligence for your innovation.
A kind of 2-amino-4,5-diarylthiazole type compound and its preparation method and application
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
A technology of thiazole type and compound, which is applied to 2-amino-4,5-diarylthiazole type compound and the field of preparation method and application thereof, can solve the problems of low bioavailability, drug resistance, high toxicity and the like, Achieving a good inhibitory effect
Inactive Publication Date: 2018-02-09
南京信卓化工科技有限公司
View PDF1 Cites 0 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
Problems solved by technology
However, many anti-tumor drugs currently used clinically have many disadvantages, such as high toxicity, low bioavailability, 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
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
Examples
Experimental program
Comparison scheme
Effect test
Embodiment 1
[0029] Example 1: Preparation of 4-(5-methoxy-2,2-dimethyl-2H-benzopyran-8-yl)-5-phenylthiazol-2-amine (1)
[0030]
[0031] Step 1: Add 1-(2-hydroxy-4-methoxyphenyl)ethanone (4.85g, 10mmol) to 100mL CH 3 After CN was dissolved, cooled to 0°C in an ice bath, and slowly added DBU (1.5mL, 15mmol), CuCl 2 (4.03mg, 0.3%mmol), 3-chloro-3-methyl-1-butyne (1.53g, 15mmol), reacted in ice bath for 5h, TLC monitoring showed that the reaction was complete. Stop the reaction, add 1N dilute hydrochloric acid dropwise to adjust pH=2, remove CH under reduced pressure 3 CN, the residue was poured into 50mL water, a large amount of solids were precipitated, filtered, and dried as solidpowder, the yield was 85%. 1 H NMR (d 6 -DMSO, 400 MHz) δ: 1.75 (s, 6H), 2.58 (s, 3H), 2.69(s, 1H), 3.84 (s, 3H), 6.58 (dd, 1H), 7.19 (d, 1H) , 7.75 (d, 1H); EIMS m / z =233.28 [M + ].
[0032] Step 2: Suspend 1-(4-methoxy-2-((2-methyl-3-yn-2-yl)oxo)phenyl)ethanone (2.32 g, 10 mmol) in 50 mL of pyridine ...
Embodiment 2
[0040] Example 2: Preparation of 5-phenyl-4-(2,2,5-trimethyl-2H-benzopyran-8-yl)thiazol-2-amine (2)
[0041]
[0042] The yield is 80%. 1 H NMR (d 6 -DMSO, 400 MHz) δ: 1.50 (s, 6H), 2.54 (s, 3H), 5.96(d, 1H), 6.67 (s, 2H), 6.79 (d, 1H), 6.88 (d, 1H), 7.42 (d, 1H), 7.45-7.56(m, 3H), 7.75-7.86(m, 2H); EIMS m / z = 349.46 [M + ].
Embodiment 3
[0043] Example 3: Preparation of 4-(5-ethyl-2,2-dimethyl-2H-benzopyran-8-yl)-5-phenylthiazol-2-amine (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
Login to View More
Abstract
The invention discloses a 2-amino-4,5-diaryl-thiazole-type compound and a preparing method and application thereof. The 2-amino-4,5-diaryl-thiazole-type compound has the structure shown in the formula (I) (please see the specification). The preparing method includes the steps that substituted 2-hydroxyacetophenone serves as a raw material, and is etherified, rearranged, brominated, subjected to ring closing through thiourea, and reacted with phthalic anhydride, the reacted product is brominated to obtain substituted 2-(5-bromine-4-(2,2-dimethyl-2H-chromene-8-base) thiazole-2-base) isoindoline-1,3-diketone, the substituted 2-(5-bromine-4-(2,2-dimethyl-2H-chromene-8-base) thiazole-2-base) isoindoline-1,3-diketone and arylboronic acid are coupled to obtain substituted 2-(4-(2,2-dimethyl-2H-chromene-8-base)-5-aryl thiazole-2-base) isoindoline-1,3-diketone, and finally protection is removed to obtain the target compound. The 2-amino-4,5-diaryl-thiazole-type compound can serve as a raw material of antitumor medicine, and raw materials of the preparing method are simple and easy to obtain, and operation is convenient.
Description
technical field [0001] The invention relates to a 2-amino-4,5-diarylthiazole compound, a preparation method thereof and an application as a tubulin inhibitor in the preparation of antitumor drugs. Background technique [0002] At present, malignant tumors have become a common and frequently-occurring disease that seriously endangers human health. Every year, 7.6 million new cases of malignant tumors are discovered in the world. It is the second leading cause of human death, second only to cardiovascular and cerebrovascular diseases. Moreover, the incidence of tumors is increasing year by year. The World Health Organization (WHO) predicts that 1.2 million people will die of cancer in 2030. Among the 27 tumor types, lungcancer, gastric cancer, liver cancer, colon cancer and breast cancer caused the most deaths. Due to the increasing tumor mortality, it is necessary to discover new, safe and efficient drugs to treat and prevent tumors. However, many anticancer drugs currentl...
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
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to View More 
Login to View More 
