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3-(3-(heteroaryl)-4-thiazolinone)-N-aryl benzamide compound and synthesis and application thereof

A technology of aryl benzamide and thiazolinone, which is applied in the field of biomedicine and synthetic medicine to achieve good inhibitory and selective effects

Pending Publication Date: 2022-04-01
SHANGHAI HONGHENG BIOMEDICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, new targets and treatment options for osteosarcoma include NK-kB ligands, folic acid inhibitors, etc., but they are all in the experimental research stage

Method used

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  • 3-(3-(heteroaryl)-4-thiazolinone)-N-aryl benzamide compound and synthesis and application thereof
  • 3-(3-(heteroaryl)-4-thiazolinone)-N-aryl benzamide compound and synthesis and application thereof
  • 3-(3-(heteroaryl)-4-thiazolinone)-N-aryl benzamide compound and synthesis and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091]

[0092] III-1 is a foamy white solid with a yield of 92%.

[0093] 1 H NMR (400MHz, Chloroform-d) δ8.20(s, 1H), 8.12(d, J=8.3Hz, 1H), 7.69(t, J=6.9Hz, 1H), 7.48(s, 1H), 7.29 (s,3H),7.18(d,J=7.1Hz,3H),7.10(d,J=8.6Hz,1H),7.02(d,J=4.6Hz,1H),6.85(s,1H),6.05 (s,1H),4.02(d,J=16.1Hz,1H),3.81(d,J=16.1Hz,1H),3.43(d,J=5.7Hz,2H),2.65(d,J=7.2Hz ,3H),1.79–1.50(m,6H).

[0094] 13 C NMR (101MHz, CDCl 3 )δ171.04,165.71,163.94,150.37,147.69,144.79,141.94,137.98,137.38,128.40,125.91,120.92,120.31,116.82,115.87,115.64,113.98,113.74,62.08,40.07,35.45,34.02,29.10,28.66.

[0095] 19 F NMR (376MHz, CDCl 3 )δ-110.94.

Embodiment 2

[0097]

[0098] Yield = 65%.

[0099] NMR spectrum:

[0100] 1 H NMR (400MHz, Chloroform-d) δ8.31(s,1H),7.90(s,1H),7.73(s,1H),7.67–7.55(m,3H),7.42(s,1H),7.31( s,2H),7.26–7.20(m,2H),7.05(s,2H),6.74(s,1H),6.68(s,2H),6.17(s,1H),4.09(s,3H),3.93 (d,J=16.1Hz,1H),3.69(d,J=16.0Hz,1H),3.33(s,2H),1.85(s,2H),1.50(s,3H).

[0101] 13 C NMR (101MHz, CDCl 3 )δ171.35,167.05,158.46,151.16,148.06,145.39,141.66,139.12,135.15,133.89,129.35,128.89,128.55,126.77,125.02,124.01,119.56,116.59,112.65,105.54,62.57,51.27,39.58,33.97,30.32 ,27.98,26.08.

Embodiment 3

[0103]

[0104] Yield = 81%.

[0105] NMR spectrum:

[0106] 1 HNMR(400MHz,Chloroform-d)δ8.16(s,1H),7.98(s,1H),7.73(s,1H),7.58(d,J=6.3Hz,1H),7.43(s,1H), 7.36–7.16(m,4H),6.90(s,2H),6.75(s,1H),6.17(s,1H),4.10(s,2H),3.93(d,J=16.2Hz,1H),3.70 (d,J=16.2Hz,1H),3.35–3.24(m,3H),1.86(s,2H),1.50(s,2H).

[0107] 13 C NMR (101MHz, CDCl 3 )δ171.34,166.98,151.35,148.17,145.35,141.72,139.18,135.18,129.30,128.51,126.70,125.01,121.10,116.63,105.54,62.58,51.26,39.59,33.98,30.32,29.69,28.01,26.05.

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Abstract

The invention discloses a 3-(3-(heteroaryl)-4-thiazolinone)-N-aryl benzamide compound or a pharmaceutically acceptable salt, and the compound belongs to a compound with a new structure. The invention further discloses application of the compound or the pharmaceutically acceptable salt or the pharmaceutical composition of the compound to treatment of osteosarcoma and other related diseases, and the compound or the pharmaceutically acceptable salt or the pharmaceutical composition of the compound has good inhibition and good selectivity to different cell lines. The invention also discloses a preparation method of the thiazolinone compound. The method has the advantage of being capable of synthesizing thiazolinone compounds with heterocyclic rings and aliphatic groups at 3 sites, which cannot be synthesized by a traditional synthesis route.

Description

technical field [0001] The invention belongs to the field of synthetic medicine and biomedicine, and mainly relates to a 3-(3-(heteroaryl)-4-thiazolinonyl)-N-arylbenzamide compound and its synthesis method and application. Background technique [0002] Osteosarcoma, also called osteosarcoma, is a malignant bone tumor that commonly occurs in adolescents or children under the age of 20 (Link MP: Osteosarcoma in adolescents and young adults: new developments and controversies. Commentary on the use of presurgical chemotherapy. Cancer Treat Res 62:383-385, 1993.), according to the epidemiological study of osteosarcoma, it is the most common in children with malignant bone tumors, accounting for 5% of children's tumors. Osteosarcoma is still a disease with a high mortality rate of malignant tumors in children and adolescents, second only to lymphoma and brain cancer, but early detection and timely treatment have greatly improved the survival rate of the disease. [0003] Treatme...

Claims

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Application Information

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IPC IPC(8): C07D417/04C07D417/14C07D277/14C07D277/44C07D277/56A61K31/4439A61K31/426A61K31/497A61K31/427A61K31/454A61P35/00A61P35/02
Inventor 刘顺英邓亚琦宋龙龙倪丹皮柔董素珍
Owner SHANGHAI HONGHENG BIOMEDICAL TECH CO LTD
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