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Compound capable of inhibiting conduction of vascular endothelial growth factor receptor signal

A growth factor receptor and signal transduction technology, applied in the field of medicine, can solve the problems of tumor cells lack of nutrition, stop growing, slow blood flow, etc.

Inactive Publication Date: 2017-08-18
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Current studies have shown that the abnormal expression of VEGFR-2 in tumor cells is related to tumor growth and migration, so blocking the VEGF / VEGFR-2 signaling pathway can effectively interfere with the angiogenesis of solid tumors, resulting in the growth of tumor cells. The required blood flow is slow, even causing tumor cells to stop growing due to lack of nutrients

Method used

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  • Compound capable of inhibiting conduction of vascular endothelial growth factor receptor signal
  • Compound capable of inhibiting conduction of vascular endothelial growth factor receptor signal
  • Compound capable of inhibiting conduction of vascular endothelial growth factor receptor signal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: Preparation of compound 5-3 in the above Table 2, namely the preparation of 3-bromo-4-chloro-N-(2-phenyl-5-benzoxazolyl)benzamide.

[0047] The 3-bromo-4-chloro-N-(2-phenyl-5-benzoxazolyl)benzamide has the following chemical structural formula:

[0048]

[0049] The preparation method of described compound 5-3 is as follows:

[0050] Select 1mmol of substituted benzoic acid or substituted phenylacetic acid 4, add it to a 20mL round bottom flask, take 20mL of DMF to dissolve, then add 1.5mmol of HOBT, 1.5mmol of EDCI, 2mmol of TEA triethylamine in turn, and then use a normal temperature magnetic stirrer Stir for about 10 minutes, then add substituted 2-phenylbenzoxazole 3 dissolved in DMF, stir at room temperature, react for 2-4 hours, TLC detects that the reaction of raw materials is complete, stop stirring, add 15 mL of ethyl acetate for extraction, and then use 50 mL of dilute hydrochloric acid After washing twice, the organic phase was dried with anhyd...

Embodiment 2

[0052] Example 2: Preparation of Compound 5-1 in the above Table 2, namely the preparation of 4-bromo-3-fluoro-N-2-(2-phenylbenzoxazol-5-yl)benzamide. The preparation method is as in Example 1, and has the following chemical structural formula:

[0053]

[0054] NMR spectrum data: yellow solid; Mp 227.9–229.9°C; IR(KBr): 3334,3064,1650,1544,1483,1279,1046,870,764,690; 1 HNMR (500MHz, DMSO-d 6 ):δ=7.58-7.61 (d, J=7.20Hz, 3H, ArH), 7.73-7.96(m, 5H, ArH), 8.16-8.18(d, J=7.15Hz, 2H, ArH), 8.27(s ,1H,ArH),10.53(s,1H,ArH); 13 CNMR (125MHz, DMSO-d 6 ):δ=110.91, 111.80, 116.08, 116.27, 119.17, 125.63, 126.74, 127.58, 127.58, 129.59, 129.59, 132.24, 133.99, 136.26, 136.64, + ): m / z calcd for C 20 h 12 BrFN 2 o 2 [M+Na] + ,432.9952; found, 432.9958.

Embodiment 3

[0055] Example 3: Preparation of Compound 5-2 in the above Table 2, namely the preparation of 4-chloro-3-fluoro-N-2-(2-phenylbenzoxazol-5-yl)benzamide. The preparation method is as in Example 1, and has the following chemical structural formula:

[0056]

[0057] NMR spectrum data: yellow solid; Mp 216.9–218.5°C; IR(KBr): 3346,3064,1654,1548,1479,1426,1058,812,694,637; 1 H NMR (500MHz, DMSO-d 6 ): δ=7.60-7.62 (d, J=6.95Hz, 3H, ArH), 7.75-7.89 (m, 4H, ArH), 7.99-8.02 (d, J=10.00Hz, 1H, ArH), 8.17-8.20 (d, J=7.20Hz, 2H, ArH), 8.27(m, 1H, ArH); 13 C NMR (125MHz, DMSO-d 6 ): δ=110.97, 111.86, 116.35, 116.53, 119.25, 125.38, 126.74, 127.61, 127.61, 129.63, 129.63, 131.13, 132.29, 135.99, 136.26, 141.97, 1463.367, TO + ):m / z calcd for C 20 h 12 ClFN 2 o 2 [M+Na] + ,389.0466; found, 389.0464.

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Abstract

The invention discloses a compound capable of inhibiting the conduction of a vascular endothelial growth factor receptor signal, and relates to the field of medicines, in particular to a benzoxazole medicine, in particular to a 2-aryl benzoxazole aryl amide compound. The compound has high activity for inhibiting tumor cell growth, especially has an obvious inhibition effect on the growth of high-expression human colon cancer cells of a vascular endothelial growth factor receptor 2 subtypes, and can be used for anti-tumor medicines.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a benzoxazole drug. Background technique [0002] Tumor is the product of abnormal expression of cells, which can be divided into benign and malignant tumors. At present, malignant tumors have become a major killer threatening human health. In recent years, the number of cancer patients in the world has increased rapidly, and it is estimated that the number of deaths from cancer in the world may increase to 19 million in 2025. Traditional tumor treatment methods all have varying degrees of toxic and side effects, and sometimes tolerance and complications occur, making it difficult to fundamentally treat tumors. [0003] One of the leading causes of death from cancer is the metastasis of tumor cells in advanced stages of cancer. At present, it is believed that tumor cell metastasis mainly takes three forms: first, tumor cells immerse into the inner wall of blood vessels to form metastas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/57A61P35/00A61P35/02
CPCC07D263/57
Inventor 金毅刘玉文杨庆益张继虹林军
Owner YUNNAN UNIV
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