Compound I and compound II as well as preparation methods and application thereof

A compound and reaction technology, applied in the field of compound I and compound II and their preparation, can solve problems such as poor therapeutic effect and adverse reactions, and achieve the effect of slowing down growth

Active Publication Date: 2016-02-10
SHENZHEN UNIV +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The object of the present invention is to provide structural formula as the compound of formula I and formula II and its preparation method and application, i.e. compound I and compound II and its preparation method and application, specifically provide T7 (the first reactant) and EA (the second Two reactant) the co

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  • Compound I and compound II as well as preparation methods and application thereof
  • Compound I and compound II as well as preparation methods and application thereof
  • Compound I and compound II as well as preparation methods and application thereof

Examples

Experimental program
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Effect test

preparation Embodiment 1

[0049] Weigh 344 mg (1 mmol) T7 and 341 mg (1.125 mmol) EA and dissolve in 8 mL DMF, add HBTU (427 mg, 1.125 mmol), triethylamine (416 μL, 3 mmol) and a catalytic amount of DMAP, and stir the reaction at room temperature for 12 hours. The reaction solution was poured into 100 mL of water, filtered with suction, and the filter residue was washed with water and dried to obtain a crude product. After separation by column chromatography (DCM:MeOH=20:1), 475 mg of T7-EA was obtained as a white solid with a yield of 75.5%. Purity: 95.08%, ESI-MS: m / z=629.1[M+H] + .(Such as Figure 1-2 shown)

preparation Embodiment 2

[0051] Weigh 172mg (0.5mmol) of T7 and 189.4mg (0.625mmol) of EA and dissolve in 6mL of a mixed solvent of benzene and toluene with a volume ratio of 2:1, add HBTU (237.2mg, 0.625mmol), triethylamine (312μL , 2.25mmol) and a catalytic amount of DMAP, stirred at room temperature for 24 hours. The reaction solution was poured into 100 mL of water, filtered with suction, and the filter residue was washed with water and dried to obtain a crude product. After separation by column chromatography (DCM:MeOH=20:1), 236.8 mg of T7-EA was obtained as a white solid, with a yield of 73.2%.

preparation Embodiment 3

[0053] Weigh 516mg (1.5mmol) of T7 and 568.3mg (1.875mmol) of EA and dissolve in 15mL of tetrahydrofuran, add HBTU (711.7mg, 1.875mmol), triethylamine (520μL, 3.75mmol) and a catalytic amount of DMAP, and stir at room temperature React for 18 hours. The reaction solution was poured into 200 mL of water, filtered with suction, and the filter residue was washed with water and dried to obtain a crude product. After separation by column chromatography (DCM:MeOH=20:1), 752 mg of T7-EA was obtained as a white solid, with a yield of 77.5%.

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Abstract

The invention relates to a compound I and a compound II as well as preparation methods and application thereof. The newly synthesized compound shown in the formula I can stimulate anti-tumor congenital immunity and cellular immunity while greatly improving the anti-tumor effect of ethacrynic acid (EA) and drug design of anti-tumor immunity synergetic integration is explored; the anti-melanoma immune response mechanism of the compound shown in the formula I is proved; the compound shown in the formula II and prepared through covalence of the compound shown in the formula I and ROR1 obviously reduces growth of breast cancer subcutaneously transplanted tumors, the breast cancer treatment immune response mechanism of the compound shown in the formula II is proved, and meanwhile, the fact that the compound shown in the formula I not only has the functions of stimulating congenital immunity and adaptive immunity, but also has the effect of immune adjuvant is proved.

Description

technical field [0001] The present invention relates to the technical field of tumor cancer disease prevention and treatment, and more specifically, relates to compound I and compound II and their preparation methods and applications. Background technique [0002] Malignant melanoma is a highly malignant tumor derived from melanocytes. It is a common malignant tumor in skin cancer and has strong metastases. At present, the main treatment methods are radiotherapy, chemotherapy and surgery. However, traditional treatments cannot completely cure it , with the development of tumor immunology and molecular biology, immunotherapy for tumors has become a research hotspot. Toll-like receptors (Tolllike receptors, TLRs) are an important class of pattern recognition receptors, which belong to type I transmembrane proteins and are expressed on various immune cells. TLRs play an important role in stimulating innate and adaptive immune responses. effect. The agonists of TLRs act on ant...

Claims

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Application Information

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IPC IPC(8): C07D473/18A61P35/00C07K14/705C07K1/107
CPCC07D473/18C07K14/70567C07K19/00A61P35/00C07D487/04A61K31/519C07K1/107C07K14/70503
Inventor 靳广毅王竹林胡云龙刘兵
Owner SHENZHEN UNIV
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