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Method for synthesizing nicotinyl amino acids and sensitizing effect thereof to tumor radiotherapy

A technology of nicotinyl amino acid and compound, which is applied in the field of medicine, can solve the problems of limiting tumors and low radiation sensitivity, and achieve the effects of simple operation, good purity and high yield

Inactive Publication Date: 2008-10-22
INST OF RADIATION MEDICINE CHINESE ACADEMY OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The presence of hypoxic cells in tumors limits the efficacy of radiation therapy for tumors because these hypoxic cells are 2-3 times less sensitive to radiation than aerobic cells

Method used

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  • Method for synthesizing nicotinyl amino acids and sensitizing effect thereof to tumor radiotherapy
  • Method for synthesizing nicotinyl amino acids and sensitizing effect thereof to tumor radiotherapy
  • Method for synthesizing nicotinyl amino acids and sensitizing effect thereof to tumor radiotherapy

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0049] Nicotinic acid hydrazide 18.7 (130mM) was dissolved in 122.2ml of 13% hydrochloric acid solution, and NaNO was added dropwise at low temperature 2 18.2g (260mM) in the solution of 45ml of water, after dripping, continue to react for 1.5 hours, the reaction mixture is washed with Na 2 CO 3 Adjust the pH to 7, extract with ether (100ml×4), wash the organic layer with water, CaCl 2 Drying and removal of solvent yielded 16.6 g of product, (86%). ,

example 2

[0051] Synthesis of N-Nicotinyliminodiacetic Acid

[0052] Add 2.3g (15.5mM) of nicotinyl azide to a solution of 2.1g (15.5mM) of iminodiacetic acid in 16ml of 1N sodium hydroxide, stir for 12 hours, then neutralize with hydrochloric acid until the pH reaches 3-4, and concentrate by rotation The reaction solution reaches a small volume (PH 3-4), and white crystals are precipitated and recrystallized with 80% methanol, mp 202-203°C.

[0053] 1HNMR (DMSO-d6), δ(ppm) 4.10(d, 4H, -CH2-, -CH2-), 7.48((dd, 1H, H5), 7.73(dd, 1H, H4), 8.50(dd, 1H , H6), 8.66 (q, 1H, H2).

example 3

[0055] 2-Nicotinamide butyric acid

[0056] Add 3.1g (21mM) of nicotinoyl azide powder to 2.16g (21mM) of DL-2-aminobutyric acid in 21ml of 1NNaOH solution in portions. After the addition is complete, continue to stir for 12 hours, rotate and concentrate to obtain a viscous substance, add dropwise Adjust the pH to 4 with 2N HCl, and 3.6 g (82%) of a white precipitate precipitated, mp 212-214°C, and recrystallized from ethanol.

[0057] 1HNMR (DMSO-d6) δppm0.968 (t, 3H, CH3), 1.810 (m, 2H, CH2), 4.317 (m, 1H, -CH-), 7.526 (dd, 1H, C53), 8.229 (m, 1H, C42), 8.727 (m, 1H, H6'), 8.821 (d, 1H, C21), 9.039 (d, 1H, NH) 12.666 (S, 1H, OH), Anal C 11 h 12 N 2 o 3 C, H, N.

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Abstract

The invention provides a nicotinoyl amino compound with a general formula I or acceptable salts in pharmacy thereof. While the maternal structure of niacinammide is maintained, compounds such as amino monoacid and amino dibasic acid, etc., are introduced into a side chain of the niacinammide; radiotherapy sensitivity experiments on tumors show that the synthesized compounds all have sensitivity effects of different degrees. The invention also provides the series compound with the general formula I or acceptable salts in pharmacy thereof, which can be used as an effective component in application of preparing the radiotherapy sensitivity drugs for curing liver cancer, lung cancer, cervical cancer, breast cancer, lymph cancer and nasopharyngeal carcinoma.

Description

technical field [0001] The invention belongs to the technical field of medicine, more specifically, the invention relates to niacinamide compounds and their preparation methods and pharmaceutical compositions containing them, and the effects of these compounds on liver cancer, lung cancer, cervical cancer, breast cancer, lymphoma , Nasopharyngeal carcinoma radiotherapy sensitization application. Background technique [0002] Malignant tumors are a large class of diseases that seriously threaten human health. Their abnormal proliferation is controlled by abnormal information in cells and is closely related to the abnormal activity and inactivation of corresponding genes in tumor cells. Radiation therapy is the main means of treating malignant tumors, and it is also one of the important means of treating middle and advanced tumors. However, since the radiation used has no special selectivity for tumor cells, a large number of normal cells are also killed while tumor cells are...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/82A61K31/455A61P35/00
Inventor 李美佳蒋铁南荘湘莲刘晓秋王荣先
Owner INST OF RADIATION MEDICINE CHINESE ACADEMY OF MEDICAL SCI