N-aryl anthranilamide compound, preparation and application thereof

An aminobenzamide and compound technology, which is applied to N-aryl anthranilamide compounds and the fields of preparation and application thereof, can solve the problems of not prolonging the median survival period, few species and the like, and achieves good resistance to various types of compounds. Human tumor activity, the effect of easy availability of raw materials

Pending Publication Date: 2021-11-16
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few types of chemotherapy drugs at present, mainly temozolomide, which can only prolong the median survival period of 2.5 months. The recently approved FDA-approved drug bevacizumab (avastin) for the treatment of relapsed glioblastoma did not prolong the median survival period. lifetime

Method used

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  • N-aryl anthranilamide compound, preparation and application thereof
  • N-aryl anthranilamide compound, preparation and application thereof
  • N-aryl anthranilamide compound, preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] A kind of N-aryl anthranilamide compound, concrete steps are as follows:

[0035] Dissolve compound IV (1.0 eq), EDCI•HCl (1.2 eq), HOBT (1.1 eq) in dichloromethane (3 mL) under argon, and add Et 3 N (2.5 eq) and compound I (1.0 eq), stirred and reacted for 8 hours, after the completion of the reaction detected by TLC, the reaction solution was removed by rotary evaporation under reduced pressure, and then the obtained residue was purified by silica gel flash column chromatography to obtain the desired The solid product of the compound of formula (a), the total yield of the two steps is 20-50%.

Embodiment 2

[0037] A kind of N-aryl anthranilamide compound, concrete steps are as follows:

[0038] Dissolve compound IV (1.0 eq), EDCI•HCl (1.2 eq), HOBT (1.1 eq) in dichloromethane (3 mL) under argon, and add Et 3 N (2.5 eq) and compound II (1.0 eq), stirred and reacted for 12 hours, after the completion of the reaction detected by TLC, the reaction solution was removed by rotary evaporation under reduced pressure, and then the obtained residue was purified by silica gel flash column chromatography to obtain the desired The compound of formula (II) is a solid product, and the total yield of the two steps is 20-50%.

Embodiment 3

[0040] A kind of N-aryl anthranilamide compound, concrete steps are as follows:

[0041] Dissolve compound IV (1.0 eq), EDCI•HCl (1.2 eq), HOBT (1.1 eq) in dichloromethane (3 mL) under argon, and add Et 3 N (2.5 eq) and compound III (1.0 eq), stirred and reacted for 12 hours, after the completion of the reaction detected by TLC, the reaction solution was removed by rotary evaporation under reduced pressure, and then the obtained residue was purified by silica gel flash column chromatography to obtain the desired The compound of formula (III) is a solid product, and the total yield of the two steps is 20-50%.

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Abstract

The invention relates to the technical field of medicine, in particular to an N-aryl anthranilamide acid compound anti-intracerebral tumor active compound, preparation and application thereof, wherein the structural general formula is shown in the specification, R1 is one or more of halogen F or Cl or Br or I, alkyl, heteroalkane, amino and nitryl, the substitution positions of R1 on a benzene ring are 2-site, 3-site and 4-site, the number of substituents is monosubstitution or polysubstitution, R2 is one or more of halogen F or Cl or Br or I, alkyl, heteroalkane, amino and nitryl, the substitution positions of R2 on the benzene ring are 2-site, 3-site and 4-site, the number of substituents is monosubstitution or polysubstitution, R3 is a heterocyclic ring or a benzoheterocyclic ring, n is 1-3, and X is N or CH. The compound disclosed by the invention has a remarkable COX-2 inhibition effect and a topoisomerase inhibition effect, has the effects of remarkably inhibiting proliferation, invasion and migration of various tumors, especially brain tumors such as glioma and the like in vivo and in vitro, retarding cycle and the like, and is a novel multi-target antitumor drug.

Description

technical field [0001] The invention belongs to the technical field of medical N-aryl anthranilamide compounds, and in particular relates to an N-aryl anthranilamide compound and its preparation and application. Background technique [0002] Glioma, the most common primary brain tumor in adults, ranks first in the incidence of intracranial tumors. The median survival period of patients with glioma is less than 2 years, and the mortality rate ranks first in intracranial tumors. Chemotherapy is currently an important means of treating glioma, especially malignant glioma. However, there are few types of chemotherapy drugs at present, mainly temozolomide, which can only prolong the median survival period of 2.5 months. The recently approved FDA-approved drug bevacizumab (avastin) for the treatment of relapsed glioblastoma did not prolong the median survival period. lifetime. Therefore, there is an urgent need to develop more effective and unique multi-target anti-glioblastoma ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/56
CPCC07D263/56C07D241/42C07D235/06C07D277/62C07D249/18C07D209/34C07D235/26C07D209/08C07D215/40C07D241/20C07D213/75C07D237/20C07D239/42C07D261/14C07D231/40C07D473/34C07D241/44C07C259/10C07C237/32C07C237/34C07D317/66C07C323/41C07C233/29C07C237/40C07C231/02C07C319/20C07D213/82A61P35/00
Inventor 王震石桃李俊芳张红花王晓东
Owner NANHUA UNIV
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