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Benzo [b][1,8]-naphthyridine-2-(1H)-imide derivative with antitumor activity and synthetic method thereof

A technology of antitumor activity and synthesis method, which is applied in the field of benzo[b][1,8]-naphthyridine-2--imine compounds and synthesis, and achieves high yield, stable product and simple synthesis process. Effect

Inactive Publication Date: 2013-05-22
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is currently no alternative treatment for 5-fluorouracil-based combination chemotherapy ineffective

Method used

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  • Benzo [b][1,8]-naphthyridine-2-(1H)-imide derivative with antitumor activity and synthetic method thereof
  • Benzo [b][1,8]-naphthyridine-2-(1H)-imide derivative with antitumor activity and synthetic method thereof
  • Benzo [b][1,8]-naphthyridine-2-(1H)-imide derivative with antitumor activity and synthetic method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 4-p-methoxybenzoyl-9-methoxy-1,2-dihydrobenzo[ g ]imidazo[1,2- aSynthesis of ][1,8]naphthyridine (compound 1): Add 2-chloro-3-formyl-7-methoxyquinoline (2 mmol, 0.44 g) and 2- After p-methoxybenzoylmethyleneimidazolinidine (2 mmol, 0.44 g), add 1,4-dioxane (15 mL) and piperidine (0.2 mL) and heat to 80 °C under magnetic stirring Next, react for 24 hours. The reaction was monitored by TLC. After the raw material point completely disappeared, the reaction solution was poured into 50 ml of water to quench, and a yellow flocculent solid was precipitated. After filtration, it was washed with a mixed solvent of petroleum ether / ethyl acetate = 2:1, and dried to obtain an orange solid product with a yield of 89%. Melting point: 289-290°C.

[0037] H NMR spectrum (deuterated dimethyl sulfoxide + perchloric acid, Bruker AM 500 instrument): δ = 8.74 (s, 1H, Ar H ), 8.01 (d, J =8.6 Hz, 2H, Ar H ), 7.92 (d, J =7.4 Hz, 3H, Ar H ), 7.71 (d, J =8.4 Hz,1H, Ar H ), 7.17 (d, ...

Embodiment 2

[0041] 4-p-methylbenzoyl-9-methoxy-1,2-dihydrobenzo[ g ]imidazo[1,2- a Synthesis of ][1,8]naphthyridine (compound 2): Replace 2-p-methoxybenzoylmethyleneimidazoline in Example 1 with 2-p-tolylmethylene imidazoline Pyridine can be reacted to give orange solid 4-p-methylbenzoyl-9-methoxy-1,2-dihydrobenzo[ g ]imidazo[1,2- a ][1,8]naphthyridine (Compound 2), the yield was 86%. Melting point: 278-279°C.

[0042] High resolution mass spectrometry C 23 h 20 N 3 o 2 [M+H] + , the theoretical value is 370.1550; the measured value is 370.1557.

Embodiment 3

[0044] 4-benzoyl-9-methoxy-1,2-dihydrobenzo[ g ]imidazo[1,2- a Synthesis of ][1,8]naphthyridine (compound 3): Replacing 2-p-methoxybenzoylmethyleneimidazolidinine in Example 1 with 2-benzoylmethyleneimidazolinidine for reaction 4-Benzoyl-9-methoxy-1,2-dihydrobenzo[ g ]imidazo[1,2- a ][1,8]naphthyridine (Compound 3), the yield was 84%. Melting point: 280-281°C.

[0045] High resolution mass spectrometry C 22 h 18 N 3 o 2 [M+H] + , theoretical value 356.1394; measured value, 356.1393.

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Abstract

The invention discloses a novel benzo [b][1, 8]-naphthyridine-2-(1H)-imide derivative which has antitumor activity, and in particular relates to anti-solid tumor activity and more accurately the anti-lung cancer and anti-colon cancer activity as well as a structure shown in formula (I). The invention further discloses a synthetic method. In formula (I), n is 1, 2 or 3, but R, R1, R2, R3 and R4 are defined as in claim 1. The synthetic method comprises the step of heating a 2-halogen-3-formyl quinoline compound with a structure in formula (II) and a compound with a structure in formula (III) in an appropriate solvent in the presence of a catalyst so as to obtain a target product in formula (I).

Description

Technical field [0001] The present invention involves the activity of antitumor activity, especially the activity of antibody tumors. It is more accurate to say that it is a benzene with anti -lung cancer and anti -colorectal cancer activity [ b ] [1,8] -Piraidine-2- (1 H )--Side compounds and synthesis methods. Background technique [0002] Lung cancer is the most common malignant tumor in the lungs.The World Health Organization survey report reports that the incidence of lung cancer in many countries and regions accounted for the first place in malignant tumors and is one of the most common tumors that lead to death.And colon-rectal cancer is one of the most common malignant tumors in my country. At present, the incidence of malignant tumors is 4th.In recent years, the incidence of colorectal cancer has increased significantly, and this trend is more obvious in large and medium cities.It is also one of the most common tumors in Western countries. [0003] About 40 ~ 50%of patie...

Claims

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Application Information

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IPC IPC(8): C07D471/14A61K31/4745A61K31/519A61K31/551A61P35/00
Inventor 严胜骄林军张怡川
Owner YUNNAN UNIV
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