Synthesis of naphthalene nucleus 4-position 1,2,3-triazole containing naphthalimide derivative and application thereof

A technology of naphthalimide and derivatives, applied in the field of synthesis of naphthalimide derivatives

Inactive Publication Date: 2014-10-01
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, they have been shown to cause side effects such as myelosuppression, vomiting, and skin rashes in c...

Method used

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  • Synthesis of naphthalene nucleus 4-position 1,2,3-triazole containing naphthalimide derivative and application thereof
  • Synthesis of naphthalene nucleus 4-position 1,2,3-triazole containing naphthalimide derivative and application thereof
  • Synthesis of naphthalene nucleus 4-position 1,2,3-triazole containing naphthalimide derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] N-(N',N'-Dimethylaminoethyl)-4-(4-morpholinomethyl-[1,2,3]-triazole)-1,8-naphthalimide (F1 )Synthesis

[0027] ①In a 50mL two-necked bottle, add 2.50g of 4-bromo-1,8-naphthalene anhydride and 35mL of DMF, stir well at room temperature, and dissolve 0.88g of NaN 3 Dissolve in 2 mL of water, drop into the reaction system, heat to 40°C for 2 hours, pour into cold water after standing, filter with suction, wash with water, and dry to obtain 2.01 g of compound (b) as a yellow-green solid with a yield of 93%.

[0028]

[0029] ②In a 50mL two-necked bottle, add 1g of compound (b) and 30mL of absolute ethanol, stir well at room temperature, add 0.6mL of N,N-dimethylethylenediamine into the reaction system, heat to 50°C for 2h, and statically Pour it into cold water, filter with suction, wash with water, and dry to obtain 1.17 g of compound (c) as a light yellow solid with a yield of 96%.

[0030]

[0031] ③In a 25mL two-necked bottle, add 0.62g compound (c), 188μL 3-mor...

Embodiment 2

[0036] N-(N',N'-dimethylaminoethyl)-4-(4-thiomorpholinomethyl-[1,2,3]-triazole)-1,8-naphthalimide ( Synthesis of F2)

[0037] Except that 3-thiomorpholinopropyne was used instead of 3-morpholinopropyne, other synthesis and purification methods were the same as in Example 1 to obtain the target product F2 as a light yellow solid with a yield of 70%. m.p.: 143.4-144.0°C.

[0038]

[0039] 1 H NMR (400MHz, CDCl 3 )δ8.72(d, J=7.2Hz, 2H), 8.27(d, J=8.8Hz, 1H), 7.97(s, 1H), 7.93–7.77(m, 2H), 4.39(t, J=6.3 Hz,2H),3.89(s,2H),2.90(t,4H),2.75(t,2H),2.74(t,4H),2.42(s,6H).

[0040] TOF MS (m / z): C 23 h 27 N 6 o 2 S+, Calculated: 451.1916, Found: 451.1918.

Embodiment 3

[0042] N-(N',N'-dimethylaminoethyl)-4-(4-piperidinylmethyl-[1,2,3]-triazole)-1,8-naphthalimide (F3 )Synthesis

[0043] Except that 3-morpholinopropyne was replaced by 3-piperidylpropyne, other synthesis and purification methods were the same as in Example 1, and the target product F3 was obtained as a yellow solid with a yield of 76%. m.p.: 142.5-144.2°C.

[0044]

[0045] 1 H NMR (400MHz, CDCl 3)δ8.71(d, J=7.7Hz, 2H), 8.30(d, J=8.5Hz, 1H), 8.10(s, 1H), 7.89–7.81(m, 2H), 4.37(t, J=6.9 Hz, 2H), 3.89(s, 2H), 2.70(t, J=6.9Hz, 2H), 2.64(t, 4H), 2.37(s, 6H), 1.74–1.63(m, 4H), 1.57–1.44 (m,2H).

[0046] 13 C NMR (101MHz, CDCl 3 )δ163.65,163.13,145.18,138.18,132.26,130.70,129.51,129.09,128.59,126.36,125.04,123.80,123.44,122.92,56.90,54.87,54.05,45.938.75,28

[0047] TOF MS (m / z): C 24 h 29 N 6 o 2 +, calculated value: 433.2352, measured value: 433.2334.

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Abstract

The invention relates to a synthesis of naphthalene nucleus 4-position 1,2,3-triazole containing naphthalimide derivative and application thereof, and belongs to the field of organic synthesis. The derivative has a compound in a general formula A structure; the preparation method of the derivative comprises the following steps: by using 4-bromo-1,8-anhydride naphthalene as raw material, amidating with the corresponding chain amine through azidation, finally reacting with an amido-propyne connected with cyclic amine; the obtained derivative is applied to a tumor cell inhibition drug.

Description

technical field [0001] The invention relates to the synthesis and application of a class of naphthalene imide derivatives containing 1,2,3-triazole at the 4-position of the naphthalene ring, and belongs to the field of organic synthesis. Background technique [0002] The research on DNA intercalators is a focus of attention in the interdisciplinary disciplines of chemistry, medicine and molecular biology. The intercalator intercalates into the base pairs of DNA, changes its conformation, causes the DNA chain to unwind and lengthen, thereby restricting its replication and exhibiting anti-tumor activity. Naphthalimide derivatives have made great progress in the research of antitumor drugs, such as the famous naphthalimide lead drugs Amonafide and Mitonafide, which have entered clinical trials. However, they have been shown to cause side effects such as bone marrow suppression, vomiting, and skin rashes in clinical trials. Therefore, the design and synthesis of new and effecti...

Claims

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Application Information

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IPC IPC(8): C07D401/04A61K31/5377A61K31/541A61K31/496A61K31/473A61P35/00
CPCC07D401/04
Inventor 李晓莲于汀汀马茹菲汪五根黄驰洲
Owner DALIAN UNIV OF TECH
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