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Anti-tumor compound containing triazole heterocyclic structure and application thereof

An anti-tumor and compound technology, applied in the field of anti-tumor compounds containing a triazole heterocyclic structure, can solve problems such as bone loss and osteoporosis, and achieve strong anti-tumor activity and good selectivity

Inactive Publication Date: 2012-07-25
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] Triazole compounds can be used as aromatase inhibitors, angiogenesis inhibitors, enzyme inhibitors, etc. to exert anti-cancer effects. Anastrozole, Letrozole and Vorozole, which are currently used in clinical practice, are the third generation of aromatase inhibitors, which are highly effective and reversible. , specificity and other characteristics, but its long-term use has the risk of bone loss and osteoporosis

Method used

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  • Anti-tumor compound containing triazole heterocyclic structure and application thereof
  • Anti-tumor compound containing triazole heterocyclic structure and application thereof
  • Anti-tumor compound containing triazole heterocyclic structure and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of N-[3'-(4-phenyl-[1,2,3]-triazole)-propyl]-4-morpholinyl-1,8-naphthalimide (compound 1):

[0025] (1) 2.77 g of 4-bromo-1,8 naphthalene anhydride (0.01 mol) was added to 20 ml of ethylene glycol monomethyl ether, and 2.6 ml of morpholine was added thereto. Heating, reflux, thin-plate chromatography tracking reaction, until the reaction is complete, let stand overnight, filter, and weigh 2.16 grams of solids, yield 76.5%.

[0026]

[0027] (2) Get 2 grams of the product synthesized by step (1), add it to 30 milliliters of absolute ethanol, and then add 0.69 grams of n-propanolamine (0.7 ml) thereto. Raise the temperature, reflux, follow the reaction by thin-plate chromatography until the reaction is complete, let stand, and filter to obtain 2.0 g of a yellow solid.

[0028]

[0029] (3) Take 1.5 grams of the product synthesized by step (2), add it to 15 ml of ethyl acetate, slowly drop 0.8 ml of PBr3 within 20 minutes at room temperature, raise the tem...

Embodiment 2

[0038] Synthesis of N-[3'-(4-phenyl-[1,2,3]-triazole)-propyl]-4-thiomorpholine-1,8-naphthalimide (compound 2) :

[0039] Except that the morpholine ring is replaced by thiomorpholine, other synthesis and purification methods are the same as in Example 1 to obtain the target compound 2

[0040] 1HNMR (d6-CDCl 3 , 400MHz): δ (ppm): 2.46 (m, 2H), 2.97 (t, J 1 = 4Hz,J 2 = 4.4Hz, 4H), 3.50(t, J 1 = 4.4Hz,J 2 = 4.0Hz, 4H), 4.31(t, J 1 =6.4Hz,J 2 =6.8Hz, 2H), 4.54(t, J 1 =6.8Hz,J 2 =7.2Hz, 2H), 7.22(d, J=8.0Hz, 1H), 7.32(t, J 1 =6.8Hz,J 2 =7.6Hz, 1H), 7.42(t, J 1 =7.6Hz,J 2 =7.6Hz, 2H), 7.71(t, J 1 =8.0Hz,J 2 =7.6Hz, 1H), 7.80(d, J=8.0Hz, 2H), 8.04(s, 1H), 8.36(d, J=8.4Hz, 1H), 8.51(d, J=8.0Hz, 1H), 8.59 (d, J=7.2Hz, 1H).

[0041] HR-MS (m / z): C 27 h 25 N 5 o 2 S, calculated value: 483.1729, measured value: 483.1728.

Embodiment 3

[0043] Synthesis of N-[3'-(4-phenyl-[1,2,3]-triazole)-propyl]-4-hexahydropyridine-1,8-naphthalimide (compound 3):

[0044] Except replacing the morpholine ring with hexahydropyridine, other synthesis and purification methods are the same as in Example 1 to obtain the target compound 3

[0045] 1HNMR (d6-CDCl 3 , 400MHz): δ(ppm): 1.89(m, 4H), 2.45(m, 2H), 3.24(t, J 1 = 4.0Hz,J 2 =4.4Hz, 4H), 3.73(m, 2H), 4.31(t, J 1 =6.4Hz,J 2 =6.4Hz, 2H), 4.54(t, J 1 =7.2Hz,J 2 =6.8Hz, 2H), 7.17(d, J=8.4Hz, 1H), 7.32(t, J 1 =7.2Hz,J 2 =7.2Hz, 1H), 7.42(t, J 1 =7.6Hz,J 2 =7.2Hz, 2H), 7.68(t, J 1 =8.0Hz,J 2 =7.6Hz, 1H), 7.80(d, J=8.0Hz, 2H), 8.04(s, 1H), 8.39(d, J=8.4Hz, 1H), 8.49(d, J=8.4Hz, 1H), 8.58 (d, J=7.2Hz, 1H).

[0046] HR-MS (m / z): C 28 h 27 N 5 o 2 , calculated value: 465.2165, measured value: 465.2162.

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Abstract

The invention discloses a class of anti-tumor compounds containing a triazole heterocyclic structure and an application thereof, belonging to the technical field of medicinal chemistry. The compounds containing the triazole heterocyclic structure introduce quintuple 1,2,3-triazole ring in the form of side chains through the amino condensation, bromination, nitrine substitution, link reaction and other reactions on the basis of naphthalimide parent structure, select tetrazolium salt reduction to test 7721 hepatocellular in the experiment of inhibiting proliferation of tumor cells, and also select sulfonyl rhodamine B protein staining method to test MCF-7 breast cancer cells. The experiment results show that the anti-tumor compounds have wide anti-tumor activity and good inhibition effect on the normal growth of tumor cells derived from different tissues of liver cancer, breast cancer and the like.

Description

technical field [0001] The invention relates to a class of anti-tumor compounds containing a triazole heterocyclic structure and applications thereof, belonging to the technical field of medicinal chemistry. Background technique [0002] Naphthalimide compounds that introduce nitrogen-containing heteroatom substituents on the aromatic ring have good anticancer activity, and amonafide (N-(β-dimethylaminoethyl)-3-amino- 1,8-naphthalimide) (Malviya V K, Liu P Y, Alberts D S, et al.Am.J.Clin.Oncol., 1992, 15:41-44.) and mitonafide (N-(β-dimethyl (aminoethyl)-3-nitro-1,8-naphthalimide) (Brana M.F, Santos A., Roldan C.M., et al.Eur.J.Med.Chem.Chim.Ther., 1981,16 , 207-212) has entered phase II clinical trials. The compound can effectively inhibit the growth of tumor cells, and its mechanism of action is to intercalate between the base pairs of DNA, inhibit the synthesis of DNA and RNA, and inhibit topoisomerase II, so as to achieve the purpose of inhibiting tumors. However, in ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/06C07D401/12A61K31/5377A61K31/541A61K31/473A61K31/496A61P35/00G01N33/15G01N21/31
Inventor 李晓莲赵雯雯
Owner DALIAN UNIV OF TECH
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