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Preparation method and use of iso-cryptolepine derivatives

A technology of isolemenine and compound, which is applied to the preparation of 8-position, 11-position derivatives and 11-position derivatives of 5-desmethyl isolemenine, and the application field of preparing antitumor drugs, which can solve the problem of High cost, few studies on antitumor activity, weak antitumor activity, etc.

Inactive Publication Date: 2015-04-15
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented chemical has been found effective against certain types of brain malignancies such as glioblastoma multiforme or lung carcinomas that are associated with these kinds of cellular growths called MCF-17/DF145.

Problems solved by technology

This patented describes different ways for making certain types of compounds that can be used effectively against cancer cells without causing harm or killing them permanently. These new chemicals have potential uses such as treatments targeted specifically towards specific molecular targets associated with tumors.

Method used

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  • Preparation method and use of iso-cryptolepine derivatives
  • Preparation method and use of iso-cryptolepine derivatives
  • Preparation method and use of iso-cryptolepine derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] The preparation method of 3-(11H-indo[3,2-c]quinolin-11-yl)propyl-1-amine

[0063] 1) Preparation of 2-nitroiodobenzene

[0064] Dissolve 1.38g (10mmol, 1equiv) of 2-nitroaniline in 5mL of concentrated hydrochloric acid, heat it to 100°C, keep it for 10 minutes to dissolve it, then cool it to 0°C with an ice-salt bath, add 0.83g ( 12mmol, 1.2equiv) Sodium nitrite was dissolved in 3mL of water, and slowly dropped into it under the condition of ice-salt bath. After dropping, the temperature of the reaction solution was raised to 70° C. for 2 to 3 hours. Cool the reaction solution to room temperature, add 15 mL of ethyl acetate to extract three times, combine the extracts, wash with dilute hydrochloric acid, sodium hydroxide solution, saturated sodium sulfite solution, and saturated sodium chloride solution in turn, dry with anhydrous sodium sulfate, and spin dry , and separated by column chromatography to obtain 2.82 g of a yellow solid, with a yield of 98.5%.

[0065]...

Embodiment 2

[0079] Preparation method of 4-(11H-indole[3,2-c]quinolin-11-yl)butyl-1-amine

[0080] Dissolve 170 mg (0.55 mmol, 1 equiv) of 11-(4-chlorobutyl) indole [3,2-c] quinoline in 5 mL of dimethyl sulfoxide, add 54 mg (0.83 mmol, 1.5 equiv) of sodium azide , reacted in an oil bath at 100°C for 12 hours. Cool the reaction solution, add 20 mL of water, extract with 60 mL of dichloromethane, wash the extract twice with water and saturated sodium chloride solution, dry over anhydrous sodium sulfate, and spin dry at low temperature to obtain 158 mg of oily azide. The rate is 91.1%.

[0081] Dissolve 158mg (0.5mmol, 1equiv) 11-(4-azidobutyl) indole [3,2-c] quinoline in a mixed solvent of 4.5mL tetrahydrofuran and 1.5mL water, add 262mg (1.0mmol, 2equiv ) triphenylphosphine, stirred at room temperature for 12 hours. The reaction solution was spin-dried, added 20 mL of water, extracted 3 times with 20 mL of ethyl acetate, combined the extracts, washed with saturated sodium chloride solut...

Embodiment 3

[0084] The preparation method of 11-(3-(1H-1,2,4-triazol-1-yl)propyl)-indole[3,2-c]quinoline

[0085] Dissolve 38 mg (0.55 mmol, 2 equiv) of 1,2,4-1H-triazole in 2 mL of dry DMF, add 13 mg (0.55 mmol, 2 equiv) of sodium hydrogen, pull out the hydrogen, stir at room temperature for 30 minutes, then dissolve 80 mg (0.27 mmol , 1equiv) 11-(3-chloropropyl)indole[3,2-c]quinoline was dissolved in 2mL DMF and dropped into the reaction solution, and reacted at room temperature for 3 hours. Add 20 mL of water to the reaction solution, extract three times with 20 mL of ethyl acetate, combine the extracts, wash with saturated sodium chloride solution, dry over anhydrous sodium sulfate, spin dry, and separate by column chromatography to obtain 32 mg of the product with a yield of 36.2%. .

[0086] Yellow solid, m.p.58-60℃; 1 H NMR (300MHz, CDCl 3 )δ9.38(s, 1H), 8.31(d, J=8.3Hz, 1H), 8.18(d, J=3.9Hz, 1H), 8.11-8.08(m, 2H), 7.71(t, J=7.4 Hz, 1H), 7.60-7.53(m, 2H), 7.48-7.40(m, 3H), 4.87...

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Abstract

The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a kind of 8-substituted and 11-substituted 5-demethylated iso-cryptolepine derivatives, structurally shown in the general formula (I). The invention further discloses a preparation method for the iso-cryptolepine derivatives and application of the iso-cryptolepine derivatives in the preparation of anti-tumor medicaments. An in-vitro anti-tumor activity test result shows that the iso-cryptolepine derivatives have higher suppression activity to MCF-7, HCT-116 and DU-145 cell strains, GI50 values of a part of the iso-cryptolepine derivatives are equivalent to that of a positive medicament adriamycin, and a novel anti-tumor medicament can be further developed and prepared (referring to the Specification for the general formula (I)).

Description

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Claims

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Application Information

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Owner CHINA PHARM UNIV
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