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1-(3-indolyl)-6,7-methylene dioxy-1,2,3,4-tetrahydro isoquinoline derivative and its prepn and use

A methylenedioxy, tetrahydroisoquinoline technology, applied in botanical equipment and methods, chemicals for biological control, biocides, etc., can solve multidrug resistance, rapid tumor cell growth, Variability, etc.

Inactive Publication Date: 2007-08-22
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the tumor has the ability to metastasize in the early stage, about 50% of the patients with clinically diagnosed primary tumors have developed distant metastases. More than 100% is related to the multidrug resistance of tumor cells, and the antitumor drugs currently used in clinical practice are far from meeting the requirements of treatment

Method used

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  • 1-(3-indolyl)-6,7-methylene dioxy-1,2,3,4-tetrahydro isoquinoline derivative and its prepn and use
  • 1-(3-indolyl)-6,7-methylene dioxy-1,2,3,4-tetrahydro isoquinoline derivative and its prepn and use
  • 1-(3-indolyl)-6,7-methylene dioxy-1,2,3,4-tetrahydro isoquinoline derivative and its prepn and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Example 1: Synthetic compound 1,1-(3-indolyl)-2-benzoyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline

[0098] 1) Preparation of 1,2-methylenedioxy-4-(2-nitro-vinyl)-benzene

[0099] Put 17.5g of piperonal (0.117mol) and 7.63g (0.096mol) of ammonium acetate into 80ml of glacial acetic acid, add 51.8ml (0.924mol) of nitromethane, heat and reflux for 2 hours under the protection of nitrogen flow, and put it in the refrigerator after cooling Leave to stand for 4 hours, filter with suction, wash the filter cake with a small amount of cold ethanol, drain the solvent, and dry under an infrared lamp. 18 g of pale yellow needle-like solid were obtained, yield: 80.0%. Melting point: 161-163°C.

[0100] 2) Preparation of 2-(1,2-methylenedioxy-4-phenyl)-ethylamine hydrochloride

[0101] 4.8g HgCl 2 Dissolve in 96ml of water, add 2.4ml of concentrated hydrochloric acid, add 60g of zinc powder under rapid stirring, and stir for 20 minutes. Suction filtration to obtain zinc-...

Embodiment 2

[0115] Example 2: Synthetic compound 2,1-(3-indolyl)-2-o-chlorobenzoyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline

[0116] 1-(3-indolyl)-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline reacts with o-chlorobenzoyl chloride, and the synthesis process is the same as 1. Yield: 36.2%. Melting point: 150-154°C. 1 HNMR (CDCl 3 )δ (ppm): 2.60 (m, 1H, Isoquinoline-C 4 -H), 3.00(m, 1H, Isoquinoline-C 4 -H), 3.35(m, 1H, Isoquinoline-C 3 -H), 3.40(m, 1H, Isoquinoline-C 3 -H), 5.94(d, 2H, OCH 2 O, J = 5.8 Hz), 6.62 (s, 1H, Isoquinoline-C 8 -H), 6.67(s, 1H, Isoquinoline-C 5 -H), 6.80(d, 1H, Isoquinoline-C 1 -H, J=6.4Hz), 7.02-7.42(m, 8H, Ar-H), 7.84(t, 1H, Indole-C 4’ -H, J=7.8 Hz), 8.22 (d, 1H, Indole-NH, J=8.3 Hz). MS (ESI) m / z (M-1) 429.1.

Embodiment 3

[0117] Example 3: Synthetic compound 3,1-(3-indolyl)-2-p-chlorobenzoyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline

[0118] 1-(3-indolyl)-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline reacts with p-chlorobenzoyl chloride, the synthesis process is the same as 1. Yield: 45.0%. Melting point: 220-222°C. 1 HNMR (CDCl 3 ) δ (ppm): 2.65 (m, 1H, Isoquinoline-C 4 -H), 2.90(m, 1H, Isoquinoline-C 4 -H), 3.43(m, 1H, Isoquinoline-C 3 -H), 3.54 (m, 1 H, Isoquinoline-C 3 -H), 5.94(d, 2H, OCH 2 O, J=5.8 Hz), 6.64 (s, 1H, Isoquinoline-C 8 -H), 6.66(s, 1H, Isoquinoline-C 5 -H), 6.78(s, 1H, Isoquinoline-C 1 -H), 7.08-7.46(m, 8H, Ar-H), 7.78(d, 1H, Indole-C 4’ -H, J=7.7 Hz), 8.37 (br-s, 1H, Indole-NH). MS (ESI) m / z (M+1) 431.1.

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Abstract

The present invention belongs to the field of medicine synthesis technology, and is especially 1- (3-indolyl)- 6, 7-methylene dioxy-1, 2, 3, 4-tetrahydro isoquinoine compounds and analogs in the general expression as shown and with substituted hydroxyl radical or acyl radical in the 2nd position, and their preparation process and medical application. Initial pharmacodynamic research of extracorporeal rice blast mold resisting experiment and extracorporeal antitumor experiment shows that these compounds has excellent activity, so that they may be developed into antifungal medicine and antitumor medicine.

Description

technical field [0001] The invention belongs to the field of medicine synthesis and relates to 1-(3-indolyl)-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline derivatives. It specifically relates to a 1-(3-indolyl)-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline derivative substituted with various hydrocarbon groups or acyl groups at the 2-position, Its preparation method and application in medicine. Background technique [0002] With the popularization and abuse of antibiotics in the world, drug resistance tends to appear in both Gram-positive bacteria and negative bacteria, and the drug resistance problem of Gram-positive bacteria is even more serious. Some non-pathogenic bacteria have become conditional pathogens, such as Proteus, Pseudomonas aeruginosa, etc.; and infections such as viruses and deep fungi still lack good prevention and treatment drugs. And with the wide application of antineoplastic drugs, immunosuppressants, etc., the mass development of organ transp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/04A61K31/4355A61P31/10A61P35/00A01N43/90A01P3/00
Inventor 闻韧郑剑斌董肖椿
Owner FUDAN UNIV
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