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Chalcone coumarins

A technology of compounds and ring atoms, applied in the fields of organic active ingredients, sexual diseases, bone diseases, etc., can solve problems such as poor bioavailability

Inactive Publication Date: 2004-03-24
英登纳股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

All these compounds are generally characterized by almost complete insolubility in water and poor bioavailability in vivo (which is related to the rapid metabolism of phenolics), and a remarkable affinity for lipids and proteins

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1. General method for preparing chalcones

[0040]

[0041] Method A.

[0042] A 50% KOH solution (3 ml) was added to an equimolar solution of ketone (0.0075 mol) and aldehyde (0.0075 mol) in 95% ethanol at room temperature with vigorous stirring. The reaction was stirred overnight, then diluted with water and acidified. The precipitate was isolated by filtration and dried under vacuum. The compound was crystallized from ethanol or chromatographically followed by crystallization from ethanol. method B.

[0043] Ketone (0.0075 mol), aldehyde (0.0075 mol), piperidine (15 ml) and acetic acid (75 ml) were added countercurrently in 95% ethanol (80 ml) for 5 hours. Molecular sieves were added to the solution to remove water and left overnight. The resulting precipitate was collected and crystallized. If the product does not precipitate under these conditions, the solvent is evaporated in vacuo and the residue is purified by column chromatography on silica gel...

Embodiment 2

[0044] 50% KOH solution (3ml) was added to equimolar 4-methyl-7-(2-methylprop-1-enyloxy)-8-acetylcoumarin (2.14g, 0.0075mol) and To a solution of pyridine-3-carbaldehyde (0.8 g, 0.0075 mol) in 95% ethanol, the addition was carried out at room temperature with vigorous stirring. The reaction was stirred overnight, then diluted with water and acidified. The precipitate was isolated by filtration and dried under vacuum. Crystallization of this compound from ethanol afforded 0.84 g of product, m.p. 156-157°C, 1 H-NMR (CDCl 3 )δ: 1.69(s, 3H); 1.72(s, 3H); 2.44(d, 3H, J=1.22Hz); 4.65(d, 2H, J=6.5Hz); 5.34-5.38(m, 1H); 6.16(d, 1H, J=1.2Hz); 6.95(d, 1H, J=8.8Hz); 7.07(d, 1H, J=18Hz); 7.36(d, 1H); 7.30-7.40(m, 1H) ; 7.64 (d, 1H, J = 8.9 Hz); 7.90 (m, 1H); 8.58-8.68 (m, 2H). Example 3. 1-[4-methyl-7-(3-methylbut-2-enyloxy)coumarin-8-yl]-3-phenyl-propen-1-one (see Attached structure diagram VIB119)

Embodiment 3

[0045] A 50% solution of KOH (3ml) was added to equimolar 4-methyl-7-(3-methylbut-2-enyloxy)-8-acetylcoumarin (2.14g, 0.0075mol) and To a solution of benzaldehyde (0.8 g, 0.0075 mol) in 95% ethanol, the addition was carried out at room temperature with vigorous stirring. The reaction was stirred overnight, then diluted with water and acidified. The precipitate was isolated by filtration and dried under vacuum. Crystallization of this compound from ethanol afforded 1.34 g of product, m.p. 114-16°C, 1 H-NMR (CDCl 3 )δ: 1.69(s, 3H); 1.72(s, 3H); 2.44(d, 3H, J=1.22Hz); 4.65(d, 2H, J=6.5Hz); 5.34-5.38(m, 1H); 6.16(d, 1H, J=1.2Hz); 6.95(d, 1H, J=8.8Hz); 7.00(d, 1H, J=18Hz); 7.10(d, 1H); 7.30-7.40(m, 3H) ; 7.45-7.52 (m, 12H); 7.61 (d, 1H, J = 8.9 Hz). Example 4. 1-[4-methyl-7-(3-methylbut-2-enyloxy)coumarin-8-yl]-3-(3,4,5-trimethoxybenzene base) propen-1-one (see attached structure diagram VIB 120)

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Abstract

Disclosed are novel chalcone derivatives having Formula (I). The compounds possess antiproliferative activity, and are useful for the manufacture of a medicament for the treatment or prevention of neoplasms, particularly those located in the uterus, ovary or breast. The compounds of the invention may also be useful in the manufacture of a medicament for the treatment or prevention of menopausal disorders and osteoporosis.

Description

technical field [0001] The present invention relates to a new class of compounds having structures related to certain naturally occurring and synthetic chalcones, processes for the preparation of these compounds and their use in medicine. Background technique [0002] The common name of the known compound 1,3-diphenyl-2-propen-1-one is chalcone. A number of naturally occurring flavonoids share the structural characteristics of chalcones and are known collectively as "chalcones". Some flavonoids, including those also classified as chalcones, have recently been shown to have anticancer activity (Cancer Research 48 , 5754, 1988) and chemopreventive activity in some tumors (J.Nat.Prod. 53 , 23, 1990). [0003] In particular quercetin, a flavonoid ubiquitous in plants, has been shown to be effective against human leukemia cells (Br.J.of Haematology, 75, 489, 1990) and other cell lines (Br.J.Cancer, 62 , 94, 942, 1990; Int. J. Cancer, 46 , 112.1990; Gynaecologic Oncology, 45,...

Claims

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Application Information

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IPC IPC(8): A61K31/37A61K31/381A61K31/4433A61P15/12A61P19/10A61P35/00C07D311/18C07D405/06C07D405/08C07D409/06C07D409/08
CPCC07D311/18C07D405/06A61K31/37C07D409/06A61P15/12A61P19/10A61P35/00A61K31/335A61K2300/00
Inventor E·博姆巴德利P·瓦伦蒂
Owner 英登纳股份有限公司
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