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Novel curcumin analogues and uses thereof

A technology of curcumin, compounds, applied in the field of new curcumin analogues and their uses

Inactive Publication Date: 2007-11-21
THE UNIV OF NORTH CAROLINA AT CHAPEL HILL +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Although antiandrogen hormone therapy is widely used in the treatment of prostate cancer, some antiandrogens can produce AR agonist effects, which can lead to "antiandrogen withdrawal syndrome"

Method used

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  • Novel curcumin analogues and uses thereof
  • Novel curcumin analogues and uses thereof
  • Novel curcumin analogues and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0167] A. Materials and methods

[0168] Commercially available curcumin (Aldrich) containing minor fractions 2 and 3 was purified by column chromatography (silica gel, CHCl 3 -MeOH), to obtain compound 1-3. Compounds 39-44 were purchased from Aldrich, Inc (Milwaukee, WI).

[0169] Dimethyl Curcumin (4)

[0170] The Et of curcumin (1) 2 The O and MeOH solutions were treated with excess diazomethane in ether for 24 h. The solvent was removed in vacuo, and the residue was purified by silica gel column chromatography and PLC to obtain yellow needles of 4 (yield 19.8%);

[0171] mp 129-130°C (MeOH) (Roughley et al., J. Chem. Soc. Perkin I, 2379-2388 (1973)) (128-130°C); 1 H NMR (300MHz, CDCl 3 ): δ3.93 (12H, s, OCH 3 x4), 5.82(1H, s, 1-H), 6.48(2H, d, 16Hz), 6.88(2H, d, J=8Hz), 7.08(2H, bs), 7.15(2H, bd), 7.61( 2H, J=16Hz); 13 CNMR (300MHz, CDCl 3 ): δ55.9, 56.0, 101.3, 109.8, 111.1, 122.0, 122.6, 128.1, 140.4, 149.2, 151.0, 183.2

[0172] Prep...

Embodiment 2

[0230] Synthesis and Characterization of Other Curcuminoid Analogs

[0231] Other curcumin analogues are shown in Table 1 below.

[0232] Table 1. Curcumin analogues

[0233]

[0234]

[0235]

[0236]

[0237] The aforementioned compounds are synthesized as follows:

[0238]

[0239] The synthetic method was improved with the strategy developed by Pedersen et al. Acetylacetone (0.2ml, 2mmol) and boric anhydride (100mg, 1.4mmol) were dissolved in 15ml ethyl acetate. The solution was stirred at 70°C for 0.5 hours. 5-Hydroxymethylfuran (506mg, 4mmol) and tributyl borate (1.08ml, 4mmol) were added. The mixture was stirred for 30 min. A solution of butylamine (0.3ml, 3mmol) in EtOAc (4ml) was then added dropwise over 15min. Stirring was continued at 85°C for 5 hours. The mixture was then hydrolyzed by adding 8 ml of 1N HCl and stirring at 60°C for 0.5 hours. The organic layer was separated. The aqueous layer was extracted with ethyl acetate. The combined o...

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Abstract

The present invention relates to compounds capable of acting as androgen receptor, antagonists, pharmaceutical formulations containing the same, and methods of use thereof. Such uses include, but are not limited to, use as antitumor agents, particularly for the treatment of cancers such as colon, skin and prostate cancer and to induce androgen receptor antagonist activity in a subject afflicted with an androgen-related affliction. Examples of androgen-related afflictions include, but are not limited to, baldness, hirsutism, behavioral disorders, acne, and uninhibited spermatogenesis wherein inhibition of spermatogenesis is so desired.

Description

[0001] related application [0002] This application is a continuation-in-part of PCT International Application No. PCT / US2003 / 009350, entitled "Novel Curcumin Analogues and Uses Thereof", filed March 27, 2003, which was filed on October 30, 2003 Published in English, it claims priority to U.S. Patent Application Serial No. 10 / 124,642, entitled "Novel Curcumin Analogs and Uses Thereof," filed April 17, 2002, now designated as U.S. Patent No. 6,790,979 promulgated, the disclosure of which is incorporated herein by reference in its entirety. [0003] Federal Government Funding Statement [0004] This invention was made with government support under Grant Numbers CA-17625 and CA-55639. The government has certain rights in this invention. field of invention [0005] The present invention relates to compounds which act as androgen receptor antagonists, pharmaceutical formulations containing such compounds and methods of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/44C07D213/46C07D213/62C07D317/72A61K31/085A61K31/12A61K31/192A61K31/216A61K31/22A61K31/222A61K31/335A61K31/357A61K31/385A61K31/415A61P15/08A61P17/10A61P17/14A61P25/02A61P31/04A61P35/00A61P35/02A61P43/00C07C49/248C07C49/255C07C49/755C07C49/84C07C59/84C07C59/90C07C69/738C07C205/45C07D231/12C07D313/00C07D339/06
CPCC07C205/45C07C69/738C07C49/248C07C49/84C07D307/58C07C49/755C07C59/84C07C49/255A61P5/28A61P15/00A61P15/08A61P15/16A61P17/00A61P17/04A61P17/10A61P17/14A61P25/00A61P25/02A61P25/14A61P25/18A61P31/04A61P35/00A61P35/02A61P35/04A61P43/00
Inventor K·-H·李L·林C·C·-Y·施C·-Y·苏J·伊施达H·奥特苏H·-K·王H·伊托卡瓦C·常
Owner THE UNIV OF NORTH CAROLINA AT CHAPEL HILL
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