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Furan-azo- [3,2-g] chromene compound and application thereof

A technology of compounds and compositions, applied in the directions of active ingredients of heterocyclic compounds, digestive system, organic chemistry, etc.

Active Publication Date: 2010-08-18
SHENYANG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But clinically used tamoxifen and raloxifene can cause adverse reactions such as endometrial cancer and hot flashes (Fisher B, Costantino JP, Wickerham DL, et al.J Nati Cancer Inst, 1998, 90: 1371- 1388; Walsh BW, Kuller LH, Wild RA, et al. J Am Med Assoc, 1998, 279:1445-1451)

Method used

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  • Furan-azo- [3,2-g] chromene compound and application thereof
  • Furan-azo- [3,2-g] chromene compound and application thereof
  • Furan-azo- [3,2-g] chromene compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1: Preparation of 2-benzoyl-3-(4-methoxyphenyl)-6,7-dihydro-5H-furo[3,2-g]chromene

[0044] Add 0.26 mol of 2', 4'-dihydroxyacetophenone into the round bottom flask, mix well with 232 mL of triethyl orthoformate, and slowly add 26.4 mL of perchloric acid thereinto. After reacting for 30 minutes, 300 mL of ether was added, and a solid was precipitated. Suction filtration, transfer the dried solid into a 1000mL round bottom flask, add 250mL hot water, reflux for two hours, suction filtration, recrystallization with ethanol to obtain 22.69g of 7-hydroxychromone, yield 53.2%, MS m / z (M) 162.

[0045] Put 0.15 mol of 7-hydroxychromone into a 1000 mL round bottom flask, add 2.50 g of 5% palladium carbon and 300 mL of ethanol, pass in hydrogen, react at 50 °C for 48 hours, remove the palladium carbon by suction filtration, and remove the ethanol by rotary evaporation. 21.39 g of 7-hydroxychroman was obtained, the yield was 92.4%, and MS m / z (M) was 150.

[0046] Dis...

Embodiment 2

[0049] Example 2: Preparation of 2-(4-methoxybenzoyl)-3-phenyl-6,7-dihydro-5H-furo[3,2-g]chromene

[0050] According to the method in Example 1, 0.65 grams of 2-(4-methoxybenzoyl)-3-phenyl-6,7-dihydro-5H-furo[3,2-g]chromene yellow crystals were obtained, Yield 60%, Mp: 130.3-132.5°C. ESI-MS m / z (M+1) 385.13; 1 HNMR (600MHz, CDCl 3 , δ: ppm) 2.04 (t, 2H, CH 2 ), 2.91(t, 2H, CH 2 ), 3.83 (s, 3H, OCH 3 ), 4.26(t, 2H, CH 2 ), 6.83(dd, 2H, ArH, J=7.0Hz, J=1.9Hz), 7.03(s, 1H, ArH), 7.30(s, 1H, ArH), 7.35-7.49(m, 5H, ArH), 7.90 (dd, 2H, ArH, J = 7.0 Hz, J = 1.9 Hz).

Embodiment 3

[0051] Example 3: Preparation of 2-(4-chlorobenzoyl)-3-(4-methoxyphenyl)-6,7-dihydro-5H-furo[3,2-g]chromene

[0052] According to the method of Example 1, 2-(4-chlorobenzoyl)-3-(4-methoxyphenyl)-6,7-dihydro-5H-furo[3,2-g]chromene was obtained 0.56 g of yellow crystals, yield 60%, Mp: 135.3-137.5°C. ESI-MS m / z (M+1) 419.13; 1 HNMR (600MHz, CDCl 3 , δ: ppm): 2.05(t, 2H, CH 2 ), 2.91(t, 2H, CH 2 ), 3.84(s, 3H, OCH 3 ), 4.27(t, 2H, CH 2 ), 6.92(dd, 2H, ArH, J=7.0Hz, J=1.9Hz), 7.00(s, 1H, ArH), 7.31-7.32(m, 3H, ArH), 7.40-7.41(m, 2H, ArH ), 7.80 (dd, 2H, ArH, J = 7.0 Hz, J = 1.9 Hz).

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Abstract

The invention relates to a furan-azo-[3,2-g] chromene derivative and application thereof, belonging to the technical field of medicine. The furan-azo-[3,2-g] chromene derivative comprises stereoisomers and pharmaceutically applicable salts of a compound of the furan-azo-[3,2-g] chromene derivative and has a structural general formula shown in the specification of the invention. The furan-azo-[3,2-g] chromene derivative and pharmaceutically applicable acid addition salts of the compound can be used as an estrogen receptor regulator singly or by combining with traditional drugs to treat or prevent various diseases related to estrogen functions, such as bone loss, fracture, osteoporosis, hot flash, LDL (Low Density Lipoprotein) cholesterol level rise, angiocardiopathy, cognitive function impairment, brain-wasting diseases, anxiety, depression caused by estrogen shortage, inflammation, inflammatory bowel diseases, sexual dysfunction, hypertension, retinosis and cancer, especially breast cancer, ovarian cancer, osteosarcoma, endometrial cancer and prostatic cancer.

Description

technical field [0001] The invention relates to a furo[3,2-g]chromene compound, its pharmaceutical application as an estrogen receptor modulator, and a preparation method thereof. Background technique [0002] Compounds that mimic estrogen-like effects have a wide range of therapeutic and prophylactic applications, including: relief of menopausal symptoms, treatment of acne, treatment of dysmenorrhea and dysfunctional uterine bleeding, osteoporosis, prostate cancer and prevention of cardiovascular disease. [0003] Studies have found that there are two types of estrogen receptors: ERα and ERβ. After the ligand binds to these two isoforms, it exerts physiological effects with different tissue specificities. [0004] What is needed in the art is a compound that can produce a positive response like estrogen replacement therapy but without adverse side effects or with reduced side effects, and exert tissue-specific estrogen-like effects on the body. [0005] Furochromene deriv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04A61K31/352A61P19/08A61P19/10A61P35/00A61P19/02A61P13/10A61P15/00A61P13/08A61P1/00A61P13/12A61P27/02A61P9/00A61P11/00A61P3/04A61P3/10A61P25/28A61P17/10A61P5/30A61P1/02A61P9/12A61P27/12A61P43/00
CPCC07D493/04A61K31/35A61K31/352A61P1/00A61P1/02A61P3/04A61P3/10A61P5/30A61P9/00A61P9/12A61P11/00A61P13/08A61P13/10A61P13/12A61P15/00A61P17/10A61P19/02A61P19/08A61P19/10A61P25/28A61P27/02A61P27/12A61P35/00A61P43/00
Inventor 胡春王世辉王岩黄二芳刘晓平李大伟
Owner SHENYANG PHARMA UNIV
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