Cryptotanshinone compound, as well as preparation method and application thereof

A technology for cryptotanshinone and compound, which is applied in the field of medicinal chemistry and can solve the problems of enzalutamide being drug-resistant and unable to be used for a long time.

Inactive Publication Date: 2017-05-24
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is currently reported that enzalutamide is also drug-resistant and cannot be used for a long time

Method used

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  • Cryptotanshinone compound, as well as preparation method and application thereof
  • Cryptotanshinone compound, as well as preparation method and application thereof
  • Cryptotanshinone compound, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0033] Example 1 2-(2-fluorophenyl)imidazol[4,5-f][10,11]-1,6,6-trimethyl-1,6,6-trimethyl-1,2,6 ,7,8,9-Hexahydrophenanthrene[1,2-b]-furan (CTS-01)

[0034]

[0035] Add cryptotanshinone (149mg, 0.5mmol), 2-fluorobenzaldehyde (65mg, 0.50mmol), 3ml glacial acetic acid, ammonium acetate (0.77g, 10mmol) into the reaction flask, and react at 100-105°C for 3-5 hours, After the reaction was completed, after the mixture was cooled to room temperature, 10ml of distilled water was added, concentrated ammonia water was added to adjust the pH to about 7, filtered, washed with water, and dried, and a bright yellow powder was prepared by silica gel column chromatography, which was the target product with a yield of 61.6% and a melting point of : 179.3~181.9°C. 1 H-NMR (300M, CDCl 3),δ=10.78(s,1H),8.58(t,J=6.7Hz,1H),7.92(d,J=8.7Hz,1H),7.52(d,J=8.7Hz,1H),7.34(dd ,J=15.1,7.5Hz,2H),7.23–7.15(m,1H),4.94(t,J=8.8Hz,1H),4.53–4.22(m,1H),4.19(d,J=6.8Hz, 1H), 3.40(s, 2H), 2.06(s, 2H), 1.82(s, 2...

example 2

[0036] Example two 2-(3-fluorophenyl)imidazol[4,5-f][10,11]-1,6,6-trimethyl-1,6,6-trimethyl-1,2,6, 7,8,9-Hexahydrophenanthrene[1,2-b]-furan (CTS-02)

[0037]

[0038] Add cryptotanshinone (149mg, 0.5mmol), 3-fluorobenzaldehyde (130mg, 1.0mmol), 15ml glacial acetic acid, ammonium acetate (2.0g, 26mmol) into the reaction flask, and react at 100-105°C for 3-5 hours, After the reaction was completed, after the mixture was cooled to room temperature, 30ml of distilled water was added, concentrated ammonia water was added to adjust the pH to about 7, filtered, washed with water, and dried, and a bright yellow powder was prepared by silica gel column chromatography, which was the target product with a yield of 55.8% and a melting point of : 105.2-109.3°C. 1 H-NMR (300M, CDCl 3 ),δ=9.99(s,1H),7.92(d,J=8.6Hz,1H),7.82(d,J=7.5Hz,1H),7.53(d,J=8.7Hz,1H),7.44(dd ,J=12.8,6.3Hz,1H),7.09(s,1H),4.87(s,1H),4.36(s,1H),4.09(s,1H),3.49(s,2H),2.08(d, J=5.1Hz, 2H), 1.83(s, 2H), 1.56(d, J=6.3Hz...

example 3

[0039] Example 3 2-(4-fluorophenyl)imidazol[4,5-f][10,11]--1,6,6-trimethyl-1,2,6,7,8,9-hexahydrophenanthrene And[1,2-b]-furan (CTS-03)

[0040]

[0041] The reaction is the same as in Example 1, and 4-fluorobenzaldehyde is used instead of 2-fluorobenzaldehyde to obtain the target product with a yield of 50.7% and a melting point of 143.8-147.2°C. 1 H-NMR (300M, CDCl 3 ),δ=9.96(s,1H),8.09–7.98(m,2H),7.92(d,J=8.5Hz,1H),7.51(d,J=8.7Hz,1H),7.17(t,J= 8.6Hz, 2H), 4.88(t, J=8.8Hz, 1H), 4.53–4.31(m, 1H), 4.05(s, 1H), 3.49(s, 2H), 2.15–1.99(m, 2H), 1.88–1.74 (m, 2H), 1.54 (s, 3H), 1.40 (d, J=3.6Hz, 6H). 13 C-NMR (125MHZ, CDCl 3 ), δ=19.74, 2.93, 30.38, 31.80, 34.48, 37.01, 38.42, 79.23, 115.99, 116.17, 120.36, 123.65, 124.23, 126.48, 128.00, 140.66, 143.868, 152.47, 164.

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Abstract

The invention provides a cryptotanshinone compound, as well as a preparation method and application thereof, and relates to the technical field of medicinal chemistry. The invention further discloses a chemical structure and medical application of the compound. The compound III has a structural general formula as shown in the specification, wherein R is phenyl containing F, Cl, Br, CH3, OCH3, NO2, OH and other substituents. The cryptotanshinone compound can be used as an anti-androgen receptor medicine for treating diseases related to androgen, including prostate cancer, prostatic hyperplasia, acne, alopecia, hirsutism, muscle failure, gonad dysfunction, high cholesterol, male infertility, male sexual dysfunction, anemia, obesity and other diseases.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, and relates to some novel anti-androgen receptor compounds, pharmaceutical formulations containing the compounds and their use methods, especially cryptotanshinone compounds and their uses. Background technique [0002] Androgen receptor (AR) belongs to the steroid receptor in the nuclear receptor superfamily, and is a member of the ligand-activated nuclear transcription factor superfamily widely distributed in organisms. Androgen and androgen receptor play an extremely important role in the growth and development of the prostate, the maintenance of its function, and the occurrence, development, progression, and metastasis of prostate cancer. Many diseases in older men are related to androgens and androgen receptors. As men age, the level of androgen in the body will decrease, accompanied by muscle loss in the body, decline in sexual function, and "male menopause" and other phenomena...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048A61P13/08A61P17/14A61P15/08A61P15/00A61P3/06A61P3/04A61P7/06A61P21/00A61P35/00A61P17/10
CPCC07D491/048
Inventor 徐德锋
Owner CHANGZHOU UNIV
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