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Tanshinone compounds, preparation method and use thereof
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Technology of a compound, tanshinone, applied in the field of medicinal chemistry
Active Publication Date: 2016-01-27
利川市常大产业技术研究院有限公司
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(Crawford et al., NewEngl.J.Med., 321,419-424(1989)), but the drug has many side effects (Neumann et al., J.Clin.Oncol., 1,41-65(1982))
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example 1
[0077] Example 1, 1,6,6-trimethyl-6,7,8,9,10,11-hexahydro-10,11-dioxophenanthrene[1,2-b]furan-2-carbaldehyde ( Tan-001)
[0078]
[0079] Add tanshinone Ⅱ A (2.94g, 19mmol) and 50ml dimethylformamide (DMF) into the reaction bottle, stir and add 7ml phosphorus oxychloride dropwise at room temperature, react at 70-80°C for 2 hours, then pour the reaction solution into 750ml In ice water with yellow precipitate, filtered, washed with water, and dried to obtain the crude product, the crude product was obtained by silica gelcolumn chromatography, and the yield was 67%. 1 H-NMR (300MHz, (CDCl 3 )), δ:9.86(s,1H),8.80(d,J=6.3Hz,1H),7.71(d,J=6.3Hz,1H),3.21(m,2H),2.65(s,3H), 1.78-1.82(m,2H),1.65-1.69(m,2H),1.42(s,6H).
example 2
[0080] Example two, 2-bromo-10,11-dioxo-1,6,6-trimethyl-6,7,8,9,10,11-hexahydrophenanthrene[1,2-b]furan ( Tan-002)
[0081]
[0082] Add tanshinone Ⅱ A (1.47g, 5mmol) and 80ml of acetic acid into the reaction flask, slowly add dropwise the solution of N-bromosuccinimide NBS (1.07g, 6mmol) in 25ml of acetic acid, react at room temperature for 6 hours, add water, Extract with dichloromethane, combine the extracts, wash with water successively, wash with aqueous sodiumsulfite solution, wash with saturated aqueous sodiumchloride solution, dry over anhydroussodiumsulfate, and use silica gelcolumn chromatography to obtain a red solid, 1 H-NMR (300MHz, (CDCl 3 )),δ:7.68(d,J=7.9Hz,1H),7.53(d,J=7.9Hz,1H),3.19(m,2H),2.21(s,3H),1.77-1.83(m,2H ), 1.64-1.71(m,2H), 1.31(s,6H).
example 3
[0083] Example three, 2-chloro-1,6,6-trimethyl-6,7,8,9,10,11-hexahydro-10,11-dioxophenanthrene[1,2-b]furan ( Tan-003)
[0084]
[0085] The reaction is the same as in Example 2, and NBS is replaced by N-chlorosuccinimide (NCS) to obtain the target product, 1 H-NMR (300MHz, (CDCl 3 ),δ:7.69(d,J=7.2Hz,1H),7.56(d,J=7.2Hz,1H),3.19(m,2H),2.23(s,3H),1.77-1.85(m,2H) ,1.64-1.75(m,2H),1.31(s,6H).
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Abstract
The invention provides tanshinone compounds, a preparation method and use thereof, and relates to the technical field of pharmaceutical chemistry. The tanshinone compounds possess a structure formula I or II as shown in the specification. The use of the tanshinone compounds includes but not limited to anticancer drugs, particularly the treatment of prostatecancer and bladder cancer, and induction of androgenreceptorantagonist activity when patients have androgen-related diseases, wherein the androgen-related diseases include but not limited to multi-disease, acne, and spermatogenesis without inhibition in need of suppressing spermatogenesis.
Description
technical field [0001] The invention relates to the technical field of medicinal chemistry, and relates to some novel anti-androgen receptor compounds, pharmaceutical dosage forms containing the compounds and their use methods, especially tanshinone compounds and their uses. Background technique [0002] Many diseases in older men are related to androgen levels. As men age, the level of androgen in the body will decrease, accompanied by the decrease of muscle in the body and the decline of sexual function. On the contrary, excessive androgen levels in the body will also bring other diseases, such as benign prostatic hyperplasia and prostatecancer, which are androgen-dependent diseases, and other diseases are related to androgen levels. The skin and hair of the body contain androgen receptors. In some people, these receptors are more sensitive to androgen, causing hair loss, and the androgen receptors in the skin of young people are more sensitive, resulting in the growth o...
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