4999-76-2Relevant articles and documents
BILE ACIDS AND STEROIDS. 28. THIOSTEROIDS. 13. FURTHER STUDY ON
TAKEDA,KOMENO,ISHIHARA
, p. 1433 - 1439 (1964)
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Preparation method for 3,5-estradiene-3,17beta-diacetate
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Paragraph 0013; 0014, (2017/12/13)
The invention relates to a preparation method for 3,5-estradiene-3,17beta-diacetate. The preparation method comprises the following steps: sequentially adding nandrolone, p-toluenesulfonic acid monohydrate, isopropyl acetate and magneton No. 15 into a reactor, introducing condensed water, carrying out a heating reaction in an oil-bath pot and slowing adding isopropenyl acetate when reflux condensation of the obtained system begins; after completion of a reaction, carrying out evaporation to remove a solvent; cooling the system, adding pyridine, and adding isopropanol drop by drop until a white solid product is precipitated; carrying out low-temperature cooling and pumping filtration and then carrying out cleaning with cold isopropanol; collecting the white solid product and then carrying out drying so as to obtain a pure 3,5-estradiene-3,17beta-diacetate product. According to the invention, nandrolone is used as a substrate and a one-pot method is employed for carbonyl and hydroxyl acetylation protection so as to synthesize the product; the method is simple in process, mild in conditions and friendly to environment and has yield of up to 85%; and the synthesized product has critical application value in the fields of medicines, veterinary drugs and pesticides and is an important pro-drug for tibolone.
Stereoselective synthesis of some methyl-substituted steroid hormones and their in vitro cytotoxic activity against human gastric cancer cell line MGC-803
Li, Chun,Qiu, Wenwei,Yang, Zhengfeng,Luo, Jian,Yang, Fan,Liu, Mingyao,Xie, Juan,Tang, Jie
experimental part, p. 859 - 869 (2010/10/18)
A series of 3-, 7-, 15-, and 16-methyl-substituted steroid analogs were synthesized via a highly stereoselective 1,6-conjugate addition. Under the catalysis of CuBr, AlMe3 reacted with four steroid dienone precursors to afford either the corresponding α-epimer of C-3 and C-7 methyl-substituted steroids as the major products, and the ratio of α/β was up to 10/1. No β-epimer has been detected for methyl addition at C-16. However, under the same reaction conditions, enantioselective methyl addition at C-15 afforded the 15β-epimer as the major product. The preliminary SAR analysis showed that the methyl substituents at C-7α and C-15β positions lead to a dramatical increase in potency against human gastric cancer cell line MGC-803.