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Synthesis method of 16-alkene-17-ketoestrone derivatives

A technology of ketoestrone and its derivatives, which is applied in the field of preparation of 16-alkene-17-ketoestrone derivatives, and achieves the effect of easy processing

Active Publication Date: 2020-06-05
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method requires a step-by-step reaction, processing with organic solvent extraction, using more organic solvents and requiring the use of carcinogen benzene solution, so the development of a simple and efficient new method for 16-alkene-17-ketoestrone derivatives has important meaning

Method used

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  • Synthesis method of 16-alkene-17-ketoestrone derivatives
  • Synthesis method of 16-alkene-17-ketoestrone derivatives
  • Synthesis method of 16-alkene-17-ketoestrone derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0022] 3-Methylestrone (1mmol), fluorine reagent (2mmol), NaAuCl 4 (5mmol%) and 2mL DMSO were added to a 15mL test tube, heated to 100°C, reacted for 8 hours, and separated by silica gel column chromatography to obtain 3-methyl 16-alkene-17-ketoestrone 3a with a yield of 85%. M.p.121-123℃. 1 H NMR (400MHz, CDCl 3 )δ7.54(d,J=7.4Hz,2H),6.48-6.43(m,1H),6.26(s,1H),6.13(s,1H),3.82(s,3H),1.45–3.08(m ,13H),1.04(s,3H).

Embodiment 2

[0024] Androstenedione (1mmol), fluorine reagent (2mmol), NaAuCl 4. h 2 O (5mmol%) and 2mL DMSO were added to a 15mL test tube, heated to 100°C, reacted for 6 hours, and separated by silica gel column chromatography to obtain 16-alkene-17-ketoandrostenedione 3b with a yield of 82%. M.p.136-138℃. 1 H NMR (400MHz, CDCl 3 )δ7.86(d,J=7.4Hz,1H),6.26(s,1H),6.13(s,1H),6.04-5.98(m,1H),3.06-3.04(m,1H),2.85-2.83 (m,1H),2.19-1.48(m,14H),1.28(s,3H),1.15(s,3H).

Embodiment 3

[0026] 1,4-androstenedione (1mmol), fluorine reagent (2mmol), NaAuCl 4. h 2 O (5mmol%) and 2mL DMSO were added to a 15mL test tube, heated to 100°C, reacted for 8 hours, and separated by silica gel column chromatography to obtain the product of 16-alkene-17-keto-1,4-androstenedione 3c The rate is 74%. M.p.110-112℃. 1 H NMR (400MHz, CDCl 3 )δ6.98(d,J=8.2Hz,1H),6.42(d,J=7.2Hz,1H),6.28(s,1H),6.12(s,1H),2.10-1.48(m,6H), 1.39(s,3H),1.28(s,3H),1.32-1.18(m,8H).

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Abstract

The invention belongs to the field of organic chemical engineering and drug synthesis, and particularly relates to a synthesis method of 16-alkene-17-ketoestrone derivatives. The synthesis method comprises the following steps that oestrone and a fluorine reagent [1-chloromethyl-4-fluoro-1, 4-diazodicyclo-2.2.2-octane bis(tetrafluoroborate)] as raw materials undergo a reaction by a gold catalyst under a heating condition, so as to obtain the 16-alkene-17-ketooestrone derivatives. By using the method provided by the invention, the 16-alkene-17-ketoestrone derivatives can be obtained by reactingfor 6-10 hours under the heating and stirring conditions, and the yield is 74%-85%. According to the reaction, the 16-alkene-17-ketoestrone derivatives are simply and conveniently synthesized from simple and easily available raw materials through a one-step method, and a novel efficient and green synthesis method is provided for the 16-alkene-17-ketoestrone derivatives.

Description

technical field [0001] The invention belongs to the technical field of organic chemical engineering and drug synthesis, and in particular relates to a preparation method of 16-alkene-17-ketoestrone derivatives. Background technique [0002] Estrogen is a substance that promotes and maintains the physiological effects of female reproductive organs and secondary sexual characteristics, and has obvious effects on endocrine, cardiovascular, metabolism, bone growth and maturation, and skin. Estrone is a type of estrogen, a female hormone secreted by the human body and animals. Estrone derivatives are a class of natural products with extensive and important pharmaceutical applications, including as receptor agonists, inhibitors of estrogen receptors, imaging agents for breast cancer treatment, etc. [1. Tapolcsányi, P.; J.; Falkay, G.; Márki, Minorics, R.; Schneider, G.; Steroids. 2002, 67, 371–377; 2. Broach, J.R.; Thorner, J. Nature 1996, 384, 14.3. Messinger, J.; Husen, B.; ...

Claims

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Application Information

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IPC IPC(8): C07J1/00
CPCC07J1/0011
Inventor 李剑徐越刘莉
Owner CHANGZHOU UNIV
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