Thiazole heterocyclic ring-containing steroid derivative as well as preparation method and application thereof

A technology of derivatives and steroids, applied in the fields of organic synthesis and medicinal chemistry, can solve the problems of lack of specific and strong drugs, and achieve the effects of easy-to-obtain raw materials, good anti-viral activity, and simple preparation methods

Active Publication Date: 2018-06-29
HUBEI BIOPESTICIDE ENG RES CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For the treatment of viral diseases, there is still a lack of specific drugs, and antiviral drugs and immunomodulatory drugs can directly interfere with the replication of viruses, which is the focus of research on the treatment of viral diseases, but among the many viruses that cause human diseases , few of these drugs

Method used

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  • Thiazole heterocyclic ring-containing steroid derivative as well as preparation method and application thereof
  • Thiazole heterocyclic ring-containing steroid derivative as well as preparation method and application thereof
  • Thiazole heterocyclic ring-containing steroid derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] [Example 1] Preparation of the compound numbered as I1 in table 1

[0038] Its reaction formula is:

[0039]

[0040] Its preparation method comprises the following steps:

[0041] 1) With 5mmol of dehydroepiandrosterone (compound 1) and 5.5mmol of thiosemicarbazide (NH 2 CSNHNH 2 ) as the starting material, the intermediate 2a was prepared by condensation reaction in absolute ethanol (30mL), the reaction temperature was 70-80°C, and the reaction time was 8h;

[0042] 2) The intermediate 2a (1mmol) and α-bromoacetophenone (1mmol) were subjected to a heterocyclization reaction in absolute ethanol (15mL) to obtain the target compound I1, the reaction temperature was 60-70°C, and the reaction time was 9h. Spectral data of target compound I1: mp 242-244°C; 1 H NMR (400MHz, CDCl 3 ):δ=8.14(bs,1H),7.75(d,J=8Hz,2H),7.36(t,J=8Hz,2H),7.27(d,J=8Hz,1H),6.81(s,1H) ,5.35(d,J=4.4Hz,1H),3.53(bs,1H),2.42-2.21(m,4H),2.10-2.02(m,2H),1.95-1.75(m,3H),1.56-1.35 (m,5H),1.25-0.93(m,1...

Embodiment 2

[0043] [Example 2] Numbering in table 1 is the preparation of the compound of I12

[0044] Its reaction formula is:

[0045]

[0046] Its preparation method comprises the following steps:

[0047] 1) With 3mmol of dehydroepiandrosterone (compound 1) and 3.3mmol of N-methylthiosemicarbazide (CH 3 NHCSNHNH 2 ) as the starting material, the intermediate 2b was prepared by condensation reaction in anhydrous methanol (20mL), the reaction temperature was 60-70°C, and the reaction time was 7h;

[0048] 2) Heterocyclization reaction of intermediate 2b (1mmol) and α-bromoacetophenone (1mmol) in anhydrous acetonitrile (10mL) to obtain the target compound I12, the reaction temperature is 65-75°C, the reaction time for 8h. Spectral data of the target compound I12: mp 206-208°C; 1 H NMR (400MHz, CDCl 3 ):δ=12.40(bs,1H),8.14(bs,1H),7.52-7.46(m,3H),7.35(q,J=8Hz,2H),6.63(s,1H),5.35(d,J =4Hz,1H),4.01(s,3H),3.52(bs,1H),3.35-2.90(m,2H),2.35-1.65(m,10H),1.55-1.35(m,4H),1.30-0.97 (m,9H)...

Embodiment 3

[0049] [embodiment 3] the preparation of the compound numbered as I21 in table 1

[0050] Its reaction formula is:

[0051]

[0052] Its preparation method comprises the following steps:

[0053] 1) With 6mmol of dehydroepiandrosterone (compound 1) and 6.6mmol of N-phenylthiosemicarbazide (PhNHCSNHNH 2 ) as the starting material, the intermediate 2c was prepared by condensation reaction in anhydrous methanol (40mL), the reaction temperature was 65-70°C, and the reaction time was 8h;

[0054] 2) The intermediate 2c (1mmol) and α-bromoacetophenone (1mmol) were subjected to a heterocyclization reaction in absolute ethanol (10mL) to obtain the target compound I21, the reaction temperature was 75-80°C, and the reaction time was 7.5h. Spectral data of the target compound I21: mp 173-175°C; 1 H NMR (400MHz, CDCl 3 ):δ=12.12(bs,1H),7.60-7.20(m,8H),7.02(d,J=8Hz,2H),6.67(s,1H),5.32(s,1H),3.51(bs,1H ),3.20-2.60(m,2H),2.40-1.75(m,7H),1.55-1.35(m,6H),1.30-0.95(m,10H); MS(ESI)m / z 5...

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Abstract

The invention discloses a thiazole heterocyclic ring-containing steroid derivative as well as a preparation method and application thereof. A thiazole unit-containing steroid derivative is as shown ina formula I as shown in the following descriptions. The invention also provides a pharmacologically acceptable salt of the thiazole unit-containing steroid derivative. The preparation method providedby the invention is started from simple and easily obtained raw materials; the thiazole heterocyclic ring-containing steroid derivative is obtained through three steps of reactions. The thiazole heterocyclic ring-containing steroid derivative provided by the invention belongs to a compound with a brand-new structure, has better antiviral activity, and is suitable for the preparation of an antiviral medicine.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and medicinal chemistry, and specifically relates to a steroid derivative containing a thiazole heterocycle, a preparation method and application thereof. Background technique [0002] Human health problems are an important field of life science research, and viral diseases have become a public health problem that seriously threatens the health of people all over the world. Different from tumors, cardiovascular and nervous system diseases, they are highly contagious and cause many other diseases. The cause of disease. There are currently hundreds of viruses that can cause disease in humans, and fewer than 10 approved antiviral therapies. According to incomplete statistics, 60-65% of epidemic infectious diseases are caused by virus infection. In recent years, with the widespread spread of viral diseases such as AIDS, hepatitis B, hepatitis C, etc. New mutant viruses or virus mutant str...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J43/00A61K31/58A61P31/12
CPCC07J43/003
Inventor 柯少勇魏艳红石丽桥张志刚方伟王开梅周荣华张亚妮梁英江爱兵张光阳杨自文
Owner HUBEI BIOPESTICIDE ENG RES CENT
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