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Preparation method of [3-14C] labeled steroid estrogen

A steroid and estrogen technology, applied in the field of radioactive isotope 14C-labeled compounds, can solve the problems of difficult control of the reaction, low total yield, and low utilization rate of labeled raw materials, and achieve easy control of the reaction, low synthesis cost, and high product yield. high effect

Inactive Publication Date: 2015-08-12
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In order to solve the introduction of the 3-position of the A ring of steroid estrogen in the prior art 14 When marking with C, there are problems such as low utilization rate of marking raw materials, difficult control of reaction, low total yield, etc., the present invention provides a CH 3 14 COCl is the labeling initiator, which is introduced at the 3-position of the steroid A ring by reacting with enol 14 C labeling, followed by subsequent reaction steps to obtain [3- 14 C]-17β-E2 and [3- 14 The preparation method of C]-E1

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  • Preparation method of [3-14C] labeled steroid estrogen
  • Preparation method of [3-14C] labeled steroid estrogen
  • Preparation method of [3-14C] labeled steroid estrogen

Examples

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Embodiment 1

[0053] Example 1: 14 C-labeled steroid estrogen [3- 14 C]-17β-estradiol ([3- 14 Synthesis of C]-17β-E2)(VIII)

[0054] combine figure 1 , 2 , 14 C-labeled steroid estrogen [3- 14 C]-17β-estradiol ([3- 14 C]-17β-E2) (VIII) synthetic steps are:

[0055] (1). Using nandrolone (I) as the starting material, the 17-position OH is protected by or benzoylation in pyridine to generate benzoyl nandrolone (II).

[0056] Take 100mL of anhydrous toluene solution containing nandrolone (I) (9.57g, 34.9mmol) and place it in a 250mL flask, stir, and slowly add 109mL of toluene solution containing 49mL of benzoyl chloride dropwise under an external bath of ice water (49mL of benzoyl chloride). Dissolve formyl chloride in 60 mL of anhydrous toluene), and then slowly add 14 mL of anhydrous pyridine. After the dropwise addition was completed, the temperature was raised to 80° C., stirred and refluxed for 4 hours. Add 60mL H 2 O, continue to stir and reflux for 1h. After the reaction wa...

Embodiment 2

[0076] Example 2: 14 C-labeled steroid estrogen [3- 14 C]-Estrone ([3- 14 Synthesis of C]-E1)(IX)

[0077] combine figure 1 , 2 , 14 C-labeled steroid estrogen [3- 14 C]-Estrone ([3- 14 C]-E1) (IX) synthetic steps are:

[0078] (1). Using nandrolone (I) as the starting material, the 17-position OH is protected by acetylation in pyridine to generate acetyl nandrolone (II).

[0079] Nandrolone acetylation: Add 10 g of nandrolone (I), 67 mL of pyridine and 67 mL of acetic anhydride in sequence in a 250 mL flask, and stir overnight at room temperature. The TLC detection reaction is basically complete (petroleum ether: ethyl acetate=3:1, acetyl nandrolone R f value is 0.42). On a rotary evaporator at 50°C, the oil pump was concentrated to dryness under reduced pressure. The residue was frozen and crystallized at -15°C in a freezer, and suction filtered. Add the filter cake into the flask, then add petroleum ether with a boiling point of 60-90°C, stir and heat to reflux ...

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Abstract

The invention discloses a preparation method of [3-14C] labeled steroid estrogen and belongs to the field of compounds labeled by a radio isotope 14C. According to the preparation method, 14C radio isotope labeling is introduced into the structure of estrogen, the 14C labeling site is a C-3 site in a loop A, and the general structural formula is shown by a figure 1. The preparation method comprises the following steps: by taking nandrolone as an initiator, performing acetyl (or benzoyl) protection, ozone oxidation ring opening and inner ester condensation to generate olefin alcohol inner ester; then performing condensation reaction on the olefin alcohol inner ester and 14C labeled acetyl chloride CH314COCl at -78 DEG C, and hydrolyzing the obtained 14C labeled olefin alcohol type transition state product under an acidic condition to generate 14C labeled acetyl nandrolone (or benzoyl nandrolone) at the 3rd site of the loop A of steroid; and aromatizing and hydrolyzing the 14C labeled acetyl nandrolone (or benzoyl nandrolone) to obtain [3-14C]-17beta-estradiol ([3-14C]-17beta-E2). The [3-14C]-17beta-E2 is oxidized by a Jones reagent to generate [3-14C]-estrone ([3-14C]-E1).

Description

technical field [0001] The present invention relates to radioisotopes 14 The field of C-labelled compounds, in particular 14 Preparation method of C-labeled steroid estrogen. It can be applied to the research on the fate of steroid estrogen in the environmental field, and it is also suitable for the research application of steroid estrogen in the field of medicine and biology. Background technique [0002] Steroid estrogens are a typical class of endocrine disruptors that widely exist in sewage, springs, rivers, oceans, sediments and soils at concentrations that can cause biological effects (ng / L level). The fate of steroid estrogens in the environment plays an important role in determining their environmental risks. However, due to the influence of environmental media, when studying the environmental fate of estrogen, it is often necessary to perform complex pretreatments on samples such as gel permeation chromatography (Gel Permeation Chromatography, GPC), solid-phase e...

Claims

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Application Information

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IPC IPC(8): C07J1/00C07J75/00
CPCC07J1/0059C07J1/0066C07J75/00
Inventor 王联红蓝贤瑾季荣王婷沈宏马旖旎
Owner NANJING UNIV
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