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18f-labeled pi3k/akt signaling pathway inhibitor s14161 and its preparation method and application

A labeling and reaction technology, applied in the field of medicine, achieves the effects of simple and easy-to-control preparation process, mild reaction conditions, and simple and convenient separation

Active Publication Date: 2018-07-24
SHANDONG UNIV QILU HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there has been no report on the radiolabeling of S14161 for tumor imaging.

Method used

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  • 18f-labeled pi3k/akt signaling pathway inhibitor s14161 and its preparation method and application
  • 18f-labeled pi3k/akt signaling pathway inhibitor s14161 and its preparation method and application
  • 18f-labeled pi3k/akt signaling pathway inhibitor s14161 and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: Synthesis of 2-hydroxyl-1-ethoxy-3-(2-nitrovinyl)benzene

[0030] Add 1.1g of ammonium acetate and 4.64ml of glacial acetic acid to the four-necked flask successively, stir, after fully dissolving, add 1mmol of 2-hydroxy-1-ethoxy-3-formylbenzene and 4mmol of nitromethane in sequence , heated to reflux, and reacted for 5 hours. After the reaction was monitored by TLC, the reaction solution was cooled to room temperature, then poured into crushed ice, stirred for 0.5 hours, and filtered with suction to obtain an orange crystalline compound, namely 2-hydroxyl-1-ethoxy Base-3-(2-nitrovinyl)benzene; purity 95%, yield 93%. ESI-MS(m / z):209(M + ); 1 H NMR (DMSO-d 6 ,,400MHz), δ:13.75(s,1H,OH),8.08(d,1H,J=7.85Hz,Ar-CH),8.19(d,1H,J=7.89Hz,CHNO 2 ), 6.61-7.15 (m, 3H, Ar-H), 4.09 (m, 2H, CH 2 O),1.4(t,3H,CH 3 CH 2 -), 13 CNMR (CDCl 3 ,125MHz) δ: 151.3, 148.1, 137.5, 138.8, 121.2, 120.1, 117.5, 114.9, 63.2, 14.5.

[0031]

Embodiment 2

[0032] Example 2: Synthesis of 8-ethoxy-2-(4-tert-butoxycarbonylaminophenyl)-3-nitro-2H-chromene

[0033] Add 10mmol of 2-hydroxyl-1-ethoxy-3-(2-nitrovinyl)benzene, 12mmol of 4-tert-butoxycarbonylaminobenzaldehyde, 1mmol of anhydrous potassium fluoride, 5mmol Triethylenediamine (DABCO), 10 mmol of dimethylamine hydrochloride, 72.6 ml of toluene, the mixture was heated to 110 ° C, and stirred for 12 h. Dichloromethane and water were added to the reaction solution, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was evaporated to obtain 8-ethoxy-2-(4-tert-butoxycarbonylaminophenyl)-3-nitrate Base-2H-chromene, the yield is 70%, ESI-MS (m / z): 368 (M + ); 1 H NMR (DMSO-d 6 ,,400MHz)δ:9.79(s,1H,NH),7.88(s,1H,NO 2 CCH), 6.61-7.58 (m, 7H, Ar-H), 5.6 (s, 1H, OCH), 4.13 (m, 2H, CH 2 O),1.48(d,9H,3×CH 3 ), 1.39(t,3H,CH 3 CH 2 -), 13 CNMR (CDCl 3 ,125MHz)δ:147.1,81.3,148.9,145.3,136.1,115.1,136.9,121.3,121.8,120.3,127.6,114.1,121.3,127.5,...

Embodiment 3

[0035] Example 3: Synthesis of the triflate salt of 8-ethoxy-2-(4-aminophenyl)-3-nitro-2H-chromene

[0036] Add 10mmol of 8-ethoxy-2-(4-tert-butoxycarbonylaminophenyl)-3-nitro-2H-chromene, 15mmol of trifluoromethanesulfonic acid, 59.3ml of dichloromethane into the reaction flask , stirred at room temperature for 0.5h, after the completion of the reaction monitored by TLC, the solvent was evaporated to dryness to obtain trifluoromethanesulfonic acid of 8-ethoxy-2-(4-aminophenyl)-3-nitro-2H-chromene. The rate is 90%. ESI-MS(m / z):459(M + ); 1 H NMR (DMSO-d 6 ,,400MHz)δ:6.63-7.56(m,7H,Ar-H),7.35(s,3H,NH 3 ),7.65(s,1H,NO 2 CCH), 5.66(s,1H,OCH), 4.11(m,2H,CH 2 O),1.39(t,3H,CH 3 CH 2 -). 13 CNMR (CDCl 3 ,125MHz) δ: 148.3, 82.0, 149.1, 145.8, 133.1, 115.5, 141.2, 121.5, 121.4, 120.3, 127.5, 114.3, 121.5, 127.3, 121.6, 28.6, 64.3, 14.9.

[0037]

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Abstract

The invention discloses a <18>F-labeled-8-ethoxy-2-(4-fluorophenyl)-3-nitro-2H-chromene (S14161) and a preparation method thereof. The preparation method has the following advantages: preparation raw materials are cheap and are easy to obtain, the synthesis process is simple, reaction conditions are mild, and the radiochemical synthesis time is short; the above product is simple and convenient to purify and separate, the radiochemical purity of the product exceeds 98%, the radiochemical yield of the product is high, the uncorrected yield reaches up to 92%, and the radioactivity of the product is high; and the product is useful in the inspection and diagnosis of tumors and the radiation therapy of the tumors. The structural formula of the <18>F-labeled-8-ethoxy-2-(4-fluorophenyl)-3-nitro-2H-chromene is shown in the description.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a 18F-labeled PI3K / Akt signaling pathway inhibitor S14161 and its preparation method and application. Background technique [0002] If cancer is diagnosed early, most patients can improve their quality of life and even prolong their lives through surgery, chemotherapy, radiotherapy or a combination of treatments. Therefore, accurate early detection can allow the primary tumor to be treated appropriately before metastases. Positron Emission Computed Tomography (PET) is a functional imaging diagnostic technology developed vigorously in the late 1990s, based on radionuclide tracer technology Non-invasive imaging technology can quantitatively and dynamically observe the drug distribution in the human body at the molecular level in vitro, and has the characteristics of high sensitivity, high spatial resolution, and three-dimensional images of the whole body. At present,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/64C07B59/00A61K51/04A61K101/02
CPCA61K51/0421C07B59/00C07B2200/05C07D311/64
Inventor 刘剑峰刘新辉梁婷苏鹏韩建奎
Owner SHANDONG UNIV QILU HOSPITAL
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