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18F-PET/CT tracer with 7-deazaneplanocin base as parent nucleus, and preparation method thereof

A technology of 18F-HX and tracer, applied in organic chemical methods, chemical instruments and methods, preparations for in vivo tests, etc.

Active Publication Date: 2019-03-22
WEST CHINA HOSPITAL SICHUAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the types of tracers that can be used for the diagnosis of lung cancer are still very limited, so it is urgent to develop new functional imaging tracers and precursor reagents for the precise diagnosis of lung cancer

Method used

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  • 18F-PET/CT tracer with 7-deazaneplanocin base as parent nucleus, and preparation method thereof
  • 18F-PET/CT tracer with 7-deazaneplanocin base as parent nucleus, and preparation method thereof
  • 18F-PET/CT tracer with 7-deazaneplanocin base as parent nucleus, and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] The preparation of embodiment 1 compound 1

[0057]

[0058] (1) Synthesis of 5-iodo-7-n-butyl-7H-pyrrolo[2,3-d]pyrimidine 4-chloro (compound 4):

[0059] 4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (compound 3) (5g, 17.90mmol) was mixed with cesium carbonate (11.66g, 4.66mmol) and dissolved in 30mL DMF and placed in ice water , after the mixture was cooled to 0°C, iodo-n-butane (6.17 mL, 53.7 mmol) was added. After 10 min, the mixture was taken out from the ice water and placed at room temperature and stirred for 5 h, and the reaction progress was detected by TLC. After the reaction was completed, the mixture was cooled and 60 mL of ice water was added, and precipitation occurred. After filtration and drying, 5.52 g of a yellow solid (compound 4) was obtained (91.9% yield).

[0060] Compound 4: 1 H NMR (600MHz, DMSO-d6) δ8.64(s, 1H), 8.06(s, 1H), 4.27(t, J=7.1Hz, 2H), 1.82–1.74(m, 2H), 1.22(h, J=7.4Hz, 2H), 0.88(t, J=7.4Hz, 3H). 13 C NMR(151MHz,DMSO-d6)δ162.75,1...

Embodiment 218

[0067] Example 2 18 Preparation of F-HX compounds

[0068]

[0069] 1. Preparation of Compound 2

[0070] Tetraethylene glycol bis(p-toluene hydrochloride) (164mg, 3.46mmol), compound 1 (100mg, 3.46mmol) and anhydrous potassium carbonate (100mg, 3.46mol) were heated under reflux in 50mL benzene solution for 4h, and in 1N HCl After and, the reaction mixture was extracted with dichloromethane. The solution was then dried under reduced pressure to obtain a solid, which was separated by column chromatography to obtain 160 mg of a brown-yellow syrupy product (compound 2) (yield 76%).

[0071] Compound 2: 1 H NMR (600MHz, Chloroform-d)δ8.29(s,1H),δ7.84-6.97(m,8H,arom-H),6.95(s,1H),5.52(s,2H),4.23-4.21 (t,J=7.2Hz,2H),4.23-3.59(t,J=7.2Hz,16H),δ2.44(s,3H),1.87-1.80(m,2H),1.44-1.35(m,2H ),0.97-0.95(t,J=7.4Hz,3H).HR-MS(ESI+): Calc.for[C 31 h 40 N 4 o 7 S]: 613.2618[M+H]+; Found 613.2694[M+H]+, 635.2521[M+Na]+.

[0072] 2, 18 Preparation of F-HX

[0073] The radionuclide la...

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Abstract

The invention discloses an 18F-PET / CT tracer with a 7-deazaneplanocin base as a parent nucleus, and a preparation method thereof. The invention first discloses a compound of the formula I or a pharmaceutically acceptable salt thereof, wherein each of R1 and R2 is independently selected from H or a C1-C5 alkyl group, and X is independently selected from 11C, 18F, 15O or 13N. The invention also discloses a preparation method and application of the compound of the formula I. The 18F-PET / CT tracer with the 7-deazaneplanocin base as the parent nucleus, namely a 18F-HX tracer, is successfully prepared. Experimental results show that the 18F-HX tracer prepared by the method can be stably absorbed in tumors, three times higher than in muscle tissues, thereby being expected to be applied to PET / CTimaging to change the scarcity of tracers in lung cancer. The formula I is shown in the description.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to a 7-deazaadenine base as the mother nucleus 18 F-PET / CT tracer and preparation method thereof. Background technique [0002] PET / CT is an advanced diagnosis and treatment equipment for functional imaging. Although its application in lung cancer has been increasingly popularized, it still has great limitations. This limitation mainly stems from the core component of functional imaging: PET / CT tracers. The current PET / CT tracers for lung cancer are mainly 18 F-FDG, due to 18 F-FDG lacks specificity at the molecular level other than glucose metabolism. On the one hand, it has the defects of false positive and false negative. On the other hand, it cannot reflect the molecular classification of lung cancer or the information of other specific molecular targets at the functional imaging level. A major technical bottleneck in the precise diagnosis and treatment of lung cancer. Based o...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07B59/00A61K51/04A61K101/02
CPCA61K51/0459C07B59/002C07B2200/05C07D487/04
Inventor 李为民何杨柴莹莹周兴龙蔡华伟吴小艾陈海黄日东
Owner WEST CHINA HOSPITAL SICHUAN UNIV
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