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Preparation process of novel PIN1 inhibitor

A technology of PIN1 and preparation process is applied in the field of preparation of novel PIN1 inhibitors to achieve the effects of reducing preparation cost, simple operation and less investment in equipment

Active Publication Date: 2021-03-12
烟台共进医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, there are no well-established methods suitable for inexpensive production scale-up

Method used

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  • Preparation process of novel PIN1 inhibitor
  • Preparation process of novel PIN1 inhibitor
  • Preparation process of novel PIN1 inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] In a 350ml sealed tube, add 200ml tetrahydrofuran, 9.8g 2-chloro-1,4 naphthoquinone, 13g 4-butylbenthiamine, 2.1eq triethylamine, 1.2eq titanium tetrachloride, react at 60°C for 15h, TLC Track the reaction, spin dry, add petroleum ether and isopropyl ether to make a slurry. After suction filtration, the solid is the intermediate. Dissolve the intermediate in 200ml tetrahydrofuran, add 11g thioglycolic acid, 1.2eq pyridine, and stir at room temperature for 2 hours to complete the reaction. Spin the reaction solution to dryness, add isopropyl ether and tertiary methyl ether for beating , the product 2-{[4-(4-tert-butylbenzenesulfonamido)-1-oxo-1,4-dihydronaphthalene-2-yl]sulfanyl}acetic acid can be obtained, two-step yield was 67.4%.

Embodiment 2

[0026] In a sealed 20ml tube, add 10ml tetrahydrofuran, 0.8g 2-chloro-1,4-naphthoquinone, 1.1g 4-butylbenthiamine, 2.1eq triethylamine, 1.2eq titanium tetrachloride, and react at 60°C for 15h. TLC traced the reaction, spin-dried, added petroleum ether and isopropyl ether to make a slurry. After suction filtration, dissolve the solid in 200ml tetrahydrofuran, add 0.8g thioglycolic acid, 1.2eq pyridine, and stir at room temperature for 2 hours to complete the reaction. The reaction solution is spin-dried, and isopropyl ether and tertiary methyl ether are added to make a slurry to obtain the product 2- {[4-

[0027] (4-tert-butylbenzenesulfonamido)-1-oxo-1,4-dihydronaphthalen-2-yl]sulfanyl}acetic acid, the two-step yield was 57.4%.

Embodiment 3

[0029] In a sealed 40ml tube, add 30ml tetrahydrofuran, 1.8g 2-chloro-1,4 naphthoquinone, 2.1g 4-butylbenthiamine, 2.1eq triethylamine, 1.2eq titanium tetrachloride, react at 60°C for 15h, TLC traced the reaction, spin-dried, added petroleum ether and isopropyl ether to make a slurry. After suction filtration, the solid was dissolved in 200ml of tetrahydrofuran, 1.8g of thioglycolic acid and 1.2eq of pyridine were added, and the reaction was completed after stirring at room temperature for 2 hours. {[4-

[0030] (4-tert-butylbenzenesulfonamido)-1-oxo-1,4-dihydronaphthalen-2-yl]sulfanyl}acetic acid, the two-step yield was 65.4%.

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Abstract

The invention relates to a preparation process of a novel PIN1 inhibitor, which comprises the following steps: 1) adding 2-chloro-1, 4-naphthoquinone, 4-butyl thiophenylamine and a catalyst into an organic solvent, performing heating, performing stirring to react, and carrying out TLC tracking reaction; 2) evaporating the organic solvent in the reaction system to dryness, adding petroleum ether, performing pulping by using isopropyl ether, and carrying out suction filtration to obtain a solid which is an intermediate; 3) dissolving the intermediate obtained in the step 2) in an organic solvent, adding thioglycolic acid and a catalyst, and performing stirring for reaction; and 4) evaporating the organic solvent in the system after the reaction in the step 3) to dryness, adding isopropyl ether and methyl tertiary ether, and performing pulping to obtain the PIN1 inhibitor 2-{[4-(4-tert-butylbenzenesulfonamido)- 1-oxo-1, 4-dihydronaphthalene-2-yl] sulfanyl} acetic acid product. The preparation process is simple in operation condition, simple in aftertreatment and purification, low in cost and suitable for industrial amplification.

Description

technical field [0001] The invention relates to a preparation process of a novel PIN1 inhibitor, which belongs to the technical field of drug synthesis. Background technique [0002] PIN1 has been shown to play a key role in carcinogenesis, PIN1 is overexpressed in most cancers and acts as a regulator of multiple cancer-driving signaling pathways, including c-MYC, NOTCH, WNT / β-catenin and RAS / MEK / ERK pathway, while inhibiting multiple tumor suppressors. Scientific studies have shown that PIN1 is necessary for the occurrence and development of certain tumors, that is, targeting PIN1 disrupts the cooperation of oncogenic pathways in CSC and non-CSC tumor cells, providing a theoretical basis for the development of PIN1-targeted therapies. [0003] 2-{[4-(4-tert-butylbenzenesulfonamido)-1-oxo-1,4-dihydronaphthalen-2-yl]sulfanyl}acetic acid stands out as a new PIN1 inhibitor. Currently, there are no well-established methods suitable for inexpensive production scale-up. Theref...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C319/28C07C323/52C07C303/38C07C311/20
CPCC07C319/14C07C319/28C07C303/38C07C2602/10C07C311/20C07C323/52
Inventor 衣永健王伟崔宁宁陈锦春
Owner 烟台共进医药科技有限公司
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