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Application of aporphine compound

A compound and hydrate technology, applied in the field of pharmacy, can solve problems such as unidentified agonists, unknown functions, unknown receptor agonists, etc.

Active Publication Date: 2021-01-05
SUZHOU UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] CN101822675A, CN 108524512 A, and CN 101407520A respectively disclose the application of aporphyrin compounds in the preparation of antibacterial drugs, anti-inflammatory drugs and antifungal drugs, but according to the above technology, it is still unknown whether such compounds can be used as receptor agonists
In 2019, it was reported in the literature that aporfil compounds were used for 5-HT 2c. Research on small molecule ligands for receptors (Bioorganic & Medicinal Chemistry Letters, 29(2):230-233), but its receptor selectivity is poor and its function is unknown, so it cannot be determined whether it is an agonist

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1: the synthesis of compound S1

[0054] The synthetic route of compound S1 is as follows:

[0055]

[0056] Among them, the reaction conditions: (a) HOBt, EDC, DCM, rt (room temperature); (b) P 2 o 5 , toluene, 110°C; NaBH 4 , MeOH, 0°C-rt (c) TEA, TFAA, DCM, 0°C-rt; (d) PhDavePhos (2-diphenylphosphine-2'-(N,N-dimethylamino)biphenyl), Pd (OAc) 2 , K 2 CO 3 , DMA, 130°C; (e) NaBH 4 , EtOH, N 2 , rt.

[0057]Synthesis of compound S1-C: 2.93mL (20mmol) of commercially available 4-methoxyphenethylamine (S1-A) and 4.73g (22mmol) of o-bromophenylacetic acid (S1-B) were dissolved in 100mL of anhydrous di In methyl chloride, 2.97 g HOBt (22 mmol), 4.22 g EDC (22 mmol) were added with stirring, and the resulting reaction mixture was stirred at room temperature overnight. The mixture was separated by extraction with dichloromethane and water, and the organic phase was washed successively with 1N dilute hydrochloric acid, saturated sodium bicarbonate and s...

Embodiment 2

[0062] Embodiment 2: the synthesis of compound S1 (R)

[0063] The compound S1-C prepared in Example 1 and the dehydrating agent were placed in toluene and refluxed for 1.5 hours. A white precipitate was precipitated in the solution. After it became a yellow solid, TLC detected that there was no raw material in the toluene, and the toluene was poured out. The solid was saturated with Sodium bicarbonate and ethyl acetate work up. Separated by extraction, the organic phase was concentrated under reduced pressure. After the ring-closing mixture was purified by column chromatography, 280 mg (848 mmol) of the above intermediate was dissolved in 2 mL of DMF, and 0.028 mmol of RuCl[(s,s)-TsDPEN](p-cymene) (S / C=30 ), add the azeotrope of formic acid and triethylamine in total 1mL (molar ratio = 5:2) under ice bath, and gradually raise to room temperature under ice bath and stir for 12h after the addition. Basified with sodium bicarbonate, extracted with dichloromethane, washed with ...

Embodiment 3

[0065] Embodiment 3: the synthesis of compound S1 (S)

[0066] The compound S1-C prepared in Example 1 and the dehydrating agent were placed in toluene and refluxed for 1.5 hours. A white precipitate was precipitated in the solution. After it became a yellow solid, TLC detected that there was no raw material in the toluene, and the toluene was poured out. The solid was saturated with Sodium bicarbonate and ethyl acetate work up. Separated by extraction, the organic phase was concentrated under reduced pressure. After the mixture obtained by ring closure was purified by column chromatography, 280 mg (848 mmol) of the above intermediate was dissolved in 2 mL of DMF, and 0.028 mmol of RuCl[(R,R)-TsDPEN](p-cymene) was added (S / C=30) 1 mL of the azeotrope of formic acid and triethylamine (molar ratio = 5:2) was added under ice-cooling, and after the addition was completed, it was gradually raised to room temperature under ice-cooling and stirred for 12 h. Basified with sodium bic...

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Abstract

The invention relates to application of an aporphine compound in preparation of a 5-hydroxytryptamine 2c receptor stimulating agent. The aporphine compound comprises a compound represented by a general formula M, isomers thereof and pharmaceutically-acceptable salts or hydrates thereof, wherein R1, R2 and R3 each is independently selected from H, C1-C8 alkyl, C2-C10 alkynyl, C2-C10 alkenyl, halogens, C1-C8 haloalkyl, cyano-, nitro-, aryl, hydroxyl, carboxyl, C1-C8 alkoxy, alkoxyacyl, oxim, amino, amido, acyloxy, acyl, sulfonyl, sulfonamido, urea, thiourea and carbamoyl-, and the R1 is a non-hydroxy group; and when the R1 is methoxy, the R2 and the R3 cannot be hydroxyl and H separately.

Description

technical field [0001] The invention relates to the field of pharmacy, in particular to the application of aporfil compounds. Background technique [0002] As a neurotransmitter, 5-hydroxytryptamine is also known as serotonin because it was first discovered in serum. Serotonin is thought to be involved in a variety of behaviors, including cognition, mood, attention, and appetite, among others. 5-HT receptors are an important class of the 7-transmembrane G protein-coupled receptor superfamily. 5-HT 2 There are three subtypes of receptors, including 5-HT 2A , 5-HT 2B , 5-HT 2C . Activation of the corresponding receptors will produce corresponding physiological activities. Activate 5-HT 2A Receptors produce hallucinogenic effects, activate 5-HT 2B Receptors can lead to primary pulmonary hypertension and valvular heart disease. 5-HT 2C Receptors are closely related to appetite and mental illness. [0003] Studies have shown that 5-HT 2C The receptor signaling pathwa...

Claims

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Application Information

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IPC IPC(8): A61K31/473A61K31/5377A61P3/04A61P25/08A61P13/00A61P25/22A61P25/24A61P25/18A61P3/10A61P29/00A61P25/30
CPCA61K31/473A61K31/5377A61P3/04A61P25/08A61P13/00A61P25/22A61P25/24A61P25/18A61P3/10A61P29/00A61P25/30
Inventor 叶娜水雯箐毛奇张冰洁
Owner SUZHOU UNIV
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