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Spiro(3,3 '-phenylpyrrolidine oxoindole) LXR(Liver X Receptor) modulator as well as preparation method and application thereof
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A technology of alkoxy and nitrogen oxides, applied in the field of biomedicine, can solve problems such as high cholesterol demand, increased efflux, and apoptosis of malignant tumors
Active Publication Date: 2019-10-15
深圳市麻王企业管理有限公司
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[0004] Recently, the research team of Professor Paul Mischel of the University of California, San Diego reported that: due to the vigorous metabolism of GBM cells and the high demand for cholesterol, LXRβ agonists lead to reduced cholesterol uptake and increased efflux, which interferes with intracellularenergy metabolism pathways, resulting in malignant tumor apoptosis
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[0110] The invention provides the preparation method of the spiro(3,3'-phenylpyrrolidinoindole) liver X receptor modulator, comprising the following steps: dissolving tryptamine and isobutyraldehyde in dichloromethane, A Pictet-Spengler reaction occurred in , to obtain intermediate 1a; 1a was dissolved in tetrahydrofuran, and under the action of N-bromosuccinimide, rearrangement occurred to obtain intermediate 1b; 1b was dissolved in dichloromethane, and triethylamine was added, React with di-tert-butyl dicarbonate to obtain intermediate 1c; 1c is dissolved in toluene, add cuprous iodide, N,N-dimethylethylenediamine, potassiumcarbonate, and react with m-chloroiodobenzene to obtain intermediate 1d; 1d Dissolved in 2,4,-dioxane, adding bis(dibenzylideneacetone) palladium, bis-linked pinacol borate, and potassium acetate reacted in a nitrogen environment to obtain intermediate 1e; 1e and bromo R a The fragment undergoes Suzuki coupling reaction to obtain intermediate 1f; 1f remo...
Embodiment 1
[0116] The synthesis of embodiment 1 compound
[0117] like figure 1 As shown, using tryptamine as a starting material, spiro(3,3'-phenylpyrrolidinoindole) compounds are obtained through six or seven steps of reaction. The reaction scheme is as follows:
[0121] 1. Dissolve tryptamine (20mmol) in 50mL dichloromethane, add 3-bromobenzaldehyde (20mmol, 1eq.), then slowly add trifluoroacetic acid (40mmol, 2eq.), and stir the reaction overnight. Petroleumether was added to the reaction solution, and a white solid was obtained by filtration to obtain intermedia...
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Abstract
The invention relates to a spiro(3,3 '-phenylpyrrolidine oxoindole) LXR (Liver X Receptor) modulator as well as a preparation method and application thereof, and specifically provides a compound shownby the formula (I) as shown in the specification, or a stereoisomer, a geometric isomer, a tautomer, an oxynitride, a hydrate, a solvate, a metabolite, pharmaceutically acceptable salt or a prodrug shown by the formula (I) as shown in the specification. The compound has significant LXR agonist activity and significant effects on cancers such as glioblastoma and the like, atherosclerosis, dyslipidemia, metabolic syndromes, Parkinson's diseases, Alzheimer's diseases, multiple sclerosis, atopic dermatitis, rheumatoid arthritis and osteoporosis, and is very broad in application prospects.
Description
technical field [0001] The present invention relates to the field of biomedicine, in particular, the present invention relates to a spiro(3,3'-phenylpyrrolidindoxindole) liver X receptor modulator and its preparation method and application. Background technique [0002] Liver X receptor (LXR) is a ligand-dependent transcription factor that binds to retinol X receptor (RXR) to form a heterodimer form: LXR / RXR. The dimer, under the premise of ligand activation, It can combine with the LXR response element (LXRE) on the target gene to regulate the transcription process of the target gene. LXR includes two subtypes, LXRα and LXRβ. LXRα is distributed in the liver, small intestine, fat and macrophages with immune function, while LXRβ is widely distributed throughout the body. It is generally believed that LXRβ selective agonists can avoid fatty liver side effects. [0003] As a nuclear receptor activated by oxysterol, LXR plays an important role in the metabolism of fat, choles...
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