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Indole derivative and medical application thereof
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A kind of indole and pharmaceutical technology, applied in the field of biomedicine, can solve problems such as cardiotoxicity
Inactive Publication Date: 2020-12-04
CHINA PHARM UNIV +1
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In addition, it has been reported that inhibition of FABP3 may cause cardiotoxicity (FASEB J.1999,13,805)
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[0125] Get compound I-1 (20g, 137mmol) and place in round-bottomed flask (1L), add water (411mL) and concentrated hydrochloric acid (137mL), under ice bath slowly add dropwise the aqueous solution of sodiumnitrite (10.4g, 151mmol) ( 82mL), after adding, continue stirring under ice bath for 45 minutes, add the concentrated hydrochloric acid solution (68.5mL) of stannous chloride dihydrate (61.8g, 274mmol) in the reaction solution, a large amount of solids are separated out, add, slowly Rising to room temperature, the reaction solution was suction-filtered, the filter cake was washed successively with saturated brine (50mL×2) and diethyl ether (50mL×2), and dried in vacuo to obtain compound I-2 (red-brown solid, 24.2g, yield 90% ): 1 H NMR (300MHz, DMSO-d 6 )δ10.53(s,3H),8.57(s,1H),7.43-7.21(m,2H),7.14-6.96(m,1H).
[0135] Suspend compound I-9 (715mg, 2.15mmol) and potassiumcarbonate (594mg, 4.30mmol) in acetonitrile (1mL), add iodoethane (1.02mL, 17.18mmol) to the reaction solution, seal the tube and heat and stir at 100°C 24 hours. After the reaction of the raw materials was completed, the heating was stopped, cooled to room temperature, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (petroleumether: ethyl acetate = 100:1) to obtain compound II-1 (yellow oily liquid, 760mg , yield 91%): 1 H NMR (300MHz, CDCl 3 )δ7.52-7.39(m,3H),7.33-7.28(m,2H),7.17(dd,J=8.8,6.8Hz,1H),6.86(d,J=8.8Hz,1H),4.13(q ,J=7.1Hz,2H),3.23-3.14(m,4H),1.09-0.99(m,9H).
[0140] Compound 3 was obtained by referring to the method of Example 1: 1 H NMR (300MHz, DMSO-d 6 )δ16.12(s,1H),7.88-7.80(m,1H),7.60-7.47(m,3H),7.44-7.36(m,2H),7.27-7.17(m,1H),7.14-7.06( m, 1H), 3.44(q, J=7.2Hz, 4H), 1.04(t, J=7.2Hz, 6H).ESI-MS: m / z 349.1[M+Na] + .
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Abstract
The invention discloses an indole compound with FABP4 / 5 inhibitory activity and a preparation method and medical application of the indole compound. The indole compound is a compound of which the structural formula is shown as a formula I, and pharmaceutically acceptable salt or ester or solvate of the compound. The compound shown in the formula I is a novel FABP4 / 5 inhibitor and can be used for preparing medicines for preventing or treating FABP4 / 5 related diseases.
Description
technical field [0001] The present invention relates to the field of biomedicine, in particular to inhibitors of fatty acidbinding protein (FABP) 4 and / or 5, more specifically to indole novel FABP4 / 5 inhibitors, and the present invention also relates to a preparation method of such compounds and their use as Medicinal uses of FABP4 / 5 inhibitors. Background technique [0002] Fatty acid binding proteins (FABPs), as intracellular lipid chaperones, can reversibly bind to lipids, increase their solubility in the cytoplasm, and reduce lipotoxicity. There are many subtypes in the FABP family, among which FABP4 (adipocyte-FABP, A-FABP) and FABP5 (epidermal-FABP, E-FABP) are members of the fatty acidbinding protein family. FABP4 is mainly distributed in adipocytes and macrophages, accounting for 1% of the total protein in adipose tissue. FABP5 is distributed in a wide range of tissues. FABP4 / 5 is closely related to the occurrence and development of metabolic inflammatory diseas...
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