Sinomenine derivative as well as preparation method and application thereof
A technology of sinomenine and derivatives, applied in the field of sinomenine derivatives and their preparation, can solve the problems of limited anti-fibrosis effect of sinomenine, and achieve good anti-fibrosis effect, good safety, and anti-fibrosis Effect of effect improvement
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Embodiment 1
[0045] The preparation of embodiment 1 sinomenine derivatives
[0046]
[0047] The specific reaction steps for the preparation of the sinomenine derivatives are as follows:
[0048] S1. Compound (II) (20mmol, 1 equivalent) was dissolved in 160mL of dichloromethane, N-iodosuccinimide (21mmol, 1.05 equivalent) was added within 5 minutes, stirred at room temperature for 5 minutes, and 120mL Quenched with saturated sodium thiosulfate solution; extracted with dichloromethane, washed with brine, dried over magnesium sulfate, and evaporated under reduced pressure; the residue was purified by column chromatography to obtain compound (III) (yield: 86%);
[0049] S2, compound (III) (1mmol, 1 equivalent), 3-benzene-1-propyne (2mmol, 2 equivalents), ditriphenylphosphine palladium dichloride (0.05mmol, 0.05 equivalents), iodine Cuprous chloride (0.05mmol, 0.05eq), triethylamine (3mmol, 3eq) were dissolved in 10mL of anhydrous acetonitrile, stirred and reacted under argon protection fo...
experiment example 1
[0051] Experimental Example 1 Toxicity test (MTT method) of sinomenine derivatives to fibrotic cells
[0052] NIH / 3T3 cells (purchased from the Chinese Academy of Sciences) were placed in DMEM medium containing 10% fetal bovine serum at 37°C, 5% CO 2 cultured in a humidified incubator. Add 100 μL of NIH / 3T3 cells at a concentration of 7000 / well to each well of a 96-well culture plate, at 37°C, 5% CO 2 Cultivate for 24 hours; Add 100 μL / well of two-fold gradient dilution of the test drug to the drug experimental group, 6 replicate wells for each concentration, set up a cell blank control and positive drug control pirfenidone (Pirfenidone) at the same time, and continue to cultivate for 24 hours; After adding 10 μl of MTT and continuing to incubate for 4 h, the supernatant was discarded, 150 μl of DMSO was added, and the absorbance at 490 nm was detected with a full-wavelength multifunctional microplate reader. The toxic effect of compounds on fibrotic cells was determined.
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experiment example 2
[0054] Experimental example 2 Inhibitory effect of sinomenine derivatives on TGF-β1-induced fibrosis target mRNA in NIH / 3T3 cells
[0055] NIH / 3T3 cells in the logarithmic growth phase (purchased from the Chinese Academy of Sciences) were selected to make a single cell suspension and seeded on a culture plate; the cells were stimulated with 5 ng / ml TGF-β1 for 24 hours to construct a fibrotic cell model. Divided into normal group, model group (TGF-β1 group), positive drug group (Pirfenidone group), sinomenine derivatives group (0.78, 1.56, 3.13, 6.25, 12.5μM), sinomenine group ( 0.78, 1.56, 3.13, 6.25, 12.5 μM).
[0056] Cells were collected, and total cellular RNA was extracted with an RNA extraction kit, reverse-transcribed into cDNA with an RNA reverse transcription kit, and PCR amplified using a SYBR Premix Ex TaqTM11 kit. The above experiments were performed in accordance with the instructions. The primers were synthesized by Sangon Biotechnology Co., Ltd., and the seque...
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