Indole guanidine compound as well as preparation method and application thereof
A compound, the technology of indoguanidine, applied in the field of preparation of indoguanidine compounds
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[0035] see figure 1 , the preparation method of the indoguanidine compound containing fatty acid ester of above-mentioned structure, comprises the following steps:
[0036] 1) thiosemicarbazide reacts with ethyl bromide to prepare thiobarbituric acid ethyl hydrazide;
[0037] 2) N-valeryl hydrazide carboxyxime amide is prepared by reacting ethyl thiobarbituryl hydrazide with pentylamine;
[0038] 3) Preparation of (E)-2-((5-hydroxy-1H-indol-3-yl)methylene)-N - Amylhydrazine-1-carboxamide;
[0039] 4) Condensation of (E)-2-((5-hydroxy-1H-indol-3-yl)methylene)-N-pentylhydrazine-1-carboxamide with fatty acid to generate indoguanidine containing fatty acid ester class of compounds.
[0040] The specific process of the step 1) is: add thiosemicarbazide and absolute ethanol into an eggplant-shaped bottle, heat up the oil bath to 55-65°C, then add bromoethane to react for 5-7h, after the reaction is completed, the reaction system Cool to room temperature, wait for a large amount...
Embodiment 1
[0046] A kind of indoguanidine compound, R is , the preparation method is as follows:
[0047] 1) Synthesis of ethyl thiobarbiturohydrazide: 2g of thiosemicarbazide (21.95mmol) and 40mL of absolute ethanol were added to a 100mL eggplant-shaped bottle, the oil bath was heated to 60°C, and 3.588g of bromoethane ( 32.925mmol) for 6h. After the reaction was completed, the reaction system was cooled to room temperature, and a large amount of white solid was precipitated in the bottle, filtered, and the filter cake was washed with anhydrous ether and dried to constant weight to obtain white crystal ethyl thiobarbiturohydrazide with a yield of 97%. EI-MS(m / z):120[M] - .
[0048] 2) Synthesis of N-valeryl hydrazide carboximide: add 1 g of ethyl thiobarbituryl hydrazide (8.390 mmol) and 20 mL of methanol into a 100 mL eggplant-shaped bottle, heat the oil bath to 65°C, and add 0.878 g of n-pentyl hydrazide Amine (10.068mmol), reflux for 5h. After the reaction was completed, the so...
Embodiment 2
[0052] A kind of indoguanidine compound, R is , the preparation method is as follows:
[0053] 1) Step 1) to step 4) are the same as in Example 1, except that 5-hexynoic acid is replaced by 6-heptynoic acid to obtain white solid compound 2 ((E)-3-((2-(N -Verylcarbamoyl)hydrazone)methyl)-1H-indol-5-ylhept-6-ynoate, yield 40%; EI-MS(m / z):396[M] - ;394[M] + . Purity: 97.560%. 1 H NMR(400MHz,DMSO)δ11.85(s,1H),11.35(s,1H),8.38(s,1H),7.95(d,J=3.7Hz,1H),7.77(s,1H),7.67 (s,1H),7.45(d,J=8.7Hz,1H),6.94(dd,J=8.7,2.2Hz,1H),3.28(d,J=4.9Hz,2H),2.80(t,J= 2.6Hz, 1H), 2.61(t, J=7.4Hz, 2H), 2.50(s, 1H), 2.23(td, J=6.9, 2.6Hz, 2H), 1.76(dt, J=15.2, 7.4Hz, 2H),1.61–1.57(m,2H),1.55(d,J=2.8Hz,2H),1.36–1.29(m,4H),0.89(t,J=6.5Hz,3H).
[0054] The synthesis steps of compound 3 are the same as those in Example 1, except that 5-hexynoic acid is replaced by levulinic acid.
[0055] Compound 3, white solid, yield 42%. EI-MS(m / z):386[M] - ;384[M] + . Purity: 95.996%; 1 HNMR(400MHz,DMSO)δ11.85...
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