Amine-containing transfection reagents and methods of making and using the same
A technology of transfection, bioactive agent, applied in the field of transfection complex
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[0104] Amine-containing transfection compounds
[0105] The present invention describes different amine-containing compounds that can be used as transfection reagents and methods for their synthesis. More specifically, according to some embodiments of the present invention, there is provided a compound having general structure I or a pharmaceutically acceptable salt thereof:
[0106]
[0107]
[0108] Where X 1 And X 2 Each of them is independently selected from the following moieties: O, S, N-A and C-A, where A is selected from hydrogen and C 1 -C 20 Hydrocarbon chain; each of Y and Z is independently selected from the following moieties: CH-OH, C=O, C=S, S=O and SO 2 ; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 And R 7 Each of them is independently selected from the following: hydrogen, cyclic or acyclic, substituted or unsubstituted, branched or straight-chain aliphatic groups, cyclic or acyclic, and Substituted or unsubstituted, branched or straight chain heteroaliphatic group, substit...
Embodiment 1
[0242] Example 1. Synthesis of bromo-N-dodecylacetamide
[0243] According to the following general reaction scheme, the title intermediate was synthesized:
[0244]
[0245] In a round bottom flask with a pressure-balanced addition funnel, 1.5 g (7.431 mmol, 1.05 equivalent) of bromoacetyl bromide was added to 200 mL of dichloromethane, and the mixture was stirred under nitrogen. Using an ice bath, the flask was cooled to about 0°C. 1.31 g (7.077 mmol) of dodecylamine and 0.716 g (983 μL, 7.077 mmol) of triethylamine were dissolved in 100 mL of dichloromethane. Transfer the solution to the addition funnel and slowly add bromoacetyl over about 1 hour Solution. The said anti The mixture was stirred at about 0°C for another about 1 hour, slowly warming to room temperature by melting the ice.
[0246] The resulting reaction mixture was transferred to a separatory funnel and extracted with 100 mL of saturated sodium bicarbonate solution. The aqueous layer was washed with 50 mL of ...
Embodiment 2
[0247] Example 2. Synthesis of tetradecyl-2-bromoacetate
[0248] According to the following general reaction scheme, the title intermediate was synthesized:
[0249]
[0250] 3g (1.3mL, 14.862mmol, 1.05 equivalent) of bromoacetyl bromide was dissolved in 50mL of dichloromethane. Using an ice bath, cool the flask to about 0°C. Dissolve 3.03 g (14.154 mmol) of tetradecyl alcohol in 50 mL of dichloromethane, and slowly add to the above mixture via a pipette, then add about 5 drops of concentrated sulfuric acid, and stir at about 0°C for about 30 minutes, then Stir overnight at room temperature.
[0251] Add about 150 mL of saturated sodium bicarbonate solution and stir quickly for about 30 minutes. The mixture was then transferred to a separatory funnel, and the organic layer was collected. Wash the aqueous layer with about 100 mL of dichloromethane. The combined organic layer was dried over sodium sulfate, filtered, and concentrated to obtain 4.095 g (89.7% yield) of product.
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