- Synthesis method and application of morpholine guanidine hydrochloride
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The invention relates to the field of organic synthesis, in particular to a synthesis method of morpholine guanidine hydrochloride. The method comprises the following steps: (1) carrying out a salt formation reaction, adding morpholine into a reactor, performing stirring, dropwise adding concentrated hydrochloric acid to start the salt formation reaction, stopping the dripping addition of concentrated hydrochloric acid when the pH value is 1-2, completing the reaction, performing dewatering by vacuum concentration to obtain morpholine hydrochloride; (2) carrying out an addition reaction, adding an organic solvent S1 and dicyandiamide into morpholine hydrochloride, starting the addition reaction, performing cooling to room temperature after the reaction is completed, performing stirring andvacuum filtration, washing the filter cake with an organic solvent S2, and performing drying to obtain a morpholine guanidine hydrochloride crude product; and (3) performing refining, performing recrystallization on the morpholine guanidine hydrochloride crude product with ethanol to obtain the morpholine guanidine hydrochloride refined product. The solvent used in the method is an edible flavorwhich is allowed to be used in GB 2760, the boiling point of the solvent is the optimum reaction temperature, the reactants are all dissolved in the solvent at the temperature, the reaction is a homogeneous reaction, the reaction product is insoluble in the solvent, the crude product is obtained by the direct filtration, and the post-treatment is simple.
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Paragraph 0024-0030
(2019/08/20)
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- Hybrid molecules composed of 2,4-diamino-1,3,5-triazines and 2-imino-coumarins and coumarins. Synthesis and cytotoxic properties
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A series of 2-imino-2H-chromen-3-yl-1,3,5-triazine compounds 5–12, which are namely hybrids of 2,4-diamino-1,3,5-triazines and 2-imino-coumarins, was synthesized by reacting 2-(4,6-diamine-1,3,5-triazin-2-yl)acetonitriles 1–4 with 2-hydroxybenzaldehydes. After this, upon heating in aqueous DMF, 2-imino-2H-chromen-3-yl-1,3,5-triazines 10 and 12 were converted into the corresponding 2H-chromen-3-yl-1,3,5-triazines 13 and 14, which are essentially hybrids of 2,4-diamino-1,3,5-triazines and coumarins. The in vitro anticancer activity of the newly prepared compounds was evaluated against five human cancer cell lines: DAN-G, A-427, LCLC-103H, SISO and RT-4. The greatest cytotoxic activity displayed 4-[7-(diethylamino)-2-imino-2H-chromen-3-yl]-6-(4-phenylpiperazin-1-yl)-1,3,5-triazin-2-amine (11, IC50 in the range of 1.51–2.60 μM).
- Makowska, Anna,Saczewski, Franciszek,Bednarski, Patrick J.,Saczewski, Jaros?aw,Balewski, ?ukasz
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- BIGUANIDE COMPOUND AND USE THEREOF
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The present invention relates to a guanidine compound and a use thereof, and more specifically, to a guanidine derivative showing excellent effects of inhibiting cancer cell proliferation, cancer metastasis, and cancer recurrence; a preparation method thereof; and a pharmaceutical composition containing the same as an active ingredient. Compared to existing drugs, the guanidine derivative according to the present invention shows excellent effects of inhibiting cancer cell proliferation, cancer metastasis, and cancer recurrence even with small doses, and may thus be effectively used in preventing or treating various cancers such as uterine cancer, breast cancer, stomach cancer, brain cancer, rectal cancer, colorectal cancer, lung cancer, skin cancer, blood cancer, liver cancer, etc., inhibiting cancer cell proliferation and cancer metastasis.
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Paragraph 0246; 0247; 0266; 0267
(2017/10/07)
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- Synthetic method of moroxydine hydrochlofide
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The invention discloses a synthetic method of moroxydine hydrochlofide. The method comprises the following steps: adding diglycol, dicyandiamide, ammonium chloride and an aqueous sulfuric acid solution with the mass concentration of 20-30% to a high pressure reaction kettle according to amass ratio of (4-6):(4-6):(2-4):(1-2), heating the obtained solution in a sealed and stirring state to 120-130DEG C, reacting under a reaction kettle pressure of 0.3-0.5MPa for 1-2h, and cooling the obtained solution to room temperature to obtain a white milk; and transferring the white milk to a reaction kettle, adding 95% ethanol according to a volume ratio of the 95% ethanol to diglycol of (7-9):1, carrying out a heating refluxing reaction for 30min to obtain a mixed solution, carrying out hot filtration on the mixed solution through a filter cylinder to a crystallization kettle, cooling the obtained filtrate in the crystallization kettle to room temperature to precipitate white crystals, centrifuging and separating the white crystals, and drying the separated white crystals in a hot wind oven at 80-85DEG C to obtain moroxydine hydrochlofide.. Moroxydine hydrochlofide is obtained through a direct reaction of dicyandiamide and morpholine hydrochloride generated through in situ reaction of diglycol and ammonium chloride under the action of sulfuric acid, so the synthetic method is simplified, side reactions are reduced, the yield is improved, and environment is protected.
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Paragraph 0056; 0057
(2016/10/10)
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- Regioselective synthesis of imidazo[1,2-a][1,3,5]triazines and 3,4-dihydroimidazo[1,2-a][1,3,5]triazines from [1,3,5]triazin-2,4-diamines
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An efficient and practical procedure was developed to prepare novel imidazo[1,2-a][1,3,5]triazines and 3,4-dihydroimidazo[1,2-a][1,3,5]triazines with a good regioselectivity and high yields, starting from dicyandiamide and the corresponding arylamines. Mechanistic studies for the subsequent cyclocondensation with chloroacetaldehyde support a pathway, which begins with the displacement of the chloro atom activated by an adjacent CO group, followed by cyclization and dehydration.
- Dao, Pascal,Garbay, Christiane,Chen, Huixiong
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p. 3867 - 3871
(2013/07/05)
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- Synthesis, crystal structure and biological properties of a new series of lipophilic s-triazines, dihydrofolate reductase inhibitors
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A number of adamantyl-group-bearing diamino-s-triazines were synthesized as potential dihydrofolate reductase (DHFR) inhibitors and their pharmacological properties were tested. The crystal structures of certain compounds were determined by X-ray crystallography. With the aid of computer graphics, model structures of the L1210 mouse DHFR-ligand ternary complex were constructed. The binding affinities of the compounds to DHFR were determined experimentally. Compounds mono-substituted at the nitrogen of the amine group appear to be slightly better inhibitors. Weak activity was also enhanced by the presence of a methylene bridge between the adamantyl group and the s-triazine ring. The majority of the compounds was shown to have weak activity against P388 and KB cell lines in vitro; some compounds showed weak anti-bacterial activity and no anti-viral activity was detected.
- Tsitsa,Antoniadou-Vyza,Hamodrakas,Eliopoulos,Tsantili-Kakoulidou,Lada-Hytiroglou,Roussakis,Chinou,Hempel,Camerman,Ottensmeyer,Vanden Berghe
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p. 149 - 158
(2007/10/02)
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- PREPARATION AND SPECTROSCOPIC INVESTIGATION ON Pt(II) AND Pd(II) CHELATES WITH MORPHOLINEBIGUANIDE AND PIPERIDINEBIGUANIDE
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A series of platinum(II) and palladium(II) coordination compounds with morpholinebiguanide and piperidinebiguanide PtLX2 and PdLX2 (X = halide, thiocyanate, hydroxide) have been obtained.The chelates have been characterized by their electronic and IR oscillation spectra.Both ligands are bidentate and bonded through nitrogen atoms with metal.It is suggested that pseudoaromatic chelate ring is formed.A square planar stereochemistry of obtained chelates has been confirmed by both electronic and oscillation spectra.
- Zawadzki, Henryk
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p. 753 - 762
(2007/10/02)
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- Process for producing amidine sulfonic acids
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An efficient synthesis of quanidines, e.g. of the formula (III), by oxidizing a thiourea, e.g. of the following formula (II): STR1 with H2 O2 and a molybdenum catalyst to yield an aminoiminomethane sulfonic acid which can then be reacted with an amine followed by optional transamination steps.
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