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1. WO2020068015 - WATER-SOLUBLE, NON-AGGREGATED SILICON PHTALGCYANINE COMPOUND HAVING IN VITRO ANTICANCER EFFECT AGAINST CANCER TYPES OF LUNG, LIVER, BREST AND MELANOMA

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CLAIMS

1. Water-soluble and non-aggregated silicon phtalocyanine compounds of Formula (I) or Formula (II) comprising functional groups of (3,5-bis{3-[3- (dlethylamino)phenoxy]propoxy}phenyl)methoxy or (3,5-bis{3-[3- (dimethylamino)phenoxy]propoxy}phenyl)methoxy.


2. A compound according to Claim 1 for use as a drug.

3. A compound according to Claim 1, comprising cytotoxicity activity on human breast (BT- 20), melanoma (SK-Mel 128), liver (SNU-398) and lung (A549) cancer cell lines.

4. A method for synthesizing the compound of bis(3,5-bis{3-[3- (diethlymethyiamino)phenoxyjpropoxy}phenyl)methoxy) phthalocyaninato silicon(IV) Iodide (7a, Formula I) or bis(3,5-bis{3-[3-trimethylamino)

phenoxy]propoxy}phenyl)methoxy)phthalocyaninato silicon(IV) iodide (3a, Formula II) for using in the treatment of human breast and/or melanoma and/or liver and/or lung cancers, comprising below steps:

® Dissolving in 100-150 mL of acetone by adding 3,5-dihydroxybenzylaicohol and dry K CO into single-necked flask,

• Removing the dissolved oxygen of the system for a couple of times in the nitrogen atmosphere by adding [3-(3-chloropropoxy)phenyl]diethylamine or [3 (3- ch!oropropoxy)pbenyi]dimethy!amine and 18-crown-6 on the mixture dissolved,

® Mixing the reaction mixture in the nitrogen atmosphere at 70 °C for 2 days,

® Evaporating completely the mixture cooled down to the room temperature,

• Dissolving the product remained at the end of evaporation in the 45-60 ml. of chloroform and extracting for more than one in 25-40 ml. of pure water,

® Evaporating the chloroform by drying the organic phase subsequent to the extraction over MgS04,

® Purifying the obtained crude product from the aluminum oxide loaded column with the solvent CHC and obtaining the compound of (3,5-bis{3-[3- (diethylamino)phenoxyjpropoxy}phenyl)methanoi or (3,5-bis{3-[3- (dimethylamino)phenoxyjpropoxy}phenyi)methanoi being a fawn colored oily substance,

® Dissolving in 10 ml of toluene by adding silicon phthalocyanine dichloride (125 mg, 0.2 mmol), (3,5-bis{3-[3-(diethylamino)phenoxy]propoxy}phenyl)methanol (171 mg, 0.32 mmol) or silicon phthalocyanine dichloride (125 mg, 0.2 mmol), (3,5-bis{3-[3- (dimethylamino)phenoxyjpropoxy} phenyl)methanol (202 mg, 0.4 mmol),

® Mixing at the room temperature in the nitrogen atmosphere for 10 minutes,

® Removing the dissolved oxygen of the system for a couple of times in the nitrogen atmosphere by swiftly adding NaH (9,6 mg, 0.4 mmol) into the obtained mixture,

® Mixing in the nitrogen atmosphere at 120 °C for 24 hours,0

® Evaporating completely the solvent of the mixture cooled down to the room temperature under low pressure,

® Purifying the obtained crude product with the solvent CHC by using the aluminum oxide filling material from the column and obtaining the compound of bis(3,5-bis{3- [3-diethylamino)phenoxy]propoxy}phenyl)methoxy)phthalocyaninato silicon(IV) or bis(3,5-bis{3-[3-dimethylamino)phenoxy]propoxy} phenyl)methoxy)phthalocyaninato silicon(IV),

® Dissolving in 4mL of chloroform by putting the compound of bis(3,5-bis{3-[3- dietbyiamino)phenoxy]propoxy}phenyl)methoxy) phthalocyaninato silicon(IV) or bis(3,5-bis{3-[3-dimethylamino)phenoxy]propoxy} phenyl)methoxy)phthalocyaninato silicon(IV) into 50 ml of a single necked flask (40 mg, 0.026 mmol),

® Mixing at the room temperature for 4 days in a lid-closed manner by adding 5 mL of methyl iodide thereon,

• Washing firstly with chloroform, acetone and lastly with diethyl ether by filtering the product precipitated in the medium and drying in vacuum oven and obtaining the water-soluble compound of bis(3,5-bis{3 -[3- diethylmethylamino)phenoxyjpropoxy}phenyl)methoxy) phthalocyaninato silicon(IV) Iodide (7a) or bis(3,5-bis{3-[3-trimethylamino)phenoxy]propoxy}phenyl)methoxy) phthalocyaninato silicon(IV) Iodide (3a).