Synthesis of gallic acid based naphthophenone fatty acid amides as cathepsin D inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 17, 2006, Pages 4603-4608

  Srivastava, Vandana ^a   Saxena, Hari Om ^a   Shanker, Karuna ^a   Kumar, J K ^a   Luqman, Suaib ^a   Gupta, M M ^a   Khanuja, S P S ^a   Negi, Arvind S ^a  

^a CSIR CENTRAL INSTITUTE OF MEDICINAL AND AROMATIC PLANTS   (India)

Author keywords

Amides; Cathepsin D; Gallic acid; Protease inhibitors; Synthesis

Indexed keywords

AMIDE; CATHEPSIN D; FATTY ACID DERIVATIVE; GALLIC ACID; PEPSTATIN; PEPTIDE HYDROLASE INHIBITOR;

ARTICLE; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; IN VITRO STUDY; STRUCTURE ACTIVITY RELATION;

AMIDES; CATHEPSIN D; FATTY ACIDS; GALLIC ACID; KETONES; MOLECULAR STRUCTURE; NAPHTHALENES; PEPSTATINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33746682540     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.06.010     Document Type: Article

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35. Syntheses. (a) General procedure for the synthesis of 12 and 13. Synthesis of 2-[1-(3,4,5-trimethoxybenzoyl) naphthalene-2-yloxy] ethanoic acid 12: In a 25 ml round-bottomed flask 2-[1-(3,4,5-trimethoxy-benzoyl)-naphthalen-2-yloxy]-ethyl ethanoate 10 (100 mg, 0.23 mmol) was taken in 5 ml of 10% aqueous methanolic (1:1, v/v) potassium hydroxide. The reaction mixture was stirred at 50 °C for 2 h. On completion, the reaction mixture was acidified with 10% HCl and extracted with ethyl acetate (3× 20 ml). The organic layer was washed with water and concentrated to get 12 as white crystalline solid. (b) Synthesis of 2-[3,4,5-trimethoxybenzoyl naphthalene-2-yloxy]-ethanoic acid amide 14: In a round-bottomed flask 2-[1-(3,4,5-trimethoxy-benzoyl) naphthalene-2-yloxy]-ethyl ethanoate 10 (100 mg, 0.25 mmol) was taken in 5 ml aqueous ammonia (30%). The reaction mixture was kept as such for overnight at room temperature. Later the reaction mixture was diluted with water and extracted with ethyl acetate (3× 25 ml). The organic layer was washed with water, dried over anhydrous sodium sulfate and distilled off to get a creamy white solid compound 14. (c) General procedure for the synthesis of amide derivatives 15-23. Synthesis of 4-[1-(3,4,5-trimethoxybenzoyl) naphthalene-2-yloxy]-but-2-enoic acid-3,4,5-trimethoxy phenyl amide 23: In a 25 ml round-bottomed flask 4-[1-(3,4,5-trimethoxy-benzoyl)-naphthalen-2-yloxy]-but-2-enoic acid 10 (100 mg, 0.171 mmol) was taken in dry dichloromethane (10 ml). To this, EDC (41 mg, 0.21 mmol), HOBt (29 mg, 0.21 mmol) and DMAP (5 mg) were added and stirred at room temperature for 20 min. Later 3,4,5-trimethoxy aniline (46 mg, 0.25 mmol) was added to the reaction mixture and refluxed for 3 h. On completion, water (10 ml) was added to it and extracted with chloroform (3× 20 ml). The organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated. The residue thus obtained was purified through a silica gel column by eluting with hexane-ethyl acetate. The desired amide was obtained at 5% ethyl acetate-hexane fraction, which on concentration yielded a creamy white solid compound.
36. 50 values were calculated from this enzyme activity value for each test compound by using Michaelis-Menten equation in 'Graph pad prism' software.
37. +.