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Volumn 18, Issue 14, 2008, Pages 3914-3918

Gallic acid-based indanone derivatives as anticancer agents

Author keywords

Anticancer; Gallic acid; HMQC; Indanones; Osmotic fragility

Indexed keywords

3 (3',4',5' TRIMETHOXYPHENYL) 4,5,6 TRIMETHOXYINDAN 1 ONE; ANTINEOPLASTIC AGENT; GALLIC ACID; INDANONE DERIVATIVE;

EID: 47349103796     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.06.039     Document Type: Article
Times cited : (124)

References (38)
  • 1
    • 47349131125 scopus 로고    scopus 로고
    • CIMAP Communication No. 2008-80J.
    • CIMAP Communication No. 2008-80J.
  • 4
    • 47349126236 scopus 로고    scopus 로고
    • Sato, Y. Jpn. Kokai Tokkyo Koho 1998, 10298126.
    • Sato, Y. Jpn. Kokai Tokkyo Koho 1998, 10298126.
  • 28
    • 47349127164 scopus 로고    scopus 로고
    • Syntheses: General procedure for preparing indanone derivatives from chalcones: Synthesis of 3-(3′,4′,5′-Trimethoxyphenyl)-4,5,6-trimethoxy-indan-1 -one (10). In a Borosil test tube, chalcone 9 (150 mg, 0.39 mmol) was taken in trifluoroacetic acid (0.5 ml) and the tube was sealed carefully with flame. The reaction mixture was heated at 120 °C for 4 h. The reaction mixture was poured into crushed ice and extracted with ethyl acetate, organic layer was washed with water, dried over anhydrous sodium sulphate and evaporated in vacuo. The crude residue thus obtained was purified through column chromatography on silica gel using ethyl acetate-hexane as eluent. The desired indanone 10 was obtained as a solid. It was recrystallised with chloroform-hexane (1:3) to get 10 as a light brown solid.
    • Syntheses: General procedure for preparing indanone derivatives from chalcones: Synthesis of 3-(3′,4′,5′-Trimethoxyphenyl)-4,5,6-trimethoxy-indan-1 -one (10). In a Borosil test tube, chalcone 9 (150 mg, 0.39 mmol) was taken in trifluoroacetic acid (0.5 ml) and the tube was sealed carefully with flame. The reaction mixture was heated at 120 °C for 4 h. The reaction mixture was poured into crushed ice and extracted with ethyl acetate, organic layer was washed with water, dried over anhydrous sodium sulphate and evaporated in vacuo. The crude residue thus obtained was purified through column chromatography on silica gel using ethyl acetate-hexane as eluent. The desired indanone 10 was obtained as a solid. It was recrystallised with chloroform-hexane (1:3) to get 10 as a light brown solid.
  • 29
    • 47349134086 scopus 로고    scopus 로고
    • Synthesis of 3-(3′,4′,5′-Trimethoxyphenyl)-4,5,6-trimethoxy-indan (20). Indanone 10 (100 mg, 0.26 mmol) was taken in trifluoroacetic acid (2.5 ml) and the reaction flask was stirred in an ice-bath. After stirring for 5 min sodium borohydride (100 mg, 2.6 mmol) was added in portions with maintaining the bath temperature 0-15 °C for an hour. After that the reaction mixture was stirred at room temperature for 6 h. On completion, 10 ml water was added to reaction mixture and it was extracted with ethyl acetate, organic layer was washed with water, dried over anhydrous sodium sulphate and evaporated in vacuo. The crude residue thus obtained was purified through column chromatography on silica gel using ethyl acetate-hexane as eluent. The desired indan 20 was obtained as oil.
    • Synthesis of 3-(3′,4′,5′-Trimethoxyphenyl)-4,5,6-trimethoxy-indan (20). Indanone 10 (100 mg, 0.26 mmol) was taken in trifluoroacetic acid (2.5 ml) and the reaction flask was stirred in an ice-bath. After stirring for 5 min sodium borohydride (100 mg, 2.6 mmol) was added in portions with maintaining the bath temperature 0-15 °C for an hour. After that the reaction mixture was stirred at room temperature for 6 h. On completion, 10 ml water was added to reaction mixture and it was extracted with ethyl acetate, organic layer was washed with water, dried over anhydrous sodium sulphate and evaporated in vacuo. The crude residue thus obtained was purified through column chromatography on silica gel using ethyl acetate-hexane as eluent. The desired indan 20 was obtained as oil.
  • 30
    • 47349108044 scopus 로고    scopus 로고
    • 2-Hydroxy, 3-(3′,4′,5′-trimethoxyphenyl)-4,5,6-trimethoxy-ind-2-e n-1-one (16). Indanone 10 (100 mg, 0.26 mmol) was taken in a round-bottomed flask with 1,4-dioxane (10 ml) and selenium dioxide (290 mg, 2.6 mmol). The reaction mixture was refluxed for 6 h. On completion, reaction mixture was filtered and filtrate was evaporated in vacuo. The crude mass thus obtained was purified through column chromatography on silica gel using ethyl acetate-hexane as eluent. The cyclised product 17 was first obtained followed by the desired derivative 16.
    • 2-Hydroxy, 3-(3′,4′,5′-trimethoxyphenyl)-4,5,6-trimethoxy-ind-2-e n-1-one (16). Indanone 10 (100 mg, 0.26 mmol) was taken in a round-bottomed flask with 1,4-dioxane (10 ml) and selenium dioxide (290 mg, 2.6 mmol). The reaction mixture was refluxed for 6 h. On completion, reaction mixture was filtered and filtrate was evaporated in vacuo. The crude mass thus obtained was purified through column chromatography on silica gel using ethyl acetate-hexane as eluent. The cyclised product 17 was first obtained followed by the desired derivative 16.
  • 31
    • 47349100022 scopus 로고    scopus 로고
    • note
    • 2 incubator at 37 °C. The concentration of DMSO were always kept below 1.25%, which was found to be non-toxic to cells. Then, 10 μL MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] was added to each well and plates were incubated at 37 °C for 4 h. DMSO (100 μL) was added to all wells and mixed thoroughly to dissolve the dark blue crystals. The plates were read on SpectraMax 190 Microplate reader (Molecular Devices Inc. USA) at 570 nm within 1 h of DMSO addition.
  • 32
    • 47349091924 scopus 로고    scopus 로고
    • note
    • 50 (mean erythrocyte fragility) value, which is the saline concentration at which 50% of the cells haemolyse at standard pH and temperature, was then obtained from the curve.
  • 34
    • 47349088717 scopus 로고    scopus 로고
    • note
    • +], 372, 357.
  • 38
    • 47349106947 scopus 로고    scopus 로고
    • Dacie, J. V.; Lewis, S. M. Practical Hematology, 1984; Orient Longman, p 152.
    • Dacie, J. V.; Lewis, S. M. Practical Hematology, 1984; Orient Longman, p 152.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.