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47349127164
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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.
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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.
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47349134086
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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.
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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.
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47349108044
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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.
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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.
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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.
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note
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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.
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0027267309
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Woerdenbag H.J., Moskal T.A., Pras N., Malingré T.M., Farouk S., EI-Feraly H., Kampinga H., and Konings A.W.T. J. Nat. Prod. 56 (1993) 849
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EI-Feraly, H.6
Kampinga, H.7
Konings, A.W.T.8
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+], 372, 357.
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Luqman S., Obli Prabu K.V., Pal A., Saikia D., Darokar M.P., and Khanuja S.P.S. Nat. Prod. Commun. 1 (2006) 481
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Obli Prabu, K.V.2
Pal, A.3
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Darokar, M.P.5
Khanuja, S.P.S.6
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Dacie, J. V.; Lewis, S. M. Practical Hematology, 1984; Orient Longman, p 152.
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Dacie, J. V.; Lewis, S. M. Practical Hematology, 1984; Orient Longman, p 152.
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