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Bioorganic and Medicinal Chemistry Letters
Volumn 27, Issue 7, 2017, Pages 1502-1507
Synthesis of extended conjugated indolyl chalcones as potent anti-breast cancer, anti-inflammatory and antioxidant agents
Author keywords

Anti inflammatory; Antioxidant; Cytotoxicity; Extended conjugation; Indole chalcones
Indexed keywords

ANTIINFLAMMATORY AGENT; ANTIOXIDANT; ASCORBIC ACID; CHALCONE DERIVATIVE; CYTOTOXIC AGENT; DICLOFENAC; DOXORUBICIN; INDOLYL CHALCONE DERIVATIVE; UNCLASSIFIED DRUG; ALBUMINOID; ANTINEOPLASTIC AGENT; EGG PROTEIN; INDOLE DERIVATIVE; NITRIC OXIDE; NONSTEROID ANTIINFLAMMATORY AGENT; SCAVENGER; SUPEROXIDE;
EID: 85014117063     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2017.02.052     Document Type: Article
Times cited : (77)
References (60)
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    • General procedure for the synthesis of extended conjugated indolyl chalcones (5a–p):To a mixture of 3-(1H-indol-3-yl)-3-oxopropanenitrile2 (1 mmol) in ethanol (15 ml) was added piperidine (0.3 ml) and stirred for 5 min
    • After completion of reaction (monitored by TLC), reaction mixture was poured over crushed ice and acidified with acetic acid. The precipitated solid was filtered, washed with water and oven dried. It was column purified by column chromatography using silica gel mesh size, 100–200 and elution with 10% ethyl acetate in hexane
    • 21 General procedure for the synthesis of extended conjugated indolyl chalcones (5a–p):To a mixture of 3-(1H-indol-3-yl)-3-oxopropanenitrile2 (1 mmol) in ethanol (15 ml) was added piperidine (0.3 ml) and stirred for 5 min. Then, added the purified β-chlorovinyl aldehyde 4 (1 mmol) and this mixture was heated to 70 °C for 1–4 h. After completion of reaction (monitored by TLC), reaction mixture was poured over crushed ice and acidified with acetic acid. The precipitated solid was filtered, washed with water and oven dried. It was column purified by column chromatography using silica gel mesh size, 100–200 and elution with 10% ethyl acetate in hexane.
    • Then, added the purified β-chlorovinyl aldehyde 4 (1 mmol) and this mixture was heated to 70 °C for 1–4 h
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    • In vitro anti-inflammatory activity by protein denaturation method: The reaction mixture (10 ml) consisted of 0.4 ml of egg albumin (from fresh hen's egg), 5.6 ml of phosphate buffered saline (PBS, pH 6.4) and 4 ml of synthetic derivative (1 mM)
    • Then the mixtures were incubated at (37 °C ± 2) in an incubator for 15 min and then heated at 70 °C for 5 min. After cooling, their absorbance was measured at 660 nm by using vehicle as blank. Diclofenac sodium (1 mM) was used as reference drug and treated similarly for the determination of absorbance. The percentage inhibition of protein denaturation was calculated by using the following formula, % inhibition = 100 × (Vt/Vc − 1); Where, Vt = absorbance of test sample, Vc = absorbance of control
    • 26 In vitro anti-inflammatory activity by protein denaturation method: The reaction mixture (10 ml) consisted of 0.4 ml of egg albumin (from fresh hen's egg), 5.6 ml of phosphate buffered saline (PBS, pH 6.4) and 4 ml of synthetic derivative (1 mM). Similar volume of double-distilled water served as control. Then the mixtures were incubated at (37 °C ± 2) in an incubator for 15 min and then heated at 70 °C for 5 min. After cooling, their absorbance was measured at 660 nm by using vehicle as blank. Diclofenac sodium (1 mM) was used as reference drug and treated similarly for the determination of absorbance. The percentage inhibition of protein denaturation was calculated by using the following formula, % inhibition = 100 × (Vt/Vc − 1); Where, Vt = absorbance of test sample, Vc = absorbance of control.
    • Similar volume of double-distilled water served as control
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    • 29 Velavan, S.; Naghlendran, K.; Mahesh, R.; HazeenaB.V. PHCOGMAG, 1998. ISSN: 0973-1296.
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    • 24 NO radicals were generated from sodium nitroprusside solution
    • The mixture was incubated at 25 °C for 150 min. After incubation the reaction mixture mixed with 1.0 ml of pre-prepared Griess reagent (1% sulphanilamide, 0.1% naphthyl ethylenediamine dichloride and 2% phosphoric acid). The absorbance was measured at 546 nm and percentage of inhibition was calculated using the same formula as above. The decreasing absorbance indicates a high nitric oxide scavenging activity
    • 31 NO radical scavenging activity: NO radical scavenging activity of compounds 5a-p was carried out as per the method. NO radicals were generated from sodium nitroprusside solution. One ml of 10 mM sodium nitroprusside was mixed with 1 ml of 1 mM synthetic compounds in phosphate buffer (0.2 M pH 7.4). The mixture was incubated at 25 °C for 150 min. After incubation the reaction mixture mixed with 1.0 ml of pre-prepared Griess reagent (1% sulphanilamide, 0.1% naphthyl ethylenediamine dichloride and 2% phosphoric acid). The absorbance was measured at 546 nm and percentage of inhibition was calculated using the same formula as above. The decreasing absorbance indicates a high nitric oxide scavenging activity.
    • One ml of 10 mM sodium nitroprusside was mixed with 1 ml of 1 mM synthetic compounds in phosphate buffer (0.2 M pH 7.4)
  • 59
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    • Superoxide radical (SOR) scavenging assay: The reaction mixture consisting of 1 ml of nitro blue tetrazolium (NBT) solution (156 mM NBT in phosphate buffer, pH 7.4)
    • The reaction was started by adding 1 ml of phenazine methosulfate (PMS) solution (60 mM PMS in phosphate buffer, pH 7.4) to the mixture. The reaction mixture was incubated at 25 °C for 5 min and the absorbance was measured at 560 nm against blank sample and compared with standards and percentage of inhibition was calculated using the same formula as above. Decreased absorbance of reaction mixture indicated increased SOR scavenging activity
    • 32 Superoxide radical (SOR) scavenging assay: The reaction mixture consisting of 1 ml of nitro blue tetrazolium (NBT) solution (156 mM NBT in phosphate buffer, pH 7.4), 1 ml NADH solution (468 mM NADH in phosphate buffer, pH 7.4), and 1 ml of synthetic compound (1 mM) solution was mixed. The reaction was started by adding 1 ml of phenazine methosulfate (PMS) solution (60 mM PMS in phosphate buffer, pH 7.4) to the mixture. The reaction mixture was incubated at 25 °C for 5 min and the absorbance was measured at 560 nm against blank sample and compared with standards and percentage of inhibition was calculated using the same formula as above. Decreased absorbance of reaction mixture indicated increased SOR scavenging activity.
    • 1 ml NADH solution (468 mM NADH in phosphate buffer, pH 7.4), and 1 ml of synthetic compound (1 mM) solution was mixed

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