One step synthesis of 2-hydroxymethylisoflavone and their osteogenic activity

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 6, 2011, Pages 1706-1709

  Kumar, Manmeet ^a   Rawat, Preeti ^a   Kureel, Jyoti ^a   Singh, Anuj Kumar ^a   Singh, Divya ^a   Maurya, Rakesh ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

1,5 Hydride shift; 2 Carbaldehydeisoflavone; 2 Hydroxymethylisoflavone; Osteoblast differentiation; Quantitative PCR

Indexed keywords

2 CARBALDEHYDEISOFLAVONE; 2 HYDROXYMETHYLISOFLAVONE; 2 ISOFLAVONE DERIVATIVE; ALKALINE PHOSPHATASE; BIOCHANIN A; BONE MORPHOGENETIC PROTEIN 2; BUTEA MONOSPERMA EXTRACT; DAIDZEIN; DEOXYBENZOIN DERIVATIVE; FORMONONETIN; GENISTEIN; GLYCITEIN; ISOFLAVONE DERIVATIVE; ISOFORMONONETIN; OSTEOCALCIN; PLANT EXTRACT; TRANSCRIPTION FACTOR RUNX2; UNCLASSIFIED DRUG;

ARTICLE; BMP 2 GENE; BONE MINERALIZATION; BUTEA; BUTEA MONOSPERMA; CALVARIA; CELL DIFFERENTIATION; CELL FUNCTION; CELL STIMULATION; CYCLIZATION; DRUG ACTIVITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; FOOD COMPOSITION; GENE; HUMAN; NONHUMAN; OSTEOBLAST; OSTEOCALCIN GENE; RUNX 2 GENE;

ANIMALS; CELLS, CULTURED; ISOFLAVONES; MAGNETIC RESONANCE SPECTROSCOPY; OSTEOBLASTS; OSTEOGENESIS; RATS;

RATTUS;

EID: 79952360746     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.01.095     Document Type: Article

References (31)

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21. General procedure for synthesis of deoxybenzoin (3a-g): The mixture of p-methoxy phenyl acetic acid (500 mg, 3.08 mmol) in boron trifluoride etherate (0.6 ml) and resorcinol (280 mg, 3.00 mmol) were heated at 80 °C for 8 h. Reaction mixture was poured in water, extracted with ethyl acetate and dried over anhydrous sodium sulphate. Reaction mixture was concentrated to give crude product. Purification was done by column chromatography using silica gel as adsorbent and hexane, ethyl acetate as eluent to yield compound 3a.
22. 4 and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate/hexane (50:50) or chloroform/methanol (98:2) as the eluting solvents.
23. 5: C, 68.54; H, 4.73. Found: C, 68.47; H, 4.75.
24. 5: C, 68.54; H, 4.73. Found: C, 68.57; H, 4.68.
25. 6: C, 65.85; H, 4.91. Found: C, 65.77; H, 4.98.
26. 4: C, 71.64; H, 4.51. Found: C, 71.59; H, 4.58.
27. 6: C, 65.85; H, 4.91. Found: C, 65.78; H, 4.97.
28. 5: C, 68.54; H, 4.73. Found: C, 68.63; H, 4.66.
29. 3: C, 76.18; H, 4.79. Found: C, 76.25; H, 4.67.
30. 2, and 10 mmol/L PNPP. ALP activity was measured colorimetrically at 405 nm as described previously.
31. Osteocalcin, Runx-2 and BMP-2 expression by using q-PCR: Total RNA was extracted from the cultured cells using Trizol (Invitrogen). cDNA was synthesized from 2 μg total RNA with the Revert Aid™ H Minus first strand cDNA synthesis kit (Fermentas, USA). SYBR green chemistry was used for quantitative determination of the mRNAs for Osteocalcin and BMP-2 and a housekeeping gene, GAPDH, following an optimized protocol. The design of sense and antisense oligonucleotide primers was based on published cDNA sequences using the Universal probe library (Roche diagnostics, USA). For real-time PCR, the cDNA was amplified with Light Cycer 480 (Roche diagnostics pvt ltd). The double-stranded DNA-specific dye SYBR Green I was incorporated into the PCR buffer provided in the Light Cycler 480 SYBER green I master (Roche diagnostics pvt ltd) to allow for quantitative detection of the PCR product in a 20-μl reaction volume. The temperature profile of the reaction was 95 °C for 5 min, 40 cycles of denaturation at 94 °C for 2 min, and annealing and extension at 62 °C for 30 s, extension at 72 °C for 30 s. GAPDH was used to normalize differences in RNA isolation, RNA degradation, and the efficiencies of the reverse transcription. Primer pairs used were; for BMP-2, 5′-CGG ACT GCG GTC TCC TAA-3′ (sense); 5′-GGG GAA GCA GCA ACA CTA GA-3′ (antisense); for osteocalcin, 5′-GGA CAT TAC TGA CCG CTC C-3′ (sense), 5′-TTT TCA GTG TCT GCC GTG AG-3′ (antisense); for Runx-2 were, 5′-GCC GGG AAT GAT GAG AAC TAC T-3′ (sense), 5'-TCC GGC CTA CAA ATC TCA GAT C-3' (antisense); for GAPDH, 5'-CAG CAA GGA TAC TGA GAG CAA GAG-3' (sense), 5'-GGA TGG AAT TGT GAG GGA GAT G-3' (antisense).