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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
7,3',4'-Trihydroxyflavone, a natural product isolated and purified from the seeds of Cassia occidentalis, can markedly inhibit the receptor activator of nuclear factor kappa B ligand (RANKL) induced osteoclastic differentiation from mouse bone marrow derived macrophages (BMMs), it inhibits osteoclastogenesis via nuclear factor of activated T cells c1 (NFATc1).
Synonyms: 7,3',4'-Trihydroxyflavone; 5-Deoxyluteolin; 3’,4’,7-Trihydroxyflavone
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| CAS No. : | 2150-11-0 |
| Formula : | C15H10O5 |
| M.W : | 270.24 |
| SMILES Code : | O=C1C=C(C2=CC=C(O)C(O)=C2)OC3=C1C=CC(O)=C3 |
| Synonyms : |
7,3',4'-Trihydroxyflavone; 5-Deoxyluteolin; 3’,4’,7-Trihydroxyflavone
|
| MDL No. : | MFCD00017434 |
| InChI Key : | PVFGJHYLIHMCQD-UHFFFAOYSA-N |
| Pubchem ID : | 5322065 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302-H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 32.4% | With palladium on activated charcoal; hydrogen; In methanol; at 20.0℃; | General procedure: 2,4-Dihydroxyacetophenone was dissolved in dry THF, and the mixture was cooled to -60 C under an atmosphere of dry nitrogen. LiHMDS (1.6M in hexane, 30mmol) was added dropwise, and the reaction was stirred for 45min at -30 C. The phenolic hydroxyl groups of 3,4-dihydroxybenzoic acid ethyl ester (1.82g, 10mmol) were protected by benzyl (RY3-c) and dissolved in dry THF (20mL). The mixture was then cooled to -60 C and to 4.36g of RY3-c, and dry THF (40mL) was added dropwise. This mixture was stirred for another 45min at -60C and then incubated at room temperature overnight. The reaction mixture was poured on ice and acidified with 2.0M HCl. The THF was removed, the crude 1-(3,4-bis-benzyloxy-phenyl)-3-(2,4-dihydroxy-phenyl)-propane-1,3-dione was dissolved in 2-propanol (50mL), 0.5g Dowex W50×8 (H+ form) was added, and the reaction was heated under reflux for 24h under an atmosphere of dry nitrogen. The solids were filtered, and then the reaction mixture was poured on water. The solids were filtered and dissolved in MeOH (50mL), and Pd-C (1g) was added under an atmosphere of dry hydrogen at room temperature overnight. The solids were filtered and MeOH was removed. Purification of the crude product by flash chromatography (30% EtOAc/hexane) yielded RY3-c (1.28g, 32.4%) as a white solid. RY3-c: 1HNMR (500MHz, DMSO-d6): δ 6.62 (s, 1H), 6.92 (m, 2H, J=10Hz), 6.95 (d, 1H, J=5Hz), 7.40 (dd, 2H, J=10Hz), 7.88 (d, 1H, J=10Hz), 9.61 (s, 2H), 10.77 (s, 1H). 13CNMR (126MHz, DMSO-d6): δ102.83, 104.97, 113.66, 115.24, 116.47, 118.99, 122.62, 126.94, 146.16, 149.61, 157.81, 163.02, 163.07, 176.63. Q-TOF (m/z): calculated m/z for C15H10O5 [M-H]-: 269.0500, found: 269.0536. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 82% | 3',4',7-trihydroxyflavone (8a) Crystallized yield: 82%; 1H NMR (CDCl3+20% DMSO): δ 6.35 (br s, OH+H2O), 6.59 (s, 1H, C3H), 6.8-6.9 (m, 3H, C8H, C6H, C5'H), 7.26 (d, 1H, J=9 Hz, C6'H), 7.34 (s, 1H, C2'H), 7.86 (d, 1H, J=8 Hz, C5H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 38% | 2.4 Synthesis of [Ru(II)([9]aneS3)(S-DMSO)(<strong>[2150-11-0]7,3',4'-trihydroxyflavone</strong>)] (1) A solution of thflv (94.5 mg, 0.35 mmol) in refluxing ethanol (15 mL) was treated with one equivalent of tetrabutylammonium hydroxide (350 μL, 0.35 mmol). The colour of the solution changed from light yellow to orange. After 20 min, the complex [Ru([9]aneS3)Cl2(DMSO)] (150 mg, 0.35 mmol) was added and the reaction mixture was left under reflux for 48 h ( Scheme 1 ). During this time the solution became dark orange and a dark green precipitate was formed. The hot solution was cannula-filtered and the remaining solid was washed with ethanol (20 mL), diethyl ether (20 mL) and dried (90 mg, 38% yield). Elemental analysis for [Ru(C6H12S3)(C15H8O5)(C2H6SO)]·3(H2O) (Mr = 681,8): C, 40.52; H, 4,73%. Found: C, 40.07; H, 4.28%. FT-IR selected bands ν(tilde) = 3443 m (νO-H), 2985 m, 2949 m, 2914 m (all three νC-H), 1624 vs (νC∸O + νC∸C (thflv)), 1595 m, 1560 s (both νC∸C (thflv)), 1490 vs (non-assigned), 1449 m, 1413 m (both δC-H([9]aneS3)), 1305 s, 1257 s, 1160 m (all three δC-H (DMSO)), 1090 s (νS = O), 721 w (νC-S (DMSO)), 680 w, 650 vw (both νC-S ([9]aneS3)), 490 w, 461 vw (both νRu-S ([9]aneS3)), 426 w (νRu-S (DMSO)), 397 vw (νRu-O). ESI+-MS (MeOH) m/z (relative intensity %): 522 ([Ru([9]aneS3-CH2CH2)(thflv)]+, 100); 628 ([Ru([9]aneS3)(S-DMSO)(thflv)]+, 95). 1H NMR (300.13 MHz, DMSO-d6): δ(ppm) = 10.58 (1H, br s, OH-7), 7.78 (1H, d, J 8.7 Hz, H-5), 6.90 (1H, dd, J 2.0, 8.4 Hz, H-6'), 6.85 (2H, d, J 2.0 Hz, H-2',8), 6.81 (1H, dd, J 2.0, 8.7 Hz, H-6), 6.35 (1H, d, J 8.4 Hz, H-5'), 6.30 (1H, s, H-3), 3.19 (6H, s, SO(CH3)2), 2.87-2.58 (12H, m, CH2 of trithiacyclononane). 13C NMR (75.47 MHz, DMSO-d6): δ (ppm) = 176.0 (C-4), 170.1 (C-4'), 165.0 (C-2), 163.5 (C-3'), 162.4 (C-9), 157.5 (C-7), 125.9 (C-5), 116.8 (C-10), 115.7 (C-1'), 114.7 (C-5',6'), 113.9 (C-6), 110.5 (C-2'), 102.1 (C-8), 100.8 (C-3), 43.6 (SO(CH3)2), 34.1, 31.9 and 30.7 (CH2 of trithiacyclononane). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 68% | With hydrogen bromide; In water;Reflux; | General procedure: An aqueous solution of hydrogen bromide (48%; 1 mL per0.10 mmol of substrate) was mixed with flavone. The reactionmixturewas refluxed for 6e9 h, during which the reaction progresswas monitored by UPLC-MS. After the disappearance of partially Odemethylatedintermediates, the reaction mixture was evaporatedunder reduced pressure. |