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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.
trans-Cinnamic acid, a natural product isolated and purified from the barks of Cinnamomum cassia, with phytotoxic, anti-diabetic, anti-cancer, antioxidant and anaesthetic activities, is cell differentiation inducer, protein isoprenylation inhibitor, shows a significant radio-protective effect by reducing the DNA damage induced by X-rays, inhibits feeding by detritivores, and the diphenolase activity of mushroom tyrosinase and the inhibition is reversible, the IC 50 values are estimated to be 2.10, 0.50 and 0.42 mM, respectively.
Synonyms: trans-3-Phenylacrylic acid; Cinnamylic acid; Isocinnamic acid
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 140-10-3 |
Formula : | C9H8O2 |
M.W : | 148.16 |
SMILES Code : | O=C(O)/C=C/C1=CC=CC=C1 |
Synonyms : |
trans-3-Phenylacrylic acid; Cinnamylic acid; Isocinnamic acid
|
MDL No. : | MFCD00004369 |
InChI Key : | WBYWAXJHAXSJNI-VOTSOKGWSA-N |
Pubchem ID : | 444539 |
GHS Pictogram: |
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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 |
---|---|---|
86% | With tert.-butylhydroperoxide; iodine; In water; toluene; at 90℃; for 12h; | General procedure: A 25 mL tube was charged with cinnamic acid (0.3 mmol), sodiumbenzene sulfinate (1.2 mmol), iodine (2 equiv), TBHP in H2O(0.6 mmol) and toluene (2 mL). The resulting reaction mixture waskept stirring at 90 C for 12 h. Upon completion of the reaction, thereaction mixturewas cooled to room temperature. After removal ofthe solvent, the residue was subjected to column chromatographyon silica gel using ethyl acetate and petroleum ether mixtures toafford the desired product in high purity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 12h; | General procedure: To a stirred solution of 1,2-diol/1,2-aminoalcohol (1 mmol) in dry DCM (5 mL), corresponding acid (2.5 mmol), DCC (2.5mmol) and DMAP (4.0 mmol) were added and stirred at rt for 12 h. Aftercompletion of the reaction (TLC), reaction mixture was filtered to removeinsoluble DCU and the filtrate was washed with water (10 mL), brine (10 mL),dried over anhydrous Na2SO4 and concentrated to furnish acrude residue, which was purified by silica gel column chromatography (100-200mesh) using EtOAc/petroleum ether (1:1) to afford the final compound in 75-80%yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | Cinnamic acid (88.1 mg, 0.59 mmol) was dissolved in CH2Cl2/DMF (1:3, 3.0 mL). EDC (105 mL, 0.89 mmol) and HOBt (80.3 mg,0.59 mmol) were added to the solution. After the mixture wascooled in an ice-water bath for 15 min, Et3N (166 mL, 1.18 mmol)and compound a (147.2 mg, 0.59 mmol) were added to the mixture.After stirring at room temperature for 9 h, the mixture waspoured into H2O (50 mL), extracted with EtOAc (50 mL 3),washed with 5% NaHCO3 (150 mL) and brine (150 mL), dried overMgSO4, filtered, and the solvent removed in vacuo. The residuewas purified by silica gel column chromatography to afford cinnamoyl-DOPA methyl ester (83.7 mg, 41%) as a yellow powder. | |
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; | General procedure: As shown in Scheme 1, the synthetic route of the analogues (1-7) involved a two-step sequence viamethyl esterification of L-amino acidand amide condensation. 100 muL SOCl2was added in portions to 4 mL methanol at -10 C,then 1 mmol L-amino acid was addedand the mixture was warmed to room temperature and stirred overnight. After thesolvent was removed, 5 mL CH3CN, 500 muL DIPEA (N,N-Diisopropyl ethylamine), 1.1 mmolcorresponding substituted acid and 1.1 mmol HBTU (O-Benzotriazole-N,N,N',N'-tetramethyl-uronium-hexafluorophosphate)was added into the residue. The mixture was stirred for 1 h at room temperatureto finish condensation. The reaction solution was added 20 mL 1 M HCl, andextracted with ethyl acetate (4 × 20 mL). The combined organic phasewas dried over anhydrous Na2SO4 and finally evaporated invacuum. The residue was purified by silica-gel chromatography using mixtures ofPE/EtOAcas eluent to afford compounds 1-7.At this stage, all compounds were fully analyzed and characterized by nuclearmagnetic resonance (NMR), high resolution massspectrum (HRMS). |