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[ CAS No. 1929-29-9 ] {[proInfo.proName]}

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Chemical Structure| 1929-29-9
Chemical Structure| 1929-29-9
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Product Citations

Product Citations

Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto , et al. DOI: PubMed ID:

Abstract: The prenylated-flavin mononucleotide-dependent decarboxylases (also known as UbiD-like enzymes) are the most recently discovered family of decarboxylases. The modified flavin facilitates the decarboxylation of unsaturated carboxylic acids through a novel mechanism involving 1,3-dipolar cyclo-addition chemistry. UbiD-like enzymes have attracted considerable interest for biocatalysis applications due to their ability to catalyse (de)carboxylation reactions on a broad range of aromatic substrates at otherwise unreactive carbon centres. There are now ～35[thin space (1/6-em)]000 protein sequences annotated as hypothetical UbiD-like enzymes. Sequence similarity network analyses of the UbiD protein family suggests that there are likely dozens of distinct decarboxylase enzymes represented within this family. Furthermore, many of the enzymes so far characterized can decarboxylate a broad range of substrates. Here we describe a strategy to identify potential substrates of UbiD-like enzymes based on detecting enzyme-catalysed solvent deuterium exchange into potential substrates. Using ferulic acid decarboxylase (FDC) as a model system, we tested a diverse range of aromatic and heterocyclic molecules for their ability to undergo enzyme-catalysed H/D exchange in deuterated buffer. We found that FDC catalyses H/D exchange, albeit at generally very low levels, into a wide range of small, aromatic molecules that have little resemblance to its physiological substrate. In contrast, the sub-set of aromatic carboxylic acids that are substrates for FDC-catalysed decarboxylation is much smaller. We discuss the implications of these findings for screening uncharacterized UbiD-like enzymes for novel (de)carboxylase activity.

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Product Details of [ 1929-29-9 ]

CAS No. :1929-29-9 MDL No. :MFCD00002777
Formula : C10H12O3 Boiling Point : -
Linear Structure Formula :CH3OC6H4CH2CH2COOH InChI Key :FIUFLISGGHNPSM-UHFFFAOYSA-N
M.W : 180.20 Pubchem ID :95750
Synonyms :

Calculated chemistry of [ 1929-29-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.29
TPSA : 46.53 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.69
Log Po/w (XLOGP3) : 1.9
Log Po/w (WLOGP) : 1.71
Log Po/w (MLOGP) : 1.67
Log Po/w (SILICOS-IT) : 1.91
Consensus Log Po/w : 1.78

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.23
Solubility : 1.06 mg/ml ; 0.00586 mol/l
Class : Soluble
Log S (Ali) : -2.5
Solubility : 0.57 mg/ml ; 0.00316 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.71
Solubility : 0.354 mg/ml ; 0.00196 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.12

Safety of [ 1929-29-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1929-29-9 ]

* 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.

  • Downstream synthetic route of [ 1929-29-9 ]

[ 1929-29-9 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1929-29-9 ]
  • [ 15893-42-2 ]
YieldReaction ConditionsOperation in experiment
100% With phosgene; In water monomer; at 20℃; for 4h; General procedure: Cinnamoyl chlorides - Derivatives of cinnamic acid were stirred with oxalyl chloride (5 ml g-1) for up to 4 h. The stirring time differed depending on the dissolution rate of the starting cinnamic acid derivative. For derivatives with 4-NO2 or 4-N(CH3)2 substituents, a drop of dry N,N-DMF was added to catalyze the reaction. The excess reagent was evaporated under reduced pressure. The hydroxy groups in the hydroxycinnamic acid derivatives were acetylated prior to reaction with oxalyl chloride by stirring the derivative (0.0244 mol) in acetic anhydride (5 ml g-1) and pyridine (0.5 ml) at room temperature (rt, ~20 C) overnight. Cold water (~50 ml) was added to the mixture and stirred for further 5-10 min with cooling in an ice-water bath, and the resulting precipitate of acetoxycinnamic acid was obtained by vacuum filtration, washed with cold water and dried.Methyl N-cinnamoylanthranilates - The cinnamoyl chloride (0.014 mol) was added to a solution of excess methyl anthranilate (0.017 mol) in dry pyridine (10 ml g-1), and the mixture was stirred for an hour at rt. Cold water (250 ml) was added to the reaction mixture and the resulting precipitate was filtered and washed with cold water until free of pyridine, and was recrystallized from hot ethanol. In contrast, methyl N-hydrocinnamoylanthranilate derivatives, with a low melting point, were extracted in diethyl ether (2 × 70 ml), washed with cold water (2 × 50 ml) and the solvent evaporated under reduced pressure.N-Cinnamoylanthranilic acids - The methyl N-cinnamoylanthranilate (0.010 mol) was stirred in a mixture of THF (100 ml) and methanol (20 ml), and LiOH.H2O (0.050 mol) [LiOH dissolved in water 0.2 g per 10 ml] was added to the reaction mixture and stirred at rt overnight. The excess reagent and solvents were evaporated under reduced pressure. The crude product was dissolved in water (~350 ml) and acidified slowly to pH 4 using dilute HCl (1 M) with stirring. The precipitate was obtained by vacuumfiltration, washed with water and dried, and was recrystallized from hot aqueous ethanol (water-ethanol, 1:4). In the case of N-hydroxycinnamoylanthranilate derivatives, water was added to the resulting solution to aid crystallization.α-Methylcinnamic acid - To a mixture of benzaldehyde (5 ml, 0.0492 mol) and propionic anhydride61 (10 ml, 0.0780 mol), anhydrous sodium acetate (2.5 g) was added and heated under reflux for 4 h. Once the mixture has cooled down to rt, cold water (50 ml) was added and alkalized with saturated aqueous sodium carbonate (85 ml). The resulting solid suspension was heated up to dissolve completely, and the unreacted benzaldehyde was extracted in DCM (2 × 25 ml) and the aqueous layer was acidified with concentrated HCl (12 M) with cooling. The pale yellowish white crystals (yield 2.098 g, 26 %) of α-methylcinnamic acid was obtained by vacuum filtration, washed with little cold water (~10 ml) and dried.
With thionyl chloride; In toluene; a) Preparation of 3-(4-methoxyphenyl)propionyl Chloride To a suspension of 3-(4-methoxyphenyl)propionic acid (10 g) in 150 ml of toluene are added 8 ml of thionyl chloride and the mixture is heated to 65 C. for 4 hours. The solvent is evaporated off under reduced pressure and the residue is redissolved in toluene and concentrated to dryness. Such steo is repeated twice. 11 g of the product are obtained as a yellow oil.
With thionyl chloride; In dichloromethane; for 3h;Reflux; General procedure: A solution of 3-(4-fluorophenyl)propionic acid (300 mg, 1.8 mmol) in dry CH2Cl2 (20 mL) was treated with thionyl chloride (2.2 mL, 30.2 mmol). The reaction mixture was refluxed for 3 h and the solvent was then removed until dryness. A translucent oil, corresponding to 3-(4-fluorophenyl)propanoyl chloride, was obtained and used directly in the next reaction under the same conditions described in the general procedure.
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 2h; Step 1 Oxalyl chloride (5 eq) was added to a solution of 4-methoxyphenyl)propionic acid (1 eq) in CH2CI2 (0.1 M), and then a catalytic amount of DMF was added to the reaction mixture to initiate the reaction and bubbling occurred. The reaction was complete in 2 hours, and the solution was dried with N2 for one hour to give the acid chloride, which was used immediately in the next step.
With thionyl chloride; In N,N-dimethyl-formamide; toluene; at 75℃; for 3h; A solution of p-methoxyphenylpropionic acid (12a, 2.99 mmol), SOCl2 (2 mL) and DMF (2 drops) was added to toluene (20 mL) and stirred at 75C for 3 h. The reaction was terminated and the solution was concentrated to dryness under reduced pressure to give p-methoxyphenylpropionyl chloride (13a). (6,2.61 mmol), pyridine (1 mL) in CH2Cl2 (10 mL) was added dropwise with stirring Oxyphenylpropionyl chloride (13a). After completion of the dropwise addition, the reaction was refluxed for 2 h. The reaction was completed, cooled to room temperature, poured into dilute hydrochloric acid, stirred. Extracted with dichloromethane, and washed with saturated brine. The solvent was concentrated to dryness under reduced pressure to give crude product. Column chromatography (petroleum ether / ethyl acetate: 15/1, V / V) gave a white solid in 66.8%
With phosphorus(V) chloride; In dichloromethane;Reflux; General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 5h; General procedure: An oven-dried flask was charged with aliphatic carboxylic acid (1.00 equiv) and CH2Cl2 (0.50 M). Three drops of N,N-dimethylformamide (DMF) and oxalyl chloride (1.20 equiv, 1.00 M) in DCM were added dropwise. The reaction mixture was stirred vigorously at room temperature for 5 h and then evaporated DCM and redundant oxalyl chloride under the vacuum. The crude acid chloride was used for the next reaction without any further purification
With oxalyl dichloride; N,N-dimethyl-formamide; at 20℃; for 1h;Inert atmosphere; General procedure: Oxalyl chloride (2equiv) was added at room temperature into asolutioncarboxylic acids(1equiv) in anhydrous dichloromethane. Added one drop ofN,N-dimethylformamide and reacted under nitrogen atmosphere for 1h. The solvent was removed under vacuum, yielding a crude product that were stored in a nitrogen atmosphere for subsequent use without further purified.

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[5]Journal of the Chemical Society,1909,vol. 95,p. 1722
[6]Journal of Medicinal Chemistry,1981,vol. 24,p. 451 - 454
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[8]Phytochemistry,1981,vol. 20,p. 1097 - 1104
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[10]Journal of Heterocyclic Chemistry,2003,vol. 40,p. 519 - 522
[11]Synlett,2004,p. 477 - 480
[12]Pharmazie,2004,vol. 59,p. 744 - 752
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[14]Journal of Organic Chemistry,2000,vol. 65,p. 4179 - 4184
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[16]Patent: US6110924,2000,A
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[22]Molecular Crystals and Liquid Crystals,2011,vol. 545,p. 149 - 155
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  • 2
  • [ 109-72-8 ]
  • [ 1929-29-9 ]
  • [ 3282-30-2 ]
  • [ 70-07-5 ]
  • [ 104-21-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; hexane; L-phenylalanine; B. Preparation of 13, 15 2-p-Methoxybenzyl acetic acid 12 (3.92 g, 0.02 mol) was dissolved in 100 mlof ether and cooled to -78 C. under a nitrogen atmosphere. Triethylamine was added (2.86 ml, 0.0205 mol) followed by pivaloyl chloride (2.52 ml, 0.0205 mol). The mixture was warmed to 0 C. over 30 min. and then stirred at 0 C. for 2 hr. to give mixed anhydride 13. The solution was then cooled to -78 C. (SOLUTION A). In a separate flask the (S) phenylalanine derived oxazolidinone 14 (3.45 g,0.0195 mol) was dissolved in 30 ml of tetrahydrofuran and cooled to -78 C. under a nitrogen atmosphere. n-Butyllithium (14.3 ml of a 1.36M solution in hexane) was added via cannula, and then was stirred for 15 min at -78 C. (SOLUTION B). Solution B was then added, via cannula, to solution A at -78 C. Theresulting mixture was stirred 15 min at -78 C., warmed to 0C. over 30 min, and then stirred for 1 hr at 0 C. Sixty ml of waterwas then added and the mixture was extracted with 3*50 ml of methylene chloride. The combined organic extracts were washed with 50 ml of saturated sodium bicarbonate solution and 50 ml of saturated sodium chloride solution and were dried over sodium sulfate. Concentration in vacuo and flash chromatography with silica gel (elution with 3:1, hexanes:ethyl acetate) gave the desired p-methoxybenzyl acetate derived oxazolidinone imide 15 (5.51 g).
With triethylamine; In tetrahydrofuran; hexane; L-phenylalanine; water; B. Preparation of 17. 19 2-p-Methoxybenzyl acetic acid 16 (3.92 g, 0.02 mol) was dissolved in 100 ml of ether and cooled to -78 C. under a nitrogen atmosphere. Triethylamine was added (2.86 ml, 0.0205 mol) followed by Pivaloyl chloride (2.52 ml, 0.0205 mol). The mixture was warmed to 0 C. over 30 min. and then stirred at 0 C. for 2 hr. to give mixed anhydride 17. The solution was then cooled to -78 C. (SOLUTION A). In a separate flask the (S) phenylalanine derived oxazolidinone 18 (3.45 g, 0.0195 mol) was dissolved in 30 ml of tetrahydrofuran and cooled to -78 C. under a nitrogen atmosphere. n-Butyllithium (14.3 ml of a 1.36 M solution in hexane) was added via cannula, and then was stirred for 15 min. at -78 C. (SOLUTION B). Solution B was then added, via cannula, to solution A at -78 C. The resulting mixture was stirred 15 min. at -78 C., warmed to 0 C. over 30 min., and then stirred for 1 hour at 0 C. Sixty ml of water was then added and the mixture was extracted with 3*50 ml of methylene chloride. The combined organic extracts were washed with 50 ml of saturated sodium bicarbonate solution and 50 ml of saturated sodium chloride solution and were dried over sodium sulfate. Concentration in vacuo and flash chromatography with silica gel (elution with 3:1, hexanes:ethyl acetate) gave the desired p-methoxybenzyl acetate derived oxazolidinone imide 19 (5.51 g).
  • 3
  • [ 1929-29-9 ]
  • [ 4654-08-4 ]
  • 4
  • [ 1929-29-9 ]
  • [ 15893-42-2 ]
  • [ 40608-04-6 ]
YieldReaction ConditionsOperation in experiment
General procedure: To a flamed-dried flask with magnetic stir bar, was added aliphatic acid (1.0 equiv), dried DCM (1.0 M) and triethylamine (1.05 equiv) successively. The solution was stirred for 30 minutes at 0 0C. Then acyl chloride (1.05 equiv) was added dropwise to the mixture and stirred overnight at rt. The solvent was evaporated by vacuum to afford the crude mixture. And the mixture was dissolved in n-hexane. Then the residue was filtered through a small plug of celite and concentrated to afford the anhydrides. This product was used to next catalytic reaction without any further purification.
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