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[ CAS No. 90719-32-7 ] {[proInfo.proName]}

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Chemical Structure| 90719-32-7
Chemical Structure| 90719-32-7
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Product Citations

Product Citations

Berg, Kaja ; Hegde, Pooja ; Pujari, Venugopal , et al. DOI: PubMed ID:

Abstract: The electron transport chain (ETC) in the cell membrane consists of a series of redox complexes that transfer electrons from electron donors to acceptors and couples this electron transfer with the transfer of protons (H+) across a membrane. This process generates proton motive force which is used to produce ATP and a myriad of other functions and is essential for the long-term survival of Mycobacterium tuberculosis (Mtb), the causative organism of tuberculosis (TB), under the hypoxic conditions present within infected granulomas. Menaquinone (MK), an important carrier molecule within the mycobacterial ETC, is synthesized de novo by a cluster of enzymes known as the classic/canonical MK biosynthetic pathway. MenA (1,4-dihydroxy-2-naphthoate prenyltransferase), the antepenultimate enzyme in this pathway, is a verified target for TB therapy. In this study, we explored structure-activity relationships of a previously discovered MenA inhibitor scaffold, seeking to improve potency and drug disposition properties. Focusing our campaign upon three molecular regions, we identified two novel inhibitors with potent activity against MenA and Mtb (IC50 = 13-22 μM, GIC50 = 8-10 μM). These analogs also displayed substantially improved pharmacokinetic parameters and potent synergy with other ETC-targeting agents, achieving nearly complete sterilization of Mtb in combination therapy within two weeks in vivo. These new inhibitors of MK biosynthesis present a promising new strategy to curb the continued spread of TB.

Keywords: 1,4-dihydroxy-2-naphthoate prenyltransferase ; MenA ; MenA inhibitors ; Menaquinone ; Mtb ; Mycobacterium tuberculosis ; Piperidine derivatives ; SAR

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Product Details of [ 90719-32-7 ]

CAS No. :90719-32-7 MDL No. :MFCD00064496
Formula : C10H11NO2 Boiling Point : -
Linear Structure Formula :C3H4NO2CH2C6H5 InChI Key :OJOFMLDBXPDXLQ-VIFPVBQESA-N
M.W : 177.20 Pubchem ID :736225
Synonyms :
(-)-4-Benzyl-2-oxazolidinone
Chemical Name :(S)-4-Benzyloxazolidin-2-one

Calculated chemistry of [ 90719-32-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.11
TPSA : 38.33 ?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) : -6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.72
Log Po/w (XLOGP3) : 1.74
Log Po/w (WLOGP) : 0.96
Log Po/w (MLOGP) : 1.42
Log Po/w (SILICOS-IT) : 1.9
Consensus Log Po/w : 1.55

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.24
Solubility : 1.01 mg/ml ; 0.0057 mol/l
Class : Soluble
Log S (Ali) : -2.16
Solubility : 1.22 mg/ml ; 0.00689 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.08
Solubility : 0.147 mg/ml ; 0.000832 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.18

Safety of [ 90719-32-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 90719-32-7 ]

* 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 [ 90719-32-7 ]

[ 90719-32-7 ] Synthesis Path-Downstream   1~11

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  • [ 195877-48-6 ]
  • 3
  • [ 90719-32-7 ]
  • [ 459-04-1 ]
  • [ 159707-16-1 ]
YieldReaction ConditionsOperation in experiment
81% (S)-4-Benzyl-3-(2-(4-fluorophenyl)acetyl)oxazolidin-2-one; To a cooled (-78 C.) solution of (S)-4-benzyloxazolidin-2-one (10.26 g, 58 mmol, 1.0 equiv) in 100 mL THF was added dropwise n-BuLi (40 mL, 1.6 M, 64 mmol, 1.1 equiv). After stirring for 30 minutes, 4-fluorophenylacetyl chloride (10.0 g, 0.58 mmol, 1.0 equiv) was added dropwise. After stirring for an additional 30 minutes, the reaction mixture was allowed to warm to room temperature. The reaction was quenched with sat'd. aq. NH4Cl, extracted with DCM, and washed with brine. The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by silica gel (10-20% EtOAc/Hexanes) provided the title compound as a thick oil (14.7 g, 81%). m/z=314.3 [M+H]+.
81% (S)-4-Benzyl-3-(2-(4-fluorophenyl)acetyl)oxazolidin-2-one To a cooled (-78 C.) solution of (S)-4-benzyloxazolidin-2-one (10 g, 58 mmol, 1.0 equiv) in 100 mL THF was added dropwise n-BuLi (40 mL, 1.6 M in hexanes, 64 mmol, 1.1 equiv). After stirring for 30 minutes, 4-fluorophenylacetyl chloride (10 g, 0.58 mmol, 1.0 equiv) was added dropwise. After stirring for an additional 30 minutes, the reaction mixture was allowed to warm to room temperature. The reaction was quenched with saturated aq. NH4Cl, extracted with dichloromethane, and washed with brine. The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by silica gel (10-20% EtOAc/hexanes) provided the title compound as a thick oil (14.7 g, 81%).
Combine (S)-4-benzyl-2-oxazolidinone (22.9 g, 129 mmol) and tetrahydrofuran (120 mL). Cool in a dry-ice/acetone bath. Add dropwise a solution of n-butyl lithium (52 mL, 2.5 M, 130 mmol). After 15 minutes, slowly add a solution of 4-fluorophenylacetyl chloride (22.3 g, 129 mmol) in tetrahydrofuran (50 mL). Warm to ambient temperature. After 2 hours, quench the reaction mixture by the addition of a saturated aqueous sodium bicarbonate solution. Separate the layers and extract the aqueous layer with diethyl ether. Combine the organic layers, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting wit 15% ethyl acetate/hexane. Combine the product containing fractions, evaporate, and recrytallize from diethyl ether/hexane to give (S)-4-benzyl-3-(4-fluorophenyl)acetyl-2-oxazolidinone.
Alternately, combined (S)-benzyl-2-oxazolidinone(55.4 g, 313 mmol) and tetrahydrofuran (550 ml). Cool in a dry-ice/acetone bath. Add n-butyl lithium (125 ml, 1 M in hexane, 312 mmol). After 30 minutes, add dropwise 4-fluorophenylacetyl chloride (56.7 g, 328 mmol). After 30 minutes, warm to ambient temperature, add a saturated aqueous sodium bicarbonate solution, and stir. After 45 minutes, separate the layers and extract the aqueous layer three times with ethyl acetate, combine the organic layers, extract with brine, dry over MgSO4, filter, and evaporate in vacuo to give a viscous oil. Stir the viscous oil under vacuum to remove residual solvent and triturate with isopropanol to give a solid. Collect the solid by the filtration and rinse with isopropanol to give, after drying, (S)-4-benzyl-3-(4-fluorophenyl)acetyl-2-oxazolidinone.

  • 4
  • [ 16957-70-3 ]
  • [ 90719-32-7 ]
  • [ 635758-46-2 ]
  • 5
  • [ 79-37-8 ]
  • [ 1643-16-9 ]
  • [ 90719-32-7 ]
  • [ 223127-28-4 ]
  • [ 223128-33-4 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; (a) (S)-4-benzyl-3-[(4-isopropylphenoxy)acetyl]oxazolidine-2-one Oxalyl chloride (16.8 ml) and N,N-dimethylformamide (three drops) were added to a solution of <strong>[1643-16-9]4-isopropylphenoxyacetic acid</strong> (15.0 g) in dichloromethane (75 ml) at ambient temperature. The reaction mixture was stirred for 1.5 hours. The reaction mixture was concentrated at reduced pressure and residual reagents were azeotropically evaporated off with toluene. The residue was dried under reduced pressure. A solution of n-butyl lithium in hexane (1.61N, 48.0 ml) was added dropwise to a solution of (S)-4-benzyloxazolidine-2-one (12.4 g) in tetrahydrofuran (150 ml) at -78 C. and the mixture was stirred at the same temperature for 30 minutes. To this solution a solution of 4-isopropylphenoxyacetyl chloride, which had been obtained above, in tetrahydrofuran (100 ml) was added at -78 C. The mixture was stirred at 0 C. for 1 hour. The reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with aqueous hydrogen chloride solution (1N), saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution. The ethyl acetate solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from a mixture of hexane/ethyl acetate=6/1 to afford the desired compound (20.9 g) as colorless crystals. mp 104.5-105 C. 1H-NMR (270 MHz, CDCl3): delta ppm 1.23 (6H, d, J=7.0 Hz), 2.79-2.92 (2H, m), 3.36 (1H, dd, J=3.0, 13.5 Hz), 4.24-4.37 (2H, m), 4.68-4.78 (1H, m), 5.22 (2H, s), 6.91 (2H, d, J=8.5 Hz), 7.13-7.38 (7H, m).
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  • [ 1194551-71-7 ]
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  • [ 154775-43-6 ]
  • [ 721455-06-7 ]
YieldReaction ConditionsOperation in experiment
A solution of the acid of Step 1 (1.6g, 6.2 mmol) in 50 ml of THF was added 1 ml of triethyl- amine and the resulting solution was cooled TO-78 C. To the solution was then added pivaloy chloride (0.88 ml, 6.8 mmol). It was allowed to warm to 0 C over 1 h. It was cooled to-78 C and was added a solution that was generated from (S)-benzyl-2-oxazolidinone (1. 1 g, 6.2 mmol) and nBuLi (4.25 ml as a 1.6 M solution in hexanes) in 25 ml of THF at-78 C for 45 min. After 2.5 h, it was warmed to rt and was quenched by NH4CL solution. The mixture was extracted with EtOAc. The organic layer was dried with MGS04, filtered through celite and concentrated. The residue was purifed by flash chromatography with acetone/hexane = 1: 4 to give 2.4 g of tert- butyl 4- {3- [ (4R)-4-BENZYL-2-OXO-1, 3-OXAZOLIDIN-3-YL]-3-OXOPROPYL} PIPERIDINE-1-CARBOXYLATE.
  • 8
  • [ 90719-32-7 ]
  • [ 149437-76-3 ]
  • [ 852148-48-2 ]
YieldReaction ConditionsOperation in experiment
78% Example 35. (4S)-4-Benzyl-3- [5- (4-fluorophenyl)-5-oxopentanoyl]-1, 3- oxazolidin-2-one 5- (4-Fluorophenyl)-5-oxopentanoic acid (10.08 g, 47.9 mmol) and triethylamine (6.8 mL, 4.94 g, 48.8 mmol) were dissolved in tetrahydrofuran (50 mL). The reaction was cooled to-5 C (ice/brine bath), trimethylacetyl chloride (6.0 mL, 5.87 g, 48.7 mmol) was added quickly drop-wise and the mixture was warmed to room temperature and stirred for 1.5 h. The reaction was cooled to-5 C (ice/brine bath) again for 30 min, filtered through Celte, washed with cold 1: 1 hexane-tetrahydrofuran (60 mL) and hexane (120 mL). The filtrate was concentrated, dissolved in N, N-dimethylformamide (16 mL) and to this mixture was added (S)-benzyl-2-oxazolidinone (8.47 g, 47.8 mmol) and 4- dimethylaminopyridine (8.57 g, 70.2 mmol) as solids. The reaction was stirred at room temperature for 20 h, poured into 1.0 N hydrochloric acid (400 mL) and extracted with ethyl acetate (2 x 300 mL). The organic layer was washed with water (400 mL), quarter saturated sodium bicarbonate solution (400 mL), brine (200 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by crystallization from hot isopropyl alcohol (75 mL) with slow cooling to room temperature over 16 h. The crystals were filtered cold and washed with cold isopropyl alcohol (50 mL) to afford (4S)-4- benzyl-3- [5- (4-fluorophenyl)-5-oxopentanoyl]-1, 3-oxazolidin-2-one (13. 87 g, 78% yield) as a white crystalline solid; mp 114. 5 C ; Rf 0.29 (1: 2 ethyl acetate-hexane) ;'H NMR (300 MHz, CDC13) b 8.03-7. 98 (m, 2H), 7. 37-7. 19 (m, 5H), 7.14 (t, J= 8.7 Hz, 2H), 4.72- 4.64 (m, 1H), 4.25-4. 15 (m, 2H), 3.32 (dd, J= 13.3, 3.4 Hz, 1H), 3.12-3. 01 (m, 4H), 2.78 (dd, J= 13.3, 9.6 Hz, 1H), 2.15 (quint. , J= 7.2 Hz, 2H) ppm
  • 9
  • [ 90719-32-7 ]
  • [ 149437-76-3 ]
  • [ 852148-48-2 ]
  • [ 914777-32-5 ]
  • [ 914777-33-6 ]
YieldReaction ConditionsOperation in experiment
78% 5-(4-Fluorophenyl)-5-oxopentanoic acid (372.0 g, 1.77 mol) and 4-dimethylamino- pyridine (286.9 g, 2.35 mol) were dissolved in LambdazetaN-dimethylformamide (1770 rnL, 1.0 M) to afford a copious white precipitate suspended in solution. The reaction was cooled to 6 0C (ice/water bath), trimethylacetyl chloride (290 mL, 2.35 mol) was added quickly drop-wise over 17 min to afford a pale yellow mixture. The rate of addition was controlled in order to keep the temperature below 8.5 C. The mixture was stirred for 1 h at 9 C (ice/water bath) then for 2 h at 20 C (colorless solution with copious white thick precipitate). The mixture was charged with (S)-benzyl-2- oxazolidinone (313.5 g, 1.77 mol) and 4-dimethylaminopyridine (216.4 g, 1.77 mol) both as solids to afford a bright yellow colored suspension. The reaction was stirred at 27 C for 3.3 h. The pale olive colored solution was poured into water (4300 mL) while stirring vigorously (an exotherm was detected to 39 C), transferred with water (1000 mL) and stirred at room temperature for 2 h to afford a pale orange-brown solution with an off-white precipitate. The compound was filtered, transferred with water (2 x 300 mL), washed with water (400 mL) and air dried for 1.5 h to afford an off-white moist clumpy powder. The material was crystallized from isopropanol (2600 mL, 4.0 mL/g theoretical yield) by heating to near reflux to afford a dark golden yellow colored solution. The mixture was cooled slowly from 81 C to 74 C in 20 min, a seed crystal was added and crystals began to precipitate. The mixture was cooled slowly to room temperature over H h, cooled to 2 C in an ice/water bath and stirred for 3 h. The crystals were filtered, transferred with cold mother liquor (350 mL), washed with cold isopropanol (2 x 350 mL), air dried and vacuum dried to constant weight to afford (4iotaS)-4-benzyl-3-[5-(4-fluorophenyl)-5-oxopentanoylj-l,3- oxazolidin-2-one (Al) (510.6 g, 78 % yield) as a white crystalline solid; m.p. 113.4 + EPO <DP n="33"/>1.2 C; R/ 0.37 (1 :2 ethyl acetate-hexane); HPLC purity 99.7 A% (96.4 A% by NMR); 1H NMR (300 MHz, CDCl3) delta 8.03-7.98 (m, 2H), 7.37-7.19 (m, 5H), 7.14 (t, J= 8.7 Hz, 2H), 4.72-4.64 (m, IH), 4.25-4.15 (m, 2H), 3.32 (dd, J= 13.3, 3.4 Hz, IH), 3.12-3.01 (m, 4H), 2.78 (dd, J= 13.3, 9.6 Hz, IH), 2.15 (quint, J= 7.2 Hz, 2H) ppm.
  • 10
  • [ 6964-21-2 ]
  • [ 90719-32-7 ]
  • (S)-4-benzyl-3-(2-(thiophen-3-yl)acetyl)oxazolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% General procedure: Toa stirred solution of arylacetic acid (1.0 eq.) in THF under nitrogen was addedDIPEA (1.3 eq.) and the solution was cooled to 0 C. To the solution was addedPivCl (1.0 eq.) and after stirring for 1 h, the resulting suspension was cooledto -78 C.Simultaneouslyin a separate flask, a stirred solution of (S)-4-benzyloxazolidin-2-one/(R)-4-benzyloxazolidin-2-one (1.5 eq.) in THF under nitrogen wascooled to -78 C and n-BuLi (1.6 eq.)was added dropwise. After stirring for 45 min, the metalated oxazolidinone wastransferred to the mixed anhydride viacannula. Afterfull consumption of starting material, the reaction was quenched by addition ofsat. NH4Cl. The phases were separated and the aqueous phase wasextracted using ethyl acetate (2x). The combined organics were passed through ahydrophobic frit and concentrated invacuo. The residue was purified by automated flash chromatography to affordthe title compound.
  • 11
  • [ 1798-06-7 ]
  • [ 90719-32-7 ]
  • (S)-4-benzyl-3-(2-(4-iodophenyl)acetyl)oxazolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With 4-methyl-morpholine; pivaloyl chloride; In toluene; at 80 - 112℃; for 45.25h; To a cloudy solution of (S)-benzyl-2-oxazolidinone (10A, 290.1 g, 1.3 eq) and NMM (1.65 L, 1.3 eq) in toluene (1.65 L, 5 vol) was added pivaloyl chloride (169.6 mL, 1.1 eq) at 19.5-20.2 C over 9 min. The cloudy solution was heated to 80 C and a solution of 4- iodophenyl acetic acid (11A, 330.0 g, 1.0 eq) and NMM (235.4 mL, 1.7 eq) in toluene (660 m L, 2 vol) was added over 135 min. The mixture was then heated at 107-112 C for 5 h. The mixture was cooled to 90-95 C, and another portion of pivaloyl chloride (66.0 mL, 0.43 eq) was added and the mixture was heated at 107-112 C for another 14 h. The mixture was cooled to 90-95 C, and another portion of pivaloyl chloride (46.2 mL, 0.30 eq) was added and the mixture was heated at 107-112 C for another 7 h. The mixture was cooled to 90-95 C, and another portion of pivaloyl chloride (18.5 mL, 0.12 eq) was added and the mixture was heated at 107-112 C for another 17 h, and at this point the reaction was deemed to be complete. The reaction was cooled to <35 C and 7% NaHCCL in H2O (1.32 L) was added (endothermic). After being stirred for 20 min, two layers were separated. The organic phase was washed with 7% NaHCCL in H2O (1.32 L), H2O (1.32 L), and 13% NaCl in H2O (1.32 L). The organic layer (2810 mL) was concentrated to 2.5 vol (-824 mL) containing toluene (-330 mL, 1 vol). The solution was held at rt overnight and some crude product precipitated. The mixture was heated at 35-40 C to dissolve most solids. IPA (1980 mL, 6 vol) was added over 30 min. The resulting slurry was stirred at 35-40 C for 2 h, and IPA (1980 mL, 6 vol) was added over 20 min at 35-40 C. The slurry was stirred at 35-40 C for 3 h and at rt for 44 h. The slurry was then gradually cooled to 0-5 C and stirred for 3 h. The solids were filtered, washed with IPA (660 mL x 2), dried under high vacuum at 45 C to provide 12A (405.2 g, 76% yield, 98.5% (AUC)) as an off-white solid. 'H NMR is consistent with the structure.
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