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[ CAS No. 371-41-5 ] {[proInfo.proName]}

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Chemical Structure| 371-41-5
Chemical Structure| 371-41-5
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Product Citations

Product Citations      Expand+

Kaustav Khatua ; Yugendar R. Alugubelli ; Kai S. Yang , et al. DOI:

Abstract: The main (MPro) of SARS-CoV-2, the causative agent of COVID-19, is a pivotal nonstructural critical for viral replication and pathogenesis. Its function relies on three active site pockets for substrate recognition and a catalytic for enzymatic activity. To develop potential SARS-CoV-2 , we successfully synthesized a diverse range of azapeptide inhibitors with various covalent warheads to target MPro's catalytic . Our characterization identified potent MPro inhibitors, including MPI89 that features an aza-2,2-dichloroacetyl warhead with a remarkable EC50 value of 10 nM against SARS-CoV-2 infection in ACE2+ A549 cells and a selective index of 875. MPI89 is also remarkably selective and shows no potency against SARS-CoV-2 papain-like and several human proteases. Crystallography analyses demonstrated that these inhibitors covalently engaged the catalytic and used the aza-amide carbonyl oxygen to bind to the oxyanion hole. MPI89 stands as one of the most potent MPro inhibitors, suggesting the potential for further exploration of azapeptides and the aza-2,2-dichloroacetyl warhead for developing effective therapeutics against COVID-19.

Keywords: COVID-19 ; SARS-CoV-2 ; Main protease ; Azapeptide ; Covalent inhibitor

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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

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; 25952-53-8 ; ; ; ; ; ; 22246-18-0 ; ; ; ; ; ; ; ; ; ; ; ; ;

Product Details of [ 371-41-5 ]

CAS No. :371-41-5 MDL No. :MFCD00002316
Formula : C6H5FO Boiling Point : -
Linear Structure Formula :- InChI Key :RHMPLDJJXGPMEX-UHFFFAOYSA-N
M.W : 112.10 Pubchem ID :9732
Synonyms :

Calculated chemistry of [ 371-41-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 28.42
TPSA : 20.23 ?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) : -5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.36
Log Po/w (XLOGP3) : 1.77
Log Po/w (WLOGP) : 1.95
Log Po/w (MLOGP) : 1.9
Log Po/w (SILICOS-IT) : 1.84
Consensus Log Po/w : 1.76

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.21
Solubility : 0.699 mg/ml ; 0.00624 mol/l
Class : Soluble
Log S (Ali) : -1.81
Solubility : 1.73 mg/ml ; 0.0154 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.04
Solubility : 1.02 mg/ml ; 0.0091 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 371-41-5 ]

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 [ 371-41-5 ]

* 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 [ 371-41-5 ]

[ 371-41-5 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 371-41-5 ]
  • [ 42864-24-4 ]
  • [ 5724-56-1 ]
  • [ 394-33-2 ]
  • [ 52962-97-7 ]
  • [ 52911-59-8 ]
  • 2
  • [ 371-41-5 ]
  • [ 42864-24-4 ]
  • [ 5724-56-1 ]
  • [ 394-33-2 ]
  • [ 52962-97-7 ]
  • [ 52911-65-6 ]
  • 3
  • [ 530-46-1 ]
  • [ 106-44-5 ]
  • [ 371-41-5 ]
  • [ 456-22-4 ]
  • [ 99-94-5 ]
  • 4
  • [ 13195-50-1 ]
  • [ 371-41-5 ]
  • [ 190966-75-7 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N-methyl-acetamide; Example 1 A specific procedure for the synthesis of: N-[(4-fluoro)-5-phenoxythien-2-yl]methanesulfonamide (1) STR10 <strong>[13195-50-1]2-Nitro-5-bromothiophene</strong> (2.97 g, 14.2 mmol) was dissolved in dimethyl-formamide (40 mL). To this was added 4-fluorophenol (1.59 g, 14.2 mmol) and potassium carbonate (3.92 g, 28.4 mmol). This was stirred at 70° C. for 5 hours after which time the mix was poured into water and the crude solid was filtered and washed with water to give 2-Nitro-5(4-fluoro)phenoxythiophene 2.67 g (78percent), mp=69°-70° C.
  • 5
  • [ 371-41-5 ]
  • [ 92-55-7 ]
  • [ 141580-53-2 ]
  • 6
  • [ 371-41-5 ]
  • [ 619-60-3 ]
  • N,N-dimethyl-p-(p-hydroxyphenoxy)aniline [ No CAS ]
  • 7
  • [ 371-41-5 ]
  • [ 26690-80-2 ]
  • [ 263409-78-5 ]
  • [ 97308-23-1 ]
  • 8
  • [ 371-41-5 ]
  • [ 59782-86-4 ]
  • methyl 2-(4-fluorophenoxy)-5-iodonicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of 4-fluorophenol (224 mg, 2.0 mmol) in DMF (5.0 mL) was added sodium hydride (48 mg, 2.0 mmol) at room temperature. After stirring for 10 min, methyl <strong>[59782-86-4]2-chloro-5-iodonicotinate</strong> (J. Org. Chem. 1989, 54, 3618-3624, 594 mg, 2.0 mmol) was added to the reaction mixture. The reaction mixture was stirred under reflux for 16 h. Then the reaction mixture was poured into water (50 mL) and extracted with ether (50 mL x 3). The combined organic extracts were washed with brIne (50 m(at)-) and dr*(at)--d, (sod.uTY: s.1l(at)a(at)e). After removal o4 the 3ci'.3(at)f:(at) t'e (at)3(at):::(at)(at) <";zs ;'.(at)-Z?"(at)'(at)(at)3(at) hy7 '(at):(at):1B(at)(at) xt(at)l:r- :-;(at)(at)(at)(at)(at).(at)5..t:;,?"￡;:(at).;/ 8(at)(at)(at)0E. ￡ ,q], L .-.."I.: -'-(at)2(at)::'(at)0/;:/::*-(at),(at)(at) ::_=J'(at)(at)'(at)(at)- (J.>,'. ] .:: ilf=No.= (at):<.No...---'(at) (I? lflXJ i:.: ..:.:,i .::":.1 compound: (at)H-NMR (CDCl3) No. 8.51 (1 H, d, J=2.3 Hz), 8.41 (1 H, s), 7.09 (4H, d, J=6.2 Hz), 3.95 (3H, s) ; MS (ESI) m/z 374 (M + H)+.
  • 9
  • [ 371-41-5 ]
  • [ 4876-10-2 ]
  • [ 1091595-24-2 ]
  • 10
  • [ 371-41-5 ]
  • [ 57641-66-4 ]
  • [ 162398-65-4 ]
  • 11
  • [ 371-41-5 ]
  • [ 84851-56-9 ]
  • methyl 4-(1-(4-fluorophenoxy)ethyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 12h; Methyl 4-(l-(4-fluorophenoxy)ethyl)benzoate. To a solution of methyl 4-(l- hydroxyethyl)benzoate (0.9 g, 5 mmol), 4-fluorophenol (627 mg, 5.6 mmol), triphenylphosphine (2.2 g, 8.4 mmol) in tetrahydrofuran (30 mL) was added diisopropyl azodicarboxylate (1.7 g, 8.4 mmol) at 0C. The mixture was stirred at 20C for 12 hours. Water (15 mL) was added to the mixture and then extracted with ethyl acetate (35 mL x 3). The combined organic phase was dried by sodium sulfate, and then filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 5: 1) to give methyl 4-(l-(4-fluorophenoxy)ethyl)benzoate (490 mg, 35%).
35% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 12h; To a solution of methyl 4-(1-hydroxyethyl)benzoate (0.9 g, 5 mmol), 4-fluorophenol (627 mg, 5.6 mmol), triphenylphosphine (2.2 g, 8.4 mmol) in tetrahydrofuran (30 mL) was added diisopropyl azodicarboxylate (1.7 g, 8.4 mmol) at 0 C. The mixture was stirred at 20 C. for 12 hours. Water (15 mL) was added to the mixture and then extracted with ethyl acetate (35 mL×3). The combined organic phase was dried by sodium sulfate, and then filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to give methyl 4-(1-(4-fluorophenoxy)ethyl)benzoate (490 mg, 35%).
  • 12
  • [ 371-41-5 ]
  • [ 21560-29-2 ]
  • [ 1613479-64-3 ]
YieldReaction ConditionsOperation in experiment
49.3% With sodium hydride; In N,N-dimethyl acetamide; mineral oil; at 20 - 200℃; for 0.3h;Inert atmosphere; Microwave irradiation; A solution of <strong>[21560-29-2]1-chloro-6,7-dimethoxyisoquinoline</strong> (50 mg, 0.22 mmol) and 4-fluorophenol (25.06mg, 0.22 mmol) in DMA (3 mL) was stirred under a nitrogen atmosphere for 5 minutes.Sodium hydride (22.35 mg, 0.56 mmol; 60% in mineral oil) was added to the reaction mixture and stirred at ambient temperature for 15 minutes. Next the mixture was stirred and heated at 200C for 3 minutes under microwave irradiation. The reaction mixture was quenched with methanol (0.5 mL) and the crude material was purified by flash column chromatography eluting with a gradient of ethyl acetate and methanol (1:0 to 1:1) to give a gum. The product was purified by reverse phase chromatography and the desired product (33.0 mg,49.3%) was obtained as a solid. HPLC purity:>99% (215 nM), >99% (254 nM), >99% (280 nM). 1H NMR (400MHz, DMSO-d6) d ppm 3.94 (s, 3 H), 3.92 (s, 3 H), 7.23- 7.31 (m, 4 H), 7.36 - 7.43 (m, 2 H), 7.58 (s, 1 H), 7.76 (d, J=5.5 Hz, 1 H).HRMS m/z calcd for C17H14FNO3 [M+H]+300.1031, found 300.1030.
49.3% A solution of <strong>[21560-29-2]1-chloro-6,7-dimethoxyisoquinoline</strong>(50 mg, 0.22 mmol) and 4-fluorophenol (25.06 mg, 0.22 mmol) in DMA (3 mL) wasstirred under a nitrogen atmosphere for 5 minutes. Sodium hydride (22.35 mg,0.56 mmol; 60% in mineral oil) was added to the reaction mixture and stirred atambient temperature for 15 minutes. Next the mixture was stirred and heated at 200C for 3 minutes undermicrowave irradiation. The reaction mixture was quenched with methanol (0.5 mL)and the crude material was purified by flash column chromatography eluting witha gradient of ethyl acetate and methanol (1:0 to 1:1) to give a gum. Theproduct was purified by reverse phase chromatography and the desired product (33.0mg, 49.3%) was obtained as a solid. HPLCpurity: >99% (215 nM), >99% (254 nM), >99% (280 nM). 1H NMR(400 MHz, DMSO-d6) dppm 3.94 (s, 3 H), 3.92 (s, 3 H), 7.23 - 7.31 (m, 4 H), 7.36- 7.43 (m, 2 H), 7.58 (s, 1 H), 7.76 (d, J=5.5 Hz, 1 H). HRMS m/z calcd for C17H14FNO3[M+H]+ 300.1031, found 300.1030.
  • 13
  • [ 371-41-5 ]
  • [ 1147557-97-8 ]
  • C17H22FNO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 0 - 20℃;Inert atmosphere; Preparation of intermediate EV A solution of DIAD (0.74 mL, 3.75 mmol) in toluene (5 mL) was added to a solution of 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate (CAS [1147557-97-8], 0.8 g, 3.75 mmol), 4-fluorophenol (0.421 g, 3.75 mmol) and triphenylphosphine (1.48 g, 5.63 mmol) in toluene (35 mL) at 0 °C under N2. The reaction mixture was then allowed to warm up to room temperature slowly overnight. Additional 4-fluorophenol (0.21 g, 1.88 mmol) was added and the reaction was stirred further at room temperature for 3d. The reaction mixture was evaporated to dryness, then dissolved in a minimum of diethyl ether and cooled to 0 °C. A large excess of heptane was added and the resulting mixture was evaporated under vacuum which induced the precipitation of PPh30, which was filtered off and washed with diethyl ether. The filtrate was evaporated to dryness and purified by preparative LC (irregular SiOH, 15-40 muiotaeta, 40 g, Grace, dry loading (silica), mobile phase gradient: Heptane/EtOAc from 90/10 to 50/50) to give 1.07 g of intermediate EV as a yellow solid (not obtained pure but engaged as such in the next step).
  • 14
  • [ 371-41-5 ]
  • [ 2991-28-8 ]
  • [ 104961-03-7 ]
  • 15
  • [ 371-41-5 ]
  • [ 33742-70-0 ]
  • C12H10FN3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In N,N-dimethyl-formamide; at 80℃; for 10.0h;Inert atmosphere; General procedure: NaH (12.0mmol) was added to a solution of 1 or 722 (1.88g, 10.0mmol) and substituted phenol (12.0mmol) in DMF (50mL) at room temperature under N2, and the mixture was stirred at 80C for 10h. Water was added to the cooled mixture, and the mixture was extracted with EtOAc several times. The combined organic layers were washed with water, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography to obtain purified compound 2, or crude 2 was used directly for the next reaction without further purification.
  • 16
  • [ 41014-43-1 ]
  • [ 371-41-5 ]
  • 2-((4-fluorophenoxy)methyl)benzo[d]oxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.13% With potassium carbonate; In acetone; for 4h;Reflux; General procedure: To a solution of various substituted phenols (1 mmol) in dry acetone (30 mL) K2CO3 (1 mmol)and compound 3 or 4 (1 mmol) were added. After being stirred for 4 h at reflux temperature, thereaction mixture was cooled, filtered, and concentrated under vacuum. Then the residue was dilutedwith 30 mL ethyl acetate and sequentially washed with 30 mL 1 M HCl, aq. NaHCO3 solution andbrine in order. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification of theresidue by chromatography on silica gel furnished target compounds. 1H-NMR, 13C-NMR and massspectroscopy (MS) of compounds 5a-m and 6a-m are shown in Supplementary Materials.
  • 17
  • [ 371-41-5 ]
  • [ 1835-65-0 ]
  • 4-(4-fluorophenoxy)-3,5,6-trifluorophthalonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With potassium fluoride; In acetone; at 0℃; for 0.5h; In a 50 ml reactor, 7 g of <strong>[1835-65-0]tetrafluorophthalonitrile</strong>,2.25 g of potassium fluoride and 30 g of acetone were added and stirred at 0 ° C. A solution prepared by mixing 3.9 g of 4-fluorophenol with 5 g of acetone was dropped there, and kept at 0 ° C. for 30 minutes.After raising the temperature to 25 ° C., the reaction solution is suction filtered.The solvent was distilled off from the filtrate under reduced pressure, and then crystallization was performed by adding methanol.The crystallized material is collected by filtration and then dried under reduced pressure.5.72 g (yield 56 molpercent based on <strong>[1835-65-0]tetrafluorophthalonitrile</strong>) of 4- (4-fluorophenoxy) -3,5,6-trifluorophthalonitrile was obtained.5 g of 4- (4-fluorophenoxy) -3,5,6-trifluorophthalonitrile thus obtained,2.61 g of potassium carbonate, 1.56 g of ethyl 3,4-dihydroxybenzoate and 50 g of acetonitrile were charged into a 100 ml reactor and reacted at 80 ° C. for 2 hours.Thereafter, 3.84 g of 4-fluorophenol and 5.21 g of potassium carbonate were further added, and reacted at 80 ° C. for about 7 hours.The reaction solution is filtered while hot to remove inorganic components,The solvent was distilled off under reduced pressure from the filtrate to obtain 9.21 g of phthalonitrile mixture (A) (yield: 98 molpercent based on 4- (4-fluorophenoxy) -3,5,6-trifluorophthalonitrile).
  • 18
  • [ 52092-47-4 ]
  • [ 371-41-5 ]
  • 5-(4-fluorophenoxy)-2-nitropyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 12h; Dissolve <strong>[52092-47-4]2-nitro-5-chloropyridine</strong> (3.17g, 20mmol), p-fluorophenol (2.24g, 20mmol), and potassium carbonate (4.14g, 30mmol) in 50mL of DMF solution. The reaction was carried out at 100 C for 12 hours. The reaction was cooled to room temperature, and 100 mL of ice water was added and stirred. A solid precipitated out, filtered with suction, washed with water, and dried.The target compound was obtained (brown solid, 4.03 g, yield: 86%).
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