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

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Structure of 371-41-5 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 371-41-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 371-41-5 ]

SDS Specification

Alternatived Products of [ 371-41-5 ]

Product Citations Expand+

Azapeptides with unique covalent warheads as SARS-CoV-2 main protease inhibitors

Kaustav Khatua ; Yugendar R. Alugubelli ; Kai S. Yang , et al. Antivir. Res.,2024,225,105874. DOI: 10.1016/j.antiviral.2024.105874

Abstract: The main protease (MPro) of SARS-CoV-2, the causative agent of COVID-19, is a pivotal nonstructural protein critical for viral replication and pathogenesis. Its protease function relies on three active site pockets for substrate recognition and a catalytic cysteine for enzymatic activity. To develop potential SARS-CoV-2 antivirals, we successfully synthesized a diverse range of azapeptide inhibitors with various covalent warheads to target MPro's catalytic cysteine. 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 protease and several human proteases. Crystallography analyses demonstrated that these inhibitors covalently engaged the catalytic cysteine 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

Purchased from AmBeed: 371-41-5 ; 1187431-43-1 ; 60-00-4 ; 3483-12-3

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 Å²

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 1~13

1
[ 371-41-5 ]
[ 42864-24-4 ]
[ 5724-56-1 ]
[ 394-33-2 ]
[ 52962-97-7 ]
[ 52911-59-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1983,p. 1003 - 1010

2
[ 371-41-5 ]
[ 42864-24-4 ]
[ 5724-56-1 ]
[ 394-33-2 ]
[ 52962-97-7 ]
[ 52911-65-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1983,p. 1003 - 1010

3
[ 530-46-1 ]
[ 106-44-5 ]
[ 371-41-5 ]
[ 456-22-4 ]
[ 99-94-5 ]

Reference： [1]Journal of Fluorine Chemistry,1994,vol. 67,p. 41 - 46

4
[ 13195-50-1 ]
[ 371-41-5 ]
[ 190966-75-7 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 779 - 786
[2]Patent: US5783597,1998,A

5
[ 371-41-5 ]
[ 619-60-3 ]
N,N-dimethyl-p-(p-hydroxyphenoxy)aniline [ No CAS ]

Reference： [1]Chemical Communications,2005,p. 2486 - 2488

6
[ 371-41-5 ]
[ 26690-80-2 ]
[ 263409-78-5 ]
[ 97308-23-1 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 4591 - 4595

7
[ 371-41-5 ]
[ 4876-10-2 ]
[ 1091595-24-2 ]

Reference： [1]European Journal of Medicinal Chemistry,2008,vol. 43,p. 2178 - 2188

8
[ 371-41-5 ]
[ 57641-66-4 ]
[ 162398-65-4 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 6898 - 6915

9
[ 371-41-5 ]
[ 1147557-97-8 ]
C₁₇H₂₂FNO₃ [ No CAS ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Patent: WO2017/1660,2017,A1 .Location in patent: Page/Page column 148; 149

10
[ 371-41-5 ]
[ 2991-28-8 ]
[ 104961-03-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1186 - 1192

11
[ 41014-43-1 ]
[ 371-41-5 ]
2-((4-fluorophenoxy)methyl)benzo[d]oxazole [ No CAS ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Molecules,2018,vol. 23

12
[ 371-41-5 ]
[ 1835-65-0 ]
4-(4-fluorophenoxy)-3,5,6-trifluorophthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Patent: JP2019/6747,2019,A .Location in patent: Paragraph 0170

13
[ 52092-47-4 ]
[ 371-41-5 ]
5-(4-fluorophenoxy)-2-nitropyridine [ No CAS ]

Yield	Reaction Conditions	Operation 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%).

Reference： [1]Patent: CN110452238,2019,A .Location in patent: Paragraph 0196-0199; 0226-0229

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Technical Information

• Acidity of Phenols • Alkyl Halide Occurrence • Chan-Lam Coupling Reaction • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Halogenation of Phenols • Oxidation of Phenols • Pechmann Coumarin Synthesis • Preparation of Aldehydes and Ketones • Reactions of Benzene and Substituted Benzenes • Reimer-Tiemann Reaction

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[ 371-41-5 ]

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Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
P402	Store in a dry place.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H351	Suspected of causing cancer
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H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
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H371	May cause damage to organs
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H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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

Quality Control of [ 371-41-5 ]

Related Doc. of [ 371-41-5 ]

Product Citations Expand+

Product Details of [ 371-41-5 ]

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

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 371-41-5 ]

Application In Synthesis of [ 371-41-5 ]

[ 371-41-5 ] Synthesis Path-Downstream 1~13

Technical Information

Related Functional Groups of [ 371-41-5 ]

Fluorinated Building Blocks

Aryls

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 371-41-5 ]