[ CAS No. 403-43-0 ] {[proInfo.proName]}

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Quality Control of [ 403-43-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 403-43-0 ]

SDS Specification

Alternatived Products of [ 403-43-0 ]

Product Citations

Rebamipide and Derivatives are Potent, Selective Inhibitors of Histidine Phosphatase Activity of the Suppressor of T Cell Receptor Signaling Proteins

Faisal Aziz ; Kanamata Reddy ; Virneliz Fernandez Vega , et al. JMC,2024,67(3):1949-1960. DOI: 10.1021/acs.jmedchem.3c01763

Abstract: The suppressor of T cell receptor signaling (Sts) proteins are negative regulators of immune signaling. Genetic inactivation of these proteins leads to significant resistance to infection. From a 590,000 compound high-throughput screen, we identified the 2-(1H)-quinolinone derivative, rebamipide, as a putative inhibitor of Sts phosphatase activity. Rebamipide, and a small library of derivatives, are competitive, selective inhibitors of Sts-1 with IC50 values from low to submicromolar. SAR analysis indicates that the quinolinone, the acid, and the amide moieties are all essential for activity. A crystal structure confirmed the SAR and reveals key interactions between this class of compound and the protein. Although rebamipide has poor cell permeability, we demonstrated that a liposomal preparation can inactivate the phosphatase activity of Sts-1 in cells. These studies demonstrate that Sts-1 enzyme activity can be pharmacologically inactivated and provide foundational tools and insights for the development of immune-enhancing therapies that target the Sts proteins.

Purchased from AmBeed: 2251-65-2 ; 90098-04-7 ; 4876-14-6 ; 90098-08-1 ; 874-60-2 ; 4876-10-2 ; 7158-32-9 ; 5271-67-0 ; 118-45-6 ; 73-22-3 ; 56-41-7 ; 34893-92-0 ; 403-43-0 ; 58757-38-3 ; 76903-88-3 ; 52-90-4 ; 6068-72-0 ; 2243-83-6 ; 38818-50-7 ; 16331-45-6 ; 36823-88-8 ; 90098-06-9 ; 90098-05-8 ; 3024-72-4 ; 618-46-2 ; 63024-43-1 ; 4122-68-3 ; 22980-09-2 ; 681806-75-7 ; 39544-74-6 ...More

Product Details of [ 403-43-0 ]

CAS No. :	403-43-0	MDL No. :	MFCD00000684
Formula :	C₇H₄ClFO	Boiling Point :	-
Linear Structure Formula :	(FC₆H₄)COCl	InChI Key :	CZKLEJHVLCMVQR-UHFFFAOYSA-N
M.W :	158.56	Pubchem ID :	67879
Synonyms :

Calculated chemistry of [ 403-43-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	36.58
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.82
Log Po/w (XLOGP3) :	3.05
Log Po/w (WLOGP) :	2.62
Log Po/w (MLOGP) :	2.48
Log Po/w (SILICOS-IT) :	2.76
Consensus Log Po/w :	2.55

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.12
Solubility :	0.12 mg/ml ; 0.000754 mol/l
Class :	Soluble
Log S (Ali) :	-3.07
Solubility :	0.134 mg/ml ; 0.000842 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.23
Solubility :	0.0938 mg/ml ; 0.000592 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.08

Safety of [ 403-43-0 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3265
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 403-43-0 ]

* 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.

Upstream synthesis route of [ 403-43-0 ]
Downstream synthetic route of [ 403-43-0 ]

[ 403-43-0 ] Synthesis Path-Upstream 1~1

1
[ 462-06-6 ]
[ 403-43-0 ]
[ 345-71-1 ]
[ 342-25-6 ]
[ 345-92-6 ]

Reference： [1] Chemical Communications, 2004, # 12, p. 1368 - 1369

[ 403-43-0 ] Synthesis Path-Downstream 1~8

1
[ 67198-21-4 ]
[ 403-43-0 ]
N-((1S,2S)-2-Dimethylamino-cyclohexyl)-4-fluoro-benzamide [ No CAS ]

Reference： [1]Patent: BE860727,1978,
Patent: DE2749984,1978,
Chem.Abstr.,1978,vol. 89

2
[ 21109-25-1 ]
[ 403-43-0 ]
[ 943188-10-1 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 4983 - 4989
[2]Organic Letters,2013,vol. 15,p. 4266 - 4269

3
[ 403-43-0 ]
[ 192130-34-0 ]
1-[2-(4-Fluorobenzoylamino)ethyl]-4-(t-butoxycarbonyl)piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium hydrogencarbonate; triethylamine; In tetrahydrofuran;	64-1) 1-[2-(4-Fluorobenzoylamino)ethyl]-4-(t-butoxycarbonyl)piperazine The 1-(2-aminoethyl)-4-(t-butoxycarbonyl)piperazine (1.33 g) obtained in Example 58 and 4-fluorobenzoyl chloride (1.1 g) were dissolved in tetrahydrofuran (20 ml), then triethylamine (1.6 ml) was added thereto, and the mixture was stirred overnight at room temperature. The organic layer was partitioned by adding aqueous saturated sodium bicarbonate and ethyl acetate, and the organic layer was washed with water, dried, and evaporated. The residue was purified by Cromatorex NH silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound (1.42 g, 70 percent) was obtained as a colorless oil.

Reference： [1]Patent: EP1099692,2001,A1
[2]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 2597 - 2602

4
[ 2040-90-6 ]
[ 403-43-0 ]
[ 1443037-87-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine; In dichloromethane; at 0 - 20℃; for 3h;	2-Chloro-6-fluoro phenol (1, 30 g, 0.2054 mol) was dissolved in DCM, triethylamine (TEA, 45.73 g, 0.4519 mol) was added and the reaction mixture was cooled to 0 °C. A solution of 4-fluorobenzoyl chloride (2a, 33.9 g, 0.2157 mol) in DCM was added slowly to the above mixture and internal temperature was maintained to 0-10 °C. Finally the reaction mixture was stirred at ambient temperaturefor 3 h. Then the reaction mass was diluted with DCM (200 mL),washed with 10percent sodium hydroxide solution (3 x 30 mL), water (3 30 mL), brine (2 x 60 mL), and again with water (3 x 30 mL). The organic layer was dried over sodium sulfate and the solvent was evaporated to achieve compound 3a as white solid. Yield: 94percent; m.p.: 52.6-54.1 °C; IR (KBr) numax (cm-1): 1738 (ester,C]O); 1H NMR (400 MHz) (DMSO-d6) d (ppm): 7.42-7.53 (m, 4H,Ar-H), 8.25-8.28 (m, 3H, Ar-H); MS (EI): m/z (75percent) M 268.5;Anal. Calcd. for C13H7ClF2O2 (268.5): C, 58.12; H, 2.63; Cl, 13.20; F,14.14. Found: C, 58.22; H, 2.43; Cl, 13.30; F, 14.29percent.
92%	With triethylamine; In dichloromethane; at 0 - 20℃; for 3h;	General procedure: 2-Chloro-6-fluoro phenol (1, 0.20 mol) was dissolved indichloro methane (DCM) and triethylamine (TEA, 0.45 mol) wasadded to it. Then the reaction mixture was cooled to 0 C. Further,a solution of substituted benzoyl chloride 2a?d (0.21 mol) in DCMwas slowly added to the reaction mixture and stirred for 3 h andthe completion of the reaction was monitored by TLC using 4:1n-hexane: ethyl acetate solvent mixture. Then the reaction masswas diluted with DCM (100 ml), washed with 10percent sodium hydroxidesolution (3 40 ml), followed by water (3 30 ml). Theorganic layer was dried over sodium sulphate and the solidobtained after evaporation of the solvent was recrystallized fromethanol to give compounds 3a?d. [21] Compound (3a) is taken asa representative example to explain physical and characterizationdata.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 63,p. 536 - 543
[2]MedChemComm,2018,vol. 9,p. 639 - 656
[3]Bioorganic Chemistry,2016,vol. 65,p. 73 - 81
[4]Archiv der Pharmazie,2013,vol. 346,p. 901 - 911

5
[ 369-26-6 ]
[ 403-43-0 ]
C₁₅H₁₀FNO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9.1 mg		Methyl 3-amino-4-f uorobenzoate (21.0 mg, 0.124 mmol) and 4-fluorobenzoyl chloride (0.124 mmol) in toluene (2 ml) were heated at 110 °C for 1.5 h. Lawesson's reagent (40 mg, 0.100 mmol) was added and the mixture stirred at 110 °C overnight. Solvent was evaporated and residue purified by flash chromatography using 5-10percent EtOAc in hexanes as eluent. Yield: 9.1 mg

Reference： [1]Patent: WO2017/108282,2017,A1 .Location in patent: Page/Page column 102

6
[ 369-26-6 ]
[ 403-43-0 ]
2-(4-fluorophenyl)-N-hydroxy-1,3-benzothiazole-5-carboxamide [ No CAS ]

Reference： [1]Patent: WO2017/108282,2017,A1

7
[ 39745-40-9 ]
[ 403-43-0 ]
N-(2-chloro-6-methylpyridin-3-yl)-4-fluorobenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16.3 g	With triethylamine; In tetrahydrofuran; at 10 - 35℃; for 16h;	A) N-(2-chloro-6-methylpyridin-3-yl)-4-fluorobenzamide (1166) To a mixture of 850 <strong>[39745-40-9]2-chloro-6-methylpyridine-3-amine</strong> (10 g), 851 4-fluorobenzoyl chloride (11 g) and 38 THF (100 ml) was added 121 triethylamine (21.3 g), and the mixture was stirred at room temperature for 16 hr. To the reaction mixture was added 29 water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the 852 title compound (16.3 g). 1H NMR (400 MHz, DMSO-d6) delta 2.51 (3H, s), 7.34-7.46 (3H, m), 7.91 (1H, d, J = 8.0 Hz), 8.08 (2H, dd, J = 8.8, 5.6 Hz), 10.19 (1H, brs).

Reference： [1]Patent: EP3225618,2017,A1 .Location in patent: Paragraph 1166

8
[ 116668-47-4 ]
[ 403-43-0 ]
C₁₈H₁₂FNO₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 7697 - 7707

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Isomers

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Robinson Annulation • Rosenmund Reduction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Historical Records

Similar Product of
[ 403-43-0 ]

A1483303[ 91742-47-1 ]

4-Fluorobenzoyl chloride-1-13C

Reason: Stable Isotope

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Code	Phrase
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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.
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P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
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P243	Take precautionary measures against static discharge.
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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.
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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.
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Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
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P311	Call a POISON CENTER or doctor/physician.
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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:
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P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
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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.
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P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P361	Remove/Take off immediately all contaminated clothing.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
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P391	Collect spillage. Hazardous to the aquatic environment
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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.
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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H302	Harmful if swallowed
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
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H316	Causes mild skin irritation
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H319	Causes serious eye irritation
H320	Causes eye irritation
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H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
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H372	Causes damage to organs through prolonged or repeated exposure
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. 403-43-0 ] {[proInfo.proName]}

Quality Control of [ 403-43-0 ]

Related Doc. of [ 403-43-0 ]

Product Citations

Product Details of [ 403-43-0 ]

Calculated chemistry of [ 403-43-0 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 403-43-0 ]

Application In Synthesis of [ 403-43-0 ]

[ 403-43-0 ] Synthesis Path-Upstream 1~1

[ 403-43-0 ] Synthesis Path-Downstream 1~8

Technical Information

Similar Product of [ 403-43-0 ]

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Similar Product of
[ 403-43-0 ]