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[ CAS No. 122536-76-9 ] {[proInfo.proName]}

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Quality Control of [ 122536-76-9 ]

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Product Citations

Product Citations

Design and synthesis of novel arylurea derivatives of aryloxy (1-phenylpropyl) alicyclic diamines with antimicrobial activity against multidrug-resistant Gram-positive bacteria

Canale, Vittorio ; Czekajewska, Joanna ; Klesiewicz, Karolina , et al. Eur. J. Med. Chem.,2023,251,115224. DOI: 10.1016/j.ejmech.2023.115224 PubMed ID: 36958177

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Abstract: The alarming increase in the resistance of bacteria to the currently available antibiotics necessitates the development of new effective antimicrobial agents that are active against bacterial pathogens causing major public health problems. For this purpose, our inhouse libraries were screened against a wide panel of clin. relevant Gram-pos. and Gram-neg. bacteria, based on which compound I was selected for further optimization. Synthetic efforts in a group of arylurea derivatives of aryloxy(1-phenylpropyl) alicyclic diamines, followed with an in vitro evaluation of the activity against multidrug-resistant strains identified compound 44 (1-(3-chlorophenyl)-3-(1-{3-phenyl-3-[3-(trifluoromethyl)phenoxy] propyl}piperidin-4-yl)urea). Compound 44 showed antibacterial activity against Gram-pos. bacteria including fatal drug-resistant strains i.e., Staphylococcus aureus (methicillin-resistant, MRSA; vancomycin-intermediate, VISA) and Enterococcus faecium (vancomycin-resistant, VREfm) at low concentrations (0.78-3.125 μg/mL) comparable to last resort antibiotics (i.e., vancomycin and linezolid). It is also potent against biofilm-forming S. aureus and Staphylococcus epidermidis (including linezolid-resistant, LRSE) strains, but with no activity against Gram-neg. bacteria (Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa). Compound 44 showed strong bactericidal properties against susceptible and drug-resistant Gram-pos. bacteria. Depolarization of the bacterial cytoplasmic membrane induced by compound 44 suggests a dissipation of the bacterial membrane potential as its mechanism of antibacterial action. The high antimicrobial activity of compound 44, along with its selectivity over mammalian cells (lung MCR-5 and skin BJ fibroblast cell lines) and no hemolytic properties toward horse erythrocytes, proposes arylurea derivatives of aryloxy(1-phenylpropyl) alicyclic diamines for development of novel antibacterial agents.

Keywords: Arylurea derivatives ; Antibacterial properties ; Anti-MRSA activity ; Anti-VRE activity ; Anti-LRSE activity ; Depolarization of bacterial cell membrane

Purchased from AmBeed: 122536-76-9 ; 936-59-4 ; 135632-53-0 ; 404-71-7 ; 73874-95-0 ; 372-20-3 ; 98-17-9 ; 402-45-9 ; 57260-71-6 ; 122536-77-0 ; 444-30-4 ; 165800-03-3 ; 150-19-6 ; 1195-45-5 ; 2909-38-8 ; 165800-03-3 ...More

Product Details of [ 122536-76-9 ]

CAS No. :	122536-76-9	MDL No. :	MFCD00143194
Formula :	C₉H₁₈N₂O₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	DQQJBEAXSOOCPG-ZETCQYMHSA-N
M.W :	186.25	Pubchem ID :	1514396
Synonyms :		Chemical Name :	(S)-tert-Butyl pyrrolidin-3-ylcarbamate

Calculated chemistry of [ 122536-76-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.89
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	54.49
TPSA :	50.36 ?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) :	-6.94 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.29
Log Po/w (XLOGP3) :	0.7
Log Po/w (WLOGP) :	0.49
Log Po/w (MLOGP) :	0.56
Log Po/w (SILICOS-IT) :	0.55
Consensus Log Po/w :	0.92

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.17
Solubility :	12.5 mg/ml ; 0.0673 mol/l
Class :	Very soluble
Log S (Ali) :	-1.34
Solubility :	8.61 mg/ml ; 0.0462 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.76
Solubility :	3.21 mg/ml ; 0.0173 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.64

Safety of [ 122536-76-9 ]

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

Application In Synthesis of [ 122536-76-9 ]

* 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.

Upstream synthesis route of [ 122536-76-9 ]
Downstream synthetic route of [ 122536-76-9 ]

[ 122536-76-9 ] Synthesis Path-Upstream 1~1

1
[ 100-52-7 ]
[ 122536-76-9 ]
[ 131852-53-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: at 20℃; for 0.166667 h; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 20℃; for 5 h;	EXAMPLE 67 Synthesis of (S)-4-((1-benzylpyrrolidin-3-yl)amino)-3-chloro-/V-(1 ,2,4-thiadiazol-5- yl)benzenesulfonamide 2,2,2-trifluoroacetate Step 1. Preparation of te/f-butyl (S)-(1-benzylpyrrolidin-3-yl)carbamate To a solution of terf-butyl (S)-pyrrolidin-3-ylcarbamate (0.30 g, 1.60 mmol) in anhydrous 1 ,2-dichloroethane (2 mL) and anhydrous A/,A/-dimethylformamide (2 mL) was added benzaldehyde (0.26 g, 2.40 mmol). The reaction mixture was stirred at ambient temperature for 10 minutes and then sodium triacetoxyborohydride (0.68 g, 3.20 mmol) was added to it. The reaction mixture was stirred at ambient temperature for 5 h. After dilution with ethyl acetate (50 mL), the mixture was washed with brine (3 x 50 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo provided the title compound as colorless oil (0.37 g, 84 percent yield). H NMR (300 MHz, CDCI₃) 7.58-7.53 (m, 2H), 7.46-7.39 (m, 3H), 4.55-4.49 (m, 1 H), 4.16 (s, 2H), 3.67-3.52 (m, 1 H), 3.40-3.36 (m, 1 H), 3.12-3.06 (m, 1 H), 2.91-2.81 (m, 1 H), 2.52-2.40 (m, 1 H), 2.25-2.12 (m, 1 H), 1.39 (s, 9H), NH not observed; MS (ES+) m/z 277.2 (M + 1).

Reference： [1] Patent: WO2017/201468, 2017, A1, . Location in patent: Page/Page column 180-181

[ 122536-76-9 ] Synthesis Path-Downstream 1~10

1
[ 130622-08-1 ]
[ 122536-76-9 ]

Reference： [1]Synthetic Communications,1998,vol. 28,p. 3919 - 3926
[2]Heterocycles,1997,vol. 44,p. 213 - 225

2
[ 128427-10-1 ]
[ 122536-76-9 ]

Reference： [1]Synthetic Communications,1998,vol. 28,p. 3919 - 3926
[2]Heterocycles,1997,vol. 44,p. 213 - 225

3
[ 17794-48-8 ]
[ 122536-76-9 ]
[ 857650-89-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In DMF (N,N-dimethyl-formamide); at 0 - 20℃;	tert-Butyl [(3S)-1-([3-(Trifluoromethyl)benzoyl]amino}acetyl)pyrrolidin-3-yl]carbamate. To a solution of the carboxylic acid (2.7 g, 11 mmol) from step A and tert-butyl (3S)-pyrrolidin-3-ylcarbamate (2.0 g, 11 mmol) in DMF (30 mL) cooled in an ice bath was added BOP (5 g, 11 mmol) followed by triethylamine (3 mL, 22 mmol). The mixture was allowed to warm to temperature and stirred overnight. Ethyl acetate (150 mL) was added. The resulting solution was washed with NaHCO3 and brine each three times, dried over MgSO4 and concentrated. Chromatography on silica gel eluting with EtOAc provided 4.4 g (96%) of the desired product. MS (M-Boc+H)+ 316.
96%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃;cooling with ice;	Step BBocHN'tert-Butyl [(3S)-1 -([3-(Trifluoromethyl)benzoyl]amino}acetyl)pyrrolidin-3-yl]carbamate. To a solution of the carboxylic acid (2.7 g, 1 1 mmol) from step A and tert-butyl (3S)-pyrrolidin-3-ylcarbamate (2.0 g, 1 1 mmol) in DMF (30 mL) cooled in an ice bath was added BOP (5 g, 1 1 mmol) followed by triethylamine (3 mL, 22 mmol). The mixture was allowed to warm to temperature and stirred overnight. Ethyl acetate (150 mL) was added. The resulting solution was washed with NaHC03 and brine each three times, dried over MgS04 and concentrated. Chromatography on silica gel eluting with EtOAc provided 4.4 g (96%) of the desired product. MS (M-Boc+H)+ 316.

Reference： [1]Patent: US2005/192302,2005,A1 .Location in patent: Page/Page column 21
[2]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 913 - 918
[3]Patent: WO2012/114223,2012,A1 .Location in patent: Page/Page column 37

4
[ 122536-76-9 ]
[ 28992-50-9 ]
[ 875899-61-9 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; for 12h;	Step B: tert-buty {(3i?)-l-[l//-l,2,3-benzotriazol-l-yl(imino)methyl]pyrrolidin-3-yl}carbamate; To a stirred solution of l,l-di(lH-l,2,3-benzotriazol-l-yl)methanimine (1.0 g, 3.8 mmol) in dry THF (75 mL) was added (3S)-(-)-3-(tert-butoxycarbonylamino)pyrrolidine (0.71 g, 3.8 mmol). After 12 hours, the reaction was concentrated and the residue was dissolved in methylene chloride. The organic layer was washed with saturated sodium carbonate, dried over sodium sulfate, filtered and concentrated to give the title compound (850 mg) as a white solid. This material was sufficiently pure for the next step. MS 331 (M+l).

Reference： [1]Patent: WO2006/17409,2006,A2 .Location in patent: Page/Page column 106

5
[ 383-31-3 ]
[ 122536-76-9 ]
[ 870859-17-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In dimethyl sulfoxide; at 130℃; for 24h;	(2) In 600 ml of DMSO were suspended 25 g of (S)-(-)-3-(tert-butoxycarbonylamino)pyrrolidine, 47.9 g of 4-fluoro-N,N-dimethyl-benzenesulfonamide and 139 g of potassium carbonate, and the mixture was stirred at 130C for 1 day. To the reaction mixture were added water and ethyl acetate, the resulting mixture was stirred and the liquids were separated. The organic layer was washed with water, and then dried, and the solvent was evaporated. The residue was dissolved in chloroform, NH silica gel was added thereto and the mixture was allowed to stand for a while, and silica gel was filtered off. The silica gel was further washed with ethyl acetate. The filtrate and the washed solution were combined, and the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=80:20? 67:33) to obtain 8.39 g of tert-butyl [(S)-1-(4-dimethylsulfamoylphenyl)-pyrrolidin-3-yl]carbamate. MS·APCI (m/z): 370 [M+H] +

Reference： [1]Patent: EP1757582,2007,A1 .Location in patent: Page/Page column 31

6
[ 14190-59-1 ]
[ 122536-76-9 ]
[ 1373525-53-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; HATU; In dichloromethane; at 20℃; for 18h;	To a solution of compound 1a (4.47 g, 24 mmol), 2-thiazole carboxylic acid 1b (2.58 g, 20 mmol), and Et3N (1.4 mL, 100 mmol) in CH2Cl2 (50 mL) was added HATU (9.89 g, 26 mmol). The reaction mixture was stirred at room temperature for 18 h. The resultant mixture was diluted with CH2Cl2 and washed with aq. NaHCO3. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification of the residue by flash column chromatography (silica gel, 50percent EtOAc/hexanes) gave compound 1c (5.5 g). 1H NMR (300 MHz, CDCl3): delta 7.89 (m, 1H), 7.52 (m, 1H), 4.65 (m, 1H), 4.39-4.22 (m, 2.5H), 4.03 (m, 0.5H), 3.91 (m, 0.5H), 3.81-3.74 (m, 1H), 3.61 (m, 0.5H), 2.28-2.19 (m, 1H), 2.05-1.86 (m, 1H), 1.44 (s, 9H).

Reference： [1]Patent: US2012/101081,2012,A1 .Location in patent: Page/Page column 20; 21

7
[ 24424-99-5 ]
[ 79286-79-6 ]
[ 122536-76-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 132 - 137

8
[ 122536-76-9 ]
[ 79286-79-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; In 1,4-dioxane; at 20℃; for 16h;Inert atmosphere;	A solution of Boc compound in 1,4-dioxane (10 vol) was added to 4 N HCl in dioxane (5 vol) at room temperature under N2 atmosphere and the reaction mixture was stirred at room temperature for 16 h. Solvent was evaporated under reduced pressure and triturated with diethyl ether to afford corresponding amines in quantitative yields.

Reference： [1]Synthetic Communications,2016,vol. 46,p. 263 - 274

9
[ 60211-57-6 ]
[ 122536-76-9 ]
[ 530-62-1 ]
3,5-dichlorobenzyl (S)-3-((tert-butoxycarbonyl)amino)pyrrolidine-1-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 2006 - 2017

10
[ 42860-10-6 ]
[ 122536-76-9 ]
tert-butyl N-[(3S)-1-(3-bromo-4-chlorobenzoyl)pyrrolidin-3-yl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl acetamide; at 20℃; for 1h;	<strong>[42860-10-6]3-bromo-4-chlorobenzoic acid</strong> (10 g) was dissolved in DMA (85 mL). At room temperature, HATU (24 g), TEA(12 mL), and tert-butyl N-[(3S)-pyrrolidin-3-yl]carbamate (8.7 g) were added thereto, followed by stirring at room temperaturefor 1 hour. Ethyl acetate was added thereto, and the resulting mixture was washed sequentially with water andsaturated brine. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off. The residuewas purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate) to give tert-butyl N-[(3S)-1-(3-bromo-4-chlorobenzoyl)pyrrolidin-3-yl]carbamate.

Reference： [1]Patent: EP3381896,2018,A1 .Location in patent: Paragraph 0193

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Technical Information

? Acyl Group Substitution ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Complex Metal Hydride Reductions ? Hydride Reductions ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Amines ? Reactions of Amines ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Specialized Acylation Reagents-Vilsmeier Reagent ? Ugi Reaction

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P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
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.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

Physical hazards
Code	Phrase
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
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
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
H280	Contains gas under pressure; may explode if heated
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
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
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

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