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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

More

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 1~3

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

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

2
[ 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

3
[ 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

Historical Records

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