Home Cart Sign in  
Chemical Structure| 57260-71-6 Chemical Structure| 57260-71-6
Chemical Structure| 57260-71-6

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

{[proInfo.proName]}

CAS No.: 57260-71-6

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Product Citations

Canale, Vittorio ; Czekajewska, Joanna ; Klesiewicz, Karolina ; Papiez, Monika ; Kuziak, Agata ; Witek, Karolina , et al.

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

Alternative Products

Product Details of N-Boc-piperazine

CAS No. :57260-71-6
Formula : C9H18N2O2
M.W : 186.25
SMILES Code : O=C(N1CCNCC1)OC(C)(C)C
MDL No. :MFCD00075265
InChI Key :CWXPZXBSDSIRCS-UHFFFAOYSA-N
Pubchem ID :143452

Safety of N-Boc-piperazine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501

Application In Synthesis of N-Boc-piperazine

* 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 [ 57260-71-6 ]
  • Downstream synthetic route of [ 57260-71-6 ]

[ 57260-71-6 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 110-85-0 ]
  • [ 24424-99-5 ]
  • [ 76535-75-6 ]
  • [ 57260-71-6 ]
YieldReaction ConditionsOperation in experiment
60% at 0℃; for 1 h; To a cold methylene chloride solution (10 ml) of piperazine (30.23 mmol, 2.60 g) was added methylene chloride solution (10 ml) of BOC anhydride (1.50 mmol) and the mixture was stirred at 0°C for 1 hour. After the reaction is complete, water is added and the aqueous K2CO3 solution is added to make the reaction mixture basic. All of the reaction mixture was extracted with methylene chloride and the product was isolated by column chromatography.
References: [1] Green Chemistry, 2014, vol. 16, # 7, p. 3635 - 3642.
[2] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 6, p. 1559 - 1563.
[3] Russian Journal of Organic Chemistry, 2009, vol. 45, # 5, p. 788 - 791.
[4] Patent: KR2015/111825, 2015, A, . Location in patent: Paragraph 0722-0734.
[5] Journal of Medicinal Chemistry, 1992, vol. 35, # 21, p. 3845 - 3857.
[6] Journal of Medicinal Chemistry, 1992, vol. 35, # 21, p. 3845 - 3857.
[7] Tetrahedron Letters, 2006, vol. 47, # 46, p. 8039 - 8042.
[8] Patent: KR2016/108281, 2016, A, . Location in patent: Paragraph 0721-0724.
  • 2
  • [ 24424-99-5 ]
  • [ 57260-71-6 ]
  • [ 76535-75-6 ]
References: [1] Journal of Organic Chemistry, 2006, vol. 71, # 21, p. 8283 - 8286.
  • 3
  • [ 124-63-0 ]
  • [ 57260-71-6 ]
  • [ 161357-89-7 ]
References: [1] Patent: US9335320, 2016, B2, . Location in patent: Page/Page column 74.
  • 4
  • [ 57260-71-6 ]
  • [ 118753-66-5 ]
References: [1] Patent: WO2015/22663, 2015, A1, .
[2] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 247 - 258.
[3] Patent: US10213433, 2019, B2, .
  • 5
  • [ 57260-71-6 ]
  • [ 627-18-9 ]
  • [ 132710-90-8 ]
YieldReaction ConditionsOperation in experiment
80% With potassium carbonate In acetonitrile at 95℃; for 4 h; Intermediate 121: tert-Butyl 4-(3-hvdroxypropyr)piperazine-l -carboxylate A mixture of tert-butyl piperazine-1 -carboxylate (2.75 g, 14.8 mmol), l-bromo-3- propanol (1.43 mL, 16.2 mmol) and potassium carbonate (2.25 mL, 27.5 mmol) in acetonitrile (75 mL) was heated at 950C for 4 hours. The solvent was removed under reduced pressure, and the residue was taken up in dichloromethane (300 mL) and washed with water, brine, EPO <DP n="118"/>dried over sodium sulfate and concentrated under reduced pressure. Chromatography on silica gel with methanol in dichloromethane (0-10percent) gave a tan solid 2.88 g (80percent yield). MS (ESV 245 (MH+) for C12H24N2O3,1H-NMR TCDCl1) δ: 1.44 (m, 9H); 1.70-1.82 (m, 2H); 2.40-2.53 (m, 2H); 2.62-2.65 (m, 2H); 3.43-3.50 (m, 4H); 2.77 (m, 2H); 3.73-3.82 (m, 2H).
References: [1] Patent: WO2006/134378, 2006, A1, . Location in patent: Page/Page column 116-117.
 

Historical Records

Technical Information

Categories