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[ CAS No. 2565-18-6 ] {[proInfo.proName]}

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Chemical Structure| 2565-18-6
Chemical Structure| 2565-18-6
Structure of 2565-18-6 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Shao, Zeyu ; Luo, Hao ; Nguyen, Thi Hanh Quyen , et al. DOI: PubMed ID:

Abstract: Cationic amphipathic antimicrobial agents inspired by antimicrobial peptides (AMPs) have shown potential in combating multidrug-resistant bacteria because of minimal resistance development. Here, this study focuses on the development of novel cationic amphipathic macromolecules in the form of dendrons and polymers with different molecular weights that employ secondary amine piperidine derivative as the cationic moiety. Generally, secondary amine compounds, especially at low molecular weights, have stronger bacteriostatic, bactericidal, and inner membrane disruption abilities than those of their primary amine counterparts. Low molecular weight D2 dendrons with two cationic centers and one hydrophobic dodecyl chain produce outstanding synergistic activity with the rifampicin against Escherichia coli, where one-eighth of the standalone dose of D2 dendrons could reduce the concentration of rifampicin required by up to 4000-fold. The low molecular weight compounds are also less toxic and therefore have higher therapeutic index values compared to compounds with larger molecular weights. This study thus reveals key information that may inform the design of future synthetic AMPs and mimics, specifically, the design of low-molecular-weight compounds with secondary amine as the cationic center to achieve high antimicrobial potency and biocompatibility.

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Product Details of [ 2565-18-6 ]

CAS No. :2565-18-6 MDL No. :MFCD00080433
Formula : C7H13NO Boiling Point : No data available
Linear Structure Formula :- InChI Key :YRVUCYWJQFRCOB-UHFFFAOYSA-N
M.W : 127.18 Pubchem ID :642908
Synonyms :

Calculated chemistry of [ 2565-18-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.57
Num. rotatable bonds : 5
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.29
TPSA : 29.1 ?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) : -6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 0.86
Log Po/w (WLOGP) : 1.09
Log Po/w (MLOGP) : 1.11
Log Po/w (SILICOS-IT) : 1.17
Consensus Log Po/w : 1.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.84
Solubility : 18.4 mg/ml ; 0.144 mol/l
Class : Very soluble
Log S (Ali) : -1.05
Solubility : 11.2 mg/ml ; 0.0882 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.89
Solubility : 1.65 mg/ml ; 0.0129 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.18

Safety of [ 2565-18-6 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P201-P202-P261-P264-P270-P271-P280-P302+P352-P304+P340-P308+P313-P310-P330-P361-P403+P233-P405-P501 UN#:2810
Hazard Statements:H301-H311-H331-H341 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 2565-18-6 ]

* 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 [ 2565-18-6 ]

[ 2565-18-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 2565-18-6 ]
  • [ 13667-12-4 ]
  • 4,8-bis(4-bromophenyl)-2,6-dibutyl-3,7-diphenyl-2,6-dihydro-2,6-naphthyridin-1,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With dirhodium tetraacetate; silver hexafluoroantimonate; silver carbonate; In tetrahydrofuran; at 20℃;Reflux; The preparation method is as follows: Add a solution of N-butyl acrylamide in tetrahydrofuran at a concentration of 1 M in a clean 30 mL round bottom flask filled with stirring magnets. Then adding the catalyst cerium acetate (10 mol%), Oxidant silver carbonate (3 eq), additive potassium hexafluorophosphate (0.5 eq), <strong>[13667-12-4]1-bromo-4-phenylethynylbenzene</strong> (1.0 eq). This mixture was stirred at room temperature for one hour and then heated to reflux overnight. The reaction was detected by thin plate chromatography, and after cooling, the reaction was cooled to room temperature. Quenching the reaction with water, Extract 4×20 mL with ethyl acetate and wash with saturated brine. Dry over anhydrous sodium sulfate and remove sodium sulfate by filtration. The solvent was evaporated under reduced pressure to give a crude material. Using petroleum ether/ethyl acetate as the eluent, Purified by column chromatography (mobile phase: ethyl acetate / petroleum ether = 1/2) The white solid product was obtained in a yield of 60%.
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