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[ CAS No. 27578-60-5 ] {[proInfo.proName]}

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Chemical Structure| 27578-60-5
Chemical Structure| 27578-60-5
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Product Citations

Product Citations      Expand+

álvaro Pe?a ; Juan Heredero ; Beatriz Blandín , et al. DOI:

Abstract: Ionizable lipids are an essential component of lipid nanoparticles (LNPs) for an efficient mRNA delivery. However, optimizing their chemical structures for high protein expression, efficient endosomal escape, and selective organ targeting remains challenging due to complex structure-activity relationships and multistep synthesis. In this study, we introduce a rapid, high-throughput platform for screening ionizable lipids using a two-step, scalable synthesis involving a one-pot 3-component click-like reaction. This method, herein known as the STAAR approach, standing for Sequential Thiolactone Amine Acrylate Reaction, allowed for the combinatorial synthesis and in vivo screening of 91 novel lipids, followed by a structure-activity study. This led to the development of CP-LC-0729, an ionizable lipid that significantly surpasses the benchmark in protein expression while showing no in vivo toxicity. Additionally, the STAAR lipid platform was further validated by incorporating a one-step strategy to yield a permanently cationic lipid which was tested following a fifth-lipid formulation strategy. The in vivo results showed a highly selective lung delivery with a 32-fold increase in protein expression, outperforming current endogenous targeting strategies. All these findings underscore the potential of lipid CP-LC-0729 and the STAAR lipid platform in advancing the efficiency and specificity of mRNA delivery systems, while also advancing the development of new ionizable lipids.

Keywords: lipid nanoparticle ; ionizable lipid ; drug delivery ; lipids ; extrahepatic ; lung targeting ; mRNA therapeutics

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Li, Bowen ; Manan, Rajith Singh ; Liang, Shun-Qing , et al. DOI: PubMed ID:

Abstract: The expanding applications of nonviral genomic medicines in the lung remain restricted by delivery challenges. Here, leveraging a high-throughput platform, we synthesize and screen a combinatorial library of biodegradable ionizable lipids to build inhalable delivery vehicles for mRNA and CRISPR-Cas9 gene editors. Lead lipid nanoparticles are amenable for repeated intratracheal dosing and could achieve efficient gene editing in lung epithelium, providing avenues for gene therapy of congenital lung diseases.

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Product Details of [ 27578-60-5 ]

CAS No. :27578-60-5 MDL No. :MFCD00006516
Formula : C7H16N2 Boiling Point : No data available
Linear Structure Formula :NH2C2H4NC5H10 InChI Key :CJNRGSHEMCMUOE-UHFFFAOYSA-N
M.W : 128.22 Pubchem ID :33944
Synonyms :
Chemical Name :N-(2-Aminoethyl)piperidine

Calculated chemistry of [ 27578-60-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.17
TPSA : 29.26 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.97
Log Po/w (XLOGP3) : 0.44
Log Po/w (WLOGP) : 0.05
Log Po/w (MLOGP) : 0.57
Log Po/w (SILICOS-IT) : 0.83
Consensus Log Po/w : 0.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.78
Solubility : 21.3 mg/ml ; 0.166 mol/l
Class : Very soluble
Log S (Ali) : -0.62
Solubility : 30.6 mg/ml ; 0.239 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.01
Solubility : 12.4 mg/ml ; 0.0966 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.01

Safety of [ 27578-60-5 ]

Signal Word:Danger Class:8,3
Precautionary Statements:P280-P305+P351+P338-P310 UN#:2734
Hazard Statements:H226-H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 27578-60-5 ]

* 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 [ 27578-60-5 ]

[ 27578-60-5 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 110-89-4 ]
  • [ 926-39-6 ]
  • [ 27578-60-5 ]
  • 2
  • [ 27578-60-5 ]
  • [ 42926-52-3 ]
  • 2-ethoxy-benzoic acid-(2-piperidino-ethylamide) [ No CAS ]
  • 3
  • [ 27578-60-5 ]
  • [ 33045-53-3 ]
  • [ 102535-21-7 ]
  • 4
  • [ 27578-60-5 ]
  • [ 6492-86-0 ]
  • 6-Amino-2-(2-piperidin-1-yl-ethyl)-benzo[de]isoquinoline-1,3-dione [ No CAS ]
  • 5
  • [ 27578-60-5 ]
  • [ 27018-76-4 ]
  • 1-benzyl-1<i>H</i>-indole-3-carboxylic acid (2-piperidin-1-yl-ethyl)-amide [ No CAS ]
  • 6
  • [ 27578-60-5 ]
  • [ 5147-80-8 ]
  • [(2-piperidinoethylamino)(3-piperidinopropylamino)methylene]malononitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% Example 1 [(2-Piperidinoethylamino)(3-piperidinopropylamino) methylene]malononitrile (Compound 1) <strong>[5147-80-8][Bis(methylthio)methylene]malononitrile</strong> (300 mg, 1.76 mmol) was dissolved in THF (4 mL), and a solution obtained by dissolving 3-piperidinopropylamine (251 mg, 1.76 mmol) in THF (1 mL) was added thereto. After stirring the mixture at room temperature for 1.5 hours, a solution obtained by dissolving 1-(2-aminoethyl) piperidine (226 mg, 1.76 mmol) in THF (1 mL) was added thereto, followed by stirring at room temperature for 1.5 hours, and further stirring at 30C for 5 hours. After cooling, the resulting mixture was added with water, and the pH of the mixture was adjusted to 4 with 2 mol/L hydrochloric acid. Then, the pH of the mixture was adjusted to 9 with a saturated aqueous sodium hydrogen carbonate solution, and the precipitated solid was obtained by filtration. The obtained solid was washed with water, triturated with diisopropyl ether and recrystallized from n-hexane/ethyl acetate, to obtain the titled compound (273 mg, 45%) as a white solid.
  • 7
  • [ 27578-60-5 ]
  • [ 5147-80-8 ]
  • [(2-piperidinoethylamino)(4-piperidinopiperidino)methylene]malononitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Example 143 [(2-Piperidinoethylamino)(4-piperidinopiperidino) methylene]malononitrile (Compound 143) <strong>[5147-80-8][Bis(methylthio)methylene]malononitrile</strong> (242 mg, 1.42 mmol) was dissolved in ethanol (2 mL) and the solution was added with a solution of 4-piperidinopiperidine (251 mg, 1.49 mmol) in ethanol (3 mL), followed by stirring at room temperature for 0.5 hour. The mixture was added with 1-(2-aminoethyl)piperidine (0.319 mL, 2.24 mmol) and stirred at 70C for 6 hours. Further, the mixture was added with 1-(2-aminoethyl) piperidine (0.213 mL, 1.49 mmol) and stirred at 70C for 2 hours. After cooling, the reaction mixture was added with saturated brine and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (n-hexane/ethyl acetate (1:1)) to obtain the titled compound (465 mg, 88%) as a yellow oily substance. 1H NMR (CDCl3, δppm): 1.38-1.69 (m, 13H), 1.94 (d, J=11.2Hz, 2H), 2.34-2.57 (m, 12H), 3.08 (t, J = 12.9 Hz, 2H), 3.31-3.38 (m, 2H), 3.88 (d, J = 12.9 Hz, 2H), 5.97 (br s, 1H). APCIMS m/z: [M+H]+371. Melting point: 198-200C.
  • 8
  • [ 27578-60-5 ]
  • [ 58656-98-7 ]
  • [ 733785-78-9 ]
YieldReaction ConditionsOperation in experiment
64% at 120℃; Step 1: tert-Butyl 4- (2- (piperidin-1-yl) ethylamino) benzoate (187) [0348] tert-Butyl 4-FLUOROBENZOATE 185 (0.502g, 2.55 MMOL) and 24PIPERIDIN-1-YL) ETHANAMINE 186 (1.46 mL, 10.21 MMOL) were stirred neat at 120C overnight then diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate (LX), brine (LX), dried over magnesium sulfate and evaporated to give 187 (0.501g, 64%). H NMR: (DMSO) 6 (ppm): 400 MHz, (DMSO) d (ppm): 7.59 (d, J= 8.8 Hz, 2H), 6.55 (d, J= 8.8 Hz, 2H), 6.24 (t, J= 5.1 Hz, 1H), 4.11 (m, 2H), 3.21 to 3.13 (m, 6H), 2.44 (t, J= 7.1 Hz, 2H), 2.37 (m, 2H), 1.49 (s, 9H), 1.47 to 1.38 (m, 2H). MS: 304.22 (CALC), 249.1 (M-T8U).
  • 9
  • [ 27578-60-5 ]
  • [ 207399-07-3 ]
  • [ 1255954-14-3 ]
  • 10
  • [ 27578-60-5 ]
  • [ 171243-30-4 ]
  • [ 1415400-66-6 ]
YieldReaction ConditionsOperation in experiment
65% In dichloromethane; at 20℃; for 0.5h; General procedure: To a solution of benzoyl chloride (1 mmol) in dry dichloromethane (10 ml) was added amine (1 mmol), and the mixture was stirred for 0.5 h at room temperature. After solvent evaporation, the crude product was purified by column chromatography on silica (CHCl3:CH3CH2OH = 9:1) resulting in yellow thick oil and crystallized from the dichloromethane-petroleum ether mixture.
  • 11
  • [ 27578-60-5 ]
  • copper(II) nitrate trihydrate [ No CAS ]
  • [ 32596-43-3 ]
  • C22H33ClCu2N5O5(1+)*NO3(1-)*H2O [ No CAS ]
  • 12
  • [ 27578-60-5 ]
  • [ 23351-91-9 ]
  • 5-bromo-N1,N3-bis[2-(piperidin-1-yl)ethyl]benzene-1,3-dicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 16h; To a solution of <strong>[23351-91-9]5-bromoisophthalic acid</strong> 1(200 mg, 0.82 mmol) and 1-piperidineethanamine (240 mL, 1.17mmol) in DMF (2.5 mL) was added EDC*HCl (330 mg, 1.73 mmol) and HOBt-H2O (25.2 mg, 0.165 mmol). The reaction mixture was stirred for 16 h at room temperature. 10 mL of saturated NaHCO3 solution was added. The aqueous layer was extracted with DCM(3 10 mL). The combined organic layer was dried over MgSO4 and evaporated. The residue was purified by flash chromatography(DCM/MeOH(NH3), 10:0 to 9.7:0.3 (v/v)). The title compound 14(340 mg, 0.73 mmol, 89percent) was obtained as a white solid. Mp:127.3 C. 1H NMR (300 MHz), d (ppm, CDCl3): 8.23 (t, J = 1.5 Hz,1H); 8.04 (d, J = 1.5 Hz, 2H); 7.46 (t, J = 4.7 Hz, 2H); 3.48 (td, J =5.9 Hz, J = 5.5 Hz, 4H); 2.50 (t, J = 6.1 Hz, 4H); 2.38 (m, 8H); 1.54(m, 8H); 1.40 (m, 4H). 13C NMR (75 MHz), d (ppm, CDCl3): 165.3;136.3; 133.2; 123.7; 123.0; 57.4; 54.3; 36.6; 25.7; 24.2. LC?MS(ESI) m/z Calculated: 465.2?467.2, Found: 465.0?466.9, 233.1?234.0 [(M+2H)/2]+.
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