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[ CAS No. 1484-84-0 ] {[proInfo.proName]}

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Chemical Structure| 1484-84-0
Chemical Structure| 1484-84-0
Structure of 1484-84-0 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

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 [ 1484-84-0 ]

CAS No. :1484-84-0 MDL No. :MFCD00005989
Formula : C7H15NO Boiling Point : No data available
Linear Structure Formula :(CH2)4CHNHCH2CH2OH InChI Key :PTHDBHDZSMGHKF-UHFFFAOYSA-N
M.W : 129.20 Pubchem ID :15144
Synonyms :

Calculated chemistry of [ 1484-84-0 ]      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 : 2.0
Molar Refractivity : 41.53
TPSA : 32.26 ?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) : -6.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.83
Log Po/w (XLOGP3) : 0.38
Log Po/w (WLOGP) : 0.13
Log Po/w (MLOGP) : 0.57
Log Po/w (SILICOS-IT) : 1.23
Consensus Log Po/w : 0.83

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.75
Solubility : 23.1 mg/ml ; 0.178 mol/l
Class : Very soluble
Log S (Ali) : -0.62
Solubility : 30.8 mg/ml ; 0.238 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.28
Solubility : 6.7 mg/ml ; 0.0519 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.79

Safety of [ 1484-84-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338 UN#:3263
Hazard Statements:H302+H312+H332-H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 1484-84-0 ]

* 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 [ 1484-84-0 ]

[ 1484-84-0 ] Synthesis Path-Downstream   1~4

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YieldReaction ConditionsOperation in experiment
Into a flask was placed N-acetyl-L-Leucine (8.65 g) dissolved in 10 ml of methanol. The solution was heated, maintaining the temperature at from 35° C. to 40° C. with stirring. A tetrahydrofuran (THF) solution prepared from 50 ml of THF and 12.9 g (0.1 mol.) of 2-piperidine-2-yl-ethanol (mixture of R and S isomers) was added to the methanol solution maintaining the temperature of the combined solutions at 35° C. to 40° C. An additional 30 ml of THF was added and the resulting mixture was heated and maintained at a temperature of from 50° C. to 55° C. for 30 minutes. The reaction mixture was cooled over two hours to 15° C. and held at that temperature for one hour, during which time salt precipitated. The precipitate was recovered by vacuum filtration and dried under vacuum at ambient temperature (about 25° C.). The recovered precipitate was tested for ee purity by HPLC through derivatization of the product with benzoyl chloride and found to be 94.5percent ee S-isomer. A yield of 37.7percent based on the weight of the unresolved alcohol starting material was calculated (11.4 g isolated S-isomer), accordingly a loss of about 25percent S-isomer. Purification of Precipitate An aliquot of the precipitate salt thus formed (7.0 g) was suspended with stirring in a solvent comprising 50 ml of acetonitrile and 2.5 ml of methanol by heating the mixture to 55° C. and held for 30 minutes. The resultant suspension was cooled over a period of 2 hours to a temperature of 15° C. The resulting crystals were obtained by filtration and tested by HPLC for purity and a yield was calculated based on recovered weight. The precipitation yielded 6.7 g of precipitate (calculated yielded 95.7percent based on starting precipitated complex) and had a isomeric purity of 97.7percent ee based on HPLC analysis. Conversion to Free Base A salt of the piperidine ethanol is converted to the free base by dissolving 13 mmol. of the purified salt in 24 ml of 3N NaOH and stirring the resulting solution vigorously for about 1.5 hours. At the end of 1.5 hours of stirring, 7.5 ml of water is added to the solution. This mixture is then extracted with methylene chloride three times. The methylene chloride extracts are concentrated to yield approximately 13 mmol. of free piperidine ethanol. The chiral purity of the product is found to be the same as that of the original salt.
The stereoisomer of the 2-Piperidin-2-yl-ethanol (Compound G1a) was prepared as described in the '878 publication in accordance with preparative Example 500, therein. Thus, a mixture of R and S enantiomers of piperidine-2-ethanol obtained from Acros and used as received (127 g, 980 mmol) was dissolved in 95percent EtOH (260 mL). To the aliphatic alcohol solution was added to (S)-(+)-camphorsulfonic acid obtained from Acros (228.7 g, 1.0 eq.) in 95percent EtOH (150 mL) and the resulting solution was warmed to reflux. To the warm solution was added Et2O (600 mL) and the solution cooled to room temperature and let stand 3 days. The resulting crystals were filtered and dried in vacuo (25 g): and analyzed by mp 173° C. (lit. 168° C.). The salt was then dissolved in NaOH (3M, 100 mL) and stirred 2 hours and the resulting solution was extracted with CH2Cl2 (5.x.100 mL). The combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give (S)-piperidine-2-ethanol (7.8 g) a portion of which was recrystallized from Et2O: mp=69-70° C. (lit. 68-69° C.); [alpha]D=14.09° (CHCl3, c=0.2). Overall yield of S-isomer isolated, based on initial weight of starting alcohol was 6.1percent.
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