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Chemical Structure| 1484-84-0 Chemical Structure| 1484-84-0

Structure of 1484-84-0

Chemical Structure| 1484-84-0

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CAS No.: 1484-84-0

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Product Citations

Product Citations

Li, Bowen ; Manan, Rajith Singh ; Liang, Shun-Qing ; Gordon, Akiva ; Jiang, Allen ; Varley, Andrew , et al.

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.

Alternative Products

Product Details of [ 1484-84-0 ]

CAS No. :1484-84-0
Formula : C7H15NO
M.W : 129.20
SMILES Code : OCCC1NCCCC1
MDL No. :MFCD00005989
InChI Key :PTHDBHDZSMGHKF-UHFFFAOYSA-N
Pubchem ID :15144

Safety of [ 1484-84-0 ]

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

Computational Chemistry of [ 1484-84-0 ] Show Less

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 ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

32.26 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.83
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.38
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.13
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.57
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.23
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.83

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.75
Solubility 23.1 mg/ml ; 0.178 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.62
Solubility 30.8 mg/ml ; 0.238 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.28
Solubility 6.7 mg/ml ; 0.0519 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.82 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 1.79

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   1~5

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  • [ 1484-84-0 ]
  • [ 6414-69-3 ]
  • [ 74012-89-8 ]
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  • [ 24686-78-0 ]
  • [ 62835-13-6 ]
  • 3
  • [ 1484-84-0 ]
  • [ 103639-57-2 ]
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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  • [ 1484-84-0 ]
  • [ 103639-57-2 ]
  • [ 68419-38-5 ]
  • 5
  • [ 1484-84-0 ]
  • C15H20O2 [ No CAS ]
  • (2R)-1-(3-mesitylpropanoyl)-2-(2-methoxyethyl)piperidine [ No CAS ]
  • (2S)-1-(3-Mesitylpropanoyl)-2-(2-methoxyethyl)piperidine [ No CAS ]
  • [ 103639-57-2 ]
  • [ 68419-38-5 ]
 

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