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[ CAS No. 183673-66-7 ] {[proInfo.proName]}

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Chemical Structure| 183673-66-7
Chemical Structure| 183673-66-7
Structure of 183673-66-7 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 183673-66-7 ]

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Product Details of [ 183673-66-7 ]

CAS No. :183673-66-7 MDL No. :MFCD01318741
Formula : C26H30N2O6 Boiling Point : No data available
Linear Structure Formula :- InChI Key :BOFOACPQHWDRLH-UHFFFAOYSA-N
M.W : 466.53 Pubchem ID :2734399
Synonyms :

Calculated chemistry of [ 183673-66-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 34
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.42
Num. rotatable bonds : 9
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 130.07
TPSA : 105.17 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.25
Log Po/w (XLOGP3) : 3.88
Log Po/w (WLOGP) : 4.0
Log Po/w (MLOGP) : 2.8
Log Po/w (SILICOS-IT) : 3.0
Consensus Log Po/w : 3.39

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -4.84
Solubility : 0.00668 mg/ml ; 0.0000143 mol/l
Class : Moderately soluble
Log S (Ali) : -5.79
Solubility : 0.000764 mg/ml ; 0.00000164 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.95
Solubility : 0.000528 mg/ml ; 0.00000113 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.18

Safety of [ 183673-66-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 183673-66-7 ]

* 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 [ 183673-66-7 ]

[ 183673-66-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 102774-86-7 ]
  • [ 183673-71-4 ]
  • [ 183673-66-7 ]
  • 2
  • [ 35661-40-6 ]
  • [ 96402-49-2 ]
  • [ 183673-66-7 ]
  • C73H78N11O10Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Each of the reaction wells contained 0.0675 mmol of Rink Amide MBHA resin(substitution = 0.72 mmol/g, Novabiochem, San Diego, CA). The following Fmoc amino acids (Novabiochem, San Diego, CA; Chem-Impex International, Wood Dale, IL; SyntheTech, Albany, OR; Pharma Core, High Point, NC) were used: Fmoc-Lys(Boc)-OH, EPO <DP n="112"/>Fmoc-Phe-OH, Fmoc-H-Inp-OH, Fmoc-D-lNal-OH, Fmoc-D-2Nal-OH, Fmoc-D- TrP(BoC)-OH, Fmoc-3Pal-OH, Fmoc-4Pal-OH/ FmOc-Om(BoC)-OH, Fmoc-D-Bip-OH, FmOC-ThT(BzI)-OH, Fmoc-Pff-OH, Fmoc-2Thi-OH, Fmoc-Taz-OH, Fmoc-D-Dip-OH, Fmoc-D-Bpa-OH, Fmoc-D-Bal-OH, and Fmoc-Apc(Boc)-OH.Each of the Fmoc amino acids was dissolved in a 0.3 N solution of HOBt in DMF wherein the concentration of the resulting Fmoc amino acid was 0.3 N. A four fold excess (0.27 mmol, 0.9 mL of the 0.3 N solution) of Fmoc amino acid was used for each coupling. DIC (0.27 mmol, 0.6 mL of 0.45N DIC solution in DMF) was used as the coupling reagent for each coupling. Deprotection was performed by using 20percent piperidine in DMF (2 X 1.5 mL per residue). The peptides were cleaved from the resin by treating the peptide-resins with 8percent trsopropylsilane (TIP) in trifluoroacetic acid (TFA) (1.5 mL per reaction well) at room temperature for 2h. The resin was removed by filtration. Each filtrate was diluted to 25 mL with ether in a centrifuge tube. The resulting precipitate in each tube was centrifuged and the solvents were decanted from the precipitate. The precipitate in each tube was then dissolved in methanol (3 mL) and diluted with water (1 mL). The purification of the crude products was done on a reverse-phase preparative HPLC using a column (100 X 21.20 mm, 5mu) of LUNA 5mu C8(2) (Phenomenex, Torrance, CA). For each peptide, the column was eluted with a linear gradient from 85percent A and 15percent B to 25percent A and 75percent B in 15 min with a flow rate of 25 mL/min. A was 0.1percent TFA in water and B was 0.1percent TFA in acetonitrile/water (80/20, v/v). The fractions were checked by analytical HPLC and those containing the pure product were combined and lyophilized to dryness.Yields ranged from 13percent to 71percent and purity of each of Examples 1 - 65 exceeded 94percent based upon analytical HPLC analysis. Electro-spray ionization mass spectrometry (ES-MS) analysis was performed and observed molecular weights were in agreement with calculated molecular weights. The results are detailed in Table I, below
  • 3
  • [ 82911-69-1 ]
  • [ 183673-71-4 ]
  • [ 183673-66-7 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; In tetrahydrofuran; water; at 20℃; for 18h;pH 8 - 9; General procedure: To 250 mL round-bottomed flask add 1a or 1c or 1g or 1h, 2.5 equiv Fmoc-OSu, 50 mL THF/H2O (1:1, v/v), pH of the solution was adjusted with saturated sodium carbonate to 8?9, and the reaction continued at room temperature for about 18h. After that, the solution was extracted twice with ether, and pH of aqueous layer was adjusted with concentrated HCl to 5, white precipitation was obtain and dried in vacuum to gave corresponding product (2a or 2c or 2g or 2h).
  • 4
  • [ 28920-43-6 ]
  • [ 183673-71-4 ]
  • [ 183673-66-7 ]
YieldReaction ConditionsOperation in experiment
42% With sodium carbonate; In tetrahydrofuran; at 0 - 25℃; for 12h; 4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-1-(tert- butoxycarbonyl)piperidine-4-carboxylic acid (Scheme 1, compound 8) [0225] A solution of 4-amino-1 -(terf-butoxycarbonyl)piperidine-4- carboxylic acid (5 g, 20.5 mmol) in THF (300 mL) and Na2CO3 (6.45 g, 61 .5 mmol, 3.0 eq in 64.5 mL of water) was cooled to 0C before the dropwise addition of a solution of Fmoc chloride (5.3 g, 30.7 mmol, 1 .5 eq) in THF (30 mL). The resulting mixture was slowly warmed to 25C and stirred for an additional 12 hours. Upon completion, the reaction contents were carefully acidified with HCI (1 M), and the crude material was extracted with EtOAc (three times). The combined organic layers were dried (Na2SO4), concentrated, and the crude material was purified by combiflash 0 to 10% MeOH in DCM to provide 4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-1 -(te/t- butoxycarbonyl)piperidine-4-carboxylic acid (Scheme 1 , compound 8) (4.02 g, 42% yield). [0226] 1 H NMR (400 MHz, Ch lore-form -c/) delta 7.75 (d, J = 7.5 Hz, 2H), 7.57 (d, J = 7.5 Hz, 2H), 7.45-7.34 (m, 2H), 7.30 (td, J = 6.9, 6.3, 1 .4 Hz, 2H), 4.68-4.26 (m, 2H), 4.19 (t, J = 6.5 Hz, 1 H), 3.96-3.65 (m, 3H), 3.08 (s, 2H), 1 .91 -1 .77 (m, 2H), 1 .48 (s, 9H). 13C NMR (101 MHz, CDCI3) 177.19, 154.73, 143.67, 141 .32, 127.72, 127.08, 124.95, 1 19.97, 80.06, 67.90, 66.86, 57.49, 47.19, 31 .98, 28.42, 25.57. HRMS (m/z): [M+] cald for C26H30N2O6, 466.53, found 466.2
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