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[ CAS No. 5317-89-5 ] {[proInfo.proName]}

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Chemical Structure| 5317-89-5
Chemical Structure| 5317-89-5
Structure of 5317-89-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5317-89-5 ]

CAS No. :5317-89-5 MDL No. :MFCD00159342
Formula : C9H11NO3S Boiling Point : -
Linear Structure Formula :- InChI Key :BQBFGIIQPXLTKM-UHFFFAOYSA-N
M.W : 213.25 Pubchem ID :684083
Synonyms :

Calculated chemistry of [ 5317-89-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.91
TPSA : 71.62 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.15
Log Po/w (XLOGP3) : 0.91
Log Po/w (WLOGP) : 2.15
Log Po/w (MLOGP) : 0.35
Log Po/w (SILICOS-IT) : 0.7
Consensus Log Po/w : 1.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.85
Solubility : 2.98 mg/ml ; 0.014 mol/l
Class : Very soluble
Log S (Ali) : -2.0
Solubility : 2.13 mg/ml ; 0.01 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.1
Solubility : 0.168 mg/ml ; 0.000787 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.47

Safety of [ 5317-89-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5317-89-5 ]

* 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.

  • Upstream synthesis route of [ 5317-89-5 ]
  • Downstream synthetic route of [ 5317-89-5 ]

[ 5317-89-5 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 99-92-3 ]
  • [ 124-63-0 ]
  • [ 5317-89-5 ]
YieldReaction ConditionsOperation in experiment
95% at 0 - 20℃; for 2 h; A cooled solution of 4'-aminoacetophenon (10 mmol) in pyridine (10 mL) at 0 °C was treated with METHANESULFONYL chloride (15 mmol) and stirred at room temperature for 2 h. The reaction mixture was diluted with HZ0 and extracted with EtOAc several times. The combined organic layers were washed with H20 and brine, dried over MGS04, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc: hexanes to afford 4'- (Methylsulfonylamino) acetophenone (13-5, LJO-298). 95percent yield, mp = 161 °C 1H NMR (CDC13) 8 7.97 (dd, 2 H, J= 2,6. 8 Hz, ), 7.26 (dd, 2 H, J= 2, 6.8 Hz), 6. 87 (bs, 1 H), 3.10 (s, 3 H), 2.59 (s, 3 H)
66% With pyridine In tetrahydrofuran at 20℃; for 12 h; General procedure: To a solution of 4-aminoacetophenone (0.68g, 5mmol) and pyridine (1.6mL, 20mmol) in THF (10mL) was slowly added the substituted sulfonyl chloride (5mmol). The reaction mixture was stirred at room temperature for 12h. Water (50mL) was added and the mixture was extracted with ethyl acetate (10mL×3), the combined organic phase was washed with 1N hydrochloric acid (30mL×2) and water (30mL×2), dried over anhydrous Na2SO4 and concentrated under vacuum to afford the product.
Reference: [1] Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 6, p. 846 - 867
[2] Organic Process Research and Development, 1998, vol. 2, # 2, p. 71 - 77
[3] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 18, p. 6043 - 6053
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2685 - 2688
[5] Patent: WO2005/3084, 2005, A1, . Location in patent: Page 79
[6] Journal of Organic Chemistry, 1987, vol. 52, # 19, p. 4377 - 4379
[7] Journal of Organic Chemistry, 2001, vol. 66, # 25, p. 8293 - 8296
[8] Journal of the American Chemical Society, 2015, vol. 137, # 11, p. 3731 - 3734
[9] Arkivoc, 2016, vol. 2016, # 4, p. 227 - 245
[10] Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1316 - 1318
[11] Chemistry - A European Journal, 2016, vol. 22, # 47, p. 16998 - 17005
[12] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 48 - 65
[13] Journal of medicinal chemistry, 1966, vol. 9, # 1, p. 88 - 97
[14] Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 1982, vol. 38, # 7, p. 791 - 796
[15] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 2, p. 1056 - 1061
[16] Synthesis, 2012, vol. 44, # 9, p. 1329 - 1338
[17] Medicinal Chemistry Research, 2014, vol. 23, # 10, p. 4383 - 4394
[18] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2685 - 2688
  • 2
  • [ 3144-09-0 ]
  • [ 99-90-1 ]
  • [ 5317-89-5 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 43, p. 7295 - 7298
[2] Organic Letters, 2011, vol. 13, # 10, p. 2564 - 2567
[3] Green Chemistry, 2014, vol. 16, # 3, p. 1480 - 1488
  • 3
  • [ 99-92-3 ]
  • [ 7143-01-3 ]
  • [ 5317-89-5 ]
Reference: [1] Patent: US2003/153596, 2003, A1,
  • 4
  • [ 1197-22-4 ]
  • [ 108-24-7 ]
  • [ 5317-89-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 7, p. 1751 - 1755
  • 5
  • [ 367-27-1 ]
  • [ 5317-89-5 ]
Reference: [1] Organic Process Research and Development, 1998, vol. 2, # 2, p. 71 - 77
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