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[ CAS No. 4382-54-1 ] {[proInfo.proName]}

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Chemical Structure| 4382-54-1
Chemical Structure| 4382-54-1
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Product Details of [ 4382-54-1 ]

CAS No. :4382-54-1 MDL No. :MFCD00005614
Formula : C10H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :YEBJVSLNUMZXRJ-UHFFFAOYSA-N
M.W : 191.18 Pubchem ID :20401
Synonyms :

Calculated chemistry of [ 4382-54-1 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 51.75
TPSA : 62.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.41
Log Po/w (XLOGP3) : 2.28
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 0.8
Log Po/w (SILICOS-IT) : 1.87
Consensus Log Po/w : 1.65

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.81
Solubility : 0.299 mg/ml ; 0.00157 mol/l
Class : Soluble
Log S (Ali) : -3.23
Solubility : 0.114 mg/ml ; 0.000594 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.79
Solubility : 0.312 mg/ml ; 0.00163 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.4

Safety of [ 4382-54-1 ]

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 [ 4382-54-1 ]

* 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 [ 4382-54-1 ]
  • Downstream synthetic route of [ 4382-54-1 ]

[ 4382-54-1 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 4382-54-1 ]
  • [ 10601-19-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 25, p. 6270 - 6282
  • 2
  • [ 124-38-9 ]
  • [ 169383-96-4 ]
  • [ 4382-54-1 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.166667 h;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5 h;
Stage #3: at -20℃; for 0.5 h;
To a solution of 2-Bromo-5-methoxy-1H-indole (1.0 g,4.4 mmol, 1.0 equiv.) in dry THF (20 mL) at 0 C was added a 2 M solution of i-PrMgCl in THF(2.2 mL, 4.4 mmol, 1.0 equiv.) during 5 min. The clear solution was stirred at that temperature for anadditional 5 min, and a 2.5 M solution of n-BuLi in hexanes (3.5 mL, 8.8 mmol, 2.0 equiv.) was addeddropwise during 5 min, while maintaining the temperature below 20 C. The resulting mixture wasstirred at that temperature for 0.5 h, dry CO2 (0.20 g, 1.0 equiv.) was added to 20 C. The resultingmixture was warmed to 20 C in 0.5 h and quenched with water (6 mL). After stirring the mixturebelow 20 C for 10 min, the phases were separated and the water phase was extracted one additionaltime with ethyl acetate. The resulting suspension was allowed to reach room temperature and ®teredthrough a 0.5 1 cm pad of silica gel eluted with 10 mL of ethyl acetate. The ®ltrate was concentratedand the residue was puri®ed by ash chromatography on silica gel (eluent: petroleum ether/ethylacetate = 3:1) to afford product 3f as brown solid, 0.68 g (yield: 80percent), m.p.: 199–201 C. 1H-NMR(600 MHz, DMSO) 7.36 (d, J = 8.9 Hz, 1H), 7.06 (d, J = 23.6 Hz, 2H), 6.90 (d, J = 8.8 Hz, 1H), 3.73 (s, 3H).13C-NMR (151 MHz, DMSO) 163.25, 154.31, 133.07, 129.10, 127.65, 116.28, 113.83, 107.47, 102.44, 55.61.
Reference: [1] Molecules, 2017, vol. 22, # 11,
  • 3
  • [ 4792-58-9 ]
  • [ 4382-54-1 ]
Reference: [1] European Journal of Medicinal Chemistry, 1990, vol. 25, # 3, p. 257 - 265
[2] Advanced Synthesis and Catalysis, 2016, vol. 358, # 24, p. 3938 - 3942
[3] Gazzetta Chimica Italiana, 1958, vol. 88, p. 574,589
[4] Gazzetta Chimica Italiana, 1955, vol. 85, p. 1445,1447
[5] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
  • 4
  • [ 67929-86-6 ]
  • [ 4382-54-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 25, p. 6270 - 6282
[2] Chemistry - A European Journal, 2012, vol. 18, # 16, p. 4859 - 4865
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 3, p. 950 - 954
  • 5
  • [ 104-94-9 ]
  • [ 4382-54-1 ]
Reference: [1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
[2] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
[3] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
[4] Angewandte Chemie - International Edition, 2016, vol. 55, # 6, p. 2243 - 2247
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 3, p. 950 - 954
  • 6
  • [ 4346-59-2 ]
  • [ 4382-54-1 ]
Reference: [1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
[2] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
[3] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
  • 7
  • [ 4792-56-7 ]
  • [ 4382-54-1 ]
Reference: [1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
  • 8
  • [ 4792-57-8 ]
  • [ 4382-54-1 ]
Reference: [1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
  • 9
  • [ 18437-68-8 ]
  • [ 4382-54-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 6, p. 2243 - 2247
  • 10
  • [ 3471-32-7 ]
  • [ 4382-54-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 3, p. 950 - 954
  • 11
  • [ 82204-34-0 ]
  • [ 4382-54-1 ]
Reference: [1] Journal of the Chemical Society, 1924, vol. 125, p. 313
  • 12
  • [ 4382-54-1 ]
  • [ 21778-81-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1987, vol. 30, # 11, p. 2074 - 2080
[2] Patent: US2003/181496, 2003, A1,
[3] Patent: EP1479384, 2004, A1,
[4] Chemical Communications, 2013, vol. 49, # 28, p. 2894 - 2896
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 5, p. 2489 - 2512
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