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[ CAS No. 40928-13-0 ] {[proInfo.proName]}

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Chemical Structure| 40928-13-0
Chemical Structure| 40928-13-0
Structure of 40928-13-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 40928-13-0 ]

CAS No. :40928-13-0 MDL No. :MFCD00090431
Formula : C8H4ClNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :QRUPDIJQZCABTC-UHFFFAOYSA-N
M.W : 197.58 Pubchem ID :329105
Synonyms :

Calculated chemistry of [ 40928-13-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.11
TPSA : 63.07 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) : -6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.23
Log Po/w (XLOGP3) : 1.65
Log Po/w (WLOGP) : 1.13
Log Po/w (MLOGP) : 1.59
Log Po/w (SILICOS-IT) : 2.71
Consensus Log Po/w : 1.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.67
Solubility : 0.419 mg/ml ; 0.00212 mol/l
Class : Soluble
Log S (Ali) : -2.59
Solubility : 0.51 mg/ml ; 0.00258 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.77
Solubility : 0.0339 mg/ml ; 0.000171 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.57

Safety of [ 40928-13-0 ]

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 [ 40928-13-0 ]

* 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.

  • Upstream synthesis route of [ 40928-13-0 ]
  • Downstream synthetic route of [ 40928-13-0 ]

[ 40928-13-0 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 32315-10-9 ]
  • [ 89-77-0 ]
  • [ 40928-13-0 ]
YieldReaction ConditionsOperation in experiment
74% With pyridine In dichloromethane; acetonitrile at 50℃; for 2 h; Intermediate G: 7-chloro-1H-benzo[d][1,3]oxazine-2,4-dione
To a stirred solution of 2-amino-4-chloro benzoic acid (10 g, 0.058 mmol) in acetonitrile (60 mL, 1 M), was added pyridine (9.4 mL, 0.117 mmol, 2 equiv), and triphosgene (17.3 g, 0.058 mmol, 1 equiv) in dichloromethane (85 mL, 0.7 M). The orange reaction solution was heated at 50° C. for two hours then cooled to room temperature. The solution was diluted with water (50 mL), and the organic and aqueous layers were separated. The aqueous layer was washed with dichloromethane (3×50 mL), and the combined organic layers were washed once with brine (50 mL), and dried over magnesium sulfate. The solvent was removed in vacuo leaving a yellow solid. The solid was titrated with hexanes to yield 7-chloro-1H-benzo[d][1,3]oxazine-2,4-dione (9.1 g, 74percent) as a yellow solid.1H NMR (Acetone, 500 MHz): δ (ppm) 7.13-7.14 (1H, s), 7.28-7.30 (1H, d, J=8.5 Hz), 7.90-7.92 (1H, d, J=8.6 Hz), 11.84 (1H, bs).
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 17, p. 6928 - 6937
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2311 - 2319
[3] Patent: US9126978, 2015, B2, . Location in patent: Page/Page column 57; 58
[4] European Journal of Medicinal Chemistry, 1994, vol. 29, # 12, p. 925 - 940
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 10, p. 2295 - 2299
[6] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 31, p. 6883 - 6889
[7] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 2, p. 437 - 440
[8] Biochemistry, 2017, vol. 56, # 49, p. 6491 - 6502
[9] Chemical Biology and Drug Design, 2018, vol. 92, # 5, p. 1914 - 1919
  • 2
  • [ 75-44-5 ]
  • [ 89-77-0 ]
  • [ 40928-13-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 7, p. 1257 - 1263
[2] European Journal of Medicinal Chemistry, 1983, vol. 18, # 3, p. 241 - 247
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 8, p. 2075 - 2088
  • 3
  • [ 75-44-5 ]
  • [ 497-19-8 ]
  • [ 89-77-0 ]
  • [ 40928-13-0 ]
  • [ 252232-80-7 ]
Reference: [1] Patent: US6087368, 2000, A,
  • 4
  • [ 201230-82-2 ]
  • [ 6828-35-9 ]
  • [ 40928-13-0 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 9, p. 4196 - 4200
  • 5
  • [ 112733-44-5 ]
  • [ 40928-13-0 ]
Reference: [1] Patent: US4734419, 1988, A,
  • 6
  • [ 79-37-8 ]
  • [ 89-77-0 ]
  • [ 40928-13-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 1, p. 138 - 147
  • 7
  • [ 40928-13-0 ]
  • [ 5900-59-4 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 31, p. 6883 - 6889
[2] Biochemistry, 2017, vol. 56, # 49, p. 6491 - 6502
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