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[ CAS No. 19840-99-4 ] {[proInfo.proName]}

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Chemical Structure| 19840-99-4
Chemical Structure| 19840-99-4
Structure of 19840-99-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 19840-99-4 ]

CAS No. :19840-99-4 MDL No. :MFCD00134256
Formula : C10H10N2O Boiling Point : -
Linear Structure Formula :- InChI Key :MJXYFLJHTUSJGU-UHFFFAOYSA-N
M.W :174.20 Pubchem ID :88277
Synonyms :
Carbostyril 124

Calculated chemistry of [ 19840-99-4 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.1
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 53.94
TPSA : 58.88 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) : -6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.39
Log Po/w (XLOGP3) : 0.57
Log Po/w (WLOGP) : 1.43
Log Po/w (MLOGP) : 1.34
Log Po/w (SILICOS-IT) : 2.31
Consensus Log Po/w : 1.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.85
Solubility : 2.47 mg/ml ; 0.0142 mol/l
Class : Very soluble
Log S (Ali) : -1.38
Solubility : 7.28 mg/ml ; 0.0418 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.63
Solubility : 0.0406 mg/ml ; 0.000233 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 19840-99-4 ]

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

Application In Synthesis of [ 19840-99-4 ]

* 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 [ 19840-99-4 ]
  • Downstream synthetic route of [ 19840-99-4 ]

[ 19840-99-4 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 141-97-9 ]
  • [ 108-45-2 ]
  • [ 19840-99-4 ]
YieldReaction ConditionsOperation in experiment
65% at 150℃; for 20 h; General procedure: 1,3-Diaminobenzene (1.0 g, 9.3 mmol), was added to substituted ethyl acetoacetates (1.2 equiv, 2-3, 6) and the mixture was refluxed for 20 h. It was then poured on ice (100 g) and the precipitate was filtered. The product was obtained through column chromatography using silica gel (100-200 mesh) in methanol/chloroform (1:99).
38% at 130℃; for 30 h; Inert atmosphere A mixture of 1,3-phenylenediamine (19.7 g,182.0  mmol) and ethyl acetoacetate (23.7 g, 182.0 mmol) was heated at 130 °C for 30 h under an argon atmosphere. After cooling to room temperature, yellowish green solid thus precipitated was collected. Recrystallization from methanol (40 mL) yielded needle crystals (11.9 g, 38 percent). 1H NMR (DMSO-d6, 270 MHz): d 2.27 (s, 3H), 5.72 (br s, 2H), 5.93 (s, 1H), 6.35 (d, J = 2.2 Hz, 1H), 6.44 (dd, J = 8.7, 2.2 Hz, 1H), 7.33 (d, J = 8.7Hz, 1H), 11.25 (s, 1H).
Reference: [1] Medicinal Chemistry Research, 2013, vol. 22, # 11, p. 5227 - 5235
[2] Medicinal Chemistry Research, 2010, vol. 19, # 2, p. 193 - 209
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 4, p. 1624 - 1638
[4] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8712 - 8728
[5] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1648 - 1653
[6] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 6, p. 1031 - 1034
[7] Inorganica Chimica Acta, 2010, vol. 363, # 14, p. 4048 - 4058
[8] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 17, p. 5143 - 5146
[9] Journal of Organic Chemistry, 1991, vol. 56, # 3, p. 980 - 983
[10] ChemMedChem, 2010, vol. 5, # 1, p. 103 - 117
[11] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7410 - 7413
[12] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 5, p. 713 - 716
[13] Tetrahedron Letters, 1999, vol. 40, # 24, p. 4505 - 4506
[14] Collection of Czechoslovak Chemical Communications, 2006, vol. 71, # 9, p. 1333 - 1349
[15] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 18, p. 8713 - 8718
[16] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 589 - 602
[17] Chinese Journal of Chemistry, 2015, vol. 33, # 12, p. 1353 - 1358
[18] Bioconjugate Chemistry, 2016, vol. 27, # 10, p. 2540 - 2548
[19] Acta Poloniae Pharmaceutica - Drug Research, 2018, vol. 75, # 4, p. 903 - 910
  • 2
  • [ 137324-44-8 ]
  • [ 19840-99-4 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 4, p. 1112 - 1118
  • 3
  • [ 127556-39-2 ]
  • [ 19840-99-4 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 10, p. 2802 - 2808
  • 4
  • [ 156942-37-9 ]
  • [ 19840-99-4 ]
Reference: [1] Liebigs Annalen der Chemie, 1994, # 4, p. 365 - 368
  • 5
  • [ 156942-38-0 ]
  • [ 19840-99-4 ]
Reference: [1] Liebigs Annalen der Chemie, 1994, # 4, p. 365 - 368
  • 6
  • [ 1210052-44-0 ]
  • [ 19840-99-4 ]
Reference: [1] ChemMedChem, 2010, vol. 5, # 1, p. 103 - 117
  • 7
  • [ 19840-99-4 ]
  • [ 114058-79-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1988, vol. 31, # 7, p. 1347 - 1351
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