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[ CAS No. 29914-81-6 ] {[proInfo.proName]}

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Chemical Structure| 29914-81-6
Chemical Structure| 29914-81-6
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Product Details of [ 29914-81-6 ]

CAS No. :29914-81-6 MDL No. :MFCD00623252
Formula : C20H14N4 Boiling Point : -
Linear Structure Formula :- InChI Key :DNYDWFIQGPJANT-UHFFFAOYSA-N
M.W : 310.35 Pubchem ID :280940
Synonyms :

Calculated chemistry of [ 29914-81-6 ]

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 96.62
TPSA : 57.36 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.97
Log Po/w (XLOGP3) : 4.47
Log Po/w (WLOGP) : 4.77
Log Po/w (MLOGP) : 3.64
Log Po/w (SILICOS-IT) : 5.03
Consensus Log Po/w : 3.97

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.19
Solubility : 0.00201 mg/ml ; 0.00000648 mol/l
Class : Moderately soluble
Log S (Ali) : -5.39
Solubility : 0.00125 mg/ml ; 0.00000403 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -8.44
Solubility : 0.00000112 mg/ml ; 0.0000000036 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.1

Safety of [ 29914-81-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 29914-81-6 ]

* 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 [ 29914-81-6 ]
  • Downstream synthetic route of [ 29914-81-6 ]

[ 29914-81-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 121-91-5 ]
  • [ 95-54-5 ]
  • [ 29914-81-6 ]
YieldReaction ConditionsOperation in experiment
57% at 190℃; for 24 h; Isophthalic acid (1.130 g, 6.8 mmol) and 1,2-diaminobenzene (1.417 g, 13.1 mmol) were dissolved in 20 mL of polyphosphoric acid. The stirred mixture was maintained at 190 °C for 24 h. The solution was allowed to cool at room temperature (20 – 25 °C) and slowly stirred in 50 mL of ice. The reaction mixture was neutralized with NaOH and the precipitate was filtered out and washed with cold water. The solid was recrystallized from methanol to yield a white-off solid (1.06 g, yield 57percent, mp 183-186 °C). 1H NMR (DMSO-d6, 400 MHz): 13.16 (s, 2H, Hc), 9.06 (t, 4Jf-d = 1.6 Hz, 1H, Hf), 8.26 (dd, 4Jd-f = 1.6 Hz, 3Jd-e = 7.8 Hz, 2H, Hd), 7.74 (t, 3Je-d = 7.8 Hz, 1H, He), 7.69 (bs, 2H, Hb’), 7.58 (bs, 2H, Hb), 7.24 (d, 3Ja-b = 4.3 Hz, 4H, HaHa’). 13C NMR (DMSO-d6, 100 MHz): 125.3 (Cf), 128.0 (Cd), 130.2 (Ce), 119.5-112.1 (Cb), 123.3-122.4 (Ca). HRMS-ESI (m/z): calcd for [BBB+H]+ C20H15N4, 311.1291; found, 311.1294 (error: 1 ppm).
Reference: [1] Organometallics, 2013, vol. 32, # 6, p. 1807 - 1814
[2] Asian Journal of Chemistry, 2013, vol. 25, # 7, p. 4013 - 4016
[3] Indian Journal of Chemistry, Section A: Inorganic, Bio-inorganic, Physical, Theoretical & Analytical Chemistry, 1993, vol. 32, # 1-3, p. 33 - 38
[4] Journal of Materials Chemistry, 2012, vol. 22, # 42, p. 22496 - 22500,5
[5] Journal of the American Chemical Society, 1992, vol. 114, # 11, p. 4230 - 4237
[6] Tetrahedron Letters, 2015, vol. 56, # 45, p. 6177 - 6182
[7] Organic and Biomolecular Chemistry, 2016, vol. 14, # 35, p. 8232 - 8236
[8] Chemistry - A European Journal, 2012, vol. 18, # 7, p. 1961 - 1968
[9] RSC Advances, 2015, vol. 5, # 109, p. 90001 - 90009
[10] Journal of Materials Chemistry C, 2018, vol. 6, # 31, p. 8495 - 8501
  • 2
  • [ 626-19-7 ]
  • [ 95-54-5 ]
  • [ 29914-81-6 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 43, p. 6237 - 6240
[2] Farmaco (Societa chimica italiana : 1989), 2002, vol. 57, # 7, p. 543 - 548
  • 3
  • [ 36323-28-1 ]
  • [ 95-54-5 ]
  • [ 29914-81-6 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 50, p. 6493 - 6497
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