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[ CAS No. 64224-21-1 ] {[proInfo.proName]}

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Chemical Structure| 64224-21-1
Chemical Structure| 64224-21-1
Structure of 64224-21-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 64224-21-1 ]

CAS No. :64224-21-1 MDL No. :
Formula : C8H6N2S3 Boiling Point : -
Linear Structure Formula :- InChI Key :CKNAQFVBEHDJQV-UHFFFAOYSA-N
M.W : 226.34 Pubchem ID :47318
Synonyms :
RP 35972;NSC 347901;CD1400

Calculated chemistry of [ 64224-21-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 59.02
TPSA : 114.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.88
Log Po/w (XLOGP3) : 1.07
Log Po/w (WLOGP) : 3.3
Log Po/w (MLOGP) : 0.25
Log Po/w (SILICOS-IT) : 5.83
Consensus Log Po/w : 2.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.48
Solubility : 0.754 mg/ml ; 0.00333 mol/l
Class : Soluble
Log S (Ali) : -3.06
Solubility : 0.196 mg/ml ; 0.000865 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.63
Solubility : 0.0529 mg/ml ; 0.000234 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.14

Safety of [ 64224-21-1 ]

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 [ 64224-21-1 ]

* 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 [ 64224-21-1 ]
  • Downstream synthetic route of [ 64224-21-1 ]

[ 64224-21-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 324737-10-2 ]
  • [ 64224-21-1 ]
YieldReaction ConditionsOperation in experiment
14% With tetraphosphorus decasulfide In 5,5-dimethyl-1,3-cyclohexadiene; toluene at 135℃; for 4 h; General procedure: P4S10 (12 g, 27.0 mmol), toluene (90 ml) and xylene (90 ml)were added to a reactor and heated to a temperature of 120 C.Compound 5a (8.1 g, 45.1 mmol) was added to the reactor. Thereaction mixture was allowed to proceed under reflux at 135 Cfor 4 h and then cooled to 20 C and filtered through Celite. The solventwas then removed under reduced pressure and the resultantred solid was extracted with CH2Cl2. The organic layer was washedwith aqueous K2CO3 solution, dried over Na2SO4, and filtered. Thesolvent was removed under reduced pressure and the crude solidwas dried in vacuo. The dried solid was washed with cold EtOAc,and then recrystallized in acetonitrile to give 1a (0.9 g, 10percent) as ared solid.
13.6% With phosphorous (V) sulfide In toluene; xylene at 135℃; for 4 h; Example 3; Synthesis and recrystallization of oltipraz. 300 mL of toluene, 350 mL of xylene, and 48.0 g (216 mmole) of phosphorus pentasulfide were added to a reactor and heated to a temperature of 120 to 122°C. 40.0 g (206 mmole) of methyl 2-metbyl-3-(pyrazin-2-yl)-3-oxopropionate prepared in Example 2 was dissolved in 100 mL of toluene and then dropwise added to the reactor. The reaction solution was allowed to proceed under reflux at 135°C for 4 hours and then cooled to 20 C. After addition of 500 mL of distilled water and 500 mL of methanol, the pH of the resultant reaction solution was adjusted to 8.5 with adding a 28percent ammonia solution (about 51 mL). An organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. 150 mL of methanol was added to the resultant concentrate, stirred for one hour, and filtered. A filtrate was washed with 100 mL of methanol to give a humid oltipraz crude crystal (12.0 to 13.0 g). The oltipraz crude crystal was placed in a reactor. 400 mL of acetonitrile was added and dissolved at 80 °C. 1.4 g of activated carbon was added and stirred for 30 minutes. The resultant solution was filtered, washed with 100 mL of acetonitrile, crystallized with stirring at a temperature of 20 to 25°C for 2 hours, and again stirred at 10°C for one hour. The obtained crystal was filtered, washed with 20 mL of acetonitrile, and vacuum dried at 40 °C to give 6.37 g of oltipraz (13.6percent yield, >99.5percent purity). NMR (6 CDC13) : 2.51 (s, 3H), 8.70 (d, 1H), 8.80 (d, 1H), 9.21 (s, 1H)
Reference: [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 12, p. 2843 - 2851
[2] Molecular Pharmacology, 2008, vol. 73, # 5, p. 1502 - 1512
[3] Patent: WO2004/48369, 2004, A1, . Location in patent: Page 9-10
[4] Patent: US2004/53989, 2004, A1,
[5] Patent: WO2016/207914, 2016, A2, . Location in patent: Page/Page column 4; 16; 17
  • 2
  • [ 7440-44-0 ]
  • [ 324737-10-2 ]
  • [ 64224-21-1 ]
Reference: [1] Patent: US2004/53989, 2004, A1,
  • 3
  • [ 98-97-5 ]
  • [ 64224-21-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 12, p. 2843 - 2851
[2] Patent: WO2016/207914, 2016, A2,
  • 4
  • [ 6164-79-0 ]
  • [ 64224-21-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 12, p. 2843 - 2851
  • 5
  • [ 62124-77-0 ]
  • [ 64224-21-1 ]
Reference: [1] Patent: US4110450, 1978, A,
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