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[ CAS No. 71203-35-5 ] {[proInfo.proName]}

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Chemical Structure| 71203-35-5
Chemical Structure| 71203-35-5
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Product Details of [ 71203-35-5 ]

CAS No. :71203-35-5 MDL No. :MFCD05987165
Formula : C22H21N3O3S Boiling Point : -
Linear Structure Formula :- InChI Key :QBNZBMVRFYREHK-UHFFFAOYSA-N
M.W : 407.49 Pubchem ID :2950007
Synonyms :
CID-2950007

Calculated chemistry of [ 71203-35-5 ]

Physicochemical Properties

Num. heavy atoms : 29
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.14
Num. rotatable bonds : 5
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 119.75
TPSA : 93.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.79
Log Po/w (XLOGP3) : 3.56
Log Po/w (WLOGP) : 3.69
Log Po/w (MLOGP) : 2.51
Log Po/w (SILICOS-IT) : 2.79
Consensus Log Po/w : 3.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.74
Solubility : 0.00744 mg/ml ; 0.0000183 mol/l
Class : Moderately soluble
Log S (Ali) : -5.21
Solubility : 0.00253 mg/ml ; 0.00000622 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.01
Solubility : 0.0000398 mg/ml ; 0.0000000977 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.66

Safety of [ 71203-35-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H320-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 71203-35-5 ]

* 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 [ 71203-35-5 ]
  • Downstream synthetic route of [ 71203-35-5 ]

[ 71203-35-5 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 22252-15-9 ]
  • [ 71203-35-5 ]
YieldReaction ConditionsOperation in experiment
37% With acetic acid In ethanol at 150℃; for 1 h; Microwave irradiation; Sealed tube 4-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]benzenesulfonamide
For the synthesis of this compound, the requisite chalcone starting material was commercially available. 4-Methoxychalcone (3, R1=H, R2=4-OMe, CASNo.959-33-1) was purchased from Sigma-Aldrich and 4-hydrazinobenzene-1-sulfonamide hydrochloride (4, CASNo.17852-52-7) was purchased from Acros Organics. (STEP 2):
To a 20 mL microwave vial was added 4-methoxychalcone (0.238 g, 1.00 mmol, 1 eq), EtOH (200 proof, 10 mL), 4-hydrazinobenzene-1-sulfonamide hydrochloride (0.252 g, 1.13 mmol, 1.1 eq), and glacial AcOH (0.29 mL, 5.0 mmol, 5 eq).
The vessel was sealed and then submitted to microwave irradiation at 150° C. for 1 h.
Once the reaction mixture had cooled to room temperature, the cap was removed and the vessel was placed in a dry-ice/acetone bath.
While stirring, hexane (10 mL) was added, and the resulting precipitate was collected by filtration.
The precipitate was rinsed with hexane (3*10 mL) and then the solid was transferred to another flask and recrystallized from EtOH (6 mL).
The solid was filtered, rinsed with hexanes (3*10 mL) and dried to afford 4-(5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1Hpyrazol-1-yl)benzenesulfonamide (0.150 g, 37percent yield, 97percent purity) as white needles. 1H NMR (400 MHz, DMSO-d6) δ 7.80 (m, 2H), 7.58 (d, J=9.0 Hz, 2H), 7.43 (m, 3H), 7.18 (d, J=8.7 Hz, 2H), 7.09 (d, J=9.0 Hz, 2H), 7.02 (s, 2H), 6.90 (d, J=8.7 Hz, 2H), 5.60 (dd, J=12.0, 5.1 Hz, 1H), 3.95 (dd, J=17.6, 12.0 Hz, 1H), 3.71 (s, 3H), 3.17 (dd, J=17.7, 5.1 Hz, 1H).
13C NMR (101 MHz, DMSO-d6) δ 158.59, 149.58, 145.87, 133.48, 132.98, 13 1.83, 129.24, 128.69 (*2), 127.06 (*2), 126.99 (*2), 126.02 (*2), 114.42 (*2), 112.02 (*2), 61.88, 55.02, 42.97.
Compounds of this chemotype submitted to LCMS analysis routinely showed a parent mass and/or a parent mass-2, the latter of which resulted presumably due to an analytical instrument artifact that resulted in oxidation/aromatization of the central dihydropyrazoline ring on the LCMS column, in the MS detector, or both.
In this case, both ions were observed in the same peak. LCMS retention time: 3.057 min. HRMS m/z calculated for C22H21N3NaO3S [M++Na]: 430.1196. found 430.1180.
For aromatized/oxidized signal, HRMS m/z calculated for C22H20N3O3S [M+-2+1] 406.1225. found 406.1217.
White needles, mp 185-187° C. (Faid-Allah, 1988).
Reference: [1] Patent: US2013/345277, 2013, A1, . Location in patent: Paragraph 0135
  • 2
  • [ 122259-16-9 ]
  • [ 71203-35-5 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 245 - 249
  • 3
  • [ 4392-54-5 ]
  • [ 959-33-1 ]
  • [ 71203-35-5 ]
Reference: [1] Pharmazie, 1981, vol. 36, # 11, p. 754 - 756
  • 4
  • [ 17852-52-7 ]
  • [ 959-33-1 ]
  • [ 71203-35-5 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 245 - 249
  • 5
  • [ 17852-52-7 ]
  • [ 71203-35-5 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 245 - 249
  • 6
  • [ 959-33-1 ]
  • [ 71203-35-5 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 245 - 249
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