Alternatived Products of [ 138977-28-3 ]
Product Details of [ 138977-28-3 ]
CAS No. : 138977-28-3
MDL No. : MFCD00153778
Formula :
C19 H21 ClN2 O2 S
Boiling Point :
-
Linear Structure Formula : -
InChI Key : DRCMAZOSEIMCHM-UHFFFAOYSA-N
M.W :
376.90
Pubchem ID : 2733484
Synonyms :
Calculated chemistry of [ 138977-28-3 ]
Physicochemical Properties
Num. heavy atoms :
25
Num. arom. heavy atoms :
12
Fraction Csp3 :
0.32
Num. rotatable bonds :
5
Num. H-bond acceptors :
2.0
Num. H-bond donors :
3.0
Molar Refractivity :
109.24
TPSA :
87.82 Ų
Pharmacokinetics
GI absorption :
High
BBB permeant :
No
P-gp substrate :
No
CYP1A2 inhibitor :
Yes
CYP2C19 inhibitor :
Yes
CYP2C9 inhibitor :
Yes
CYP2D6 inhibitor :
Yes
CYP3A4 inhibitor :
Yes
Log Kp (skin permeation) :
-5.82 cm/s
Lipophilicity
Log Po/w (iLOGP) :
2.5
Log Po/w (XLOGP3) :
3.91
Log Po/w (WLOGP) :
3.08
Log Po/w (MLOGP) :
2.87
Log Po/w (SILICOS-IT) :
4.58
Consensus Log Po/w :
3.39
Druglikeness
Lipinski :
0.0
Ghose :
None
Veber :
0.0
Egan :
0.0
Muegge :
0.0
Bioavailability Score :
0.55
Water Solubility
Log S (ESOL) :
-4.67
Solubility :
0.00815 mg/ml ; 0.0000216 mol/l
Class :
Moderately soluble
Log S (Ali) :
-5.45
Solubility :
0.00133 mg/ml ; 0.00000353 mol/l
Class :
Moderately soluble
Log S (SILICOS-IT) :
-5.78
Solubility :
0.000625 mg/ml ; 0.00000166 mol/l
Class :
Moderately soluble
Medicinal Chemistry
PAINS :
1.0 alert
Brenk :
2.0 alert
Leadlikeness :
2.0
Synthetic accessibility :
2.86
Safety of [ 138977-28-3 ]
Application In Synthesis of [ 138977-28-3 ]
* 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.
Downstream synthetic route of [ 138977-28-3 ]
1
[ 17608-10-5 ]
[ 113853-92-2 ]
[ 138977-28-3 ]
Yield Reaction Conditions Operation in experiment
79%
With triethylamine In tetrahydrofuran for 18h;
70%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 4h;
With triethylamine In DMF (N,N-dimethyl-formamide) for 65h;
10
The hydrobromic salt of the bicyclic amine (1 eq.) was dissolved in DMF and triethylamine (3 eq.) was added. This mixture was stirred for 15-30 minutes and then was the isothiocyanate (1.2 eq.) added. This mixture was stirred for 65 hours and then concentrated. The residue was dissolved in EtOAc and washed with water. The organic phase was dried (MgSO4) and concentrated to give the crude product, typically as a yellow oil. The thiourea was chromatographed on silicagel (heptane:EtOAc). The substituted thioureas thus prepared are listed in Table 5.
Reference:
[1]Walpole, Christopher S. J.; Bevan, Stuart; Bovermann, Guenter; Boelsterli, Johann J.; Breckenridge, Robin; et al.
[Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 1942 - 1954]
[2]Dalence-Guzman, Maria F.; Berglund, Magnus; Skogvall, Staffan; Sterner, Olov
[Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 5, p. 2499 - 2512]
[3]Current Patent Assignee: RESPIRATORIUS - US2005/165004, 2005, A1
Location in patent: Page/Page column 16
2
[ 95469-38-8 ]
[ 138977-28-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 58 percent / 48percent aq. HBr / 24 h / Heating
2: 79 percent / Et3 N / tetrahydrofuran / 18 h
3
[ 72584-69-1 ]
[ 138977-28-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 75 percent / B2 H6 / tetrahydrofuran / 15 h / Heating
2: 58 percent / 48percent aq. HBr / 24 h / Heating
3: 79 percent / Et3 N / tetrahydrofuran / 18 h