Alternatived Products of [ 142596-50-7 ]
Product Details of [ 142596-50-7 ]
CAS No. : 142596-50-7
MDL No. : MFCD18382535
Formula :
C8 H6 N2 O3
Boiling Point :
-
Linear Structure Formula : -
InChI Key : OXWWZQUPPXKYQB-UHFFFAOYSA-N
M.W :
178.14
Pubchem ID : 10374991
Synonyms :
Calculated chemistry of [ 142596-50-7 ]
Physicochemical Properties
Num. heavy atoms :
13
Num. arom. heavy atoms :
6
Fraction Csp3 :
0.12
Num. rotatable bonds :
2
Num. H-bond acceptors :
4.0
Num. H-bond donors :
0.0
Molar Refractivity :
46.47
TPSA :
78.84 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) :
-6.36 cm/s
Lipophilicity
Log Po/w (iLOGP) :
1.19
Log Po/w (XLOGP3) :
1.44
Log Po/w (WLOGP) :
1.48
Log Po/w (MLOGP) :
0.03
Log Po/w (SILICOS-IT) :
-0.35
Consensus Log Po/w :
0.76
Druglikeness
Lipinski :
0.0
Ghose :
None
Veber :
0.0
Egan :
0.0
Muegge :
1.0
Bioavailability Score :
0.55
Water Solubility
Log S (ESOL) :
-2.06
Solubility :
1.55 mg/ml ; 0.00868 mol/l
Class :
Soluble
Log S (Ali) :
-2.7
Solubility :
0.355 mg/ml ; 0.00199 mol/l
Class :
Soluble
Log S (SILICOS-IT) :
-1.99
Solubility :
1.82 mg/ml ; 0.0102 mol/l
Class :
Soluble
Medicinal Chemistry
PAINS :
0.0 alert
Brenk :
2.0 alert
Leadlikeness :
1.0
Synthetic accessibility :
1.98
Safety of [ 142596-50-7 ]
Signal Word: Warning
Class: N/A
Precautionary Statements: P280-P305+P351+P338
UN#: N/A
Hazard Statements: H302
Packing Group: N/A
GHS Pictogram:
Application In Synthesis of [ 142596-50-7 ]
* 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 [ 142596-50-7 ]
Downstream synthetic route of [ 142596-50-7 ]
1
[ 186581-53-3 ]
[ 129298-23-3 ]
[ 142596-50-7 ]
2
[ 99595-85-4 ]
[ 142596-50-7 ]
Yield Reaction Conditions Operation in experiment
76%
With thionyl chloride In N,N-dimethyl-formamide at 20℃; for 19h;
74.5%
With thionyl chloride In tetrahydrofuran Ambient temperature;
With thionyl chloride
Reference:
[1]Paintner, Tobias; Björk, Jonas; Du, Ping; Klyatskaya, Svetlana; Paszkiewicz, Mateusz; Hellwig, Raphael; Uphoff, Martin; Öner, Murat A.; Cuniberto, Edoardo; Deimel, Peter S.; Zhang, Yi-Qi; Palma, Carlos-Andres; Allegretti, Francesco; Ruben, Mario; Barth, Johannes V.; Klappenberger, Florian
[Angewandte Chemie - International Edition, 2019, vol. 58, # 33, p. 11285 - 11290][Angew. Chem., 2019, vol. 131, p. 11407 - 11412]
[2]Goto; Nakamura; Morioka; Kondo; Naito; Tsutsumi
[Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 3, p. 547 - 551]
[3]Kimura; Watanabe; Matsui; Hayashi; Tanaka; Ohtsuka; Saeki; Kogushi; Kabayashi; Akasaka; Yamagishi; Saitou; Yamatsu
[Journal of Medicinal Chemistry, 1993, vol. 36, # 11, p. 1641 - 1653]
3
[ 142596-50-7 ]
[ 148932-68-7 ]
4
[ 725266-66-0 ]
[ 142596-50-7 ]
5
[ 4920-80-3 ]
[ 142596-50-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: SOCl2 / CH2 Cl2 / 2 h / Heating
2: aq. NH3 / tetrahydrofuran / 0.5 h / Ambient temperature
3: 74.5 percent / SOCl2 / tetrahydrofuran / Ambient temperature
Multi-step reaction with 3 steps
1: SOCl2
2: NH4 OH / CH2 Cl2
3: SOCl2
Multi-step reaction with 3 steps
1: thionyl chloride / tetrahydrofuran / 2 h / Reflux
2: ammonium hydroxide / tetrahydrofuran / 0.58 h / 0 - 20 °C
3: thionyl chloride / N,N-dimethyl-formamide / 19 h / 20 °C
Reference:
[1]Goto; Nakamura; Morioka; Kondo; Naito; Tsutsumi
[Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 3, p. 547 - 551]
[2]Kimura; Watanabe; Matsui; Hayashi; Tanaka; Ohtsuka; Saeki; Kogushi; Kabayashi; Akasaka; Yamagishi; Saitou; Yamatsu
[Journal of Medicinal Chemistry, 1993, vol. 36, # 11, p. 1641 - 1653]
[3]Paintner, Tobias; Björk, Jonas; Du, Ping; Klyatskaya, Svetlana; Paszkiewicz, Mateusz; Hellwig, Raphael; Uphoff, Martin; Öner, Murat A.; Cuniberto, Edoardo; Deimel, Peter S.; Zhang, Yi-Qi; Palma, Carlos-Andres; Allegretti, Francesco; Ruben, Mario; Barth, Johannes V.; Klappenberger, Florian
[Angewandte Chemie - International Edition, 2019, vol. 58, # 33, p. 11285 - 11290][Angew. Chem., 2019, vol. 131, p. 11407 - 11412]
6
[ 15865-57-3 ]
[ 142596-50-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: aq. NH3 / tetrahydrofuran / 0.5 h / Ambient temperature
2: 74.5 percent / SOCl2 / tetrahydrofuran / Ambient temperature
Multi-step reaction with 2 steps
1: NH4 OH / CH2 Cl2
2: SOCl2
Multi-step reaction with 2 steps
1: ammonium hydroxide / tetrahydrofuran / 0.58 h / 0 - 20 °C
2: thionyl chloride / N,N-dimethyl-formamide / 19 h / 20 °C
Reference:
[1]Goto; Nakamura; Morioka; Kondo; Naito; Tsutsumi
[Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 3, p. 547 - 551]
[2]Kimura; Watanabe; Matsui; Hayashi; Tanaka; Ohtsuka; Saeki; Kogushi; Kabayashi; Akasaka; Yamagishi; Saitou; Yamatsu
[Journal of Medicinal Chemistry, 1993, vol. 36, # 11, p. 1641 - 1653]
[3]Paintner, Tobias; Björk, Jonas; Du, Ping; Klyatskaya, Svetlana; Paszkiewicz, Mateusz; Hellwig, Raphael; Uphoff, Martin; Öner, Murat A.; Cuniberto, Edoardo; Deimel, Peter S.; Zhang, Yi-Qi; Palma, Carlos-Andres; Allegretti, Francesco; Ruben, Mario; Barth, Johannes V.; Klappenberger, Florian
[Angewandte Chemie - International Edition, 2019, vol. 58, # 33, p. 11285 - 11290][Angew. Chem., 2019, vol. 131, p. 11407 - 11412]
7
[ 142596-50-7 ]
[ 176718-55-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 87.5 percent / H2 / 10percent Pd/C / ethyl acetate / 2 h / 760 Torr
2: 78.6 percent / NBS / dimethylformamide / 1 h / Ambient temperature
3: 72.6 percent / BBr3 / CH2 Cl2 / Ambient temperature
8
[ 142596-50-7 ]
[ 176718-54-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 87.5 percent / H2 / 10percent Pd/C / ethyl acetate / 2 h / 760 Torr
2: 78.6 percent / NBS / dimethylformamide / 1 h / Ambient temperature
9
[ 142596-50-7 ]
sodium 2-amino-5-bromo-3-cyanophenyl sulfate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: 87.5 percent / H2 / 10percent Pd/C / ethyl acetate / 2 h / 760 Torr
2: 78.6 percent / NBS / dimethylformamide / 1 h / Ambient temperature
3: 72.6 percent / BBr3 / CH2 Cl2 / Ambient temperature
4: 49.7 percent / SO3 *NMe3 , NaOH, NaHCO3 / H2 O / 72 h / Ambient temperature
10
[ 142596-50-7 ]
[ 148726-44-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: H2 / 10percent Pd/C / ethyl acetate / 1 h / 760 Torr
2: CHCl3
3: BBr3 / CH2 Cl2 / 2 h / Heating
Multi-step reaction with 4 steps
1: H2 / 10percent Pd/C / ethyl acetate / 1 h / 760 Torr
2: pyridine / 2 h / 60 °C
3: toluene / 1 h / Heating
4: BBr3 / CH2 Cl2 / 2 h / Heating
11
[ 142596-50-7 ]
[ 1026065-48-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: H2 / 10percent Pd/C / ethyl acetate / 1 h / 760 Torr
2: CHCl3
Multi-step reaction with 3 steps
1: H2 / 10percent Pd/C / ethyl acetate / 1 h / 760 Torr
2: pyridine / 2 h / 60 °C
3: toluene / 1 h / Heating
12
[ 142596-50-7 ]
(2-Cyano-6-methoxy-phenyl)-carbamic acid phenyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: H2 / 10percent Pd/C / ethyl acetate / 1 h / 760 Torr
2: pyridine / 2 h / 60 °C
13
[ 142596-50-7 ]
N-[6-Cyano-2-{3-(5-methyl-4-phenyl-1H-imidazol-1-yl)-propoxy}]phenyl-N'-pentylurea
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: H2 / 10percent Pd/C / ethyl acetate / 1 h / 760 Torr
2: CHCl3
3: BBr3 / CH2 Cl2 / 2 h / Heating
4: NaI, K2 CO3 / dimethylformamide / 2 h / 60 °C
Multi-step reaction with 5 steps
1: H2 / 10percent Pd/C / ethyl acetate / 1 h / 760 Torr
2: pyridine / 2 h / 60 °C
3: toluene / 1 h / Heating
4: BBr3 / CH2 Cl2 / 2 h / Heating
5: NaI, K2 CO3 / dimethylformamide / 2 h / 60 °C
14
[ 142596-50-7 ]
[ 1427420-70-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: potassium hydroxide; water / 1,2-dimethoxyethane / 1 h / -5 - 0 °C / Inert atmosphere
2: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 2 h / 65 °C / Inert atmosphere
3: palladium diacetate; cesium bicarbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 18 h / 100 °C / Schlenk technique; Inert atmosphere
Reference:
[1]Romagnoli, Romeo; Baraldi, Pier Giovanni; Kimatrai Salvador, Maria; Preti, Delia; Aghazadeh Tabrizi, Mojgan; Bassetto, Marcella; Brancale, Andrea; Hamel, Ernest; Castagliuolo, Ignazio; Bortolozzi, Roberta; Basso, Giuseppe; Viola, Giampietro
[Journal of Medicinal Chemistry, 2013, vol. 56, # 6, p. 2606 - 2618]
15
[ 142596-50-7 ]
[ 1427420-46-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: potassium hydroxide; water / 1,2-dimethoxyethane / 1 h / -5 - 0 °C / Inert atmosphere
2: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 2 h / 65 °C / Inert atmosphere
Reference:
[1]Romagnoli, Romeo; Baraldi, Pier Giovanni; Kimatrai Salvador, Maria; Preti, Delia; Aghazadeh Tabrizi, Mojgan; Bassetto, Marcella; Brancale, Andrea; Hamel, Ernest; Castagliuolo, Ignazio; Bortolozzi, Roberta; Basso, Giuseppe; Viola, Giampietro
[Journal of Medicinal Chemistry, 2013, vol. 56, # 6, p. 2606 - 2618]
16
[ 142596-50-7 ]
[ 2365-48-2 ]
[ 198204-08-9 ]
Yield Reaction Conditions Operation in experiment
68%
With water; potassium hydroxide In 1,2-dimethoxyethane at -5 - 0℃; for 1h; Inert atmosphere;
Reference:
[1]Romagnoli, Romeo; Baraldi, Pier Giovanni; Kimatrai Salvador, Maria; Preti, Delia; Aghazadeh Tabrizi, Mojgan; Bassetto, Marcella; Brancale, Andrea; Hamel, Ernest; Castagliuolo, Ignazio; Bortolozzi, Roberta; Basso, Giuseppe; Viola, Giampietro
[Journal of Medicinal Chemistry, 2013, vol. 56, # 6, p. 2606 - 2618]