3-(2-Ethylphenyl)-2-methylquinazolin-4(3H)-one (Etaqualone) [C17H16N2O]

Query Query

Results

Date

1 substances in Reaxys

2018-08-20 22h:18m:19s (UTC)

N

N

1. Query O

Search as: As drawn ))

Copyright Š 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

1/7

2018-08-20 22:18:56

Reaxys ID 887484 View in Reaxys

1/1 CAS Registry Number: 7432-25-9 Chemical Name: etaqualone; 3-(2-ethyl-phenyl)-2-methyl-3H-quinazolin-4-one; 3-(2-ethyl-phenyl)-2-methyl-3H-quinazolin-4-one; 3-(2Ethyl-phenyl)-2-methyl-4-oxo-3.4-dihydro-chinazolin; 2-Methyl-3-(2aethylphenyl)-chinazolin-4(3H)-on; 3-Methyl-3-(o-ethylphenyl)-4(3H)-chinazolinon; 2-Methyl-3-(2-ethyl-phenyl)-chinazolon-(4) Linear Structure Formula: C17H16N2O Molecular Formula: C17H16N2O Molecular Weight: 264.327 Type of Substance: heterocyclic InChI Key: UVTJKLLUVOTSOB-UHFFFAOYSA-N Note:

N

N

O

Substance Label (5) Label References 3d

Su; Wu; Xie; Li; Organic Preparations and Procedures International; vol. 38; nb. 1; (2006); p. 89 - 94, View in Reaxys

4j

Errede et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 1765, View in Reaxys

IV

Patent; Stroh; DD65928; (1968); Chem.Abstr.; vol. 71; nb. 124485x; (1969), View in Reaxys

II

Pflegel; Wagner; Pharmazie; vol. 22; (1967); p. 643,649, View in Reaxys

I

Patent; Biersdorf and Co.;AG; BE615282; (1961); Chem.Abstr.; vol. 58; nb. 13971; (1963), View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.331

H Bond Donors

0

H Bond Acceptors

3

Rotatable Bonds

2

TPSA

32.67

Lipinski Number

4

Veber Number

2

Highest Clinical Phase (1) Highest Clinical Phase Marketed Derivative (1) Comment (Derivative)

References

HCl: F = 247grad

Patent; Biersdorf and Co.;AG; BE615282; (1961); Chem.Abstr.; vol. 58; nb. 13971; (1963), View in Reaxys

Melting Point (3) 1 of 3

Melting Point [°C]

249 - 250

Errede et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 1765, View in Reaxys 2 of 3

Melting Point [°C]

240 - 243

Parmar; Kishor; Seth; Arora; Journal of medicinal chemistry; vol. 12; nb. 1; (1969); p. 138 - 141, View in Reaxys 3 of 3

Melting Point [°C]

76 - 78

Patent; Stroh; DD65928; (1968); Chem.Abstr.; vol. 71; nb. 124485x; (1969), View in Reaxys Crystal Property Description (1) Colour & Other Location Properties yellow

References

supporting informa- Kumar, R. Arun; Maheswari, C. Uma; Ghantasala, Satheesh; Jyothi; Reddy, K. Rajender; tion Advanced Synthesis and Catalysis; vol. 353; nb. 2-3; (2011); p. 401 - 410, View in Reaxys

Electrochemical Behaviour (1) Description (Elec- References trochemical Behaviour) Polarography

Pflegel; Wagner; Pharmazie; vol. 22; (1967); p. 643,649, View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

2/7

2018-08-20 22:18:56

Electrochemical Characteristics (1) 1 of 1

Description (Electrochemical Characteristics)

polarographic half-wave potential

Pflegel; Wagner; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 9; nb. 4; (1969); p. 151, View in Reaxys NMR Spectroscopy (4) 1 of 4

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 300 scopy) [MHz] Location

supporting information

Kumar, R. Arun; Maheswari, C. Uma; Ghantasala, Satheesh; Jyothi; Reddy, K. Rajender; Advanced Synthesis and Catalysis; vol. 353; nb. 2-3; (2011); p. 401 - 410, View in Reaxys 2 of 4

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 75 scopy) [MHz] Kumar, R. Arun; Maheswari, C. Uma; Ghantasala, Satheesh; Jyothi; Reddy, K. Rajender; Advanced Synthesis and Catalysis; vol. 353; nb. 2-3; (2011); p. 401 - 410, View in Reaxys 3 of 4

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectroscopy)

CDCl3

Su; Wu; Xie; Li; Organic Preparations and Procedures International; vol. 38; nb. 1; (2006); p. 89 - 94, View in Reaxys 4 of 4

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Su; Wu; Xie; Li; Organic Preparations and Procedures International; vol. 38; nb. 1; (2006); p. 89 - 94, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

neat (no solvent)

Kumar, R. Arun; Maheswari, C. Uma; Ghantasala, Satheesh; Jyothi; Reddy, K. Rajender; Advanced Synthesis and Catalysis; vol. 353; nb. 2-3; (2011); p. 401 - 410, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Su; Wu; Xie; Li; Organic Preparations and Procedures International; vol. 38; nb. 1; (2006); p. 89 - 94, View in Reaxys Mass Spectrometry (2)

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

3/7

2018-08-20 22:18:56

Description (Mass Spectrometry)

References

ESI (Electrospray ionisation); Spectrum

Kumar, R. Arun; Maheswari, C. Uma; Ghantasala, Satheesh; Jyothi; Reddy, K. Rajender; Advanced Synthesis and Catalysis; vol. 353; nb. 2-3; (2011); p. 401 - 410, View in Reaxys

spectrum; electron impact (EI)

Su; Wu; Xie; Li; Organic Preparations and Procedures International; vol. 38; nb. 1; (2006); p. 89 - 94, View in Reaxys

Medchem (9) 1 of 9

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Lethal dose of compound in mice following intravenous administration

Biological Species/NCBI ID

mouse

Substance RN

887484View in Reaxys

Substance Route of Adm.

intravenous administration

Measurement Parameter

LD50

Unit

mg/kg

Measurement Object

Lethal dose

Qualitative value

=

Quantitative value

320

vol. NX#03782, View in Reaxys 2 of 9

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibition of pyruvic acid (10 mM) oxidation in rat brain homogenate in the presence of NAD (0.5 mM) with compound concentration at 3 mM upon incubation at 37 degree C in pH 7.4

Biological Species/NCBI ID

rat

Cells/Cell Lines

brain cell

Substance RN

887484View in Reaxys

Measurement Parameter

inhibition rate

Unit

%

Qualitative value

=

Quantitative value

23.32

Deviation

0.18

Concomitants: Compound name

NAD (0.5 mM)

Concomitants: Compound role

COM

Parmar; Kishor; Seth; Arora; Journal of medicinal chemistry; vol. 12; nb. 1; (1969); p. 138 - 141, View in Reaxys 3 of 9

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibition of pyruvic acid (10 mM) oxidation in rat brain homogenate in the absence of NAD with compound concentration at 1 mM upon incubation at 37 degree C in pH 7.4 at time interval of 30-60 minutes

Biological Species/NCBI ID

rat

Cells/Cell Lines

brain cell

Copyright Š 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

4/7

2018-08-20 22:18:56

Substance RN

887484View in Reaxys

Measurement Parameter

inhibition rate

Unit

%

Qualitative value

=

Quantitative value

20.5

Deviation

0.37

Parmar; Kishor; Seth; Arora; Journal of medicinal chemistry; vol. 12; nb. 1; (1969); p. 138 - 141, View in Reaxys 4 of 9

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibition of pyruvic acid (10 mM) oxidation in rat brain homogenate in the absence of NAD with compound concentration at 3 mM upon incubation at 37 degree C in pH 7.4

Biological Species/NCBI ID

rat

Cells/Cell Lines

brain cell

Substance RN

887484View in Reaxys

Measurement Parameter

inhibition rate

Unit

%

Qualitative value

=

Quantitative value

49.88

Deviation

0.9

Parmar; Kishor; Seth; Arora; Journal of medicinal chemistry; vol. 12; nb. 1; (1969); p. 138 - 141, View in Reaxys 5 of 9

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibition of pyruvic acid oxidation in rat brain homogenate in the absence of NAD with compound concentration at 1 mM upon incubation at 37 degree C in pH 7.4 at time interval of 0-30minutes

Biological Species/NCBI ID

rat

Cells/Cell Lines

brain cell

Substance RN

887484View in Reaxys

Measurement Parameter

inhibition rate

Unit

%

Qualitative value

=

Quantitative value

20.21

Deviation

0.46

Parmar; Kishor; Seth; Arora; Journal of medicinal chemistry; vol. 12; nb. 1; (1969); p. 138 - 141, View in Reaxys 6 of 9

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibition of pyruvic acid (10 mM) oxidation in rat brain homogenate in the presence of NAD (0.5 mM) with compound concentration at 1 mM upon incubation at 37 degree C in pH 7.4 at time interval of 30-60 minutes

Biological Species/NCBI ID

rat

Cells/Cell Lines

brain cell

Copyright Š 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

5/7

2018-08-20 22:18:56

Substance RN

887484View in Reaxys

Measurement Parameter

inhibition rate

Unit

%

Qualitative value

=

Quantitative value

8.74

Deviation

0.45

Concomitants: Compound name

NAD (0.5 mM)

Concomitants: Compound role

COM

Parmar; Kishor; Seth; Arora; Journal of medicinal chemistry; vol. 12; nb. 1; (1969); p. 138 - 141, View in Reaxys 7 of 9

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibition of pyruvic acid (10 mM) oxidation in rat brain homogenate in the presence of NAD (0.5 mM) with compound concentration at 2 mM upon incubation at 37 degree C in pH 7.4

Biological Species/NCBI ID

rat

Cells/Cell Lines

brain cell

Substance RN

887484View in Reaxys

Measurement Parameter

inhibition rate

Unit

%

Qualitative value

=

Quantitative value

15.31

Deviation

0.47

Concomitants: Compound name

NAD (0.5 mM)

Concomitants: Compound role

COM

Parmar; Kishor; Seth; Arora; Journal of medicinal chemistry; vol. 12; nb. 1; (1969); p. 138 - 141, View in Reaxys 8 of 9

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibition of pyruvic acid (10 mM) oxidation in rat brain homogenate in the absence of NAD with compound concentration at 2 mM upon incubation at 37 degree C in pH 7.4

Biological Species/NCBI ID

rat

Cells/Cell Lines

brain cell

Substance RN

887484View in Reaxys

Measurement Parameter

inhibition rate

Unit

%

Measurement Object

Inhibition

Qualitative value

=

Quantitative value

35.34

Deviation

0.93

Parmar; Kishor; Seth; Arora; Journal of medicinal chemistry; vol. 12; nb. 1; (1969); p. 138 - 141, View in Reaxys 9 of 9

Substance Action on Target

Inhibitor

Copyright Š 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

6/7

2018-08-20 22:18:56

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibition of pyruvic acid (10 mM) oxidation in rat brain homogenate in the presence of NAD (0.5 mM) with compound concentration at 1 mM upon incubation at 37 degree C in pH 7.4 at time interval of 0-30minutes

Biological Species/NCBI ID

rat

Cells/Cell Lines

brain cell

Substance RN

887484View in Reaxys

Measurement Parameter

inhibition rate

Unit

%

Qualitative value

=

Quantitative value

6.64

Deviation

0.32

Concomitants: Compound name

NAD (0.5 mM)

Concomitants: Compound role

COM

Parmar; Kishor; Seth; Arora; Journal of medicinal chemistry; vol. 12; nb. 1; (1969); p. 138 - 141, View in Reaxys

Copyright Š 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

7/7

2018-08-20 22:18:56