(1H-indol-3-yl)(naphthalen-1-yl)methanone

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1 substances in Re2016-03-09 09h:33m:45s (EST) axys

O HN

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Reaxys ID 210669 View in Reaxys

HN

1/1 CAS Registry Number: 109555-87-5 Chemical Name: 3-(1-naphthylcarbonyl)indole; 3-(1-naphthoyl)-1H-indole; indol-3-yl-[1]naphthyl ketone; Indol-3-yl-[1]naphthyl-keton Linear Structure Formula: C19H13NO Molecular Formula: C19H13NO Molecular Weight: 271.318 Type of Substance: heterocyclic InChI Key: QIXQGVQLBPQVOR-UHFFFAOYSA-N Note:

O

Substance Label (4) Label References 1

Patent; Randox Laboratories Ltd.; EP2487155; (2012); (A1) English, View in Reaxys

9

Banerji, Avijit; Bandyopadhyay, Debasish; Basak, Bidyut; Heterocycles; vol. 63; nb. 10; (2004); p. 2371 2377, View in Reaxys

10

Oda, Kazuaki; Hiratsuka, Rin; Machida, Minoru; Heterocycles; vol. 43; nb. 2; (1996); p. 463 - 470, View in Reaxys

pr. step a,t.I, cmpd.30

D'Ambra, Thomas E.; Eissenstat, Michael A.; Abt, Jeffrey; Ackerman, James H.; Bacon, Edward R.; Bell, Malcolm R.; Carabateas, Philip M.; Josef, Kurt A.; Kumar, Virendra; Weaver III, John D.; Arnold, Renee; Casiano, Frances M.; Chippari, Susan M.; Haycock, Dean A.; Kuster, Joan E.; Luttinger, Daniel A.; Stevenson, Joan I.; Ward, Susan J.; Hill, W. Adam; Khanolkar, Atmaram; Makriyannis, Alexandros; Bioorganic and Medicinal Chemistry Letters; vol. 6; nb. 1; (1996); p. 17 - 22, View in Reaxys

Patent-Specific Data (2) Location in Patent References Page/Page column

Patent; Randox Laboratories Ltd.; Fitzgerald, Stephen Peter; Innocenzi, Paul John; Lowry, Philip Andrew; McConnell, Ivan Robert; Benchikh, Elouard; EP2698385; (2014); (A1) English, View in Reaxys

Claim

Patent; RANDOX LABORATORIES LIMITED; US2012/208213; (2012); (A1) English, View in Reaxys; Patent; Randox Laboratories Ltd.; EP2487155; (2012); (A1) English, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

216

Banerji, Avijit; Bandyopadhyay, Debasish; Basak, Bidyut; Heterocycles; vol. 63; nb. 10; (2004); p. 2371 - 2377, View in Reaxys 2 of 2

Melting Point [°C]

236

Solvent (Melting Point)

benzene

Buu-Hoi et al.; Journal of the Chemical Society; (1957); p. 625,627, View in Reaxys Crystal Property Description (2) Colour & Other Location Properties white

Page/Page column

yellow

References Patent; Randox Laboratories Ltd.; Fitzgerald, Stephen Peter; Innocenzi, Paul John; Lowry, Philip Andrew; McConnell, Ivan Robert; Benchikh, Elouard; EP2698385; (2014); (A1) English, View in Reaxys Banerji, Avijit; Bandyopadhyay, Debasish; Basak, Bidyut; Heterocycles; vol. 63; nb. 10; (2004); p. 2371 - 2377, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

27

Frequency (NMR Spectroscopy) [MHz]

125.77

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Banerji, Avijit; Bandyopadhyay, Debasish; Basak, Bidyut; Heterocycles; vol. 63; nb. 10; (2004); p. 2371 - 2377, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

27

Frequency (NMR Spectroscopy) [MHz]

500.134

Banerji, Avijit; Bandyopadhyay, Debasish; Basak, Bidyut; Heterocycles; vol. 63; nb. 10; (2004); p. 2371 - 2377, View in Reaxys 3 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

27

Frequency (NMR Spectroscopy) [MHz]

500.134

Banerji, Avijit; Bandyopadhyay, Debasish; Basak, Bidyut; Heterocycles; vol. 63; nb. 10; (2004); p. 2371 - 2377, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Banerji, Avijit; Bandyopadhyay, Debasish; Basak, Bidyut; Heterocycles; vol. 63; nb. 10; (2004); p. 2371 - 2377, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 213.5; 256.5 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

54954; 20417

Banerji, Avijit; Bandyopadhyay, Debasish; Basak, Bidyut; Heterocycles; vol. 63; nb. 10; (2004); p. 2371 - 2377, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Buu-Hoi et al.; Journal of the Chemical Society; (1957); p. 625,627, View in Reaxys; Oda, Kazuaki; Hiratsuka, Rin; Machida, Minoru; Heterocycles; vol. 43; nb. 2; (1996); p. 463 - 470, View in Reaxys; D'Ambra, Thomas E.; Eissenstat, Michael A.; Abt, Jeffrey; Ackerman, James H.; Bacon, Edward R.; Bell, Malcolm R.; Carabateas, Philip M.; Josef, Kurt A.; Kumar, Virendra; Weaver III, John D.; Arnold, Renee; Casiano, Frances M.; Chippari, Susan M.; Haycock, Dean A.; Kuster, Joan E.; Luttinger, Daniel A.; Stevenson, Joan I.; Ward, Susan J.; Hill, W. Adam; Khanolkar, Atmaram; Makriyannis, Alexandros; Bioorganic and Medicinal Chemistry Letters; vol. 6; nb. 1; (1996); p. 17 - 22, View in Reaxys; Banerji, Avijit; Bandyopadhyay, Debasish; Basak, Bidyut; Heterocycles; vol. 63; nb. 10; (2004); p. 2371 - 2377, View in Reaxys; Patent; Sterling Drug Inc.; US5068234; (1991); (A1) English, View in Reaxys; Patent; RANDOX LABORATORIES LIMITED; US2012/208213; (2012); (A1) English, View in Reaxys; Patent; Randox Laboratories Ltd.; EP2487155; (2012); (A1) English, View in Reaxys; Lai, Qiu Yu; Liao, Rong Su; Wu, Shao Yong; Zhang, Jia Xin; Duan, Xin Hong; New Journal of Chemistry; vol. 37; nb. 12; (2013); p. 4069 - 4076, View in Reaxys; Patent; Randox Laboratories Ltd.; Fitzgerald, Stephen Peter; Innocenzi, Paul

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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John; Lowry, Philip Andrew; McConnell, Ivan Robert; Benchikh, Elouard; EP2698385; (2014); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

antibody raised to Immunogen I (Hapten A-BTG); binding to

Species or Test-System (Pharmacological Data)

Ig fraction of the antiserum raised to Immunogen I (Hapten A-BTG)

Kind of Dosing (Pharma- title compound prepared in Tris buffered saline containing Tween 20 (TBST) solution cological Data) Method (Pharmacological Data)

The wells of an enhanced binding 96 well polystyrene microtiter plate were coated with the Ig fraction of the antiserum raised to Immunogen I (Hapten A-BTG - example 5) and diluted in 10mM Tris, pH8.5 (125μl/well). The appropriate antibody coating concentration was determined using standard ELISA checkerboard techniques. The plate was incubated for 2 hours at 37°C, washed 4 times over a 10-minute period with Tris buffered saline containing Tween 20 (TBST) and tapped dry. Standard solutions of JWH synthetic cannabinoids, metabolites and selected molecules were prepared in TBST and 50μl of each was added to the appropriate wells. 75μl of conjugate (Hapten A-HRP) diluted in Tris buffer containing EDTA, D-mannitol, sucrose, thimerosal and BSA, was added to each of the wells. The appropriate dilution of conjugate was also determined using standard ELISA checkerboard techniques. The plate was incubated at 25°C for 1 hour. The excess unbound conjugate was removed by washing 6 times over a 10-minute period with TBST and tapped dry. 125μl of tetramethylbenzedine (TMB) substrate solution was added to each well of the plate that was then incubated for 15-20 minutes in the dark at room temperature. The reaction was terminated by addition of 125μl of 0.2M sulphuric acid to each well. The absorbance was then measured at 450nm using a microtiter plate reader.

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

3840 ng/l

Results

cross-reactivity (percent) = 70.57

Location

Page/Page column 12

Patent; Randox Laboratories Ltd.; EP2487155; (2012); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

antibody raised to Immunogen II (Hapten A-BTG); binding to

Species or Test-System (Pharmacological Data)

Ig fraction of the antiserum raised to Immunogen II (Hapten A-BTG)

Kind of Dosing (Pharma- title compound prepared in Tris buffered saline containing Tween 20 (TBST) solution cological Data) Method (Pharmacological Data)

The wells of an enhanced binding 96 well polystyrene microtiter plate were coated with the Ig fraction of the antiserum raised to Immunogen I (Hapten A-BTG - example 5) and diluted in 10mM Tris, pH8.5 (125μl/well). The appropriate antibody coating concentration was determined using standard ELISA checkerboard techniques. The plate was incubated for 2 hours at 37°C, washed 4 times over a 10-minute period with Tris buffered saline containing Tween 20 (TBST) and tapped dry. Standard solutions of JWH synthetic cannabinoids, metabolites and selected molecules were prepared in TBST and 50μl of each was added to the appropriate wells. 75μl of conjugate (Hapten A-HRP) diluted in Tris buffer containing EDTA, D-mannitol, sucrose, thimerosal and BSA, was added to each of the wells. The appropriate dilution of conjugate was also determined using standard ELISA checkerboard techniques. The plate was incubated at 25°C for 1 hour. The excess unbound conjugate was removed by washing 6 times over a 10-minute period with TBST and tapped dry. 125μl of tetramethylbenzedine (TMB) substrate solution was added to each well of the plate that was then incubated for 15-20 minutes in the dark at room temperature. The reaction was terminated by addition of 125μl of 0.2M sulphuric acid to each well. The absorbance was then measured at 450nm using a microtiter plate reader.

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 40000 ng/l

Results

cross-reactivity (percent) = <5.28

Location

Page/Page column 12

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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2016-03-09 09:34:38


Patent; Randox Laboratories Ltd.; EP2487155; (2012); (A1) English, View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

5/5

2016-03-09 09:34:38


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