Synthesis and 5-HT3 affinity of new 3-substituted indoles at central nervous system
A series of 3-imino and 3-aminomethyl-N-methylindoles, in which the amine substituents were 3-quinuclidyl and 1-adamantyl groups, were synthesized and their in vitro affinity towards 5-HT3 central receptors evaluated. Of the nine compounds tested, three caused displacement of 3H-BRL 43694 binding to 5-HT3. 2-Chloro-3-(3-quinuclidylimino)-1-methylindole, 4, was the most potent compound with an IC50 = 5.15 10(-8) M. Moreover, the monoamine oxidase inhibition activity was tested and three compounds were shown to be MAO inhibitors, their IC50 was in the range of that of (-)-Deprenyl. Again, 4 was the most potent compound. Structure-activity relationships within the series are briefly discussed.
| Medienart: |
Artikel |
|---|
| Erscheinungsjahr: |
1996 |
|---|---|
| Erschienen: |
1996 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:14 |
|---|---|
| Enthalten in: |
Drug design and discovery - 14(1996), 2 vom: 09. Okt., Seite 157-70 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Monge, A [VerfasserIn] |
|---|
| Anmerkungen: |
Date Completed 28.05.1997 Date Revised 15.11.2006 published: Print Citation Status MEDLINE |
|---|
| Förderinstitution / Projekttitel: |
|
|---|
| PPN (Katalog-ID): |
NLM089760247 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM089760247 | ||
| 003 | DE-627 | ||
| 005 | 20231222080721.0 | ||
| 007 | tu | ||
| 008 | 231222s1996 xx ||||| 00| ||eng c | ||
| 028 | 5 | 2 | |a pubmed24n0300.xml |
| 035 | |a (DE-627)NLM089760247 | ||
| 035 | |a (NLM)9010621 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Monge, A |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Synthesis and 5-HT3 affinity of new 3-substituted indoles at central nervous system |
| 264 | 1 | |c 1996 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ohne Hilfsmittel zu benutzen |b n |2 rdamedia | ||
| 338 | |a Band |b nc |2 rdacarrier | ||
| 500 | |a Date Completed 28.05.1997 | ||
| 500 | |a Date Revised 15.11.2006 | ||
| 500 | |a published: Print | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a A series of 3-imino and 3-aminomethyl-N-methylindoles, in which the amine substituents were 3-quinuclidyl and 1-adamantyl groups, were synthesized and their in vitro affinity towards 5-HT3 central receptors evaluated. Of the nine compounds tested, three caused displacement of 3H-BRL 43694 binding to 5-HT3. 2-Chloro-3-(3-quinuclidylimino)-1-methylindole, 4, was the most potent compound with an IC50 = 5.15 10(-8) M. Moreover, the monoamine oxidase inhibition activity was tested and three compounds were shown to be MAO inhibitors, their IC50 was in the range of that of (-)-Deprenyl. Again, 4 was the most potent compound. Structure-activity relationships within the series are briefly discussed | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 7 | |a 2-chloro-3-(3-quinuclidylimino)-1-methylindole |2 NLM | |
| 650 | 7 | |a Indoles |2 NLM | |
| 650 | 7 | |a Monoamine Oxidase Inhibitors |2 NLM | |
| 650 | 7 | |a Quinuclidines |2 NLM | |
| 650 | 7 | |a Receptors, Dopamine D2 |2 NLM | |
| 650 | 7 | |a Receptors, Serotonin |2 NLM | |
| 650 | 7 | |a Receptors, Serotonin, 5-HT3 |2 NLM | |
| 700 | 1 | |a Palop, J A |e verfasserin |4 aut | |
| 700 | 1 | |a Orts, L |e verfasserin |4 aut | |
| 700 | 1 | |a Oset, C |e verfasserin |4 aut | |
| 700 | 1 | |a Lasheras, B |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Drug design and discovery |d 1997 |g 14(1996), 2 vom: 09. Okt., Seite 157-70 |w (DE-627)NLM012603031 |x 1055-9612 |7 nnns |
| 773 | 1 | 8 | |g volume:14 |g year:1996 |g number:2 |g day:09 |g month:10 |g pages:157-70 |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 14 |j 1996 |e 2 |b 09 |c 10 |h 157-70 | ||