80749-33-3Relevant articles and documents
Direct Synthesis of 3-Acylindoles through Rhodium(III)-Catalyzed Annulation of N-Phenylamidines with α-Cl Ketones
Zhou, Jianhui,Li, Jian,Li, Yazhou,Wu, Chenglin,He, Guoxue,Yang, Qiaolan,Zhou, Yu,Liu, Hong
supporting information, p. 7645 - 7649 (2018/12/11)
In the present study, a novel synthetic strategy to directly produce versatile 3-acylindoles through Rh(III)-catalyzed C-H activation and annulation cascade of N-phenylamidines with α-Cl ketones was developed, in which α-Cl ketones serve as unusual one-carbon (sp3) synthons. This strategy features high regioselectivity, efficiency, wide substrate tolerance, and mild reaction conditions, which further underscore its synthetic utility in drug molecule synthesis.
Detection of synthetic cannabinoids
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, (2014/03/22)
The invention describes methods and kits for detecting and determining current and future synthetic cannabinoids from the JWH and CP families. Unique antibodies derived from immunogens enable said methods and kits.
Detection of synthetic cannabinoids
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Page/Page column, (2014/03/22)
The invention describes methods and kits for detecting and determining current and future synthetic cannabinoids from the JWH and RCS families. Unique antibodies derived from immunogens enable said methods and kits.
Multitarget Compounds Active at a PPAR and Cannabinoid Receptor
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Page/Page column 47, (2011/04/13)
There is a need for pharmaceutical compounds which have activity at, at least one of a PPAR and a cannabinoid receptor. Thus there are provided such compounds, wherein the compound comprises: a PPAR pharmacophore and a cannabinoid pharmacophore linked together by a moiety comprising a fused bicyclic ring comprising a five membered ring fused with a six membered ring or a six membered ring fused with a six membered ring; wherein the cannabinoid pharmacophore comprises the fused bicyclic ring; and the PPAR pharmacophore comprises a salicylic acid, alkoxybenzylacetic acid or a alkoxyphenylacetic acid functionality; and wherein the PPAR pharmacophore is linked to the bicyclic ring of the cannabinoid pharmacophore through a linker comprising an amine or an amide functional group.
New class of potent ligands for the human peripheral cannabinoid receptor
Gallant, Michel,Dufresne, Claude,Gareau, Yves,Guay, Daniel,Leblanc, Yves,Prasit, Petpiboon,Rochette, Chantal,Sawyer, Nicole,Slipetz, Deborah M.,Tremblay, Nathalie,Metters, Kathleen M.,Labelle, Marc
, p. 2263 - 2268 (2007/10/03)
A new class of potent ligand for the human peripheral cannabinoid (hCB2) receptor is described. Two indole analogs 13 and 17 exhibited nanomolar potencies (K(i)) with good selectivity for the hCB2 receptor over the human central cannabinoid (hCB1) receptor.
C-attached aminoalkylindoles: Potent cannabinoid mimetics
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
, p. 17 - 22 (2007/10/03)
Aminoalkylindoles (AAIs) with potent cannabinoid agonist activity have been synthesized where the aminoalkyl chain is attached to the indole ring via a carbon atom of the cyclic amine.
Antinociceptive (Aminoalkyl)indoles
Bell, Malcolm R.,D'Ambra, Thomas E.,Kumar, Virendra,Eissenstat, Michael A.,Herrmann, John L.,et al.
, p. 1099 - 1110 (2007/10/02)
The (aminoalkyl)indole (AAI) derivative pravadoline (1a) inhibited prostaglandin (PG) synthesis in mouse brain microsomes in vitro and ex vivo and exhibited antinociceptive activity in several rodent assays.In vitro structure-activity relationship studies of this new class of PG synthesis inhibitors revealed a correspondence in three respects to those reported for the arylacetic acids: (1) "α-methylation" caused an increase in PG inhibitory potency, (2) the (R)-α-methyl isomer was more active than the S isomer, (3) the hypothesized aroyl group conformation of the 2-methyl derivatives corresponded to the proposed and reported "active" conformations of the aroyl and related aromatic acetic acid derivatives.The 1H NMR chemical shift of the C-4 hydrogen of pravadoline in comparison to the deshielding seen with 50, which lacks a substituent at C-2, suggested that the carbonyl group of pravadoline is located near C-2 but is located near C-4 in 50.Associated with this conformational change of the carbonyl group of 1a is a diminution of PG synthetase inhibitory activity.The results of UV and difference nuclear Overhauser studies of the two compounds were consistent with these conformational assignments.The low eudismic ratios of the α-methyl derivatives and the observation that the side chain may be extended by three methylene groups without significant loss of PG inhibitory potency suggests that this class of inhibitors bound less strongly and less selectively to the active site of PG synthetase than do the arylacetic acids.Two AAIs, 1a and 30, were found to be metabolized to the corresponding acetic acid derivatives, both of which inhibited PG synthesis.An exception to the observation that the antinociceptive activity of the AAIs was associated with PG synthetase inhibitory activity was the 1-naphthoyl derivative 67 since neither it nor its acetic acid metabolite 74 inhibited PG synthesis.Yet 67 was antinociceptive in four different rodent assays.This naphthoyl derivative, like opioids, also inhibited electrically stimulated contractions in the mouse vas deferens (MVD) preparation.Unlike opioids, however, the inhibition was not antagonized by naloxone.A subseries of AAIs was identified, of which 67 was prototypic.These compounds lacked PG synthetase inhibitory activity, but their inhibitory potency in MVD preparations correlated roughly with their antinociceptive potency in vivo.Pravadoline was also inhibitory in MVD.Is antinociceptive activity, therefore, may be a consequence of both its PG synthease inhibitory potency and another antinociceptive mechanism, the latter associated with its inhibitory potency in the MVD.The evidence is summarized which suggests that this second antinociceptive mechanism is associated with binding to the recently characterized cannabinoid receptor.
