145554-63-8Relevant articles and documents
2,3-Dihydro and Carbocyclic Analogues of Tryptamines: Interaction with Serotonin Receptors
Glennon, Richard A.,Jacyno, John M.,Salley, John J.
, p. 68 - 70 (1982)
Several dihydro and carbocyclic analogues of tryptamine were evaluated in order to determine the role of the heterocyclic portion of the indole nucleus on the interaction of indolealkylamines with the serotonin receptors of the rat fundus.Reduction of the C2-C3 double bond or replacement of the indole nitrogen with sp3-hybridized carbon atom results in a 50percent decrease in receptor affinity.Complete removal of the five-membered ring of N,N-dimethyltryptamine reduces affinity by an order of magnitude.It appears that an intact indole nucleus, though not entirely necessary, results in an optimal receptor interaction for the indolealkylamines examined.
Cu-Catalyzed Chemoselective Reduction of N-Heteroaromatics with NH3·BH3 in Aqueous Solution
Gao, Chao,Xuan, Qingqing,Song, Qiuling
supporting information, p. 2504 - 2508 (2021/07/31)
An efficient catalytic system was successfully developed on reduction of N-heteroaromatics with H3N?BH3 as hydrogen source in CuSO4 solution, featuring excellent chemoselectivity as well as very broad functional group tolerance. Various challenging substrates, such as OH-, NH2-, Cl-, Br-, etc., contained quinolines, quinoxalines, 1,5-naphthyridines and quinazolines were all reduced smoothly. Mechanistic studies suggested that [Cu-H] intermediate might be generated from NH3?BH3, which was believed to form with H3N?BH3 in CuSO4 solution.
INDOLE AHR INHIBITORS AND USES THEREOF
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, (2020/05/21)
The present invention provides compounds useful as inhibitors of AHR, compositions thereof, and methods of using the same.
Boron-Catalyzed Hydrogenative Reduction of Substituted Quinolines to Tetrahydroquinolines with Hydrosilanes
Gandhamsetty, Narasimhulu,Park, Sehoon,Chang, Sukbok
supporting information, p. 2396 - 2400 (2017/11/04)
A metal-free procedure for the hydrogenative reduction of substituted N-heteroaromatics has been developed by using hydrosilanes as reducing agents. The optimized conditions were successfully applied to the reactions of quinolines, quinoxalines, and quinoline N -oxides. They were also effective for the reduction of quinolines bearing amino or hydroxy groups, where H 2 was evolved through dehydrogenative silylation of the amine or hydroxy moieties. Preliminary mechanistic studies revealed that the initial step in the catalytic cycle involves 1,4-addition of the hydrosilane to the quinoline to give a 1,4-dihydroquinoline; this is followed by (transfer) hydrogenation to deliver the tetrahydroquinoline as the final product.
Novel Analogues of (R)-5-(Methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (Sumanirole) Provide Clues to Dopamine D2/D3 Receptor Agonist Selectivity
Zou, Mu-Fa,Keck, Thomas M.,Kumar, Vivek,Donthamsetti, Prashant,Michino, Mayako,Burzynski, Caitlin,Schweppe, Catherine,Bonifazi, Alessandro,Free, R. Benjamin,Sibley, David R.,Janowsky, Aaron,Shi, Lei,Javitch, Jonathan A.,Newman, Amy Hauck
, p. 2973 - 2988 (2016/05/19)
Novel 1-, 5-, and 8-substituted analogues of sumanirole (1), a dopamine D2/D3 receptor (D2R/D3R) agonist, were synthesized. Binding affinities at both D2R and D3R were higher when determined in competition with the agonist radioligand [3H]7-hydroxy-N,N-dipropyl-2-aminotetralin (7-OH-DPAT) than with the antagonist radioligand [3H]N-methylspiperone. Although 1 was confirmed as a D2R-preferential agonist, its selectivity in binding and functional studies was lower than previously reported. All analogues were determined to be D2R/D3R agonists in both GoBRET and mitogenesis functional assays. Loss of efficacy was detected for the N-1-substituted analogues at D3R. In contrast, the N-5-alkyl-substituted analogues, and notably the n-butyl-arylamides (22b and 22c), all showed improved affinity at D2R over 1 with neither a loss of efficacy nor an increase in selectivity. Computational modeling provided a structural basis for the D2R selectivity of 1, illustrating how subtle differences in the highly homologous orthosteric binding site (OBS) differentially affect D2R/D3R affinity and functional efficacy.
2,9-DIAMINO- AND 2-AMINO-8-CARBAMOYL-4-HYDROXY-ALKANOIC ACID AMIDE DERIVATIVES
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, (2008/06/13)
Compounds of the formula I STR1 in which R 1 is arylamino, N-aryl-N-(lower alkoxy-lower alkyl)-amino, N-aryl-N-aryl-lower alkyl-amino or heterocyclyl bonded via a ring carbon atom, X is a carbonyl or methylene group, R 2 and R 3 independently of one another are hydrogen or lower alkyl or, together with the carbon atom with which they are bonded, are a cycloalkylidene radical, R 4 is hydrogen, lower alkyl, lower alkanoyl or lower alkoxycarbonyl, R 5 is hydroxyl, lower alkanoyloxy or lower alkoxycarbonyloxy, R 6 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl, cycloalkyl-lower alkyl, aryl-lower alkyl or heteroaryl-lower alkyl having 5 to 7 ring atoms in the heteroaryl ring and R 7 is hydrogen or lower alkyl, or R 6 and R. sub.7, together with the carbon atom with which they are bonded, are a cydoalkylidene radical and R 8 denotes an aliphatic, cycloaliphatic-aliphatic or heteroarylaliphatic radical, and their salts can be used as active ingredients for medicaments for treatment of high blood pressure.
