6831-57-8Relevant academic research and scientific papers
In vitro functional evaluation of isolaureline, dicentrine and glaucine enantiomers at 5-HT2 and α1 receptors
Heng, Hui Li,Chee, Chin Fei,Thy, Chun Keng,Tee, Jia Ti,Chin, Sek Peng,Herr, Deron R.,Buckle, Michael J. C.,Paterson, Ian C.,Doughty, Stephen W.,Abd. Rahman, Noorsaadah,Chung, Lip Yong
, p. 132 - 138 (2018/10/15)
Compounds with activity at serotonin (5-hydroxytryptamine) 5-HT2 and α1 adrenergic receptors have potential for the treatment of central nervous system disorders, drug addiction or overdose. Isolaureline, dicentrine and glaucine enantiomers were synthesized, and their in vitro functional activities at human 5-HT2 and adrenergic α1 receptor subtypes were evaluated. The enantiomers of isolaureline and dicentrine acted as antagonists at 5-HT2 and α1 receptors with (R)-isolaureline showing the greatest potency (pKb?=?8.14 at the 5-HT2C receptor). Both (R)- and (S)-glaucine also antagonized α1 receptors, but they behaved very differently to the other compounds at 5-HT2 receptors: (S)-glaucine acted as a partial agonist at all three 5-HT2 receptor subtypes, whereas (R)-glaucine appeared to act as a positive allosteric modulator at the 5-HT2A receptor.
COMPOUNDS AND METHODS FOR THE TREATMENT OF NON?ALCOHOLIC STEATOHEPATITIS
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Paragraph 00350; 00351; 00352; 00353, (2019/06/23)
Compounds and compositions are provided having the structure of Formula (I) or a pharmaceutically acceptable salt, tautomer, or stereoisomer thereof, wherein T, T', U, U', V, W, R1, R2, R3', n, o, o', o'', and o''' are as
Novel Series of Dihydropyridinone P2X7 Receptor Antagonists
Lopez-Tapia, Francisco,Walker, Keith A. M.,Brotherton-Pleiss, Christine,Caroon, Joanie,Nitzan, Dov,Lowrie, Lee,Gleason, Shelley,Zhao, Shu-Hai,Berger, Jacob,Cockayne, Debra,Phippard, Deborah,Suttmann, Rebecca,Fitch, William L.,Bourdet, David,Rege, Pankaj,Huang, Xiaojun,Broadbent, Scott,Dvorak, Charles,Zhu, Jiang,Wagner, Paul,Padilla, Fernando,Loe, Brad,Jahangir, Alam,Alker, André
, p. 8413 - 8426 (2015/11/24)
Identification of singleton P2X7 inhibitor 1 from HTS gave a pharmacophore that eventually turned into potential clinical candidates 17 and 19. During development, a number of issues were successfully addressed, such as metabolic stability, plasma stability, GSH adduct formation, and aniline mutagenicity. Thus, careful modification of the molecule, such as conversion of the 1,4-dihydropyridinone to the 1,2-dihydropyridinone system, proper substitution at C-5″, and in some cases addition of fluorine atoms to the aniline ring allowed for the identification of a novel class of potent P2X7 inhibitors suitable for evaluating the role of P2X7 in inflammatory, immune, neurologic, or musculoskeletal disorders.
DIHYDROPYRIDONE AMIDES AS P2X7 MODULATORS
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Page/Page column 24-25, (2010/07/04)
Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein m, n, R1, R2, R3, R4 and R5 are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of diseases associated with the P2X7 purinergic receptor.
First total syntheses of (±)-isopiline, (±)-preocoteine, (±)-oureguattidine and (±)-3-methoxynordomesticine and the biological activities of (±)-3-methoxynordomesticine
Nimgirawath, Surachai,Udomputtimekakul, Phansuang,Taechowisan, Thongchai,Wanbanjob, Asawin,Shen, Yuemao
experimental part, p. 368 - 376 (2009/12/27)
A convenient and economical synthesis of 4-hydroxy-2,3- dimethoxybenzaldehyde has been developed. This was used as the starting material for the first total syntheses of (±)-isopiline, (±)-preocoteine, (±)-oureguattidine and (±)-3-methoxynordomesticine in
The palladium-catalyzed preparation of condensed tetracyclic heterocycles and their application to the synthesis of rac-mangochinine
Vincze, Zoltan,Biro, A. Beatrix,Csekei, Marton,Timari, Geza,Kotschy, Andras
, p. 1375 - 1385 (2007/10/03)
Dihydroisoquinoline derivatives and their analogues, prepared by the Bischler-Napieralsky reaction, were converted to their indole-fused derivatives. Scope and limitations of the palladium-catalyzed reaction, proceeding through the tautomeric enamine forms of these compounds, were studied and the process was extended to the preparation of racemic mangochinine. Georg Thieme Verlag Stuttgart.
Bischler-napieralski reaction of n-[2-(2-bromo-4,5-dialkyloxyphenyl)ethyl]-n-(1-phenylethyl)-2- (2-bromo-4,5-dimethoxyphenyl)acetamides
Hashimoto, Naomi,Miyatani, Kumiko,Ohkita, Keiko,Ohishi, Yoshitaka,Kunitomo, Jun-Ichi,Kawasaki, Ikuo,Yamashita, Masayuki,Ohta, Shunsaku
, p. 2149 - 2161 (2007/10/03)
Direction of Bischler-Napieralski reaction of N-[2-(2-bromo- or 2-unsubstituted 4,5-dialkoxyphenyl)ethyl]-N-(1-phenylethyl)-2- (2-bromo-4,5-dimethoxyphenyl)acetamides is discussed.
Revisiting the Ullmann-ether reaction: A concise and amenable synthesis of novel dibenzoxepino[4,5-d]pyrazoles by intramolecular etheration of 4,5-(o,o′-halohydroxy)arylpyrazoles
Olivera, Roberto,SanMartin, Raul,Churruca, Fatima,Dominguez, Esther
, p. 7215 - 7225 (2007/10/03)
A concise synthesis of a series of novel dibenzoxepino[4,5-d]pyrazoles was accomplished by implementation of an intramolecular Ullmann-ether reaction on o,o'-halohydroxy-4,5-diarylpyrazoles mediated by CuBr·DMS. An alternative useful approach based on the palladium-catalyzed biarylether linkage formation (Buchwald-Hartwig reaction) was also successfully applied, offering limitations with regard to the steric demand of the substituents. The synthesis of the key o,o′-halohydroxy-4,5-diarylpyrazole intermediates proceeds through the construction of the heterocyclic ring by a tandem amine-exchange/heterocyclization sequence of 3-N,N-(dimethylamino)-1,2-diarylpropenones with phenylhydrazine followed by basic hydrolysis for deprotection. The enamino ketone precursors were conveniently prepared from the corresponding O-sulfonyloxy and O-benzoyloxy ortho-substituted 1,2-diarylethanones, starting from inexpensive salicylaldehyde or phenylacetic derivatives. Preliminary binding affinity experiments against peripheral and central nervous system receptors have been done with negative results.
FORMATION OF ANOMALOUS PRODUCTS IN THE LEUCKART REACTION OF THE 2-BROMO-4,5-DIMETHOXYBENZYL 2-HYDROXY-3,4-DIMETHOXYPHENYL KETONE
Dominguez, Esther,Lete, Esther,Villa, M. Jesus,Iriondo, Carmen
, p. 1217 - 1224 (2007/10/02)
The Leuckart reaction of the 2-bromo-4,5-dimethoxybenzyl 2-hydroxy-3,4-dimethoxyphenyl ketone (2) afforded, not the expected amine, but three anomalous products: the stilbene (3), the isoflavone (4) and the pyrimidine (5).Their structures have been establ
