72503-43-6Relevant academic research and scientific papers
Synthesis and Docking of Novel 3-Indolylpropyl Derivatives as New Polypharmacological Agents Displaying Affinity for 5-HT1AR/SERT
Pessoa-Mahana, Hernán,Silva-Matus, Paul,Pessoa-Mahana, C. David,Chung, Hery,Iturriaga-Vásquez, Patricio,Quiroz, Gabriel,M?ller-Acu?a, Patricia,Zapata-Torres, Gerald,Saitz-Barría, Claudio,Araya-Maturana, Ramiro,Reyes-Parada, Miguel
, (2017/01/10)
A series of novel 3-indolylpropyl derivatives was synthesized and evaluated for their binding affinities at the serotonin-1A receptor subtype (5-HT1AR) and the 5-HT transporter (SERT). Compounds 11b and 14b exhibited the highest affinities at the 5-HT1AR (Ki = 43 and 56 nM), whereas compounds 11c and 14a were the most potent analogs at the SERT (Ki = 34 and 17 nM). On the other hand, compounds 14b and 11d showed potent activity at both targets, displaying a profile that makes them promising leads for the search for novel potent ligands with a dual mechanism of action. Molecular docking studies in all the compounds unveiled relevant drug–target interactions, which allowed rationalizing the observed affinities.
Synthesis and anticonvulsant evaluation of some new 1,3,4,5-tetrahydro-6- Alkoxy-2H-1-benzazepin-2-one derivatives
Han, Rong-Bi,Shao, Yun-Peng,Wu, Hui-Fan,Zhang, Duo,Piao, Feng-Yu
, p. 2810 - 2820 (2014/05/06)
A series of new 1,3,4,5-tetrahydro-6-Alkoxy-2H-1-benzazepin-2-one derivatives were synthesized and screened for their anticonvulsant activities by the maximal electroshock (MES) test, subcutaneous pentylenetetrazol (scPTZ) test, and their neurotoxicity was evaluated by the rotarod neurotoxicity test. The results of these tests showed that 1,3,4,5-tetrahydro-6-octyloxy-2H-1- benzazepin-2-one (4f) was the most promising compound, with median effective dose (ED50) of 20.4 mg/kg, and protective index (PI) value of 20.1 in the MES test, which is much higher than the PI value of the prototype antiepileptic drug carbamazepine (PI = 8.1), phenytoin (PI = 6.9), phenobarbital (PI = 3.2), and sodium valproate (PI = 1.6). The scPTZ test displayed that 1,3,4,5-tetrahydro-6-heptyloxy-2H-1-benzazepin-2-one (4e) was the most active compound (ED50 = 64.4, PI = 2.6). The possible structure-Activity relationship was discussed.
2,4-DIAMINO-6,7-DIHYDRO-5H-PYRROLO[2,3]PYRIMIDINE DERIVATIVES AS FAK/Pyk2 INHIBITORS
-
Page/Page column 54-55, (2012/07/27)
The invention relates to a novel class of 2,4-diamino-6,7-dihydro-5H-pyrrolo[2,3]pyrimidine derivatives as a FAK and/or Pyk2 inhibitor, to a process for their preparation, and to a composition thereof, as well as to use of the compounds for the inhibiting FAK and/or Pyk2 and method for the treatment of a FAK and/ or Pyk2 mediated disorder or disease.
The application of the schmidt reaction and beckmann rearrangement to the synthesis of bicyclic lactams: Some mechanistic considerations
Crosby, Ian T.,Shin, James K.,Capuano, Ben
experimental part, p. 211 - 226 (2011/06/21)
The syntheses of some methoxy-substituted bicyclic lactams, of the types 3 and 4, are reported employing two different conditions for the Schmidt reaction of appropriate ketones and employing two different conditions for the Beckmann rearrangement of the corresponding ketoximes. The alkyl to aryl migration ratios of the reactions were determined by high-performance liquid chromatography analysis of the reactions. The mechanisms of the reactions reported are discussed, some limitations of the reported mechanisms identified, and an alternative mechanism proposed in light of the outcomes of the various reactions. Application of the Schmidt reaction and Beckmann rearrangement was used for the synthesis of some chloro bicyclic lactams, of the types 3 and 4. CSIRO 2010.
Dynamic and static conformational analysis of acylated tetrahydrobenzazepines
Hassner, Alfred,Amit, Boaz,Marks, Vered,Gottlieb, Hugo E.
, p. 6853 - 6858 (2007/10/03)
A detailed high-field NMR analysis of several acylated tetrahydrobenzazepines, supported by molecular mechanics calculations, indicates that the heterocyclic ring in these compounds exists in a chair conformation, with the carbonyl oriented anti to the aryl moiety in the dominant rotamer. Surprisingly, ring methylenes are typically diastereotopic at room temperature, as the barriers for the process of enantiomerization of the seven-membered ring are much higher than expected. It is shown that ring inversion is correlated (but not concerted) with rotation of the amide moiety, as the carbonyl is forced out of conjugation with the nitrogen in the transition state.
Studies on quinones. Part 22. Synthesis of 1-benzazepine-6,9-quinone derivatives
Valderrama,Pessoa-Mahana,Tapia
, p. 629 - 639 (2007/10/02)
A facile synthesis of 1,2,3,4-tetrahydro-5H-1-benzazepine-quinone derivatives starting from 5-methoxy-1-tetralone is described.
Aminopropanol derivatives of 6-hydroxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one and pharmaceutical formulations containing the said compounds
-
, (2008/06/13)
Aminopropanol derivatives of 6-hydroxy-2,3,4,5-tetrahydro-1-H-1-benzazepin-2-one of the formula STR1 where R is alkyl of 1 to 6 carbon atoms, which is unsubstituted or substituted by hydroxyl or by alkoxy of 1 to 3 carbon atoms, or is alkenyl or alkynyl o
