37648-63-8Relevant academic research and scientific papers
Design, synthesis and structure-activity relationship of novel quinoxalin-2-carboxamides as 5-HT3 receptor antagonists for the management of depression
Mahesh, Radhakrishnan,Devadoss, Thangaraj,Pandey, Dilip Kumar,Bhatt, Shvetank,Yadav, Shushil Kumar
scheme or table, p. 6773 - 6776 (2010/12/20)
A novel series of quinoxalin-2-carboxamides were designed based on the ligand-based approach, employing a three-point pharmacophore model; it consists of an aromatic residue and a linking carbonyl group and a basic nitrogen. The target new chemical entities were synthesized from the key intermediate, quinoxalin-2-carboxylic acid, by coupling it with various amines in the presence of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl) and 1-hydroxybenzotriazole (HOBt). The obtained compounds' structures were confirmed by spectral data. The target new chemical entities were evaluated for their 5-HT3 receptor antagonisms in longitudinal muscle myenteric plexus preparation from guinea pig ileum against 5-HT3 agonist, 2-methyl-5-HT, which was expressed in the form of pA2 value. All the synthesized compounds showed antagonism towards 5-HT3 receptor; based on this result, a structure-activity relationship was derived, which reveals that the aromatic residue in 5-HT3 receptor antagonists may have hydrophobic interaction with 5-HT3 receptor. Regardless of their antagonistic potentials, all the synthesized molecules were screened for their anti-depressant potentials by using forced swim test in mice model; interestingly none of the tested compounds affect the locomotion of mice in the tested dose levels. Compounds with significant pA2 values exhibited good anti-depressant-like activity as compared to the vehicle-treated group.
Azole-N-acetonitriles as carbonyl synthons: A one-pot preparation of heteroaryl amides from halides
Zhang, Zhongxing,Yin, Zhiwei,Kadow, John F.,Meanwell, Nicholas A.,Wang, Tao
, p. 2323 - 2326 (2007/10/03)
Azole-N-acetonitrile derivatives were utilized as synthons for an ambident carbonyl moiety via a strategy relying upon sequential base-mediated S NAr substitution of a 2-halo heterocycle, in situ oxidation, and amine displacement. This strategy allows prompt and efficient synthesis of N-containing heteroaryl amides directly from the corresponding halides via a one-pot process.
SYNTHESE VON CHINOXALIN- UND INDOL-2,3-DICARBONSAUREIMIDEN
Augustin, M.,Kohler, M.,Faust, J.,Al-Holly, M. M.
, p. 1801 - 1805 (2007/10/02)
Quinoxaline- and indole-2,3-dicarboxylic imides 7,8 are prepared by reaction of halogenactive maleimides 1,2 with sodium azide.Further derivatives of these heterocyclic series are available by secondary reactions of the imides.
