Armed Imidazo [1,2-a] Pyrimidines (Pyridines): Evaluation of Antibacterial Activity

Synthesis of a series of fourteen novel 2,3',4'-tri-subsituted-1,2-dihydro-4H,4'Hspiro[isoquinoline-3,5'-isoxazol]-4-ones was accomplished in good yield by regio and stereoselective 1,3-dipolar cycloaddition of p-R 2 -benzadoxime 4-8 with dipolarophiles (3Z)-3-The structure of the isolated products 9-23 was established through different spectroscopic techniques. X-Ray crystal structure analysis of one of the products confirms the structure and the selective region and stereochemistry of this cycloaddition. Their antitubercular activity is also evaluated.

Section: And Antibacterial Agents (Gram+ Andmentioning

confidence: 99%

Looking for a new antitubercular pharmacophore site: synthesis and bioactivity of spiroheterocycles 2,3',4'-tri-subsituted-1,2-dihydro-4H,4'H-spiro[isoquinoline-3,5'-isoxazol]-4-ones

Hadda¹,

Rahima²,

Kerbal³

et al. 2007

“…These studies have shown that compounds bearing a formyl-, hydroxyl-or nitroso-side chains in position 3 are highly active as antitubercular agents 5 as well as antibacterial agents. 6 General structure/activity relationship observations allowed us to suggest that functionalized side chain(s) characterized by groups such as [N-C-N=O], [N-C-C-O] or [N-C-C=O] are crucial for the bioactivity of certain chemical compounds. The two terminal atoms (N and O) are critical for the interactions with the bacterial cell receptor, therefore are responsible for antimicrobial activities, in particularly against Mycobacterium Tuberculosis (MBT).…”

Section: Introductionmentioning

confidence: 99%

Drug design of new antitubercular agents: 1,3-dipolar cycloaddition reaction of arylnitriloxides and 3-para-methoxy-benzylidene-isochroman-4-ones

Houari¹,

Kerbal²,

Bennani³

et al. 2008

Five new 3',4'-substituted-spiro[isochromene-3,5'-isoxazolin]-4(1H)-ones 7-11 have been prepared in the reaction of p-R-benzadoxime 2-6 with 3-para-methoxy-benzylidene-isochroman-4-one 1. The reaction occurs by a 1,3-dipolar cycloaddition mechanism which leads to the regiospecific formation of various spiro-isoxazolines 7-11. It is concluded that rigid (O 1'group may be responsible for the biological activity observed in antitubercular test with these hyper inter-organised spiro-isoxazoline derivatives. However, subtle alteration by addition of a substituted aryl groups affecting the charge distribution of the terminal heteroatom O 1' confers significant improvements in biological effects.

“…5 We have also demonstrated the direct impact of dipolar in drug design of functionalised bisarmed quinoxaline 6 and imidaz[1,2-a]pyridine (or pyrimidine) ligands. 7,8 In connection with our research aimed at developing new pharmacophore site(s) leading us to efficient and selective antitubercular, 9 antitumoral 10 or anti-HIV drugs, 11 we became interested in the pharmacomodulation of parent drugs, as like the ethambutol; a clinical antitubercular agent.…”

Section: Introductionmentioning

confidence: 99%

3LYP theoretical calculations and structure of 4-[(2-{[(1E)-1-methyl-3-oxobutylidene]amino}ethyl)imino]pentan-2-one

Benjelloun¹,

Akkurt²,

Yıldırım³

et al. 2008

In this work we present the synthesis 4-[(2-{[(1E)-1-methyl-3-oxobutylidene]amino} ethyl)imino]pentan-2-one. We also propose evidence for the presence of various tautomers for this molecule, and theoretical density functional theory (DFT)-B3LYP/6-31G* calculations to characterize the potential energy surface of these species. NMR, IR, MS techniques and X-ray are also used to analyze the molecule 3 and its tautomeric preferential form.