75401-65-9Relevant academic research and scientific papers
Synthesis, biological evaluation, Structure ? Activity relationship studies of quinoline-imidazole derivatives as potent antimalarial agents
Anas, Mohammad,Kumar, Niti,Manhas, Ashan,Panda, Gautam,Roy, Deblina,Saha, Satyen
, (2022/02/17)
In our efforts to identify novel chemical scaffolds for the development of antimalarial agents, a series of quinoline ? imidazole hybrid compounds were synthesized and their blood-stage antimalarial activity was evaluated in both drug-sensitive and –multi drug-resistant (MDR) P. falciparum strains. The new analogs possess sub-micromolar activities against Plasmodium falciparum. Among all synthesized derivatives, 11(xxxii) exhibited significant antimalarial efficacy in-vitro against both CQ-sensitive (IC50-0.14 μM) and MDR strain (IC50- 0.41 μM) with minimal cytotoxicity and high selectivity. Structure-activity relationships revealed that Br and OMe substitutions on quinoline ring improved the antimalarial activity and selectivity index. The role of stereochemistry in the inhibitory activity was assessed by enantiomeric separation of a racemic mixture of 11(xxxii). The enantiomer (?)-11(xxxii) had potent antimalarial activity over the other isomer, with IC50 of 0.10 μM.
Base-Mediated 1,6-Aza-Michael Addition of Heterocyclic Amines and Amides to para-Quinone Methides Leading to Meclizine-, Hydroxyzine-and Cetirizine-like Architectures
Panda, Gautam,Roy, Deblina
, p. 4434 - 4442 (2019/11/21)
An expeditious, cost-effective synthetic methodology for a wide range of nitrogen-containing unsymmetrical trisubstituted methanes (TRSMs) is reported. The synthesis involves base-mediated 1,6-conjugate addition of heterocyclic amines and amides to substituted para-quinone methides, giving the unsymmetrical TRSMs in moderate to very good yields (up to 83percent) in one pot. The low cost, mild temperature, high atom economy and yields, easy scale-up and broad substrate scope are some of the salient features of this protocol. Further, the methodology could be extended for the synthesis of meclizine-, -hydroxyzine-and cetirizine-like molecules. The structure of one such compound, 2,6-di-tert-butyl-4-((4-chlorophenyl)(4-methylpiperazin-1-yl)methyl)phenol, was determined by single crystal X-ray analysis.
Nucleophilic reactivities of the anions of nucleobases and their subunits
Breugst, Martin,Corralbautista, Francisco,Mayr, Herbert
supporting information; experimental part, p. 127 - 137 (2012/03/09)
The kinetics of the reactions of different heterocyclic anions derived from imidazoles, purines, pyrimidines, and related compounds with benzhydrylium ions and structurally related quinone methides have been studied in DMSO and water. The second-order rate constants (logk2) correlated linearly with the electrophilicity parameters E of the electrophiles according to the correlation logk2 = sN(N+E) (H. Mayr, M. Patz, Angew. Chem. 1994, 106, 990-1010; Angew. Chem. Int. Ed. Engl. 1994, 33, 938-957) allowing us to determine the nucleophilicity parameters N and sN for these anions. In DMSO, the reactivities of these heterocyclic anions vary by more than six orders of magnitude and are comparable to carbanions, amide and imide anions, or amines. The azole anions are generally four to five orders of magnitude more reactive than their conjugate acids. Copyright
Synthesis of Mannich Bases of Bioactive Benzylphenols
Jurd, Leonard
, p. 81 - 83 (2007/10/02)
2,4-Bis(1,1-dimethylethyl)-6-phenol (4), prepared by oxidation of 2,4-bis(1,1-dimethylethyl)-6-phenol (1) with silver oxide in methanol, reacts with secondary amines in boiling toluene to give Manni
