Synthesis of (R)-(6-Methoxyquinolin-4-yl)[(1S,2S,4S,5R)-5-vinylquinuclidin-2-yl]methanol Tetraphenylborate Ion-Pair Complex: Characterization, Antimicrobial, and Computational Study
-
Published:2023-10-08
Issue:19
Volume:28
Page:6974
-
ISSN:1420-3049
-
Container-title:Molecules
-
language:en
-
Short-container-title:Molecules
Author:
Yousef Tarek A.1, Alrabiah Haitham2, Al-Agamy Mohamed H.3ORCID, Al-Salahi Rashad2ORCID, Ali Essam A.2ORCID, Mostafa Gamal A. E.2ORCID
Affiliation:
1. Chemistry Department, College of Science, Imam Mohammad Ibn Saud Islamic University (IMSIU), Riyadh 11623, Saudi Arabia 2. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia 3. Department of Pharmaceutics, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.
Abstract
The (R)-(6-Methoxyquinolin-4-yl)[(1S,2S,4S,5R)-5-vinylquinuclidin-2-yl]methanol (quinine)-tetraphenylborate complex was synthesized by reacting sodium tetraphenyl borate with quinine in deionized water at room temperature through an ion-pair reaction (green chemistry) at room temperature. The solid complex was characterized by several physicochemical methods. The formation of ion-pair complex between bio-active molecules and/or organic molecules is crucial to comprehending the relationships between bioactive molecules and receptor interactions. The complex under study was examined for antimicrobial activity. All theoretical calculations were carried out in vacuum and water using the B3LYP level 6–311G(d,p) levels of theory. The theoretical computation allowed for the prediction and visualization of ionic interactions, which explained the complex’s stability. The results of energy optimization showed that the Q-TPB complex is stable with a negative complexation energy. The obtained geometries showed that the boron (B−) and nitrogen (N+) in piperidine of the two molecules tetraphenylborate and quinine are close to each other, which makes it possible for ions to interact. The modest energy gap between HOMO and LUMO showed that the compound was stable. The computation of the electron transitions of the two models by density functional theory (TD-DFT) in the solvent at the theoretical level B3LYP/6–311G(d,p) allowed for the detection of three UV/visible absorption bands for both models and the discovery of a charge transfer between the host and the guest. The UV absorption, infrared, and H NMR are comparable with the experimental part.
Funder
Deputyship for Research and Innovation, “Ministry of Education” in Saudi Arabia
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Reference40 articles.
1. Pósa, S.P., Dargó, G., Nagy, S., Kisszékelyi, P., Garádi, Z., Hámori, L., Szakács, G., Kupai, J., and Tóth, S. (2022). Cytotoxicity of cinchona alkaloid organocatalysts against MES-SA and MES-SA/Dx5 multidrug-resistant uterine sarcoma cell lines. Bioorg. Med. Chem., 67. 2. Antimalarial pharmacokinetics and treatment regimens;White;Br. J. Clin. Pharmacol.,1992 3. Drug development: Holding out for reinforcements;Eisenstein;Nature,2012 4. Construction and performance of probe-type cells connected in a series assembly;Wanli;Talanta,1992 5. Fabrication of Quinine-Sensitive Membrane Electrodes and Their Properties;Anzai;Chem. Pharm. Bull.,1985
Cited by
1 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献
|
|