Facile Synthesis of Propranolol and Novel Derivatives

Abstract

Propranolol is one of the first medications of the beta-blocker used for antihypertensive drugs. This study reports the facile route for the synthesis of propranolol and its novel derivatives. Herein, propranolol synthesis proceeded from 1-naphthol and isopropylamine under mild and less toxic conditions. Novel propranolol derivatives were designed by reactions of propranolol with benzoyl chloride, pyridinium chlorochromate, and n-butyl bromide through esterification, oxidation reduction, and alkylation, respectively. The isolation and purity of compounds were conducted using column chromatography and thin-layer chromatography. Mass spectrometry and 1H-NMR spectroscopy were applied to identify new compounds structure. Propranolol derivatives from 2-chlorobenzoyl chloride (compound 3), 2-fluorobenzoyl chloride (compound 5), and especially acetic anhydride (compound 6) manifested high yields and significantly increased water solubility. Six semisynthetic propranolol derivatives promise to improve antioxidative and biological activities.

Propranolol and nifedipine efficacy against hypertension

“…The total mechanism is from the 1-naphthol and isopropylamine to propranolol [20]. The first step involves 1naphthol dissolved in the ethanol/water mixture with the ratio of 9 over 1, potassium hydroxide as the base, epichlorohydrin to form the product glycidyl 1-naphthyl ether [20].…”

“…The total mechanism is from the 1-naphthol and isopropylamine to propranolol [20]. The first step involves 1naphthol dissolved in the ethanol/water mixture with the ratio of 9 over 1, potassium hydroxide as the base, epichlorohydrin to form the product glycidyl 1-naphthyl ether [20]. Two intermediates will be formed during this process in the graph shown as 1-chloro-3-(naphthalen-1-yloxy) propan-2-ol and 2-chloro-3-(naphthalen-1yloxy)propan-1-ol [20].…”

Dual Stimuli-Responsive Multifunctional Silicon Nanocarriers for Specifically Targeting Mitochondria in Human Cancer Cells

“…Cancer cells predominantly produce chemical energy via a high rate of glycolysis, even in the presence of abundant oxygen. Therefore, this organelle is increasingly paid attention as a "prime target" for pharmacological intervention [3][4][5]. However, it is difficult for drug molecules to enter the mitochondria due to the extensively folded and compartmentalized structure of the inner mitochondrial membrane.…”

Novel α-Mangostin Derivatives from Mangosteen (Garcinia mangostana L.) Peel Extract with Antioxidant and Anticancer Potential

“…Various parts of plants, including roots, stems, leaves, fruits, flowers, and seeds, can be used as sources for the extraction of natural bioactive compounds [5][6][7][8][9]. Many studies have recently focused on the utilization of inexpensive or waste sources from the consumption and food industry for the production of valuable natural substances [2,[10][11][12]. Additionally, peels of several fruits, e.g., pomegranate, citrus, longan, sapodilla, dragon fruit, banana, and apple, have been reported to be rich in bioactive components (vitamins, flavonoids, and phenolic compounds), which promote high free radical scavenging activity [13][14][15].…”

“…Additionally, peels of several fruits, e.g., pomegranate, citrus, longan, sapodilla, dragon fruit, banana, and apple, have been reported to be rich in bioactive components (vitamins, flavonoids, and phenolic compounds), which promote high free radical scavenging activity [13][14][15]. Antioxidants scavenge the oxidants or free radicals created by multiple degenerative and disease processes, e.g., diabetes, cancer, and cardiovascular disorders [12,16,17]. erefore, finding, extraction, and semisynthesis of these active ingredients from traditional medicine play an important role in discovering the new active ingredients in antioxidant, healing, and cancer treatment processes [4,9,18,19].…”