Synthesis of new propanolamine derivatives with potential antihypertensive activity.

number: 
513
إنجليزية
department: 
Degree: 
Imprint: 
Chemistry
Author: 
Omar Sinan Abdul-Razzak Al-Rahbi
Supervisor: 
Dr. Nazar Al-Nasiry
Dr.Khulood Al-Sameraei
year: 
2001

Abstract:

This work describes the synthesis of some new propanolamine derivatives and studies some of their biological properties. Many 2-propanolamine derivatives have been extensively studied and are known to posses high degree of cardioselectivity and adrenergic blocking potency β-adrenergic blocking agents can
be used to treat many medical conditions, they are primarily used to treat high blood pressure (hypertension), but are also useful for reducing the risk of second heart attack, chest pain (angina), irregular heart beat (arrhythmias), β- blockers have been prescribed in combination with other medications for the treatment of congestive heart failure. Most compounds available for clinical uses belong to the aryloxypropanolamine series, which are considered a second generation of β-blocking agents. Four series of compounds have been synthesized, the aryloxypropanolamine series with an ether linkage i. Series two: Containing compounds [2a-e]. ii. Series four: Containing compounds [4a-e]. And others having thioemer linkage (thiopropanolamine), iii. Series three: Containing compounds [3a-e]. iv. Series five: Containing compounds [5a-e]. Compounds [laf] have been synthesized upon the reaction of 2°-amine with epichlorohydrine at room temperature under SN2 mechanism to give 1 -amino-3-chloro-2-hydroxy propane [1 a- f]. All series of compounds [2a-e], [3a-e], [4a-e] and [5a-e] have been synthesized by the reaction of p-hydroxy acetophenone, 2-mercapto benzothiazole, vaniline and 4-methyl (3-mercapto-4-phenyl-4H-l,2,4- triazole-5-yl) methyl piperazine, with propanolamines [la-e] in the presence of potassium hydroxide and ethanol as a solvent The invented compounds were designed as β-adrenoceptor antagonist to have antihypertensive activity. The biological tests were achieved on many groups of mice, the results of these tests showed that the most effective derivatives as hypotensive agents were From series [2a-e] compound [2e].- From series [3a-e] compound [3b]. From series [4a-e] compound [4b]. From series [5a-e] compound [5e]. All the synthesized compounds were characterized by IR, FTIR spectral data, and some by mass spectra.