ChemInform Abstract: Synthesis and Antihypertensive Effects of New Methylthiomorpholinphenol Derivatives.

Abstract

Antihypertensive activity X 0120Synthesis and Antihypertensive Effects of New Methylthiomorpholinphenol Derivatives. -The novel compounds (I) are evaluated for their antihypertensive activity. The results are discussed in detail in comparison with other cardiovascular drugs such as captopril, losartan and omapatrilat. LQM303 (Ic) exhibits the best decreasing effect in both systolic and diastolic pressure and the best heart rate decreasing effect. -(VELAZQUEZ, A. M.; MARTINEZ, L.; ABREGO, V.; BALBOA, M. A.; TORRES, L. A.; CAMACHO, B.; DIAZ-BARRIGA, S.; ROMERO, A.; LOPEZ--CASTANARES, R.; ANGELES*, E.; Eur.

More Sustainable Approaches for the Synthesis of N-Based Heterocycles

“…The simplest six-membered N-heterocyclic compound, piperidine, can be modified at the nitrogen position in a solvent-free Mannich reaction by the use of infrared light. The experimental procedure consists of irradiating a mixture of a phenol, formaldehyde, and piperidine with a medicinal infrared lamp (which reaches 120−180 °C) to yield methylpiperidinyl phenols in up to 25 min (Table ) . Morpholine and thiomorpholine can also be used as amines to yield the correspondent phenols after infrared irradiation.…”

Modification of Bicyclic Phosphonates Based on Resorcinols and Its Derivatives via the Mannich Reaction

“…The mixture of (0.5 g; 1.5 mmol) bicyclic phosphonate 1, (0.27 g; 3 mmol) morpholine 4b, and (0.09 g; 3 mmol) paraformaldehyde in 20 mL benzene was kept under reflux with the Dean-Stark adapter for 12 h (until the evolution of water stops). Yield: 0.23 g (27% 3,8 .0 10,15 ]-heptadeca-3,5,7,10,12,14-hexaene 1-oxide (7) The mixture of (0.3 g; 1.0 mmol) bicyclic phosphonate 2, (0.35 g; 4.0 mmol) morpholine 4b, and (0.12 g; 4.0 mmol) paraformaldehyde in 20 mL benzene was kept under reflux with the Dean-Stark adapter for 16 h (until the evolution of water stops). The formed precipitate was filtered and dried in vacuum up to a constant weight.…”

“…The reaction proceeds according to electrophilic aromatic substitution, and the attack of carbocation may be directed at both ortho-and parapositions relative to hydroxyl groups of phenol [13][14][15]. In general, these compounds are prepared by the condensation of corresponding phenol with formaldehyde and amine (primary or secondary).…”

“…Dihydroxy-4,14-dimethyl-6,12di(diethylaminomethyl)-2,16-dioxa-1phosphatetracyclo-[7.7.1.03,8 .010,15 ]-heptadeca-3,5,7,10,12,14-hexaene 1-oxide (5a)The mixture of (0.5 g; 1.5 mmol) bicyclic phosphonate 1, (0.23 g; 3 mmol) diethylamine 4a, and (0.09 g; 3 mmol) paraformaldehyde in 20 mL benzene was kept under reflux with a Dean-Stark adapter for 12 h (until the evolution of water stops).The solvent was removed; residue was grinded in diethyl ether and dried in vacuum up to a constant weight. Yield 0.30 g (39%) mp >350 о С. IR: 1266, 1613, 3436.…”

Determination of Acidity Constants, Partition Coefficients between Water and 1-Octanol, and Deprotonation Route of 4-tert-buthyl-bis-(2,6-thiomorpholin-4-ylmethyl)-1-phenol and 4-hydroxy-3,5-bis(morpholin-1-ylmethyl)benzonitrile; Compounds with Antihypert

“…These researchers proposed that the presence of phenol and pyrrolidine rings are structural key factors for the antiarrhythmic effects. More recently, Velázquez et al [8,9] synthesized a series of compounds, usually referred to as LQM's, which exhibit antihypertensive effects. Compared to changrolin derivatives, these compounds present morpholin and thiomorpholin rings instead of the pyrrolidine ring (Scheme 1).…”