ABSTRACT
The phenothiazine nucleus is known for their inhibitory activity towards the regulatory enzymes that are contributing to diseases such as asthma, autoimmune diseases including allergic rheumatoid and encephalomyelitis. In this study a number of substituted phenothiazines were synthesized and screened for their biological activity against the regulatory enzymes involved in inflammatory diseases. Our results show that the newly synthesized compounds 4a-c and 5a-c exhibited promising target specific enzyme inhibition against phosphodiesterase, prostaglandin dehydrogenase and superoxide dismutase activity depending on steric factors of the molecules.
Subject(s)
Anti-Inflammatory Agents/chemical synthesis , Phenothiazines/chemical synthesis , Anti-Inflammatory Agents/pharmacology , Asthma/drug therapy , Autoimmune Diseases/drug therapy , Enzyme Inhibitors , Humans , Inflammation/drug therapy , Inflammation/enzymology , Phenothiazines/pharmacology , Phosphodiesterase Inhibitors , Structure-Activity Relationship , Superoxide Dismutase/antagonists & inhibitorsABSTRACT
The molecules of (+/-)-2-(4-methoxyphenyl)-1-phenethyl-2,3-dihydroquinazolin-4(1H)-one, C(23)H(22)N(2)O(2), (I), and (+/-)-2-(1,3-benzodioxol-5-yl)-1-phenethyl-2,3-dihydroquinazolin-4(1H)-one, C(23)H(20)N(2)O(3), (II), have T-shaped forms in the crystal structure. The tetrahydropyrimidine ring in both structures adopts a sofa conformation. Both molecules are linked by N-H...O and C-H...O hydrogen bonds to form sheets built from alternating R(2)(2)(8) and R(4)(4)(26) [R(4)(4)(24) in (II)] edge-fused rings. Additionally, the structures are stabilized by extensive C-H...pi interactions.
Subject(s)
Quinazolinones/chemistry , Crystallography, X-Ray , Hydrogen Bonding , Molecular ConformationABSTRACT
The title compound, C22H19N3O2S, crystallizes in two polymorphic forms having the same space group, viz. P-1, with Z' = 2 and Z' = 1. In both polymorphs, the planar thiazole ring is fused cis with the dihydropyrimidine ring, the carbamoyl group is in an extended conformation with an anticlinal orientation with respect to the pyrimidine ring, and the phenyl ring is attached to the pyrimidine ring approximately at a right angle. The two polymorphs have different interplanar angles between the phenyl and thiazole rings. The molecules are linked by N-H...O and C-H...O hydrogen bonds.
