Synthesis and antioxidant, anti-inflammatory and gastroprotector activities of anethole and related compounds.
Some derivatives of trans-anethole [1-methoxy-4-(1-propenyl)-benzene] (1) were synthesized, by introducing hydroxyl groups in the double bond of the propenyl moiety. Two types of reactions were performed: (i) oxymercuration/demercuration that formed two products, the mono-hydroxyl derivative, 1-hydroxy-1-(4-methoxyphenyl)-propane (2) and in lesser extent the dihydroxyl derivative, 1,2-dihydroxy-1-(4-methoxyphenyl)-propane (3) and (ii) epoxidation with m-chloroperbenzoic acid that also led to the formation of two products, the dihydroxyl derivative (3) and the correspondent m-chloro-benzoic acid mono-ester, 1-hydroxy-1(4-methoxyphenyl)-2-m-chlorobenzoyl-propane (4). The structures of these compounds were confirmed mainly by mass, IR, 1H and 13C NMR spectral data. The activity of anethole and hydroxylated derivatives was evaluated using antioxidant, anti-inflammatory and gastroprotector tests. Compounds (2) and (3) were more active antioxidant agents than (1) and (4). In the anti-inflammatory assay, anethole showed lower activity than hydroxylated derivatives. Anethole and in lesser extent its derivatives 2 and 4 showed significant gastroprotector activity. All tested compounds do not alter significantly the total number of white blood cells.
Freire
Rosemayre S
RS
Natural Product Chemistry Laboratory, Department of Chemistry, University of Ceará State, Av. Paranjana 1700, Campus do Itaperi, CEP 60740-000 Fortaleza, Ceará, Brazil.
Morais
Selene M
SM
Catunda-Junior
Francisco Eduardo A
FE
Pinheiro
Diana C S N
DC
D000081248:Allylbenzene Derivatives; D000818:Animals; D000840:Anisoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007958:Leukocyte Count; D008297:Male; D051379:Mice; D013276:Stomach Ulcer / Q000188:drug therapy / Q000517:prevention & control*; D013329:Structure-Activity Relationship
D000081248:Allylbenzene Derivatives; D000840:Anisoles; D000893:Anti-Inflammatory Agents; D000975:Antioxidants; C006578:anethole