Demİr Şemsi Betül, SeÇİntİ Hatice, ÇelebİoĞlu Neslihan, Özdal Murat, Sezen Alev, GÜlmez Özlem, Algur Ömer Faruk, SeÇen Hasan
Department of Chemistry, Faculty of Sciences, Atatürk University, Erzurum Turkey.
Department of Biology, Faculty of Sciences, Atatürk University, Erzurum Turkey.
Turk J Chem. 2020 Jun 1;44(3):589-601. doi: 10.3906/kim-1911-61. eCollection 2020.
Four linear nonphenolic diarylheptanoids were synthesized and their antibacterial activities were studied. ( )-2-Me-CBS-catalysed reduction of alnustone with BHSMe gave ( )(-)(4 ,6 )-1,7-diphenylhepta-4,6-dien-3-ol, a natural product. Reduction of alnustone with Na in -BuOH at -15 °C under N atm gave ()-1,7-diphenylhept-5- en-3-one as a Birch-type reduction product. -BuOK catalysed condensation of benzalacetone with propionyl chloride gave (4 ,6 )-5-hydroxy-1,7-diphenylhepta-4,6-dien-3-one, a natural product. (1 ,4 ,6 )-5-Hydroxy-4-phenethyl-1,7-diphenylhepta-1,4,6-trien-3-one, a curcuminoid, was synthesized starting from pentan-2,4-dione in 3 steps. The synthesized chemical compounds were applied against 2 gram-positive bacteria ( and ), 4 gram-negative bacteria ( , , , and ), and 1 yeast (Candida albicans) by the disc diffusion method. All of the synthesized compound exhibited different degrees of antimicrobial activity at concentrations between 20-100 μg/disc against the test organisms.
合成了四种线性非酚类二芳基庚烷类化合物，并研究了它们的抗菌活性。用BHSMe在()-2-Me-CBS催化下还原阿尔努酮得到一种天然产物()-(-)(4,6)-1,7-二苯基庚-4,6-二烯-3-醇。在氮气气氛下，于-15℃用钠在正丁醇中还原阿尔努酮得到()-1,7-二苯基庚-5-烯-3-酮作为Birch型还原产物。用叔丁醇钾催化苯亚甲基丙酮与丙酰氯缩合得到一种天然产物(4,6)-5-羟基-1,7-二苯基庚-4,6-二烯-3-酮。以戊-2,4-二酮为起始原料，分三步合成了一种姜黄素类化合物(1,4,6)-5-羟基-4-苯乙基-1,7-二苯基庚-1,4,6-三烯-3-酮。采用纸片扩散法将合成的化合物应用于2种革兰氏阳性菌(和)、4种革兰氏阴性菌(、、、)和1种酵母(白色念珠菌)。所有合成的化合物在20-100μg/纸片的浓度下对受试微生物均表现出不同程度的抗菌活性。
