新型 2-[(2,4-二芳基-3-氮杂双环[3.3.1]壬-9-亚基)腙基]-4-苯基-2,3-二氢噻唑的合成、立体化学和体外抗菌评价。
Synthesis, stereochemistry and in vitro antimicrobial evaluation of novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-4-phenyl-2,3-dihydrothiazoles.
机构信息
Department of Image Science and Engineering, Pukyong National University, Busan 608 737, Republic of Korea.
出版信息
Bioorg Med Chem Lett. 2011 Nov 1;21(21):6301-4. doi: 10.1016/j.bmcl.2011.08.115. Epub 2011 Sep 1.
2-[(2,4-Diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-4-phenyl-2,3-dihydrothiazoles (3a-3k) have been synthesized by the cyclization of 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one thiosemicarbazones with phenacyl bromide and characterized by analytical (melting point and elemental analysis) and spectral (IR, (1)H NMR, (13)C NMR, D(2)O exchange, NOESY and mass) techniques. The novel Hantzsch products (3a-3k) were screened for their in vitro antibacterial and antifungal activities against some selected microorganisms. Structure activity relationship (SAR) for the reported compounds was studied by comparing their MIC values with standard drugs (Streptomycin and Amphotericin B). The results show that 3e against Escherichia coli and Cryptococcus neoformans3i against Bacillus Subtilis, 3b against Aspergillus flavus, and 3k against Rhizopus sp. were found to show significant growth inhibition.
2-[(2,4-二芳基-3-氮杂双环[3.3.1]壬烷-9-亚基)腙基]-4-苯基-2,3-二氢噻唑（3a-3k）是通过 2-[(2,4-二芳基-3-氮杂双环[3.3.1]壬烷-9-酮硫代缩氨基脲与苯乙酮溴的环化反应合成的，并通过分析（熔点和元素分析）和光谱（IR、（1）H NMR、（13）C NMR、D（2）O 交换、NOESY 和质谱）技术进行了表征。新型 Hantzsch 产物（3a-3k）对一些选定的微生物进行了体外抗菌和抗真菌活性筛选。通过比较它们的 MIC 值与标准药物（链霉素和两性霉素 B），研究了所报道的化合物的构效关系（SAR）。结果表明，化合物 3e 对大肠杆菌和新型隐球菌有抑制作用，3i 对枯草芽孢杆菌有抑制作用，3b 对黄曲霉有抑制作用，3k 对根霉有抑制作用。
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