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新型1,2-O-异亚丙基-α-D-木呋喃糖席夫碱连接硼酸酯的合成、表征及抗菌活性

Synthesis, characterization and antimicrobial activity of novel Schiff base tethered boronate esters of 1,2-O-isopropylidene-α-d-xylofuranose.

作者信息

Reddy Eda Rami, Trivedi Rajiv, Sudheer Kumar Buddana, Sirisha Katukuri, Sarma Akella Venkata Subrahmanya, Sridhar Balasubramanian, Prakasham Reddy Shetty

机构信息

Inorganic and Physical Chemistry Division, CSIR-IICT, Hyderabad 500007, India.

Inorganic and Physical Chemistry Division, CSIR-IICT, Hyderabad 500007, India.

出版信息

Bioorg Med Chem Lett. 2016 Aug 1;26(15):3447-52. doi: 10.1016/j.bmcl.2016.06.049. Epub 2016 Jun 18.

DOI:10.1016/j.bmcl.2016.06.049
PMID:27353535
Abstract

A series of twenty one Schiff bases based on boronate ester of 1,2-O-isopropylidene-α-d-xylofuranose scaffold were designed and synthesized by condensation of formyl or amino phenyl boronate esters with substituted anilines or 2-hydroxybenzaldehydes, respectively. All the imines are remarkably stable crystalline solids and were obtained in good yields. All the products were fully characterized by FT-IR, multinuclear NMR ((1)H, (13)C and (11)B) spectroscopy, and elemental analysis. Furthermore, the molecular structures of two of the Schiff bases were established by single crystal X-ray diffraction analysis. All the compounds have been screened for in vitro antimicrobial activity against various Gram-positive and Gram-negative bacterial and fungal strains. They exhibited moderate to good inhibitory activity against most of the tested organisms in comparison with standard drugs.

摘要

基于1,2-O-异亚丙基-α-D-木糖呋喃糖骨架硼酸酯设计并合成了一系列21种席夫碱,分别通过甲酰基或氨基苯基硼酸酯与取代苯胺或2-羟基苯甲醛缩合得到。所有亚胺均为非常稳定的结晶固体,产率良好。所有产物均通过傅里叶变换红外光谱(FT-IR)、多核核磁共振((1)H、(13)C和(11)B)光谱以及元素分析进行了全面表征。此外,通过单晶X射线衍射分析确定了两种席夫碱的分子结构。对所有化合物进行了针对各种革兰氏阳性和革兰氏阴性细菌及真菌菌株的体外抗菌活性筛选。与标准药物相比,它们对大多数测试生物体表现出中度至良好的抑制活性。

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