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Synthesis of (4S)‐4‐C‐spiro‐glycosyl‐chromeno‐[3,4‐d][1,2,3]triazoles: Biological evaluation and molecular docking investigation
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-09-13 , DOI: 10.1002/jhet.4151 Deepak Ranjan Mishra 1 , Sabita Nayak 1 , Bishnu Prasad Raiguru 1 , Seetaram Mohapatra 1 , Mana Bhanjan Podh 2 , Chita Ranjan Sahoo 3, 4 , Rabindra Nath Padhy 3
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-09-13 , DOI: 10.1002/jhet.4151 Deepak Ranjan Mishra 1 , Sabita Nayak 1 , Bishnu Prasad Raiguru 1 , Seetaram Mohapatra 1 , Mana Bhanjan Podh 2 , Chita Ranjan Sahoo 3, 4 , Rabindra Nath Padhy 3
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Microwave assisted a novel methodology have developed to obtain (4S)‐4‐C‐spiro‐glycosyl‐chromeno‐[3,4‐d][1,2,3]triazolesfollowing 1,3‐ dipolarcycloadditionreaction of 2‐C‐Spiro‐Glycosyl‐3‐Nitrochromenes with sodium azide in dry DMF at 100W, 120 oC for 1 minute. The structure of the product was assigned by 1H, 13C NMR and HRMS data and confirmed by single crystal X‐ray study.“2‐C‐Spiro‐Glycosyl‐3‐Nitrochromenes were synthesized byoxa‐Michael‐Aldol reaction of sugar derived 3‐C‐vinyl nitro olefin with substituted salicylaldehydes using Et3N as base in neat at rt‐40 oC.”This protocol was found to be cost effective, easily accessible, wide substrate scopewithhigh yield and high purityin a very short reaction time. Futhermore, in vitro antibacterial activity of these synthesized compounds have examined against E. coli and S. aureus. The compound 24bhave antibacterial activity against S. aureus DNA gyrase having zone of inhibition at value 19±0.5 mm and concomitant MIC value at 25 μg/ml respectively.Consequently, molecular docking results agreed with in vitrostudy and the docking results confirmed that compound 24bhad binding affinity ‐9.8 and ‐8.9 against DNA gyrase and DHPS of S. aureus.
中文翻译：
（4S）-4-C-螺-糖基-chromeno- [3,4-d] [1,2,3]三唑的合成：生物学评估和分子对接研究
微波辅助的一种新颖的方法已经开发，以获得（4-小号）-4- Ç -螺糖基- chromeno- [3,4-d] [1,2,3] triazolesfollowing 1,3- dipolarcycloadditionreaction 2- Ç -螺在干燥的DMF中于100W，120 o C的条件下将叠氮化钠中的‐Glycosyl-3-Nytrochromenes与叠氮化钠混合1分钟。该产物的结构由1 H，13 C NMR和HRMS数据确定，并由单晶X射线研究证实。“ 2 - C-螺-糖基-3-硝基苯二酮是通过糖衍生的氧杂-迈克尔-奥尔多反应合成的以Et 3 N为碱在rt-40 o处纯净的3‐ C‐乙烯基硝基烯烃与取代的水杨醛发现该方案具有成本效益，易于获得，底物范围广，产率高，纯度高，反应时间短等优点。此外，已经检查了这些合成的化合物对大肠杆菌和金黄色葡萄球菌的体外抗菌活性。化合物24b对金黄色葡萄球菌DNA促旋酶具有抑菌作用，其抑菌圈分别为19±0.5 mm和MIC值为25μg/ ml，因此，分子对接结果与体外研究相符，对接结果证实了该化合物24b对金黄色葡萄球菌的DNA促旋酶和DHPS的结合亲和力分别为9.8和8.9 。
更新日期：2020-10-02
中文翻译：
（4S）-4-C-螺-糖基-chromeno- [3,4-d] [1,2,3]三唑的合成：生物学评估和分子对接研究
微波辅助的一种新颖的方法已经开发，以获得（4-小号）-4- Ç -螺糖基- chromeno- [3,4-d] [1,2,3] triazolesfollowing 1,3- dipolarcycloadditionreaction 2- Ç -螺在干燥的DMF中于100W，120 o C的条件下将叠氮化钠中的‐Glycosyl-3-Nytrochromenes与叠氮化钠混合1分钟。该产物的结构由1 H，13 C NMR和HRMS数据确定，并由单晶X射线研究证实。“ 2 - C-螺-糖基-3-硝基苯二酮是通过糖衍生的氧杂-迈克尔-奥尔多反应合成的以Et 3 N为碱在rt-40 o处纯净的3‐ C‐乙烯基硝基烯烃与取代的水杨醛发现该方案具有成本效益，易于获得，底物范围广，产率高，纯度高，反应时间短等优点。此外，已经检查了这些合成的化合物对大肠杆菌和金黄色葡萄球菌的体外抗菌活性。化合物24b对金黄色葡萄球菌DNA促旋酶具有抑菌作用，其抑菌圈分别为19±0.5 mm和MIC值为25μg/ ml，因此，分子对接结果与体外研究相符，对接结果证实了该化合物24b对金黄色葡萄球菌的DNA促旋酶和DHPS的结合亲和力分别为9.8和8.9 。
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