2,5-Disubstituted structures of 1,3,4-oxadiazole and 1,3,4-thiodiazole for anti-inflammatory potential: DFT approach for the structural aspects

被引:3
作者
Veeramani, Vairaperumal [1 ]
Ganesh, Pothapragada S. K. Prabhakar [2 ]
Bharanidharan, Sarangapani [3 ]
Muthuraja, Perumal [4 ]
Govindasamy, Chandramohan [5 ]
Rajamohan, Rajaram [6 ,7 ]
机构
[1] Alagappa Univ, Dept Ind Chem, Karaikkudi 630006, Tamil Nadu, India
[2] Indian Inst Sci Educ & Res IISER Tirupati, Dept Chem, Tirupati 517507, Andhra Pradesh, India
[3] Panimalar Engn Coll, Dept Phys, Chennai 600123, Tamil Nadu, India
[4] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, Assam, India
[5] King Saud Univ, Coll Appl Med Sci, Dept Community Hlth Sci, POB 10219, Riyadh 11433, Saudi Arabia
[6] Yeungnam Univ, Sch Chem Engn, Organ Mat Synth Lab, Gyongsan 38541, South Korea
[7] Saveetha Univ, Saveetha Inst Med & Tech Sci SIMATS, Saveetha Dent Coll & Hosp, Dept Physiol, Chennai 600077, India
关键词
1,3,4-oxadiazole; 1,3,4-thiodiazole; B3LYP/6-311++G; (d; p); NLO property; Anti-inflammatory; NONLINEAR-OPTICAL PROPERTIES; RESISTANT PROSTATE-CANCER; ONE-POT SYNTHESIS; ZIBOTENTAN ZD4054; ACETAZOLAMIDE; DERIVATIVES; DISCOVERY; CLEAVAGE;
D O I
10.1016/j.molstruc.2024.139263
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
We suggest a [3 + 2] annulation method that combines aromatic acid with acyl hydrazide using p-TSA, resulting in the formation of highly substituted 1,3,4-oxadiazole derivatives. These reactions take place efficiently under specific conditions: microwave irradiation, employing a metal-free environment, utilizing the environmentally friendly solvent PEG-400, and requiring only a short reaction time. Furthermore, employing similar conditions in the presence of Lawesson's reagent yields 1,3,4-thiadiazole derivatives. This method exhibits several notable characteristics, including atom and step economy, utilization of easily accessible raw materials, and simplicity in operation. From the DFT approach, the optimized geometrical parameters are obtained using the B3LYP/ 6-311++G (d,p) level of theory. There is a decrease in the energy gap and NLO property increases in nature and leads to more biological activity. Notably, there was a reduction in the energy gap, accompanied by an increase in the nonlinear optical property, and suggested the synthesized compounds exhibit heightened biological activity. Furthermore, these compounds demonstrate promising anti-inflammatory and anti-diabetic activity, as evidenced by protein denaturation assay studies.
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页数:12
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