Design, synthesis, in vitro α-glucosidase inhibitory, antioxidant activity and molecular docking studies of novel pyridine linked imidazo[1,2-a]pyridine derivatives

被引:11
|
作者
Padmaja, Pannala [1 ]
Reddy, Pedavenkatagari Narayana [2 ]
Reddy, B. V. Subba [1 ]
Tiwari, Ashok Kumar [3 ]
Ugale, Vinod G. [4 ]
Komati, Anusha [3 ]
Sridhar, B. [5 ]
机构
[1] CSIR Indian Inst Chem Technol, Ctr Semio Chem, Hyderabad 500007, India
[2] Gitam Univ, Sch Sci, Dept Chem, Hyderabad, India
[3] CSIR Indian Inst Chem Technol, Ctr Nat Prod & Tradit Knowledge, Hyderabad 500007, India
[4] RC Patel Inst Pharmaceut Educ & Res, Dept Pharmaceut Chem, Shirpur 425405, Maharashtra, India
[5] CSIR Indian Inst Chem Technol, Ctr Xray Crystallog, Hyderabad 500007, India
关键词
Type 2 diabetes Imidazo[1; 2-a]pyridine; -glucosidase; Antioxidant activity; Molecular docking; Virtual screening; DIABETES-MELLITUS; IN-VITRO; IMIDAZOPYRIDINES; 2-AMINOPYRIDINES; THIAZOLES; ACCESS;
D O I
10.1016/j.molstruc.2022.134238
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
A novel series of 2-(pyridin-2-yl)H-imidazo[1,2-a]pyridine derivatives were designed and synthesised in two steps via Suzuki coupling and condensation reactions with a wide substrate scope in good yields. The structures of the synthesized compounds were characterized using different spectroscopic tech-niques. Further, their inhibitory activity against alpha-glucosidase enzyme was investigated. Among various synthesized 2-(pyridin-2-yl)H-imidazo[1,2-a]pyridines, compound 5 g exhibited the best inhibitory po-tency having IC50 value of 3.7 mu M which was 18 times more potent than acarbose as standard inhibitor (IC50 = 67.4 mu M). The antioxidant activity of these compounds was evaluated by using in vitro 2-azinobis- 3-ethylbenzothiazoline-6-sulfonic acid (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical bioas-says. Molecular docking was performed to establish the interaction with the target enzyme which also corroborated with the in vitro results. An in silico analysis was performed to set physicochemical param-eters and prediction of pharmacokinetic profiles. (c) 2022 Elsevier B.V. All rights reserved.
引用
收藏
页数:9
相关论文
共 50 条
  • [31] Molecular insights on analogs of imidazo[1,2-a]pyridine, azaindole, and pyridylurea towards ParE using pharmacophore modeling, molecular docking, and dynamic simulation
    Azam, Mohammed Afzal
    Thathan, Janarthanan
    Tripuraneni, Naga Srinivas
    STRUCTURAL CHEMISTRY, 2017, 28 (04) : 1187 - 1200
  • [32] Synthesis of new derivatives containing pyridine, investigation of MAO inhibitory activities and molecular docking studies
    Osmaniye, Derya
    Saglik, Begum Nurpelin
    Levent, Serkan
    Ozkay, Yusuf
    Kaplancikli, Zafer Asim
    Turan, Gulhan
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES, 2022, 77 (11-12): : 509 - 517
  • [33] Novel polyhydroquinoline Schiff’s base derivatives: synthesis, characterization, in vitro α-glucosidase inhibitory, and molecular docking studies
    Nazish Shahab
    Duanyang Kong
    Mumtaz Ali
    Aftab Alam
    Najeeb Ur Rehman
    Saeed Ullah
    Zainab Zainab
    Momin Khan
    Abdul Latif
    Masaud Shah
    Ajmal Khan
    Ahmed Al-Harrasi
    Manzoor Ahmad
    Research on Chemical Intermediates, 2023, 49 : 3005 - 3028
  • [34] Functionalized ionic liquid tagged Cu(II) catalyst: Design, characterization, and application in synthesis of imidazo[1,2-a]pyridine
    Ghosh, Sumit
    Kundu, Dhiman
    Dey, Amrita
    Majee, Adinath
    Hajra, Alakananda
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2020, 97 (12A) : 2533 - 2539
  • [35] Novel polyhydroquinoline Schiff's base derivatives: synthesis, characterization, in vitro α-glucosidase inhibitory, and molecular docking studies
    Shahab, Nazish
    Kong, Duanyang
    Ali, Mumtaz
    Alam, Aftab
    Rehman, Najeeb Ur
    Ullah, Saeed
    Zainab, Zainab
    Khan, Momin
    Latif, Abdul
    Shah, Masaud
    Khan, Ajmal
    Al-Harrasi, Ahmed
    Ahmad, Manzoor
    RESEARCH ON CHEMICAL INTERMEDIATES, 2023, 49 (07) : 3005 - 3028
  • [36] Hydrazinyl arylthiazole based pyridine scaffolds: Synthesis, structural characterization, in vitro α-glucosidase inhibitory activity, and in silico studies
    Ali, Farman
    Khan, Khalid Mohammed
    Salar, Uzma
    Taha, Muhammad
    Ismail, Nor Hadiani
    Wadood, Abdul
    Riaz, Muhammad
    Perveen, Shahnaz
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 138 : 255 - 272
  • [37] Design and Synthesis of Fluoroquinolone Derivatives as Potent α-Glucosidase Inhibitors: In Vitro Inhibitory Screening with In Silico Docking Studies
    Shaheen, Aasia
    Ashiq, Uzma
    Jamal, Rifat Ara
    Khan, Khalid Mohammed
    Gul, Sana
    Yousuf, Sammer
    Ali, Syed Tahir
    CHEMISTRYSELECT, 2021, 6 (10): : 2483 - 2491
  • [38] Imidazo[1,2-a]pyridine Derivatives as Aldehyde Dehydrogenase Inhibitors: Novel Chemotypes to Target Glioblastoma Stem Cells
    Quattrini, Luca
    Gelardi, Edoardo Luigi Maria
    Coviello, Vito
    Sartini, Stefania
    Ferraris, Davide Maria
    Mori, Mattia
    Nakano, Ichiro
    Garavaglia, Silvia
    La Motta, Concettina
    JOURNAL OF MEDICINAL CHEMISTRY, 2020, 63 (09) : 4603 - 4616
  • [39] Synthesis and anticancer activity evaluation of some novel imidazo[1,2-a]pyridine based heterocycles containing S-alkyl/aryl moiety
    Kaya, Betul
    Yurttas, Leyla
    Baysal, Merve
    Celikates, Buesra Korkut
    Kaplancikli, Zafer Asim
    Imamoglu, Rizvan
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2024, 199 (05) : 383 - 393
  • [40] C2-functionalized imidazo[1,2-a]pyridine: Synthesis and medicinal relevance
    Sharma, Mousmee
    Prasher, Parteek
    SYNTHETIC COMMUNICATIONS, 2022, 52 (11-12) : 1337 - 1356