Benzoxazolyl linked benzylidene based rhodanine and analogs as novel antidiabetic agents: synthesis, molecular docking, and in vitro studies

被引：6
|
作者：
Singh, Varinder [1 ]
Singh, Amanjot [1 ]
Singh, Gagandeep [1 ]
Verma, Raman K. [1 ]
Mall, Rajiv [2 ]
机构：
[1] Punjabi Univ, Dept Chem, Synthet Organ & Med Chem Lab, Patiala 147002, Punjab, India
[2] Punjabi Univ, Dept Basic & Appl Sci, Patiala 147002, Punjab, India
来源：
MEDICINAL CHEMISTRY RESEARCH | 2021年 / 30卷 / 10期
关键词：
Benzoxazole; Molecular docking; alpha-Glucosidase; Antidiabetic; ALPHA-GLUCOSIDASE INHIBITORS; BIOLOGICAL EVALUATION; POTENT; DERIVATIVES;
D O I：
10.1007/s00044-021-02781-y
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Benzoxazolyl linked meta- and para-substituted new chemical entities (5a-5h) featuring thiazolidinedione, rhodanine, hydantoin, and thiohydantoin moieties were synthesized and characterized by H-1 NMR, C-13 NMR, FT-IR, and HRMS spectral studies. In addition, all compounds were screened for alpha-glucosidase inhibitory activity and further supported by molecular docking studies carried out at the active site of alpha-glucosidase (PDB code: 3TOP) in comparison to acarbose used as a standard drug. Out of eight tested compounds, 5d was found as the most active inhibitor of alpha-glucosidase (IC50 = 9.48 +/- 0.36 mu M), having rhodanine moiety substituted at meta-position of the phenyl ring. [GRAPHICS] .
引用
收藏
页码：1905 / 1914
页数：10
相关论文
共 50 条
  • [1] Benzoxazolyl linked benzylidene based rhodanine and analogs as novel antidiabetic agents: synthesis, molecular docking, and in vitro studies
    Varinder Singh
    Amanjot Singh
    Gagandeep Singh
    Raman K. Verma
    Rajiv Mall
    Medicinal Chemistry Research, 2021, 30 : 1905 - 1914
  • [2] Novel benzoxazole derivatives featuring rhodanine and analogs as antihypergycemic agents: synthesis, molecular docking, and biological studies
    Varinder Singh
    Amanjot Singh
    Gagandeep Singh
    Raman K. Verma
    Rajiv Mall
    Medicinal Chemistry Research, 2018, 27 : 735 - 743
  • [3] Novel benzoxazole derivatives featuring rhodanine and analogs as antihypergycemic agents: synthesis, molecular docking, and biological studies
    Singh, Varinder
    Singh, Amanjot
    Singh, Gagandeep
    Verma, Raman K.
    Mall, Rajiv
    MEDICINAL CHEMISTRY RESEARCH, 2018, 27 (03) : 735 - 743
  • [4] Novel indolyl linked para-substituted benzylidene-based phenyl containing thiazolidienediones and their analogs as α-glucosidase inhibitors: synthesis, in vitro, and molecular docking studies
    Jeewanjot Kaur
    Amanjot Singh
    Gagandeep Singh
    Raman K. Verma
    Rajiv Mall
    Medicinal Chemistry Research, 2018, 27 : 903 - 914
  • [5] Novel indolyl linked para-substituted benzylidene-based phenyl containing thiazolidienediones and their analogs as α-glucosidase inhibitors: synthesis, in vitro, and molecular docking studies
    Kaur, Jeewanjot
    Singh, Amanjot
    Singh, Gagandeep
    Verma, Raman K.
    Mall, Rajiv
    MEDICINAL CHEMISTRY RESEARCH, 2018, 27 (03) : 903 - 914
  • [6] Synthesis, Antidiabetic, Antimicrobial, and Molecular Docking Studies of Some New Rhodanine Acetic Acid Derivatives
    Honavar, Premanand M.
    Shirahatti, Prithvi S.
    Ramu, Ramith
    Arunodaya, H. S.
    Kumar, Vasantha
    Swamy, P. M. Gurubasavaraja
    Kumar, Naveen
    Vishwanatha, P.
    Holla, B. Shivarama
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 30 (02) : 211 - 216
  • [7] Synthesis and Molecular Docking Studies of Novel Biheterocyclic Propanamides as Antidiabetic Agents Having Mild Cytotoxicity
    Abbasi, Muhammad Athar
    Rubab, Kaniz
    Aziz-ur-Rehman, Sabahat Zahra
    Siddiqui, Sabahat Zahra
    Hassan, Mubashir
    Raza, Hussain
    Shah, Syed Adnan Ali
    Shahid, Muhammad
    Kloczkowski, Andrzej
    ACS OMEGA, 2023, 8 (25): : 22899 - 22911
  • [8] Rhodanine Derivatives as Anticancer Agents: QSAR and Molecular Docking Studies
    Molnar, Maja
    Loncaric, Melita
    Opacak-Bernardi, Teuta
    Glavas-Obrovac, Ljubica
    Rastija, Vesna
    ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2023, 23 (07) : 839 - 846
  • [9] Thiosemicarbazone derivatives as potent antidiabetic agents: Synthesis, in vitro, molecular docking and DFT investigations
    Jan, Faheem
    Idris, Sana
    Waheed, Mahnoor
    Alam, Aftab
    Alasmari, Abdullah F.
    Alasmari, Fawaz
    Khan, Momin
    JOURNAL OF MOLECULAR STRUCTURE, 2024, 1311
  • [10] Design, synthesis, molecular docking, and in vitro antidiabetic activity of novel PPARγ agonist
    Radha Nandan Chaturvedi
    Krishnaiah Pendem
    Vipul P. Patel
    Mukta Sharma
    Sunita Malhotra
    Monatshefte für Chemie - Chemical Monthly, 2018, 149 : 2069 - 2084
12345