Synthesis and Molecular Docking of Curcumin-Derived Pyrazole-Thiazole Hybrids as Potent α-Glucosidase Inhibitors

被引:0
|
作者
Al-Humaidi, Jehan Y. [1 ]
Albedair, Lamia A. [1 ]
Maliwal, Deepika [2 ]
Zaki, Magdi E. A. [3 ]
Al-Hussain, Sami A. [3 ]
Pissurlenkar, Raghuvir [4 ]
Mukhrish, Yousef E. [5 ]
Abolibda, Tariq Z. [6 ]
Gomha, Sobhi M. [6 ]
机构
[1] Princess Nourah bint Abdulrahman Univ, Coll Sci, Dept Chem, POB 84428, Riyadh 11671, Saudi Arabia
[2] Inst Chem Technol, Dept Pharmaceut Sci & Technol, Mumbai 400019, India
[3] Imam Mohammad Ibn Saud Islamic Univ IMSIU, Fac Sci, Dept Chem, Riyadh 11623, Saudi Arabia
[4] Goa Coll Pharm, Dept Pharmaceut Chem, Panaji 403001, Goa, India
[5] Jazan Univ, Coll Sci, Dept Phys Sci, Chem Div, POB 114, Jazan 45142, Saudi Arabia
[6] Islamic Univ Madinah, Fac Sci, Chem Dept, Madinah 42351, Saudi Arabia
关键词
Curcumin; Pyrazoles; Thiazoles; Hydrazonyl halides; alpha-Glucosidase inhibitors; Docking and MD simulation studies; BIOLOGICAL EVALUATION; EFFICIENT SYNTHESIS; ANTICANCER ACTIVITY; GREEN SYNTHESIS; DERIVATIVES; DESIGN; AMYLASE; MOIETY; TYPE-1; AGENTS;
D O I
10.1002/cbdv.202401766
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
alpha-Glucosidase inhibitors are critical for diabetes management, with pyrazoles and thiazoles emerging as effective options. This research highlights curcumin-based pyrazole-thiazole hybrids as potential inhibitors, synthesizing derivatives and evaluating their inhibitory capabilities. The study involved the synthesis of novel compounds using hydrazonoyl halides, confirmed through elemental and spectral analyses. The synthesized derivatives exhibited significant alpha-glucosidase inhibition, with IC50 values ranging from 3.37 +/- 0.25 to 16.35 +/- 0.37 mu M. Among them, compound 7e demonstrated the strongest inhibition at 3.37 +/- 0.25 mu M, outperforming the standard drug acarbose (IC50=5.36 +/- 0.31 mu M). In silico assessments and molecular docking using AutoDock Vina revealed strong interactions, particularly with compounds 7b, 7e, 7f, and 7g, indicating their potential as stable and effective inhibitors. The results suggest that the synthesized pyrazole-thiazole hybrids hold promise as novel therapeutic agents for diabetes, warranting further exploration of their substituent effects for optimized inhibitor design.
引用
收藏
页数:13
相关论文
共 50 条
  • [21] Structural based investigation of novel pyrazole-thiazole Hybrids as dual CDK-1 and CDK-2 inhibitors for cancer chemotherapy
    Obakachi, Vincent A.
    Kehinde, Idowu
    Kushwaha, Narva Deshwar
    Akinpelu, Olayinka, I
    Kushwaha, Babita
    Merugu, Srinivas Reddy
    Kayamba, Francis
    Kumalo, Hezekiel M.
    Karpoormath, Rajshekhar
    MOLECULAR SIMULATION, 2022, 48 (08) : 687 - 701
  • [22] Imidazole-pyrazole hybrids: Synthesis, characterization and in-vitro bioevaluation against α-glucosidase enzyme with molecular docking studies
    Chaudhry, Faryal
    Naureen, Sadia
    Ashraf, Muhammad
    Al-Rashida, Mariya
    Jahan, Bakhat
    Munawar, Munawar Ali
    Khan, Misbahul Ain
    BIOORGANIC CHEMISTRY, 2019, 82 : 267 - 273
  • [23] Synthesis and Evaluation of Phenyltriazole-Deoxynojirimycin Hybrids as Potent α-Glucosidase Inhibitors
    Wang, Lin
    Luo, Wei
    Zhao, Yonghong
    Guo, Xinling
    Bai, Xiangru
    Guo, Leilei
    Zhu, Nailiang
    MOLECULES, 2024, 29 (21):
  • [24] Synthesis, biological evaluation and molecular docking analysis of vaniline–benzylidenehydrazine hybrids as potent tyrosinase inhibitors
    Aida Iraji
    Tina Adelpour
    Najmeh Edraki
    Mahsima Khoshneviszadeh
    Ramin Miri
    Mehdi Khoshneviszadeh
    BMC Chemistry, 14
  • [25] Design, Synthesis, DFT, Molecular Docking, and Biological Evalution of Pyrazole Derivatives as Potent Acetyl Cholinestrease Inhibitors
    Abdelwahab, Huda E.
    Ibrahim, Hesham Z.
    Omar, Alaa Z.
    JOURNAL OF MOLECULAR STRUCTURE, 2023, 1271
  • [26] Synthesis, biological evaluation and molecular docking of novel pyrazole derivatives as potent carbonic anhydrase and acetylcholinesterase inhibitors
    Turkan, Fikret
    Cetin, Adnan
    Taslimi, Parham
    Karaman, Muhammet
    Gulcin, Ilhami
    BIOORGANIC CHEMISTRY, 2019, 86 : 420 - 427
  • [27] Synthesis and molecular docking studies of imines as α-glucosidase and α-amylase inhibitors
    Aispuro-Perez, Analy
    Lopez-Avalos, Juan
    Garcia-Paez, Fernando
    Montes-Avila, Julio
    Picos-Corrales, Lorenzo A.
    Ochoa-Teran, Adrian
    Bastidas, Pedro
    Montano, Sarita
    Calderon-Zamora, Loranda
    Osuna-Martinez, Ulises
    Sarmiento-Sanchez, Juan, I
    BIOORGANIC CHEMISTRY, 2020, 94
  • [28] Design, synthesis and molecular docking of α,β-unsaturated cyclohexanone analogous of curcumin as potent EGFR inhibitors with antiproliferative activity
    Xu, Yun-Yun
    Cao, Yi
    Ma, Hailkuo
    Li, Huan-Qiu
    Ao, Gui-Zhen
    BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (02) : 388 - 394
  • [29] Synthesis, Molecular Docking and In Vitro Antimicrobial Studies of Novel Pyrazole Analogues of Curcumin
    Kumar, Dileep
    Harish, B. G.
    Gangwar, Mayank
    Kumar, Manish
    Kumar, Dharmendra
    Tilak, Ragini
    Nath, Gopal
    Kumar, Ashok
    Singh, Sushil Kumar
    LETTERS IN DRUG DESIGN & DISCOVERY, 2014, 11 (04) : 474 - 483
  • [30] Synthesis, biological evaluation and molecular docking analysis of vaniline-benzylidenehydrazine hybrids as potent tyrosinase inhibitors
    Iraji, Aida
    Adelpour, Tina
    Edraki, Najmeh
    Khoshneviszadeh, Mahsima
    Miri, Ramin
    Khoshneviszadeh, Mehdi
    BMC CHEMISTRY, 2020, 14 (01)