Cholinesterase inhibitors for the treatment of Alzheimer's disease: Synthesis, biological analysis and molecular docking study of sulphur containing heterocyclic analogues

被引:4
作者
Ullah, Hayat [1 ]
Rahim, Fazal [2 ]
Uddin, Imad [3 ]
Taha, Muhammad [4 ]
Khan, Misbah Ullah [5 ]
Khan, Fahad [2 ]
Khan, Shoaib [6 ]
Hussain, Rafaqat [2 ]
Hussain, Amjad [1 ]
Iqbal, Naveed [7 ]
Gul, Farzana [8 ]
机构
[1] Univ Okara, Dept Chem, Okara 56130, Pakistan
[2] Hazara Univ, Dept Chem, Mansehra 21300, Khyber Pakhtunk, Pakistan
[3] Univ Haripur, Dept Chem, Haripur 22620, Khyber Pakhtunk, Pakistan
[4] Imam Abdulrahman Bin Faisal Univ, Inst Res & Med Consultat IRMC, Dept Clin Pharm, POB 1982, Dammam 31441, Saudi Arabia
[5] Univ Okara, Ctr Nanosci, Okara 56130, Pakistan
[6] Abbottabad Univ Sci & Technol AUST, Dept Chem, Abbottabad, Pakistan
[7] Univ Poonch, Dept Chem, Rawalakot, Ajk, Pakistan
[8] Hazara Univ, Dept Biochem, Mansehra 21300, Khyber Pakhtunk, Pakistan
来源
CHEMICAL DATA COLLECTIONS | 2024年 / 51卷
关键词
Synthesis; Thiophene; Sulfonamide; Acetylcholinesterase; Butyrylcholinesterase; GLUTATHIONE-S-TRANSFERASE; CARBONIC-ANHYDRASE; ACETYLCHOLINE ESTERASE; ALPHA-GLUCOSIDASE; DERIVATIVES; BUTYRYLCHOLINESTERASE; ANTIOXIDANT; LACTOPEROXIDASE; THIAZOLE; BASES;
D O I
10.1016/j.cdc.2024.101132
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In synthetic medicinal chemistry thiophene and their analogues play a vital role due to the wide range of pharmacological properties. In current studies, we have synthesized a new class of thiophene-bearing sulfonamide analogues (1-11) as cholinesterase inhibitors. These newly synthesized upon esterification, hydrazide formation and finally through sulfonamide mode of synthesis and were characterized through 1H, 13C NMR and HREI-MS spectroscopic techniques. Synthesized analogues showed an excellent to moderate cholinesterase inhibitory potential. Analogues 10, 7, 9 and 11 showed an excellent potency against cholinesterase inhibition as compared to standard Donepezil. The binding interactions of the most potent analogues were confirmed through molecular docking studies. All Compounds were verified for cytotoxicity against 3T3 mouse fibroblast cell line and detected non-toxic.
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页数:9
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共 42 条
  • [1] Discovery of potent carbonic anhydrase and acetylcholine esterase inhibitors: Novel sulfamoylcarbamates and sulfamides derived from acetophenones
    Akincioglu, Akin
    Akincioglu, Hulya
    Gulcin, Ilhami
    Durdagi, Serdar
    Supuran, Claudiu T.
    Goksu, Suleyman
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (13) : 3592 - 3602
  • [2] 5-Bromo-2-aryl benzimidazole derivatives as non-cytotoxic potential dual inhibitors of α-glucosidase and urease enzymes
    Arshad, Tanzila
    Khan, Khalid Mohammed
    Rasool, Najma
    Salar, Uzma
    Hussain, Shafqat
    Asghar, Humna
    Ashraf, Mohammed
    Wadood, Abdul
    Riaz, Muhammad
    Perveen, Shahnaz
    Taha, Muhammad
    Ismail, Nor Hadiani
    [J]. BIOORGANIC CHEMISTRY, 2017, 72 : 21 - 31
  • [3] Cytotoxicity and molecular docking studies on phytosterols isolated from Polygonum hydropiper L
    Ayaz, Muhammad
    Sadiq, Abdul
    Wadood, Abdul
    Junaid, Muhammad
    Ullah, Farhat
    Khan, Nadir Zaman
    [J]. STEROIDS, 2019, 141 : 30 - 35
  • [4] Synthesis and antimicrobial evaluation of some new thiazole, thiazolidinone and thiazoline derivatives starting from 1-chloro-3,4-dihydronaphthalene-2-carboxaldehyde
    Bondock, Samir
    Khalifa, Wesam
    Fadda, Ahmed A.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2007, 42 (07) : 948 - 954
  • [5] Synthesis of azomethines derived from cinnamaldehyde and vanillin: in vitro aetylcholinesterase inhibitory, antioxidant and insilico molecular docking studies
    Chigurupati, Sridevi
    Selvaraj, Manikandan
    Mani, Vasudevan
    Mohammad, Jahidul I.
    Selvarajan, Kesavanarayanan K.
    Akhtar, Shaikh S.
    Marikannan, Maharajan
    Raj, Suthakaran
    Teh, Lay K.
    Salleh, Mohd Z.
    [J]. MEDICINAL CHEMISTRY RESEARCH, 2018, 27 (03) : 807 - 816
  • [6] Identification of novel acetylcholinesterase inhibitors: Indolopyrazoline derivatives and molecular docking studies
    Chigurupati, Sridevi
    Selvaraj, Manikandan
    Mani, Vasudevan
    Selvarajan, Kesavanarayanan Krishnan
    Mohammad, Jahidul Islam
    Kaveti, Balaji
    Bera, Hriday
    Palanimuthu, Vasanth Raj
    Teh, Lay Kek
    Salleh, Mohd Zaki
    [J]. BIOORGANIC CHEMISTRY, 2016, 67 : 9 - 17
  • [7] Thiophene-Based Compounds with Potential Anti-Inflammatory Activity
    Duarte da Cruz, Ryldene Marques
    Mendonca-Junior, Francisco Jaime Bezerra
    de Melo, Natalia Barbosa
    Scotti, Luciana
    Aquino de Araujo, Rodrigo Santos
    de Almeida, Reinaldo Nobrega
    de Moura, Ricardo Olimpio
    [J]. PHARMACEUTICALS, 2021, 14 (07)
  • [8] Design, synthesis, molecular docking and biological activity evaluation of some novel indole derivatives as potent anticancer active agents and apoptosis inducers
    El-Sharief, Ahmed M. Sh
    Ammar, Yousry A.
    Belal, Amany
    El-Sharief, Marwa A. M. Sh
    Mohamed, Yehia A.
    Mehany, Ahmed B. M.
    Ali, Gameel A. M. Elhag
    Ragab, Ahmed
    [J]. BIOORGANIC CHEMISTRY, 2019, 85 : 399 - 412
  • [9] Design, synthesis, antiproliferative evaluation, and molecular docking study of new quinoxaline derivatives as apoptotic inducers and EGFR inhibitors
    Fayed, Eman A.
    Ammar, Yousry A.
    Saleh, Marwa A.
    Bayoumi, Ashraf H.
    Belal, Amany
    Mehany, Ahmed B. M.
    Ragab, Ahmed
    [J]. JOURNAL OF MOLECULAR STRUCTURE, 2021, 1236
  • [10] Rosmarinic acid inhibits some metabolic enzymes including glutathione S-transferase, lactoperoxidase, acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase isoenzymes
    Gulcin, Ilhami
    Scozzafava, Andrea
    Supuran, Claudiu T.
    Koksal, Zeynep
    Turkan, Fikret
    Cetinkaya, Songul
    Bingol, Zeynebe
    Huyut, Zubeyir
    Alwasel, Saleh H.
    [J]. JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2016, 31 (06) : 1698 - 1702