Design and synthesis of various 1,3,4-oxadiazoles as AChE and LOX enzyme inhibitors

被引:1
|
作者
Iqbal, Javed [1 ]
Mallhi, Ali Imran [2 ]
Rehman, Aziz Ur [3 ]
Al-Mijalli, Samiah H. [4 ]
Un-Nisa, Mehr [5 ]
Zafar, Fatiqa [1 ]
Shahzad, Sohail [1 ]
Rasool, Shahid [3 ]
Iqbal, Munawar [6 ]
Shah, Syed Adnan Ali [7 ,8 ]
机构
[1] Univ Sahiwal, Dept Chem, Sahiwal 57000, Pakistan
[2] Govt Coll Univ, Dept Appl Chem, Faisalabad, Pakistan
[3] Govt Coll Univ, Dept Chem, Lahore 54000, Pakistan
[4] Princess Nourah Bint Abdulrahman Univ, Coll Sci, Dept Biol, POB 84428, Riyadh 11671, Saudi Arabia
[5] Univ Lahore, Deparatment Chem, Lahore 54000, Pakistan
[6] Univ Educ, Dept Chem, Div Sci & Technol, Lahore, Pakistan
[7] Univ Teknol Malaysia, Fac Pharm, MARA Cawangan Selangor Kampus Puncak Alam, Bandar Puncak Alam 42300, Selangor, Malaysia
[8] Univ Teknol Malaysia, Atta Ur Rahman Inst Nat Prod Discovery AuRIns, MARA Cawangan Selangor Kampus Puncak, Bandar Puncak Alam 42300, Selangor, Malaysia
关键词
1,3,4-oxadiazole; piperidine; lipoxygenase; urease; acetyl cholinesterase; BIOLOGICAL EVALUATION; MOLECULAR DOCKING; DERIVATIVES; BEARING; ANTIBACTERIAL; HETEROCYCLES; ANTIFUNGAL; MOIETY;
D O I
10.1515/hc-2022-0169
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Substituted-2-propanamide analogues of 1,3,4-oxadiazole have been synthesized using a multi-step synthetic protocol to explore new therapeutic anti-enzymatic agents. Herein, we have merged sulfonyl, piperidine, oxadiazole and amide into a single unit to synthesize a library of unique compounds, 8a-n. The molecular structures of all synthesized compounds were verified by 13C-NMR, 1H-NMR, HRMS and IR spectroscopy. Furthermore, the compounds were screened for their inhibition potential against acetylcholinesterase (AChE), urease and lipoxygenase (LOX) enzymes. A considerable inhibition potential was observed for three compounds against LOX with quercetin as a reference standard, two compounds against urease with thiourea as a reference standard and two compounds against AChE with eserine as a reference standard. Through molecular docking investigations, we were able to correlate the overall impact and inhibition criteria by the structure-activity relationship via the interactions between synthesized compounds and active sites of enzymes. Pharmacodynamics, pharmacokinetics and in vivo studies may be investigated further for the most active compounds to substantiate them as potential anti-enzymatic medications.
引用
收藏
页数:21
相关论文
共 50 条
  • [1] 1,3,4-oxadiazoles .16. Synthesis and antimicrobial activity of substituted 1,3,4-oxadiazoles
    Joshi, N
    Korgaokar, S
    Parekh, H
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 5 (03) : 241 - 242
  • [2] Synthesis and Biological Evaluation of New 1,3,4-Oxadiazoles as Potential Anticancer Agents and Enzyme Inhibitors
    Yurttas, Leyla
    Cavusoglu, Betul K.
    Ciftci, Gulsen A.
    Temel, Halide E.
    ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2018, 18 (06) : 914 - 921
  • [3] Modular and Computational Access to Innocuous Multistep MetalFree Synthesis of 1,3,4-Oxadiazoles as Enzyme Inhibitors
    Umair, Muhammad
    Rehman, Aziz ur
    Abbasi, Muhammad Athar
    Siddiqui, Sabahat Zahra
    Iqbal, Javed
    Khalid, Hira
    Rasool, Shahid
    Khan, Shafi Ullah
    Zafar, Fatiqa
    ACS OMEGA, 2023, 8 (13): : 11952 - 11965
  • [4] SYNTHESIS OF PHOSPHORYLATED 1,3,4-OXADIAZOLES
    SHISHKIN, VE
    ZOTOV, YL
    NO, BI
    ZHURNAL OBSHCHEI KHIMII, 1977, 47 (11): : 2623 - 2623
  • [5] Synthesis and Antioxidant Activity of Styrylsulfonylmethyl 1,3,4-Oxadiazoles, Pyrazolyl/Isoxazolyl-1,3,4-oxadiazoles
    Reddy, Guda Mallikarjuna
    Muralikrishna, Akkarapalli
    Padmavathi, Venkatapuram
    Padmaja, Adivireddy
    Tilak, Thandaiah Krishna
    Rao, Chippada Appa
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2013, 61 (12) : 1291 - 1297
  • [6] Synthesis of 1,3,4-oxadiazoles using dibromotriphenylphosphorane
    Bliss, Emily
    Merringer, Katlynn
    Peters, Elizabeth
    Sowers, Brittney
    Grote, Robin
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [7] Synthesis of steroidal extranucleo 1,3,4-oxadiazoles
    Siddiqui, AU
    Satyanarayana, Y
    Ahmed, I
    Siddiqui, AH
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (04) : 1385 - 1387
  • [8] Synthesis of branched polynuclear 1,3,4-oxadiazoles
    L. I. Vereshchagin
    O. N. Verkhozina
    A. G. Proidakov
    A. I. Smirnov
    V. N. Kizhnyaev
    Chemistry of Heterocyclic Compounds, 2008, 44 : 1158 - 1163
  • [9] Synthesis of substituted isoxazoles and 1,3,4-oxadiazoles
    Reddy, KV
    Sabitha, G
    Rao, AVS
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1998, 37 (07): : 697 - 699
  • [10] Synthesis of dendrimers containing 1,3,4-oxadiazoles
    Verheyde, B
    Dehaen, W
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (11): : 4062 - 4064