Synthesis of Spiro-oxindole Analogs Engrafted Pyrazole Scaffold as Potential Alzheimer's Disease Therapeutics: Anti-oxidant, Enzyme Inhibitory and Molecular Docking Approaches

被引：10

作者：

Islam, Mohammad Shahidul ^{[1
,2
]}

Al-Majid, Abdullah Mohammed ^{[1
]}

Sholkamy, Essam Nageh ^{[3
]}

Yousuf, Sammer ^{[4
]}

Ayaz, Muhammad ^{[5
]}

Nawaz, Asif ^{[5
]}

Wadood, Abdul ^{[6
]}

Rehman, Ashfaq Ur ^{[7
]}

Verma, Ved Prakash ^{[2
]}

Rahman, A. F. M. Motiur ^{[8
]}

Barakat, Assem ^{[1
,9
]}

机构：

[1] King Saud Univ, Dept Chem, Coll Sci, POB 2455, Riyadh 11451, Saudi Arabia

[2] Banasthali Vidyapith, Dept Chem, Banasthali 304022, Rajasthan, India

[3] King Saud Univ, Dept Bot & Microbiol, Coll Sci, POB 2455, Riyadh 11451, Saudi Arabia

[4] Univ Karachi, HEJ Res Inst Chem, Int Ctr Chem & Biol Sci, Karachi 75270, Pakistan

[5] Univ Malakand, Dept Pharm, Fac Biol Sci, Chakdara 18000, KP, Pakistan

[6] Abdul Wali Khan Univ Mardan, Dept Biochem, Mardan 23200, Pakistan

[7] Univ Calif Irvine, Dept Mol Biol & Biochem, Irvine, CA 92697 USA

[8] King Saud Univ, Dept Pharmaceut Chem, Coll Pharm, POB 2457, Riyadh 11451, Saudi Arabia

[9] Alexandria Univ, Dept Chem, Fac Sci, POB 426, Alexandria 21321, Egypt

来源：

CHEMISTRYSELECT | 2022年 / 7卷 / 36期

关键词：

Spirooxindoles; 3+2] cycloaddition reaction (32CA); Acetylcholinesterase; Alzheimer's disease (AD); BChE enzyme; Butyrylcholinesterase; DPPH; REGIOSELECTIVE SYNTHESIS; DERIVATIVES; DESIGN; ANTIFUNGAL; ANTICANCER; DISCOVERY;

D O I：

10.1002/slct.202203047

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

About 19 spirooxindole analogs 8 a-s engrafted with pyrazole scaffolds were designed and constructed via [3+2] cycloaddition reaction (32CA) approach. The synthesized spirooxindole analogs was screened for anti-cholinesterase against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) and antioxidant potentials against DPPH. The compounds 8 h and 8 i showed the strongest acetylcholine esterase (AChE) and butyrylcholinesterase (BChE) inhibition with IC50 values of 30 mu g/mL respectively. The highest anti-oxidant potential was demonstrated by compounds 8 p with IC50 values of 240 mu g/mL, respectively. Molecular docking was used to study their interaction with the active site of enzymes.

引用

页数：10

共 45 条

[1] Curcumin Pyrazole and its derivative (N-(3-Nitrophenylpyrazole) Curcumin inhibit aggregation, disrupt fibrils and modulate toxicity of Wild type and Mutant α-Synuclein [J].

Ahsan, Nuzhat ;

Mishra, Satyendra ;

Jain, Manish Kumar ;

Surolia, Avadhesha ;

Gupta, Sarika .

SCIENTIFIC REPORTS, 2015, 5

[2] Substituted spiro [2.3′] oxindolespiro [3.2"]-5,6-dimethoxy-indane-1"-one-pyrrolidine analogue as inhibitors of acetylcholinesterase [J].

Ali, Mohamed Ashraf ;

Ismail, Rusli ;

Choon, Tan Soo ;

Yoon, Yeong Keng ;

Wei, Ang Chee ;

Pandian, Suresh ;

Kumar, Raju Suresh ;

Osman, Hasnah ;

Manogaran, Elumalai .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (23) :7064-7066

[3] Facile one-pot synthesis of novel dispirooxindole-pyrrolidine derivatives and their antimicrobial and anticancer activity against A549 human lung adenocarcinoma cancer cell line [J].

Arun, Y. ;

Bhaskar, G. ;

Balachandran, C. ;

Ignacimuthu, S. ;

Perumal, P. T. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (06) :1839-1845

[4] Design, Synthesis, Chemical and Biochemical Insights Into Novel Hybrid Spirooxindole-Based p53-MDM2 Inhibitors With Potential Bcl2 Signaling Attenuation [J].

Aziz, Yasmine M. Abdel ;

Lotfy, Gehad ;

Said, Mohamed M. ;

El Ashry, El Sayed H. ;

El Tamany, El Sayed H. ;

Soliman, Saied M. ;

Abu-Serie, Marwa M. ;

Teleb, Mohamed ;

Yousuf, Sammer ;

Doemling, Alexander ;

Domingo, Luis R. ;

Barakat, Assem .

FRONTIERS IN CHEMISTRY, 2021, 9

[5] Synthesis and biological evaluation of a novel series of pyrazole chalcones as anti-inflammatory, antioxidant and antimicrobial agents [J].

Bandgar, Babasaheb P. ;

Gawande, Shrikant S. ;

Bodade, Ragini G. ;

Gawande, Nalini M. ;

Khobragade, Chandrahasya N. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (24) :8168-8173

[6] Synthesis of a New Class of Spirooxindole-Benzo[b]Thiophene-Based Molecules as Acetylcholinesterase Inhibitors [J].

Barakat, Assem ;

Alshahrani, Saeed ;

Al-Majid, Abdullah Mohammed ;

Ali, M. ;

Altowyan, Mezna Saleh ;

Islam, Mohammad Shahidul ;

Alamary, Abdullah Saleh ;

Ashraf, Sajda ;

Ul-Haq, Zaheer .

MOLECULES, 2020, 25 (20)

[7]

BRAND-WILLIAMS W, 1995, FOOD SCI TECHNOL-LEB, V28, P25

[8] The application of isatin-based multicomponent-reactions in the quest for new bioactive and druglike molecules [J].

Brandao, Pedro ;

Marques, Carolina ;

Burke, Anthony J. ;

Pineiro, Marta .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2021, 211

[9] A study on synthesis and antimicrobial activity of 4-acyl-pyrazoles [J].

Cetin, Adnan ;

Bildirici, Ishak .

JOURNAL OF SAUDI CHEMICAL SOCIETY, 2018, 22 (03) :279-296

[10] Identification of novel acetylcholinesterase inhibitors: Indolopyrazoline derivatives and molecular docking studies [J].

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 .

BIOORGANIC CHEMISTRY, 2016, 67 :9-17

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