(1H-Pyrrolo [2,3-B] Pyridine) 7-Azaindole as Cholinesterase/ Glycation Inhibitors
Zafar Saied Saify, Nighat Sultana, Nousheen Mushtaq, Nazia Zaheer Ul Hasan
International Journal of Biochemistry Research & Review · pp. 624–643 · Published 20 Aug 2014
10.9734/IJBCRR/2014/9721Abstract
As a part of our program to discover novel analoges of (1H-pyrrolo [2,3-b] pyridine) 7-azaindole having useful biological activities, a variety of 7-azaindole analogs 1-9 with variable substituents on phenyl ring of phenacyl moiety were synthesized and evaluated for their AChE, BChE and antiglycation Inhibitory potential. Compounds 2-5 were found to be AChE inhibitors with IC50 1.34 µM, 11.60 µM, 0.96 µM and 0.97 µM respectively, while compounds 2-5 were also found to be BChE inhibitors with IC50 1.25 µM, 3.93 µM, IC50 9.18µM and 10.20µM respectively. Compounds 2 (IC50 = 1.25±0.019uM) and 3 (IC50 = 3.93±0.36uM), showed potent BChE inhibitory potential than standard Galantamine (IC50 = 8.51±0.02uM). Besides this, compounds 2-9 were evaluated for glycation inhibition activity. Compound 5 (IC50 values 120.6+0.2uM) showed potent antiglycation potential than standard rutin (IC50=294.50+1.5uM). The size of the substituent, electron donating or withdrawing effect of substituents as well as the position of substituent on phenyl effects the activity.
References (41)
- 1 Atomic Structure of Acetylcholinesterase from Torpedo californica : A Prototypic Acetylcholine-Binding Protein [DOI]
- 2 beta-Amyloid peptides destabilize calcium homeostasis and render human cortical neurons vulnerable to excitotoxicity [DOI]
- 3 Advanced glycation endproducts—role in pathology of diabetic complications [DOI]
- 4 Glycation and Diabetic Complications [DOI]
- 5 Butyrylcholinesterase: An Important New Target in Alzheimer’s Disease Therapy [DOI]
- 6 Calcium and reactive oxygen species mediate staurosporine-induced mitochondrial dysfunction and apoptosis in PC12 cells [DOI]
- 7 Novel inhibitors of advanced glycation endproducts [DOI]
- 8 Structure of acetylcholinesterase complexed with (−)‐galanthamine at 2.3 Å resolution [DOI]
- 9 Glucose, Advanced Glycation End Products, and Diabetes Complications: What Is New and What Works [DOI]
- 10 Therapeutic potential of breakers of advanced glycation end product–protein crosslinks [DOI]
- 11 Organometallic methods for the synthesis and functionalization of azaindoles [DOI]
- 12 Antiglycation Properties of Aged Garlic Extract: Possible Role in Prevention of Diabetic Complications [DOI]
- 13 Synthesis of Novel Phenserine-Based-Selective Inhibitors of Butyrylcholinesterase for Alzheimer's Disease [DOI]
- 14 Non-Steroid Anti-Inflammatory Agents [DOI]
- 15 Pharmacotherapeutic approaches to the treatment of Alzheimer's disease [DOI]
- 16 Galantamine hydrobromide: An agent for Alzheimer’s disease [DOI]
- 17 Calcium Entry through L-type Calcium Channels Causes Mitochondrial Disruption and Chromaffin Cell Death [DOI]
- 18 Design and Synthesis of 4-Azaindoles as Inhibitors of p38 MAP Kinase [DOI]
- 19 The polyamines spermine and spermidine protect proteins from structural and functional damage by AGE precursors: a new role for old molecules? [DOI]
- 20 Luminescence and reactivity of 7-azaindole derivatives and complexes [DOI]
- 21 Tetrahydrofurobenzofuran cymserine, a potent butyrylcholinesterase inhibitor and experimental Alzheimer drug candidate, enzyme kinetic analysis [DOI]
- 22 Pharmacological and Molecular Effects of Platinum(II) Complexes Involving 7-Azaindole Derivatives [DOI]
- 23 The Response to Acetylcholine [DOI]
- 24 Syntheses and Antiproliferative Activities of 7-Azarebeccamycin Analogues Bearing One 7-Azaindole Moiety [DOI]
- 25 Molecular Modelling and QSAR of Reversible Acetylcholines-terase Inhibitors [DOI]
- 26 Cholinesterase inhibitory and spasmolytic potential of steroidal alkaloids [DOI]
- 27 Determination of acetylcholinesterase activity by a new chemiluminescence assay with the natural substrate [DOI]
- 28 Synthesis and biological activities of isogranulatimide analogues [DOI]
- 29 New natural cholinesterase inhibiting and calcium channel blocking quinoline alkaloids [DOI]
- 30 Synthesis and Antiglycation Activity of Kaempferol-3-O-rutinoside (Nicotiflorin) [DOI]
- 31 Palladium-catalyzed functionalization of 5- and 7-azaindoles [DOI]
- 32 Synthesis and biological evaluation of 7-azaindole derivatives, synthetic cytokinin analogues [DOI]
- 33 7-Azaindole derivatives as potential partial nicotinic agonists [DOI]
- 34 A secondary isotope effect study of equine serum butyrylcholinesterase-catalyzed hydrolysis of acetylthiocholine [DOI]
- 35 Synthesis and pharmacological activities of 7-azaindole derivatives.
- 36 Broadening in the scope of NADH models by using chiral and non chiral pyrrolo [2,3-bl pyridine derivatives. [DOI]
- 37 Structure‐Activity Relationship Studies of CNS Agents, Part 31[1]: Analogs of MP 3022 with a Different Number of Nitrogen Atoms in the Heteroaromatic Fragment — New 5‐HT1A Receptor Ligands [DOI]
- 38 The Indazole Analog of Serotonin [DOI]
- 39 Acetylcholinesterase inhibition by the ketone transition state analogs phenoxyacetone and 1-halo-3-phenoxy-2-propanones [DOI]
- 40 The Pharmacological Basis of Therapeutics [DOI]
- 41 Intervention against the Maillard reaction in vivo [DOI]
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