Pyrano[2,3-f]pyrazolo[3,4-b]quinoline-3-carbonitriles: A three-component synthesis and AChE inhibitory studies

被引：2

作者：

Sumesh, Remani Vasudev ^{[1
]}

Kumar, Raju Ranjith ^{[1
]}

Almansour, Abdulrahman I. ^{[2
]}

Kumar, Raju Suresh ^{[2
]}

Ashraf, Mohamed Kassim Mohamed ^{[3
]}

机构：

[1] Madurai Kamaraj Univ, Sch Chem, Dept Organ Chem, Madurai, Tamil Nadu, India

[2] King Saud Univ, Coll Sci, Dept Chem, Riyadh, Saudi Arabia

[3] Minist Sci Technol & Innovat, Malaysian Inst Pharmaceut & Nutraceut, AMIPRO SDN BHD Co 1166264 V, Gelugor, Pulau Pinang, Malaysia

来源：

SYNTHETIC COMMUNICATIONS | 2021年 / 51卷 / 07期

关键词：

Acetylcholine; AChE inhibition; Alzheimer’ s Disease; dementia; domino reaction; pyrano[2; 3-f]pyrazolo[3; 4-b]quinoline; ACETYLCHOLINESTERASE INHIBITORS; BIOLOGICAL EVALUATION; ALZHEIMERS-DISEASE; DERIVATIVES; EFFICIENT; DESIGN; POTENT;

D O I：

10.1080/00397911.2020.1866612

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The one-pot three-component reaction of 3-methyl-1-phenyl-1,6,7,8-tetrahydro-5H-pyrazolo[3,4-b]quinolin-5-one, aromatic aldehydes, and malononitrile in the presence of piperidine in ethanol has been carried out. The reaction proceeded through domino Knoevenagel condensation - Michael addition - O-cyclization sequence of reactions in a single transformation affording structurally intriguing novel pyrano[2,3-f]pyrazolo[3,4-b]quinoline-3-carbonitriles in excellent yields in short reaction time. The high-throughput AChE inhibition studies of these pyrano[2,3-f]pyrazolo[3,4-b]quinoline-3-carbonitriles disclosed one compound with maximum potency with an IC50 value of 2.6 mu M/L. The structure-activity relationship revealed that the pyrano[2,3-f]pyrazolo[3,4-b]quinoline-3-carbonitriles bearing alkyl or alkoxy substituted phenyl ring at C-4 exhibited more potency than the compounds with halogen-substituted phenyl ring.

引用

页码：1058 / 1065

页数：8

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