Synthesis, biological evaluation and molecular modelling of diversely functionalized heterocyclic derivatives as inhibitors of acetylcholinesterase/butyrylcholinesterase and modulators of Ca2+ channels and nicotinic receptors

Marco, J. L.; Rı́os, Cristóbal de los; Garcı́a, Antonio G.; Villarroya, Mércedes; Carreiras, M. Carmo; Martins, Carla P.; Eleutério, Ana; Morreale, Antonio; Orozco, Modesto; Luque, F. Javier

doi:10.1016/j.bmc.2004.02.017

Cited by 97 publications

(78 citation statements)

References 42 publications

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“…They were obtained in one step (Scheme 2) in very good yields using methods described by Freeman and Kim 7 or Hirota et al To prepare these different compounds, we used Friedländer's reaction. 9 2-Aminoselenophene-3-carbonitriles (1a-c) and 5-amino-1,3-thiazole-4-carbonitriles (2a-d) were reacted with cycloalkanones in dichloroethane in the presence of aluminium chloride. After at least 6 hours of reflux the reaction had come to an end and the expected products (3a-e, Scheme 3, and 4a0-4d2, Scheme 4) were obtained in good or moderate yields depending on the size of the ring of the cycloalkanone used.…”

Section: Synthesis Of 5-amino-13-thiazole-3-carbonitrilesmentioning

confidence: 99%

Synthesis of new selenophene and thiazole analogues of the Tacrine series

Seck¹,

Thomae²,

Perspicace³

et al. 2012

Arkivoc

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Section: Synthesis Of 5-amino-13-thiazole-3-carbonitrilesmentioning

confidence: 99%

Synthesis of new selenophene and thiazole analogues of the Tacrine series

Seck¹,

Thomae²,

Perspicace³

et al. 2012

Arkivoc

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“…These heterocycles have shown different pharmacological activities such as anti-inflammatory, anti-pyretic, analgesic [1][2][3], and antifungal properties [4]. They can also act as inhibitor of fatty acid amide hydrolaze (FAAH) [5,6], inhibitors of monoterpenoidindole alkaloid production in Catharanthus roseus cells [7], inhibitors of acetylcholinesterase/butyrylcholinesterase [8], and SIRT1 activators [9].…”

Section: Introductionmentioning

confidence: 99%

“…A number of methods have been reported for the synthesis of these heterocycles which include condensation of carboxylic acids [1,12,13], orthoesters [14], acid chlorides and nitriles [8], with o-substituted amino aromatics. Other methods include Pd-catalyzed C-2 arylation of oxazolo [4,5-b]pyridine [5], reaction of o-aminopyridinols with aldehydes under oxidative conditions and cyclization of an o-halogeno amidopyridine at very high temperature [11].…”

Section: Introductionmentioning

confidence: 99%

Facile microwave-assisted synthesis of 2-aryloxazolo[4,5-b]pyridines using SBA-Pr-NH2

et al. 2014

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In this work, amino-functionalized SBA-15 (SBA-Pr-NH 2 ) has been used as a basic nano-catalyst in the one-pot synthesis of 2-aryloxazolo [4,5-b]pyridines by the condensation reaction of 2-amino-3-hydroxypyridine and benzoyl chlorides under microwave irradiation in solvent free conditions. Among the advantages of this work are short reaction times, high yields and simple work-up. SBAPr-NH 2 as an efficient heterogeneous nanoporous solid basic catalyst which was prepared by silica functionalization with 3-aminopropyltriethoxysilane, can be easily removed from the reaction mixture by simple filtration, and also recovered and reused without noticeable loss of reactivity. 2-Aryloxazolo[4,5-b]pyridines have different pharmacological activities (anti-inflammatory, anti-pyretic, analgesic, antifungal). In the current method for the synthesis of 2-aryloxazolo [4,5-b]pyridines, no hazardous organic solvent was used and simplicity of the procedure provides significant improvements over many of other existing methods. Furthermore, the SBA-15-Pr-NH 2 with pore size of 6 nm can act as nano-reactor.

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“…6 A series of tacrine analogues has also been synthesized and evaluated as inhibitors of acetylcholinesterase/butyrylcholinesterase and modulators of Ca +2 channels and nicotinic receptors. 7 In the present study, a series of new D-glyceraldehyde heterocyclic derivatives were synthesized and were evaluated as potential inhibitors of acetylcholinesterase, so that current approaches to the treatment of cognitive and behavioral symptoms of AD make use of structurally diverse cholinesterase inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antiacetylcholinesterase activity of new D-glyceraldehyde heterocyclic derivatives

Scorzo¹,

Fascio²,

D’Accorso³

et al. 2010

J. Braz. Chem. Soc.

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Neste trabalho são apresentados os procedimentos para a síntese de diferentes compostos heterocíclicos a partir do 2,3-O-isopropilideno-D-gliceraldeído: ciclização intramolecular, cicloadição 1,3-dipolar e reação de acoplamento bimolecular. Os produtos sintetizados foram caracterizados por espectroscopia de 1 H RMN e 13 C RMN e análise elementar. Os novos heterocíclicos e seus derivados (12 compostos) foram testados como inhibidores da enzima acetilcolinesterase.We report herein the convenient procedures for the syntheses of different heterocyclic compounds from 2,3-O-isopropylidene-D-glyceraldehyde using intramolecular cyclization, 1,3-dipolar cycloaddition or bimolecular coupling reactions. The products were characterized by 1 H and 13 C NMR spectroscopy and elemental analysis. The new heterocycles and their derivatives were evaluated as inhibitors of acetylcholinesterase enzyme.

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Synthesis, biological evaluation and molecular modelling of diversely functionalized heterocyclic derivatives as inhibitors of acetylcholinesterase/butyrylcholinesterase and modulators of Ca2+ channels and nicotinic receptors

Cited by 97 publications

References 42 publications

Synthesis of new selenophene and thiazole analogues of the Tacrine series

Synthesis of new selenophene and thiazole analogues of the Tacrine series

Facile microwave-assisted synthesis of 2-aryloxazolo[4,5-b]pyridines using SBA-Pr-NH2

Synthesis and antiacetylcholinesterase activity of new D-glyceraldehyde heterocyclic derivatives

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