ChemInform Abstract: Molecular Iodine Promoted Synthesis of New Pyrazolo[3,4‐d]pyrimidine Derivatives as Potential Antibacterial Agents.

Bakavoli, Mehdi; Bagherzade, Ghodsieh; Vaseghifar, Maryam; Shiri, Ali; Pordel, Mehdi; Mashreghi, Mansour; Pordeli, Parvaneh; Araghi, Maryam

doi:10.1002/chin.201023151

Cited by 3 publications

(3 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…14 Those works indicated the chemoselective products resulted from the different reactivity of the substituted amides serving as the Vilsmeier reagent by reacting with POCl 3 . Other synthesis approaches of pyrazolopyrimidines were also found through heterocyclization reaction using 5-amino-4-formypyrazoles, 22 5-amino-1H-4-pyrazolcarbonitriles, 23 5-amino-1H-4-pyrazolcarboxamides 23 or other similar chemical reagents as the starting substrates. 15 Herein, we reported the use of Vilsmeier reagent to initiate the Vilsmeier-Haack formylation reaction, -3 -remarkable pharmaceutical applications.…”

Section: Introductionmentioning

confidence: 99%

Vilsmeier reagent-mediated synthesis of 6-[(formyloxy)methyl]-pyrazolopyrimidines via a one-pot multiple tandem reaction

Liu

Wong

2015

RSC Adv.

View full text Add to dashboard Cite

A new Vilsmeier reagent mediated one-pot reaction using 5-(2-chloroacetylamino)pyrazoles as the starting material was developed for the efficient synthesis of 6-[(formyloxy)methyl]-1H-pyrazolo[3,4-d]pyrimidine. This new multiple tandem reactions involving Vilsmeier-Haack reaction, Morgan-Walls reaction, sequential elimination, substitution reaction, and final hydrolysis reaction efficiently afforded formyloxymethyl pyrazolo[3,4-d]pyrimidine products in good yields.Morgan-Walls cyclization reaction, sequential elimination, substitution reaction, and hydrolysis for synthesis of the pyrazole fused pyrimidine derivatives via a tandem multiple reaction. 14,16Pyrimidines fused with a heterocycle such as furo-, 17 pyrazolo-, 18 pyrrolo-, 19 pyridopyrazolo-, 20 and pyrazolotriazolo-pyrimidine 21 are important classes of compounds and also currently of interest to the pharmaceutical industry due to their

show abstract

Section: Introductionmentioning

confidence: 99%

Vilsmeier reagent-mediated synthesis of 6-[(formyloxy)methyl]-pyrazolopyrimidines via a one-pot multiple tandem reaction

Liu

Wong

2015

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…They are biologically active isomeric purine analogues and have useful properties as antimetabolites in purine biochemical reactions [1][2][3] . They exhibit wide pharmacological activities like tuberculostatic 4 antimicrobial 5 , neuroleptic 6 , antitumor 7 , antihypertensive 8 and antileishmanial activities 9 . Stimulated by the successful application of pyrazolo [3,4-d]pyrimidines, our objective was to synthesize a new class of pyrazolo [3,4-d]pyrimidine analogues 3a-c, 4a-b by introducing various groups at the pyrazolopyrimidine ring and to evaluate its anti-inflammatory, nociceptive and antipyretic activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of new pyrazolo[3,4-d]pyrimidine derivatives

et al. 2014

View full text Add to dashboard Cite

Abstract:Several new pyrazolopyrimidine compounds were achieved from aminocyanopyarazole 1.The starting material 1 was initially coupled with orthoester at refluxed with various primary amines, ammonia, hydrazines and hydroxylamine to furnish a series of pyrazolo [3,4-d] activities. We start by studing the toxicity of these two molecules by measuring the corresponding DL50. The DL50 of 3a and 4c are estimated to 1333.2mg / kg and 1593.5mg / kg respectively. Pharmacological evaluation showed that compounds 3a and 4c at doses (5.5-22.2 mg / Kg, i.p) exhibited anti-inflammatory activities compared to Ibuprofen (150 mg / Kg, i.p), used as a refer ence drug. Further, our study showed that the injection of derived pyrazolopyrimidines on hyperthermic animal leads to a decrease in temperature after 1 hours of treatment compared to paracetamol used as reference. In addition, the injection of derived pyrazolopyrimidines at different doses contains a potent nociceptive activity. This effect is dose-dependent compared to aspirin.

show abstract

“…][1,2,4]triazolo[4,3-c]pyrimidines. Further, the results obtained in this study indicate that these compounds possess potent anti-inflammatory, nociceptive and antipyretic properties, which are mediated via peripheral and central inhibitory mechanisms.…”

mentioning

confidence: 99%

Synthesis and biological evaluation of new pyrazolo[3,4-d]pyrimidine derivatives

et al. 2014

View full text Add to dashboard Cite

Several new pyrazolopyrimidine compounds were achieved from aminocyanopyarazole 1. The starting material 1 was initially coupled with orthoester at refluxed with various primary amines, ammonia, hydrazines and hydroxylamine to furnish a series of pyrazolo[3,4-d]pyrimidines. The reaction of imidate 2a-b with hydrazide derivatives led to the formation of pyrazolo[3,4-d][1,2,4]triazolo[4,3-c]pyrimidines. Some of the synthesized compounds 3a and 4c were evaluated for their anti-inflammatory, antipyretic and nociceptive activities. We start by studing the toxicity of these two molecules by measuring the corresponding DL50. The DL50 of 3a and 4c are estimated to 1333.2mg / kg and 1593.5mg / kg respectively. Pharmacological evaluation showed that compounds 3a and 4c at doses (5.5-22.2 mg / Kg, i.p) exhibited anti-inflammatory activities compared to Ibuprofen (150 mg / Kg, i.p), used as a refer ence drug. Further, our study showed that the injection of derived pyrazolopyrimidines on hyperthermic animal leads to a decrease in temperature after 1 hours of treatment compared to paracetamol used as reference. In addition, the injection of derived pyrazolopyrimidines at different doses contains a potent nociceptive activity. This effect is dose-dependent compared to aspirin.

show abstract

ChemInform Abstract: Molecular Iodine Promoted Synthesis of New Pyrazolo[3,4‐d]pyrimidine Derivatives as Potential Antibacterial Agents.

Cited by 3 publications

References 1 publication

Vilsmeier reagent-mediated synthesis of 6-[(formyloxy)methyl]-pyrazolopyrimidines via a one-pot multiple tandem reaction

Vilsmeier reagent-mediated synthesis of 6-[(formyloxy)methyl]-pyrazolopyrimidines via a one-pot multiple tandem reaction

Synthesis and biological evaluation of new pyrazolo[3,4-d]pyrimidine derivatives

Synthesis and biological evaluation of new pyrazolo[3,4-d]pyrimidine derivatives

Contact Info

Product

Resources

About