Pyridazine derivatives. Part 33: Sonogashira approaches in the synthesis of 5-substituted-6-phenyl-3(2H)-pyridazinones

Coelho, Alberto; Sotelo, Eddy; Raviña, Enrique

doi:10.1016/s0040-4020(03)00263-1

Cited by 60 publications

(28 citation statements)

References 29 publications

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“…The pyridazine moiety is a versatile scaffold to develop new biological active compounds with wide varieties of biological activities and also be used to link other pharmacophoric groups. Pyridazine derivatives have various biological properties like anti-viral, anti-cancer, anti-hypertensive, antiinflammatory, anti-microbial, anti-depressant, anti-HIV and other biological activities [50][51][52][53][54][55][56] . The polyfunctional 2H-pyrano [3,2- …”

Section: Discussionmentioning

confidence: 99%

Biological Potential and Chemical Properties of Pyridine and Piperidine Fused Pyridazine Compounds: Pyridopyridazine a Versatile Nucleus

Asif¹

2016

AJCPS

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Pyridopyridazine compounds are important nitrogen atom containing heterocyclic compounds due to their pharmacological versatility. This heterocycle system characterized a structural feature for different types of bioactive compounds that exhibiting various types of biological activities which make it an attractive scaffold for the design and development of new drug molecules. This article provided information about the pharmacological properties of pyridopyridazines derivatives.

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Section: Discussionmentioning

confidence: 99%

Biological Potential and Chemical Properties of Pyridine and Piperidine Fused Pyridazine Compounds: Pyridopyridazine a Versatile Nucleus

Asif¹

2016

AJCPS

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“…In recent years, synthesis of novel pyridazinone derivatives and investigation of their chemical and biological behavior have gained more importance due to their biological, medicinal, and agricultural reason. This privileged structure attracts the interest of medicinal chemists as a nucleus of potential therapeutic utility and exhibits several pharmacological activities such as analgesic (Asif, et al, 2011), anti-inflammatory (Gokce, et al, 2009), antidepressant (Coelho, et al, 2003), antihypertensive (Demirayak, et al, 2004), anticonvulsant (Rubat, et al, 1990), cardiotonic (Amin, et al, 2010), diuretic (Akahane, et al, 1999), and anti-HIV (Livermone, et al, 1993) activities. Certain pyridazinone derivatives containing the 2-phenyl-indolyl moiety have also shown anti-cancer activity (Murty, et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Computer Aided Screening and Pharmacological Evaluation of 2/3-Substituted-6(4-Methylphenyl)-4,5-Dihydropyridazin3(2h)-Ones, and Pyridazine Substituted Triazine

Husain

Khokra

Seth

et al. 2017

Indonesian J. Pharm.

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The present research work involved synthesis of some new pyridazine derivatives and evaluation of their analgesic and antiinflammatory activities in experimental animals to obtain safer non-steroidal anti-inflammatory agents (NSAIDs). Friedel-Crafts acylation reaction of succinic anhydride with toluene in the presence of anhydrous aluminum chloride gave 4-(4-methylphenyl)-4-oxo-butanoic acid (1). The aryl propionic acid 1 on reaction with phenyl hydrazine and hydrazine hydrate yielded the pyridazinone derivative 2 and 3, respectively. Reaction of the compound 3 with phosphorus oxychloride (POCl 3 ) produced the corresponding chloropyridazine derivative 4. A 4-hydroxymethyl derivative of dihydropyridazinone (5) was synthesized by condensing 3 with methanol and formaldehyde (HCHO). The compound 5 on further treatment with guanidine hydrochloride in ethanol gave the pyridazino-triazine (6). The synthesized compounds were investigated for their analgesic activity in mice and anti-inflammatory activity in Wistar albino rats. The molecular, pharmacokinetic and toxicity properties of the synthesized compounds were calculated by Molinspiration and Osiris property explorer software. The results of in-vivo antiinflammatory studies revealed that the compound. 4 showed maximum inhibition in paw edema volume followed by compound 3 while the compound 4 exhibited excellent peripheral analgesic activity (74%) followed by the compound 5. Compound s 4 and 5 also showed good central analgesic effect increased the reaction time to 90 minutes. All the title compounds except compound 5 are predicted to be safe by Osiris online software and are likely to have good oral bioavailability as they obey Lipinski's rule of five for drug likeness.

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“…This azine heterocycle is included in chemicals with a wide range of biological activities and can also be used to link other pharmacophoric groups. 10 Pyridazine derivatives have biological properties and features, such as anti-viral and anti-cancer, 11 anti-hypertensive, 12 anti-inflammatory, 13 anti-microbial, 14 anti-depressant, 15 anti-HIV 16 and etc. 3-Arylpyrimido [4,5-c]pyridazine-5,7(6H,8H)-diones possess monoamine oxidase (MAO) inhibitory activity and substituents on the diazine nucleus modulate the inhibitory activity.…”

Section: Introductionmentioning

confidence: 99%

ZrOCl2.8H2O as a green and efficient catalyst for the expeditious synthesis of substituted 3-arylpyrimido[4,5-c]pyridazines in water

Rimaz¹,

Mousavi²,

Keshavarz³

et al. 2015

10.5267/j.ccl

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A new and simple synthetic methodology for the preparation of 3-arylpyrimido [4,5-c]pyridazine-5,7(6H,8H)-diones and 3-aryl-5-oxo-7-thioxo-7,8-dihydropyrimido[4,5-c]pyridazin-5(6H)-ones by a one-pot three component reaction of barbituric acid or thiobarbituric acid with arylglyoxals in the presence of catalytic amount of ZrOCl2•8H2O as green Lewis acid and hydrazine hydrate at ambient temperature in water was reported. All of these pyrimidopyridazines derivatives have one clustered water molecule in their molecular structure. The use of ZrOCl2•8H2O catalyst is feasible because of its easy availability, convenient handling, high stability, simple recovery, reusability, good activity and ecofriendly.

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Pyridazine derivatives. Part 33: Sonogashira approaches in the synthesis of 5-substituted-6-phenyl-3(2H)-pyridazinones

Cited by 60 publications

References 29 publications

Biological Potential and Chemical Properties of Pyridine and Piperidine Fused Pyridazine Compounds: Pyridopyridazine a Versatile Nucleus

Biological Potential and Chemical Properties of Pyridine and Piperidine Fused Pyridazine Compounds: Pyridopyridazine a Versatile Nucleus

Synthesis, Computer Aided Screening and Pharmacological Evaluation of 2/3-Substituted-6(4-Methylphenyl)-4,5-Dihydropyridazin3(2h)-Ones, and Pyridazine Substituted Triazine

ZrOCl2.8H2O as a green and efficient catalyst for the expeditious synthesis of substituted 3-arylpyrimido[4,5-c]pyridazines in water

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