Microwave-assisted synthesis and investigation of xanthine oxidase inhibition of new phthalonitrile and phthalocyanines containing morpholino substituted 1,2,4-triazole-3-one

Kantar, Günay Kaya; Baltaş, Nimet; Menteşe, Emre; Şaşmaz, Selami

doi:10.1016/j.jorganchem.2015.03.033

Cited by 28 publications

(23 citation statements)

References 51 publications

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“…The inhibitory activity of the extract was determined using the reference methods [28]. A well-known XO inhibitor (XOI), allopurinol, was used as a positive control for the inhibition test.…”

Section: Anti-xanthine Oxidase and Anti-urease Activity Of Pyrus Elaementioning

confidence: 99%

Investigation of a wild pear species (Pyrus elaeagnifoliasubsp.ElaeagnifoliaPallas) from Antalya, Turkey: polyphenol oxidase properties and anti-xanthine oxidase, anti-urease, and antioxidant activity

Baltaş

2016

International Journal of Food Properties

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Polyphenol oxidase (PPO) properties and anti-xanthine oxidase, anti-urease and antioxidant activity were investigated in Pyrus elaeagnifolia subsp. elaeagnifolia Pallas harvested from Antalya, Turkey. Optimum pH and temperature were 7.0 and 30 °C, respectively. Selected kinetic properties of PPO was evaluated.The K m and V max values, using 4-methylcatechol as substrate, were calculated as 3.57 mM and 4781 U/mg protein, respectively. IC 50 values ranged from 0.0036 to 4.0231 mM against sodium metabisulphite, ascorbic acid, sodium azide and benzoic acid, while ascorbic acid was the strongest inhibitor. Aquatic extracts of the samples exhibited strong antioxidant capacity and substantial xanthine oxidase and urease inhibition, with IC 50 values of 20.75 ± 0.11 and 2.97 ± 0.09 mg/mL, respectively.

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Section: Anti-xanthine Oxidase and Anti-urease Activity Of Pyrus Elaementioning

confidence: 99%

Investigation of a wild pear species (Pyrus elaeagnifoliasubsp.ElaeagnifoliaPallas) from Antalya, Turkey: polyphenol oxidase properties and anti-xanthine oxidase, anti-urease, and antioxidant activity

Baltaş

2016

International Journal of Food Properties

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“…Gunay and co‐workers synthesized a new series of phthalonitrile and phthalocyanines containing morpholino‐substituted 1,2,4‐triazole‐3‐one by using both microwave and conventional method and assessed their XO inhibitory activity; 4‐[4‐(3‐morpholinopropyl)‐5‐phenyl‐2 H ‐1,2,4‐triazol‐3‐one‐1‐yl] phthalonitrile ( 69 ) (IC 50 = 0.082 mM ) was found to be the most potent inhibitor of XO. However due to high aggregation tendency and poor solubility, phthalocyanine compounds did not show XO inhibition . In 2016, Rodrigues et al.…”

Section: Xanthine Oxidasementioning

confidence: 99%

Toward an Understanding of Structural Insights of Xanthine and Aldehyde Oxidases: An Overview of their Inhibitors and Role in Various Diseases

Kumar

Joshi

Kler

et al. 2017

Medicinal Research Reviews

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Almost all drug molecules become the substrates for oxidoreductase enzymes, get metabolized into more hydrophilic products and eliminated from the body. These metabolites sometime may be more potent, active, inactive, or toxic in nature compared to parent molecule. Xanthine oxidoreductase and aldehyde oxidase belong to molybdenum containing family and are well characterized for their structures and functions, in particular to their ability to oxidize/hydroxylate the xenobiotics. Their upregulated clinical levels causing oxidative stress are associated with pathways either directly involved in the progression of diseases, gout, or indirectly with the succession of other diseases such as diabetes, cancer, etc. Herein, we have put forth a comprehensive review on the xanthine and aldehyde oxidases pertaining to their structures, functions, pathophysiological role, and a comparative analysis of structural insights of xanthine and aldehyde oxidases' binding domains with endogenous ligands or inhibitors. Though both the enzymes are molybdenum containing and are likely to share some common pathways and interact with inhibitors in a similar manner but we have focused on structural prerequisites for inhibitor specificity to both the enzymes keeping in view of the existing X-ray structures. This review also provides futuristic implications in the design of inhibitors derived from inorganic complexes or small organic molecules considering the spatial features and structural insights of both the enzymes.

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“…The compound 263 exhibited promising XO inhibition with IC50 value as 0.082 mM. Anti-xanthine oxidase activity has not been observed in the case of the phthalocyanines 265 and 266; this latter result is Recently, novel phthalonitriles and zinc (II) phthalocyanines containng morpholine and/or triazole as pharmacophores have been synthesized by Kantar et al [103]. In the first step of this synthesis, the triazole 260 has been synthesized through the treatment of compound 258 with 3-morpholinopropylamine 259.…”

Section: Mw-assisted Syntheses Of Phthalocyaninesmentioning

confidence: 99%

“…The metallophthalo-cyanines 255 were obtained using corresponding anhydrous metal salts NiCl2 and ZnCl2, CoCl2, CuCl2, under MW-irradiation in 2-(dimethylamino)ethanol at 175 °C and 350 W, for 10 min (Scheme 53) [101]. Recently, novel phthalonitriles and zinc (II) phthalocyanines containng morpholine and/or triazole as pharmacophores have been synthesized by Kantar et al [103]. In the first step of this synthesis, the triazole 260 has been synthesized through the treatment of compound 258 with 3-morpholinopropylamine 259.…”

Section: Mw-assisted Syntheses Of Phthalocyaninesmentioning

confidence: 99%

Microwave-Assisted Syntheses of Bioactive Seven-Membered, Macro-Sized Heterocycles and Their Fused Derivatives

et al. 2016

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This review describes the recent advances in the microwave-assisted synthesis of 7-membered and larger heterocyclic compounds. Several types of reaction for the cyclization step are discussed: Ring Closing Metathesis (RCM), Heck and Sonogashira reactions, Suzuki-Miyaura cross-coupling, dipolar cycloadditions, multi-component reactions (Ugi, Passerini), etc. Green syntheses and solvent-free procedures have been introduced whenever possible. The syntheses discussed herein have been selected to illustrate the huge potential of microwave in the synthesis of highly functionalized molecules with potential therapeutic applications, in high yields, enhanced reaction rates and increased chemoselectivity, compared to conventional methods. More than 100 references from the recent literature are listed in this review.

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Microwave-assisted synthesis and investigation of xanthine oxidase inhibition of new phthalonitrile and phthalocyanines containing morpholino substituted 1,2,4-triazole-3-one

Cited by 28 publications

References 51 publications

Investigation of a wild pear species (Pyrus elaeagnifoliasubsp.ElaeagnifoliaPallas) from Antalya, Turkey: polyphenol oxidase properties and anti-xanthine oxidase, anti-urease, and antioxidant activity

Investigation of a wild pear species (Pyrus elaeagnifoliasubsp.ElaeagnifoliaPallas) from Antalya, Turkey: polyphenol oxidase properties and anti-xanthine oxidase, anti-urease, and antioxidant activity

Toward an Understanding of Structural Insights of Xanthine and Aldehyde Oxidases: An Overview of their Inhibitors and Role in Various Diseases

Microwave-Assisted Syntheses of Bioactive Seven-Membered, Macro-Sized Heterocycles and Their Fused Derivatives

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