Semicarbazones, thiosemicarbazone, thiazole and oxazole analogues as monoamine oxidase inhibitors: Synthesis, characterization, biological evaluation, molecular docking, and kinetic studies

Qazi, Syeda Uroos; Naz, Asia; Hameed, Abdul; Osra, Faisal Abdulrhman; Jalil, Saquib; Iqbal, Jamshed; Mirza, Agha Zeeshan

doi:10.1016/j.bioorg.2021.105209

Cited by 20 publications

(6 citation statements)

References 60 publications

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“…Such compounds might represent promising candidates for the future treatment of PD [7,8]. Also, it has been established that 1,3-oxazole derivatives also exhibit potent and specific inhibition of the MAO-B isoform [9]. This work reports a successful attempt to combine both these structural features into a single molecule (Figure 1).…”

Section: Introductionmentioning

confidence: 92%

4-(2-Methyloxazol-4-Yl)benzenesulfonamide

Shetnev,

Efimova,

Korsakov

et al. 2023

Preprint

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4-(2-Methyloxazol-4-yl)benzenesulfonamide was synthesized by the reaction of 4-(2-bromoacetyl)benzenesulfonamide with an excess of acetamide. The obtained compound was evaluated as a potential inhibitor of human monoamine oxidase (MAO) A and B and was found to inhibit these enzymes with IC50 values of 3.47 μM for MAO-B and 43.3 μM for MAO-A. Thus, the new selective MAO-B inhibitor was identified, which may be used as the lead compound for development anti-Parkinson’s disease agents.

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Section: Introductionmentioning

confidence: 92%

4-(2-Methyloxazol-4-Yl)benzenesulfonamide

Shetnev,

Efimova,

Korsakov

et al. 2023

Preprint

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“…Enzymes were found to have two isoforms: (MAO-A) and (MAO-B) The two isoforms share 73 % of their amino acid sequence, but they differ mainly, in how they are distributed in different tissues and how they respond to different types of substrates. [28][29][30][31] The binding configuration of the isoforms with the ligand is as depicted in (Figure 2). MAO-B has substrate specificity for tiny amines like -benzylamine and -phenylethylamine whereas monoamine oxidase-A isoform has substrate specificity for bigger native amines like (5-HT), epinephrine, and norepinephrine.…”

Section: Inhibition Of the Mao-a And Mao-b Enzymes For The Antidepres...mentioning

confidence: 99%

“…Multiple xenobiotic and endogenous neurotransmitters are subjected to oxidative deamination by MAOs, which control their concentration found in the brain and surrounding tissues. Enzymes were found to have two isoforms: (MAO–A) and (MAO–B) The two isoforms share 73 % of their amino acid sequence, but they differ mainly, in how they are distributed in different tissues and how they respond to different types of substrates [28–31] . The binding configuration of the isoforms with the ligand is as depicted in (Figure 2).…”

Section: Interaction With Different Receptors Responsible For Neurolo...mentioning

confidence: 99%

Targeted Development of Pyrazoline Derivatives for Neurological Disorders: A Review

Chauhan,

Salahuddin,

Mazumder

et al. 2024

ChemistrySelect

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Pyrazolines are preferred to be stable heterocycles in medication development. It has been established from previous research that the 2‐pyrazolone scaffold is a common pattern that can be found in many pharmacologically significant therapeutic compounds. They are said to have a wide range of biological actions and have been thoroughly investigated by the scientific community. 2‐pyrazoline has been used as an intriguing pharmacophore to create novel compounds with enhanced potency, less toxicity, and the necessary pharmacokinetic profile to treat unprecedented diseases and global drug resistance. Experiments done by docking confirmed the hypothesized neuropharmacological mode of action and demonstrated a strong affinity towards the monoamine oxidase, β‐amyloid plaques, and AChE. Furthermore, additional computational pharmacokinetic assessments signify that it may not have any significant risk of carcinogenic effects, neurotoxic effects, reproductive intoxication, acute toxicity, mutagenicity, or irritations suggesting their possible utility in depressive, convulsions, and anxiety disorders. This discussion outlines a reliable approach for medicinal chemists to develop pyrazolines for the establishment of neurodegenerative research as well as future research programs on neurodegenerative disorders.

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“…Qazi ve ark. 24 tarafından gerçekleştirilen bir çalışmada semikarbazon, tiyosemikarbazon, tiyazol ve oksazol analogları sentezlenerek MAO inhibitör etkinlikleri incelenmiştir. Elde edilen türevlerden semikarbazon ve tiyosemikarbazon türevleri karşılaştırıldığında semikarbazon türevlerinin daha aktif olduğu görülmüştür.…”

Section: Tartişma Ve Sonuçunclassified

Yeni Pirol Türevlerinin Sentezi ve Karakterizasyonu, Monoamin Oksidaz İnhibisyon Özelliklerinin ve Moleküler Doking Çalışmalarının Araştırılması

Osmaniye¹,

Özkay²

2022

Online Türk Sağlık Bilimleri Dergisi

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Amaç: Depresyon önemli bir psikiyatrik hastalıktır ve dünyada görülme sıklığı yüksektir. Dünya Sağlık Örgütü tarafından, 2012 yılında yaklaşık 350 milyon kişinin depresyon ile mücadele ettiğini belirtilmiştir. Özellikle monoamin oksidaz-A inhibitörleri depresyon tedavisinde kullanılmaktadır. Monoamin oksidaz inhibitörlerinin bu alanda kullanımı, yeni bileşiklerin geliştirilmesini de değerli kılmaktadır. Materyal ve Metot: 5 yeni molekülden oluşan pirol türevi (2a-2e) bileşikler sentezlenmiştir. Elde edilen bileşiklerin yapıları spektroskopik yöntemler kullanılarak aydınlatılmıştır. Bileşiklerin in vitro monoamin oksidaz enzim inhibitor etkinlikleri incelenmiştir. Bulgular: Sentezlenen bileşikler içerisinde 2b ve 2c kodlu bileşikler monoamin oksidaz-A enzimine karşı önemli düzeyde inhibitor etkinlik göstermiştir. Sonuç: Sentezlenen bileşiklerin selektif monoamin oksidaz-A inhibitör potansiyelleri incelendiğinde umut verici sonuçlara ulaşıldığı görülmektedir. Elde edilen bileşikler üzerinde yapılan modifikasyonlar ile daha etkili yeni bileşiklere ulaşılması planlanmaktadır.

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Semicarbazones, thiosemicarbazone, thiazole and oxazole analogues as monoamine oxidase inhibitors: Synthesis, characterization, biological evaluation, molecular docking, and kinetic studies

Cited by 20 publications

References 60 publications

4-(2-Methyloxazol-4-Yl)benzenesulfonamide

4-(2-Methyloxazol-4-Yl)benzenesulfonamide

Targeted Development of Pyrazoline Derivatives for Neurological Disorders: A Review

Yeni Pirol Türevlerinin Sentezi ve Karakterizasyonu, Monoamin Oksidaz İnhibisyon Özelliklerinin ve Moleküler Doking Çalışmalarının Araştırılması

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