Development of selective and reversible pyrazoline based MAO-A inhibitors: Synthesis, biological evaluation and docking studies

Karuppasamy, Muthukumar; Mahapatra, Manoj Kumar; Yabanoglu, Samiye; Uçar, Gülberk; Sinha, Barij Nayan; Basu, Arijit; Mishra, Neha; Sharon, Ashoke; Kulandaivelu, Umasankar; Jayaprakash, Venkatesan

doi:10.1016/j.bmc.2010.01.043

Cited by 47 publications

(21 citation statements)

References 32 publications

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“…After this evaluation, another research group studied new pyrazoline derivatives bearing N-arylthiocarbamoyl moiety at N1 [58]. The authors discovered some important structural insights such as: (a) 4-hydroxy substitution in the phenyl ring at C3 increased the potency towards MAO-A as well as reduced the cytotoxicity (HeLa cells), (b) approximately 10-15 fold increase in potency was observed with furan or thiophene groups at C5 in comparison with phenyl groups; (c) selectivity towards MAO-A was observed substituting the phenyl ring at N1.…”

Section: As Shown Inmentioning

confidence: 99%

The State of the Art of Pyrazole Derivatives as Monoamine Oxidase Inhibitors and Antidepressant/Anticonvulsant Agents

Secci

Bolasco²,

Chimenti³

et al. 2011

CMC

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Monoamine oxidase plays a significant role in the control of intracellular concentration of monoaminergic neurotransmitters or neuromodulators and dietary amines. The rapid degradation of these molecules ensures the proper functioning of synaptic neurotransmission and is critically important for the regulation of emotional and other brain functions. The development of human MAO inhibitors led to important breakthroughs in the therapy of several neuropsychiatric disorders. Different families of heterocycles containing 2 or 4 nitrogen atoms have been used as scaffolds for synthesizing selective monoamine oxidase inhibitors, but the early period of the MAO-inhibitors started with hydrazine derivatives. Pyrazole, pyrazoline, and pyrazolidine derivatives can be considered as a cyclic hydrazine moiety. This scaffold also displayed promising antidepressant and anticonvulsant properties as demonstrated by different and established animal models. Diversely substituted pyrazoles, embedded with a variety of functional groups, are important biological agents and a significant amount of research activity has been directed towards this chemical class.

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Section: As Shown Inmentioning

confidence: 99%

The State of the Art of Pyrazole Derivatives as Monoamine Oxidase Inhibitors and Antidepressant/Anticonvulsant Agents

Secci

Bolasco²,

Chimenti³

et al. 2011

CMC

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“…( ( ( ( ( Synthesis of 5-aryl-4,5-dihydro-3-(5-methyl-1-p-tolyl-1H-1,2,3-triazol-4-yl)pyrazole-1-carbothioamide 4a-j [28]. Compounds 3a-j (5 mmol) and thiosemicarbazide (10 mmol) was dissolved in ethanol (70 mL), the mixture was stirred at 90 C for several mintuters, and then an aqueous solution of potassium hydroxide (10 mmol) in ethanol (70 mL) was added dropwise.…”

Section: Methodsmentioning

confidence: 99%

An efficient synthesis of 5‐aryl‐4,5‐dihydro‐3‐(5‐methyl‐1‐p‐tolyl‐1H‐1,2,3‐triazol‐4‐yl)‐1‐(4‐phenylthiazol‐2‐yl)pyrazoles

Dong

Cui

Gao

et al. 2011

Journal of Heterocyclic Chem

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Some new target products 5‐aryl‐4,5‐dihydro‐3‐(5‐methyl‐1‐p‐tolyl‐1H‐1,2,3‐triazol‐4‐yl)‐1‐(4‐phenylthiazol‐2‐yl)pyrazoles 5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j have been synthesized by reaction of 2‐bromo‐1‐phenylethanone and compounds 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j which were prepared from the combination of thiosemicarbazide and (E)‐3‐aryl‐1‐(5‐methyl‐1‐p‐tolyl‐1H‐1,2,3‐triazol‐4‐yl)‐prop‐2‐en‐1‐ones 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j. All the structures were established by MS, IR, CHN, and 1H NMR spectra data. Synthesis of structure diversity is applied. J. Heterocyclic Chem., (2011).

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“…The hot reaction mixture was poured in ice-cold water to obtain the crude product, which was washed and re-crystallized from appropriate solvent (ethanol/acetone/ethyl acetate) to afford the respective pyrazoline derivative (Karuppasamy et al, 2010[17]; Tripathi et al, 2016[33]).…”

Section: Methodsmentioning

confidence: 99%

2-Pyrazoline derivatives in neuropharmacology: synthesis, ADME prediction, molecular docking and in vivo biological evaluation

Upadhyay

Tripathi

Paliwal

et al. 2017

EXCLI Journal; 16:Doc628; ISSN 1611-2156

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Development of selective and reversible pyrazoline based MAO-A inhibitors: Synthesis, biological evaluation and docking studies

Cited by 47 publications

References 32 publications

The State of the Art of Pyrazole Derivatives as Monoamine Oxidase Inhibitors and Antidepressant/Anticonvulsant Agents

The State of the Art of Pyrazole Derivatives as Monoamine Oxidase Inhibitors and Antidepressant/Anticonvulsant Agents

An efficient synthesis of 5‐aryl‐4,5‐dihydro‐3‐(5‐methyl‐1‐p‐tolyl‐1H‐1,2,3‐triazol‐4‐yl)‐1‐(4‐phenylthiazol‐2‐yl)pyrazoles

2-Pyrazoline derivatives in neuropharmacology: synthesis, ADME prediction, molecular docking and in vivo biological evaluation

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