Syntheses of Benzo[d]Thiazol-2(3H)-One Derivatives and Their Antidepressant and Anticonvulsant Effects

Jin, Qinghao; Fu, Zhiyang; Guan, Liping; Jiang, Haiying

doi:10.3390/md17070430

Cited by 15 publications

(10 citation statements)

References 26 publications

(26 reference statements)

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“…The 1 H and 13 C NMR spectra were recorded on a Bruker AVANCE III (400 MHz) spectrometer in DMSO-d6. As an internal standard, chemical shifts are expressed in δppm downfield from Tetramethylsilane (TMS).…”

Section: Experimental Section: Materials and Methodsmentioning

confidence: 99%

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2023

IJPSR

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A series of novel (Z)-3-((5-(2-((E)-arylidene) hydrazine-1carbonyl)-4-methylthiazol-2-yl)amino)-2-cyano-3-(methylthio) acrylate 4a-t molecules have been synthesized and characterized by 1 H NMR, 13 C NMRand mass spectral analysis. Starting from ethyl 2-amino-4methylthiazole-5-carboxylate 1 was reacted with hydrazine hydrate to obtain carbohydrazide molecule 2. Furthermore, reaction of molecule 2 with various aldehyde and the adduct 3a-t formed was reacted with ethyl 2-cyano-3,3-bis(methylthio) acrylate to get novel thiazole derivatives 4at, furthermore it was reacted with lithium hydroxide to form acid containing novel thiazole molecule 5a. The significant features of this reaction procedure are novel, easy and less time consuming with analytically pure product formation. INTRODUCTION:Thiazole moiety is present in several medicinal compounds and natural sources. The first widely used antibiotic penicillin, also have thiazole moiety in its core structure. Numerous medicinal drugs available for various types of illness also hold thiazole moiety, as shown in Fig. 1. Thiazoles and their derivatives also play a significant role in the field of medicinal chemistry where they found to exhibit a wide variety of activities such as, antiviral 1 , antioxidant 2 , antituberculosis 3 , antimicrobial 4 , anticancer 5 , anticonvulsant 6 , anti-inflammatory 7 , anti-infective 8 , antidiabetic 9 , anticonvulsant 10 , antifungal 11 , antiepileptic 12 , antidepressant 13 . Some of the thiazole molecules also showed inhibition against SARS-CoV-2 virus disease 14,15 . Several procedures for synthesizing thiazole derivatives are described in the literature [16][17][18][19][20][21][22][23] .

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Section: Experimental Section: Materials and Methodsmentioning

confidence: 99%

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2023

IJPSR

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“…Thiazole, a five-membered ring system carrying three carbons, one nitrogen, and one sulfur atom, is one such structure. It has been reported that thiazole-bearing compounds have some central nervous system (CNS)-related effects, such as anti-schizophrenic [4], anti-parkinsonian [5], neuroprotective [6], acetylcholinesterase inhibitory [7], anticonvulsant [8], antidepressant [9], and sedative-hypnotic [10] effects. Another heterocyclic structure, piperazine, is a 6-membered saturated ring system containing two nitrogen atoms in the first and fourth positions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antinociceptive Effect of Some Thiazole-Piperazine Derivatives: Involvement of Opioidergic System in the Activity

et al. 2021

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In this study, we aimed to design and synthesize novel molecules carrying both the thiazole and piperazine rings in their structures and to investigate their antinociceptive activity. Targeted compounds were obtained by reacting thiosemicarbazide derivative and appropriate 2-bromoacetophenone in ethanol. The structures of the obtained compounds were determined using data from various spectroscopic methods (IR, 1H-NMR, 13C-NMR, and LCMSMS). Experimental data from in vivo tests showed that test compounds 3a–3c, 3f, and 3g (50 mg/kg) significantly prolonged reaction times of animals in tail-clip and hot-plate tests compared to the controls, indicating that these compounds possess centrally mediated antinociceptive activities. Furthermore, these compounds reduced the number of writhing behaviors in the acetic acid-induced writhing tests, showing that the compounds also possess peripheral antinociceptive activity. In the mechanistic studies, naloxone pre-treatments abolished the antinociceptive activities of compounds 3a–3c, 3f, and 3g, indicating that opioidergic mechanisms were involved in their antinociceptive effects. Molecular docking studies demonstrating significant interactions between the active compounds and µ- and δ-opioid receptor proteins supported the pharmacological findings. This study is the first showing that molecules designed to bear thiazole and piperazine moieties together on their structure exert centrally and peripherally mediated antinociceptive effects by activating the opioid system.

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“…Its aromaticity makes it relatively stable, although as a heterocyclic, it has reactive sites which allow for functionalization8. Benzoxazole displays diverse pharmacological properties including antimicrobial [9][10][11][12][13][14] , multidrug resistant cancer cell activities [15][16] , antiinflammatory [17][18][19] , anticonvulsant 20 , antidepressant 21 , anti-HIV [22][23] , Antihypertensive 24 , anthelmintic 25 activities.…”

Section: Introductionmentioning

confidence: 99%

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2021

IJPSR

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Benzoxazole and its analogues play an important role as therapeutic agents and exhibit good cytotoxic as well as antimicrobial activity. In the present study, benzoxazole analogues have been prepared by synthetic route; their spectroscopic evaluation was carried out, and then the synthesized compounds were screened for their cytotoxic activity by Allium cepa root model as well as antimicrobial activity by cup plate method. The synthesis and cytotoxic activity of a novel series of Schiff's base was carried out by reacting the amino group of the 4-Benzoxazol-2yl-phenylamine with different aromatic/ heteroaromatic aldehydes in the presence of polyphosphoric acid to give 4-(1,3-Benzoxazol-2-yl)phenyl]-1-(Substituted phenyl) methanimine (4a-4h) also Diazotization reaction of (4-Benzoxazol-2-yl phenyl) with β napthol gave 2- ((4-(benzo [d]oxazole-2-yl)phenyl) diazenyl) naphthalene-2-ol (4i). The cytotoxic and antimicrobial activities of the synthesized compounds were determined by using the onion root model and cup plate method, respectively. The activity data of compounds was compared with standard drugs Cefixime for antibacterial activity and miconazole for antifungal was used as a standard, and cyclophosphamide was used as a standard for Cytotoxic activity.

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Syntheses of Benzo[d]Thiazol-2(3H)-One Derivatives and Their Antidepressant and Anticonvulsant Effects

Cited by 15 publications

References 26 publications

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Synthesis and Antinociceptive Effect of Some Thiazole-Piperazine Derivatives: Involvement of Opioidergic System in the Activity

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