Synthesis and Urease Inhibitory Properties of Some New N4-Substituted 5-Nitroisatin-3-thiosemicarbazones

Pervez, Humayun; Manzoor, Nazia; Yaqub, Muhammad; Khan, Ajmal; Khan, Khalid Mohammed; Nasim, Faiz-ul-Hassan; Choudhary, M. Iqbal

doi:10.2174/157018010790225840

Cited by 53 publications

(38 citation statements)

References 40 publications

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“…This study describes the in vitro determination of the leishma- 5-Nitroisatin-derived thiosemicarbazones 629 thiosemicarbazones 2-30, the synthesis of which has been reported elsewhere 35,36 .…”

Section: Resultsmentioning

confidence: 99%

“…The 5-nitroisatin-3-thiosemicarbazones were prepared by treating 5-nitroisatin with appropriate thiosemicarbazides. The details of the reactions along with physical, analytical and spectral data of the compounds were reported elsewhere 35,36 . In vitro leishmanicidal screening of the prepared compounds was made at Dr. Panjwani Center for Molecular Medicine and Drug Research, H.E.J.…”

Section: Methodsmentioning

confidence: 99%

“…Very recently, during random screening of the organic compounds prepared in our laboratory, we found that certain N 4 -substituted isatin-thiosemicarbazones bearing strong inductively electron-attracting substituents at position-5 of the isatin scaffold exhibited antileishmanial activity. This observation stimulated us to study the leishmanicidal properties of a series of 29 previously reported N 4 -alkyl/alkenyl/aryl substituted 5-nitroisatin-3-thiosemicarbazones 35,36 , prepared by the condensation of 5-nitroisatin with appropriate thiosemicarbazides (Scheme 1). This paper, therefore, describes the in vitro leishmanicidal potential of these compounds.…”

Section: Introductionmentioning

confidence: 99%

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5-Nitroisatin-derived thiosemicarbazones: potential antileishmanial agents

Pervez

Manzoor

Yaqub

et al. 2013

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of 29 previously reported N 4 -substituted 5-nitroisatin-3-thiosemicarbazones 2-30 has been screened for leishmanicidal potential. 7,8,[10][11][12][13][15][16][17][18][19]21,23,24,26,28 and 30 exhibited good to excellent antileishmanial activities with IC 50 values ranging from 0.44 AE 0.02 to 32.38 AE 0.66 mg/mL. Of these, 5, 7, 19 and 28 proved to be the most active antileishmanial agents, displaying activities with IC 50 values 1.78 AE 0.35, 0.44 AE 0.02, 1.91 AE 0.04 and 4.28 AE 0.75 mg/mL, respectively, which were even better than the standard drug, pentamidine (IC 50 ¼ 5.09 AE 0.04 mg/mL). This study presents the first example of exhibition of leishmanicidal potential by isatin-thiosemicarbazones and as such furnishes a solid basis for further research on these compounds to develop more potent antileishmanial agents.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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5-Nitroisatin-derived thiosemicarbazones: potential antileishmanial agents

Pervez

Manzoor

Yaqub

et al. 2013

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…SAR studies in the synthesized thiosemicarbazones disclosed that in some cases the nature and location of the substituent on the phenyl ring attached to thiosemicarbazone N 4 and/or the existence of lipophilic/inductively electron-withdrawing functions (Cl, F, F 3 CO, NO 2 ) at position 5 of the isatin moiety played a significant role in inducing and/or increasing certain activities, including urease inhibition. In view of this and as an extension of our earlier studies [36][37][38][39][40][41][42][43][44][45][46][47] aiming to the synthesis of novel isatin derivatives with enhanced or diverse biological activities, we very recently reported the synthesis of a series of N 4 -benzyl substituted 5-nitroisatin-3-thiosemicarbazones (derivatives of thiourea, a substrate-like urease inhibitor) as highly effective urease inhibitors. 48 Interestingly, all these compounds demonstrated either induced or increased urease inhibitory activity in comparison to the respective N 4 -phenyl substituted derivatives tested in our earlier assays.…”

Section: Introductionmentioning

confidence: 99%

“…48 Interestingly, all these compounds demonstrated either induced or increased urease inhibitory activity in comparison to the respective N 4 -phenyl substituted derivatives tested in our earlier assays. 38,45 Furthermore, a number of other derivatives of thiourea are reported to show promising glycation inhibitory activity. [49][50][51][52][53] Also, some isatin-derived imines (Schiff bases) have been recognized as potent inhibitors of glycation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and in vitro Bio-activity Evaluation of N4-benzyl Substituted 5-Chloroisatin- 3-thiosemicarbazones as Urease and Glycation Inhibitors

Pervez¹,

Khan²,

Iqbal³

et al. 2018

ACSi

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A series of fifteen N 4 -benzyl substituted 5-chloroisatin-3-thiosemicarbazones 5a-o were synthesized and screened mainly for their antiurease and antiglycation effects. Lemna aequinocitalis growth and Artemia salina assays were carried out to determine their phytotoxicity and cytotoxicity potential. All the compounds proved to be extremely effective urease inhibitors, demonstrating enzyme inhibition much better than the reference inhibitor, thiourea (IC 50 values 1.31 ± 0.06 to 3.24 ± 0.15 vs. 22.3 ± 1.12 μM). On the other hand, eight out of fifteen compounds tested, i.e. 5b, 5c, 5h-k, 5m and 5n were found to be potent glycation inhibitors. Of these, five viz. 5c, 5h-j and 5n proved to be exceedingly efficient, displaying glycation inhibition greater than the reference inhibitor, rutin (IC 50 values 114.51 ± 1.08 to 229.94 ± 3.40 vs. 294.5 ± 1.5 μM).

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Enzyme inhibition, molecular docking, and density functional theory studies of new thiosemicarbazones incorporating the 4‐hydroxy‐3,5‐dimethoxy benzaldehyde motif

Demir

Türkeş

Çavuş

et al. 2022

Archiv der Pharmazie

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New Schiff base-bearing thiosemicarbazones (1-13) were obtained from 4-hydroxy-3, 5-dimethoxy benzaldehyde and various isocyanates. The structures of the synthesized molecules were elucidated in detail. Density functional theory calculations were also performed to determine the spectroscopic properties of the compounds. Moreover, the enzyme inhibition activities of these compounds were investigated. They showed highly potent inhibition effects on acetylcholinesterase (AChE) and human carbonic anhydrases (hCAs) (K I values are in the range of 51.11 ± 6.01 to 278.10 ± 40.55 nM, 60.32 ± 9.78 to 300.00 ± 77.41 nM, and 64.21 ± 9.99 to 307.70 ± 61.35 nM for AChE, hCA I, and hCA II, respectively). In addition, molecular docking studies were performed, confirmed by binding affinities studies of the most potent derivatives.

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Synthesis and Urease Inhibitory Properties of Some New N4-Substituted 5-Nitroisatin-3-thiosemicarbazones

Cited by 53 publications

References 40 publications

5-Nitroisatin-derived thiosemicarbazones: potential antileishmanial agents

5-Nitroisatin-derived thiosemicarbazones: potential antileishmanial agents

Synthesis and in vitro Bio-activity Evaluation of N4-benzyl Substituted 5-Chloroisatin- 3-thiosemicarbazones as Urease and Glycation Inhibitors

Enzyme inhibition, molecular docking, and density functional theory studies of new thiosemicarbazones incorporating the 4‐hydroxy‐3,5‐dimethoxy benzaldehyde motif

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