Synthesis and theoretical calculations of carbazole substituted chalcone urea derivatives and studies their polyphenol oxidase enzyme activity

Nixha, Arleta Rifati; Arslan, Mustafa; Atalay, Yusuf; Gençer, Nahit; Ergün, Adem; Arslan, Oktay

doi:10.3109/14756366.2012.688040

Cited by 21 publications

(14 citation statements)

References 32 publications

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“…It is mentioned that the compounds have excellent inhibitory effects for all these isoforms due to the urea moiety [29]. On the other hand, it has been reported that some urea derivatives have CA inhibitor activities [30,31]. Therefore, the investigation of clinically useful ureas/thioureas is a growing field of interest.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of New Phthalazine Urea and Thiourea Derivatives as Carbonic Anhydrase Inhibitors

Berber

Arslan

Yavuz

et al. 2013

Journal of Chemistry

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A new series of phthalazine substituted urea and thiourea derivatives were synthesized, and their inhibitory effects on the activity of purified human carbonic anhydrases (hCAs I and II) were evaluated. 2H-Indazolo[2,1-b]phthalazine-trione derivative(1)was prepared with 4-nitrobenzaldehyde, dimedone, and phthalhydrazide in the presence of TFA in DMF, and nitro group was reduced to amine derivative(2)with SnCl2·2H2O. The compound was reacted with isocyanates and isothiocyanates to get the final products(3a–p). The results showed that all the synthesized compounds inhibited the CA isoenzymes activity.3a(IC50= 6.40 µM for hCA I and 6.13 µM for hCA II) has the most inhibitory effect. The synthesized compounds are very bulky to be able to bind near the zinc ion, and they much more probably bind as the coumarin derivatives.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of New Phthalazine Urea and Thiourea Derivatives as Carbonic Anhydrase Inhibitors

Berber

Arslan

Yavuz

et al. 2013

Journal of Chemistry

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“…Kojic acid, arbutin, tropolone, and 1-phenyl-2-thiourea are compound used as therapeutic agents and cosmetic products. [6,9] Only some of compounds like derivatives of carbazole substituted chalcone urea, [10] 4'-(phenylurenyl/thiourenyl)chalcone derivatives, [11] 1,2,3-triazole chalcone derivates [12] are reported as activator of the tyrosinase.…”

Section: Introductionmentioning

confidence: 99%

“…In our previous studies, it has been proven that β-lactam compounds can also be used as an enzyme inhibitor or activator. [10,18,19,20] From this point of view, we thought that the PPO enzyme assigned in phenol oxidation may be affected by the presence of β-lactam, which is sensitive to reducers. [21,22] On the other hand, the carbazole structure located in the other part of the lactam bearing molecule is a valuable side group for a potential drug because of found in many natural products and drugs.…”

Section: Introductionmentioning

confidence: 99%

Novel β‐Lactam Compounds as Activators for Polyphenoloxidase

Bytyqi-Damoni¹,

Genc

Zengin

et al. 2020

ChemistrySelect

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A copper-containing enzyme polyphenol oxidase (other name is tyrosinase) plays crucial role in melanin biosynthesis, as a compound responsible for human pigmentation. Non controlled loss of melanin can cause hypopigmentation disease. The hypopigmentatory disorder can be treated with melanogenesis stimulators. Here, twenty-four new β-lactam compounds were synthesized, characterized and in vitro effects of them on banana tyrosinase investigated. The enzyme has been purified from banana by an affinity gel comprised of Sepharose4BÀ L-tyrosine-p-aminobenzoic acid. The results showed that the compounds have an effect on increasing the activity of tyrosinase enzyme. Molecules having a notable tyrosinase activator effects are compound 3 h (79.86) and compound 4 n (61.30). The maximal activation, 131% was determined at 130 μM concentration. These results suggested that compounds 3 h and 4 n might represent a novel approach for an effective therapy for diseases associate with tyrosinase dysfunction, such as vitiligo and hair graying.

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“…A large number of natural and synthetic carbazole derivatives have been reported to exhibit diverse biological activities such as antimicrobial [1,2], antiviral [3], antimalarial [4] and potential application as pharmacological agents [5,6]. Recentlycarbazole-substitutedchalcone and its urea derivatives have been reported to exhibit antimicrobial, radical scavenger, cancer chemopreventive and polyphenol oxidase enzyme activities [7,8]. Chalcones are also key precursors in the synthesis of many biologically important heterocyclic compounds such as benzothiazepines and pyrazolines.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial and antimalarial activityof1, 4-benzothiazepine and pyrazolinederivatives incorporating carbazolemoiety

Kadnor¹,

Shelke

2019

BCC

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A series of carbazole-based 1,4-benzothiazepine and pyrazoline derivatives were synthesized and the structures of the newly synthesized compounds were confirmed by FT-IR, 1H NMR, 13C NMR and mass spectral studies. All new derivatives 4(a-f) and 5(a-e) were screened for their in vitro antimicrobial activity, and also for their antimalarial activity. Compounds 4a, 4b, 4d, 5a, 5b and 5c exhibited promising antimicrobial and antimalarial activities as compared to positive control. Notably, compounds 4a, 4b and 4d showed excellent antifungal activity against Penicillium sp. comparable to that of a standard drug.

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Synthesis and theoretical calculations of carbazole substituted chalcone urea derivatives and studies their polyphenol oxidase enzyme activity

Cited by 21 publications

References 32 publications

Synthesis and Evaluation of New Phthalazine Urea and Thiourea Derivatives as Carbonic Anhydrase Inhibitors

Synthesis and Evaluation of New Phthalazine Urea and Thiourea Derivatives as Carbonic Anhydrase Inhibitors

Novel β‐Lactam Compounds as Activators for Polyphenoloxidase

Synthesis, antimicrobial and antimalarial activityof1, 4-benzothiazepine and pyrazolinederivatives incorporating carbazolemoiety

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