Thiourea Derivatives in Drug Design and Medicinal Chemistry: A Short Review

Shakeel, Azeem

doi:10.11648/j.jddmc.20160201.12

Cited by 90 publications

(63 citation statements)

References 24 publications

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“…Thiourea and its derivatives are important structures in chemistry, biochemistry, and industry because of their various applications in pharmaceutical purposes, [1][2][3] agricultural pesticides, [4][5][6][7][8] fungicides, [9][10][11] antibacterial materials, [12,13] antitumor agents [14,15] , and antifungal compounds. [16,17] Moreover, thiourea and its derivatives are important precursors for different synthetic methodologies; [18,19] especially as a sulfur resource in the synthesis of S-containing heterocyclic compounds.…”

Section: Introductionmentioning

confidence: 99%

Theoretical study of the possible mechanisms for the synthesis of dialkyl thiourea from dithiocarbamate

Ranjbari

Tavakol

2018

Heteroatom Chemistry

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In this study, the different mechanistic ways for the conversion of dithiocarbamate to dialkyl thiourea have been investigated using the high‐accurate DFT calculations. The energy details of all mechanisms were investigated in the gas phase, simple and solvent‐assisted solvation models. Two general mechanisms and several different pathways have been considered to evaluate these mechanisms. The first mechanism (A) involved with the preparation of alkyl isothiocyanate, addition of alkyl amine to it and the final proton transfer. The second mechanism (B) is consisted of the addition of alkyl amine, proton transfer, and elimination of thiol. In the gas phase and solvent‐assisted models, the mechanism A is preferred; while in PCM model, the mechanism B is preferred. In both mechanisms, both solvation models have enhancing effects on the thermodynamics of the reactions and stabilize the product versus the reactant (comparing with the gas phase). In mechanism A, the amine should have at least 1 proton and the dithiocarbamate should also have 1 proton in its structure. Both proton transfer steps of these mechanisms have been facilitated by the proton transfer of amine molecule and both solvation models (PCM and explicit presence of water) increased the barriers and reduced the rate of this mechanism. However, in mechanism B, the PCM solvation model reduces the barriers and accelerates the reaction but the solvent‐assisted model increases the barriers and reduces the reaction's rate. The water molecule could not assist efficiently by making the proton bridge in these cases.

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Section: Introductionmentioning

confidence: 99%

Theoretical study of the possible mechanisms for the synthesis of dialkyl thiourea from dithiocarbamate

Ranjbari

Tavakol

2018

Heteroatom Chemistry

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“…Thioureas are the subject of significant interest because of their usefulness in industry, 1,2 agriculture (eg, insect and plant growth regulators, rodenticide agents, and due to antifungal and herbicidal activity), pharmacy (as enzyme inhibitors and antioxidants; antibacterials and antiallergens; anti-inflammatory agents and also antiepileptic, antihypertensive and anticancer drugs, etc), 1,2 and also in analytical and material chemistry. 2 Since several years, they have very often been used as organocatalysts. [3][4][5] It should be noted here that, among biological active thioureas, some contain the amino acid motif (eg, Walpole et al, 6 Vankatachalan and Uckun, 7 Vardhan et al, 8 and Korkmaz et al 9 ).…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, thiourea derivatives are valuable building blocks for the synthesis of many types of compounds (amides, guanidines, and heterocycles). 10 The special type of thioureas-N-arylthioureido-alkylphosphonates (Atc-AA P (OPh) 2 ) are key compounds in the synthesis of 1-amino-alkylphosphonic One of us (JD) thanks the National Science Center (Poland) for support under the OPUS grant UMO 2014/15/B/ST5/05329. [This article is part of the Special Issue: Dedicated to Prof. Jacek Gawronski.…”

Section: Introductionmentioning

confidence: 99%

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High‐performance liquid chromatographic enantioseparation of N‐aryl‐thioureidoalkylphosphonates and thiourylenedi(alkylphosphonates) on polysaccharide‐based chiral stationary phases

Drabowicz

Kudzin

et al. 2017

Chirality

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The first successful enantioseparation of representative O,O-diphenyl-N-arylthioureidoalkylphosphonates, (±)-Ptc-Val (OPh) & (±)-Ptc-Leu (OPh) and thiourylenedi(isobutyl phosphonate), Tcm[Val (OPh) ] on analytical and semipreparative scale was achieved by high-performance liquid chromatography using polysaccharide-based chiral stationary phases (CPs). Atc-AA (OPh) was obtained using modified tricomponent condensations of the corresponding aldehydes, N-arylthiourea and triphenyl phosphite whereas Tcm[Val (OPh) ] by the condensations of aldehydes, thiourea, and triphenyl phosphite. The prepared, racemic (±)-Atc-AA (OPh) [(±)-Ptc-Val (OPh) , (±)-Ptc-Leu (OPh) , (±)-Ptc-Pgly (OPh) and (±)-Ntc-Pgly (OPh) ] and racemic (±)-Tcm[AA (OPh) ] [(±)-Tcm[Nva (OPh) ] & (±)-Tcm[Val (OPh) ] ] were adequately characterized and used for chromatographic separations on high-performance liquid chromatography-chiral stationary phases. The best results were obtained for (±)-Ptc-Val (OPh) , (±)-Ptc-Leu (OPh) and (±)-Tcm[Val (OPh) ] .

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“…The thiourea functional group has been used widely in medicine, with 2-thiouracil itself used to treat thyroid disorders for some time. [19] Thioureas are investigated as antiviral agents, [20] including non-nucleoside HIV-1 reverse transcriptase inhibitors, [21] insecticidal growth regulators, [22] anti-inflammatory, [22] and anticancer drugs. [20] Thioureas show promise as anticancer drug candidates due to their sulfur atoms, [23] with sulfur itself being a versatile and biologically important element to all living organisms.…”

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confidence: 99%

Thiourea and Guanidine Compounds and Their Iridium Complexes in Drug‐Resistant Cancer Cell Lines: Structure‐Activity Relationships and Direct Luminescent Imaging

et al. 2019

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Thiourea and guanidine units are found in nature, medicine, and materials. Their continued exploration in applications as diverse as cancer therapy, sensors, and electronics means that their toxicity is an important consideration. Iridium complexes present new opportunities for drug development and imaging in terms of structure and photoactivity. We have systematically synthesised a set of thiourea and guanidine compounds and iridium complexes thereof, and elucidated structure–activity relationships for cellular toxicity in three ovarian cancer cell lines and their cisplatin‐resistant sub‐lines. We have been able to use the intrinsic luminescence of iridium complexes to visualise the effect of both structure alteration and cellular resistance mechanisms. These findings provide starting points for the development of new drugs and consideration of safety issues for novel thiourea‐, guanidine‐, and iridium‐based materials.

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Thiourea Derivatives in Drug Design and Medicinal Chemistry: A Short Review

Cited by 90 publications

References 24 publications

Theoretical study of the possible mechanisms for the synthesis of dialkyl thiourea from dithiocarbamate

Theoretical study of the possible mechanisms for the synthesis of dialkyl thiourea from dithiocarbamate

High‐performance liquid chromatographic enantioseparation of N‐aryl‐thioureidoalkylphosphonates and thiourylenedi(alkylphosphonates) on polysaccharide‐based chiral stationary phases

Thiourea and Guanidine Compounds and Their Iridium Complexes in Drug‐Resistant Cancer Cell Lines: Structure‐Activity Relationships and Direct Luminescent Imaging

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