- An efficient synthesis of polymethylene-bis-aroyl thiourea derivatives under the condition of phase transfer catalysis
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Reaction of polymethylene diamine with aroyl chloride and ammonium thiocyanate under the condition of solid-liquid phase transfer catalysis using polyethylene glycol-400(PEG-400) as the catalyst yielded polymethylene- bis-aroyl thiourea derivatives 3a - 3
- Wei, Tai-Bao,Zhang, You-Ming,Gao, Li-Ming
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- Synthesis of 1-aryloxyacetyl-4-(4-nitrobenzoyl)-thiosemicarbazides under phase transfer catalysis and microwave irradiation
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The 1-aryloxyacetyl-4-(4-nitrobenzoyl)-thiosemicarbazides (3a-m) are synthesized via reaction of 4-nitrobenzoyl chloride with ammonium thiocyanate and aryloxyacetic acid hydrazides (2a-m) under phase transfer catalysis and microwave irradiation in excelle
- Li, Zheng,Wang, Xicun
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- Preparation and characterization of copper sulfide nanoparticles from symmetrical [(Bu) 2NC(S)NC(O)C 6H 3(3,5-NO 2) 2] 2Cu(II) and [(Bu) 2NC(S)NC(O)C 6H 4(4-NO 2)] 2Cu(II) complexes by thermolysis
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Trigonal copper sulfide nanoparticles were synthesized from symmetrical [(Bu)2NC(S)NC(O)C6H3(3,5-NO2)2]2Cu(II) and [(Bu)2NC(S)NC(O)C6H4(4-NO2)]2Cu(II) complexes by thermolysis in the presence of surfactant oleylamine. The symmetrical copper complexes were
- Saeed, Sohail,Hussain, Rizwan
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- Semiconducting nanostructured copper sulfide thin films from bidentate copper(ii) complexes of N-(dialkylcarbamothioyl)-nitrosubstituted benzamides by chemical vapour deposition
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Copper(ii) complexes of various N-(dialkylcarbamothioyl)-nitrosubstituted benzamide [dialkyl = di-n-butyl (1a, 2a); hexyl, methyl (3a); butyl, ethyl (4a)] have been synthesized and characterized by elemental analysis, IR spectroscopy and atmospheric pressure chemical ionization-mass spectrometry (MS-APCI). The molecular structure of the complex 2a was determined by single-crystal X-ray diffraction. These complexes were used as single-source precursors for the deposition of copper sulfide thin films by aerosol assisted chemical vapour deposition (AA-CVD) at 350 °C. The powder X-ray diffraction (p-XRD) patterns of the thin films of complexes 3a and 4ashowed the deposition of rhombohedral digenite Cu9S5 phase, and complex 1a deposited monoclinic roxbyite Cu7S4 phase at 350 °C with spherical crystallites. Complex 2a deposited orthorhombic anilite Cu7S 4 phase with spherical crystallites. The degree of roughness of the film surface was determined by atomic force microscopy (AFM). The scanning electron microscopy (SEM) and energy dispersive X-ray analysis (EDXA) results showed the uniform distribution of copper sulfide in the films, which makes them useful semiconducting materials on a structured surface.
- Saeed, Sohail,Rashid, Naghmana,Hussain, Rizwan,Malik, Muhammad Azad,O'Brien, Paul,Wong, Wing-Tak
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- N-(4-Nitrobenzoyl)-N′-(1,5-dimethyl-3-oxo-2-phenyl-1H-3(2H) -pyrazolyl)-thiourea hydrate: Synthesis, spectroscopic characterization, X-ray structure and DFT studies
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The title molecule (C19H17N5O 4S·H2O) was synthesized and characterized by IR-NMR spectroscopy, MS and single-crystal X-ray diffraction. The molecular geometry, vibrational frequencies and gauge-independent atomic orbital (GIAO) 1H and 13C NMR chemical shift values of the compound in the ground state have been calculated by using the density functional theory (DFT) method with 6-31G(d) basis set, and compared with the experimental data. All the assignments of the theoretical frequencies were performed by potential energy distributions using VEDA 4 program. The calculated results show that the optimized geometries can well reproduce the crystal structural parameters, and the theoretical vibrational frequencies and 1H and 13C NMR chemical shift values show good agreement with experimental data. To determine conformational flexibility, the molecular energy profile of the title compound was obtained with respect to the selected torsion angle, which was varied from -180°to +180°in steps of 10°. Besides, molecular electrostatic potential (MEP), frontier molecular orbitals (FMO) analysis and thermodynamic properties of the compound were investigated by theoretical calculations.
- Arslan, N. Burcu,Kazak, Canan,Aydin, Fatma
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- Synthesis of novel acylthioureas bearing naphthoquinone moiety as dual sensor for high-performance naked-eye colorimetric and fluorescence detection of CN? and F? ions and its application in water and food samples
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In this study, six new acylthiourea, bearing naphthoquinone moiety, sensors were synthesized in high yield (88–96%) and characterized using 1H/13C NMR, FT-IR and HRMS techniques. All synthesized sensors (4a-f) showed shifts in absorb
- ?ahin, Ertan,Ayd?ner, Burcu,Efeo?lu, ?a?la,Karasu, Elize,Kele?, Ergin,Nural, Yahya,Sefero?lu, Nurgül,Sefero?lu, Zeynel
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- Theoretical and experimental verification of molecular properties of novel benzamide derivatives using computational platforms and in vitro antibacterial activity
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A series of N-(benzo[d]oxazol-2-ylcarbamothioyl)-2/4-substituted benzamides were synthesized by the reaction of 2-aminobenzoxazole with apposite benzoyl isothiocyanate. The structure of the newly synthesized compounds was confirmed by chemical tests, elemental (C, H, N, and S), and spectral (IR, 1H NMR, 13C NMR, and mass) analysis. All the synthesized compounds were evaluated experimentally for their antibacterial activity against Gram-positive and Gram-negative bacteria. The test results show moderate to potent antibacterial activity compared to the standard drug. The binding interactions of newly synthesized ligand and protein were correlated using a molecular docking study using a binding pocket of GlcN-6-P synthase. [Figure not available: see fulltext.].
- Wanjari, Poonam M.,Mokale, Santosh N.,Bharati, Avinash V.,Ingle, Vishwas N.
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p. 655 - 663
(2021/01/07)
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- A PROCESS FOR PREPARING 2-CHLORO-N-{[4-(PYRIMIDIN-2-YLSULFAMOYL)PHENYL] CARBAMOTHIOYL} BENZAMIDE AND THE PHARMACEUTICAL UTILITY THEREOF
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Disclosed is a process for preparing 2-chloro-N-{[4-(pyrimidin-2-ylsulfamoyl)phenyl] carbamothioyl} benzamide (compound 2c).
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Page/Page column 8; 9
(2021/07/10)
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- Synthesis and Investigation of the Antibacterial Activity of New Tris-Thiourea Derivatives
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An efficient procedure for the preparation of symmetrical tris-thiourea derivatives (5a – 5h) by means of one-pot condensation reaction between available benzoyl chlorides (1a –1h) with potassium thiocyanate (2) and melamine (4) under reflux conditions is
- Ghorbani, Saghi Shiroud,Montazeri, Naser,Zeydi, Masoud Mohammadi,Ghane, Masood
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- Synthesis of Novel Tris-1,2,4-triazole Derivatives and Their Antibacterial Activity
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Abstract: A series of novel 3,3′,3″-[1,3,5-triazine-2,4,6-triyltris(azanediyl)]tris(5-aryl-1H-1,2,4-triazole-1-carbothioamide) derivatives were designed and synthesized through reaction of new tris-thiourea derivatives with thiosemicarbazide and sodium hy
- Ghane, M.,Ghorbani, S. Shiroud,Montazeri, N.,Zeydi, M. M.
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p. 605 - 610
(2021/06/02)
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- Synthesis, kinetics and biological assay of some novel aryl bis-thioureas: A potential drug candidates for Alzheimer's disease
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A new series of bis-thioureas (4a-4j) was synthesized and characterized through spectroscopic and elemental analysis. The synthesized compounds 4a-4j were subjected to acetylcholinesterase enzyme (AChE) inhibition activity and free radical scavenging activity. The results of AChE inhibition assay were found to be active in inhibiting the target enzyme with different IC50 values. Among all derivatives, the 4 g showed highly potent inhibition potential against AChE enzyme with IC50 value of 0.1761±0.00768 μM, which is several times better than the reference inhibitor neostigmine methylsulfate IC50 2.469±0.069 μM. The initial structure-activity relationship (SAR) of 4 g revealed dual hydrogen bonding ability (donor and acceptor). Moreover, the electronic environment around the aromatic ring also greatly influenced the enzyme inhibition of AChE. To further explore the newly synthesized AChE inhibitors, kinetic studies were carried out to determine the mode of inhibition and it was found to be competitive inhibition. Pharmacokinetic predictions (ADMET parameters) were also evaluated and compounds showed good lead-like potential with little hepatotoxic and no skin-sensitive effects. The molecular docking studies delineated the binding affinity of the ligands with target protein and showed docking scores in the range of -10.3 to -7.6 kcal/mol.
- Abbas, Qamar,Abd-Rabboh, Hisham S. M.,Bahadur, Ali,Channar, Kashif Ali,Channar, Pervaiz Ali,Hassan, Mubashir,Iqbal, Shahid,Khan, Bilal Ahmad,Kim, Jung Min,Lal, Bhajan,Mahesar, Parvez Ali,Nawaz, Muhammad,Rajoka, Muhammad Shahid Riaz,Rashid, S. G.,Raza, Hussain,Saeed, Aamer,Shah, Mazloom,Siyal, Ali Nawaz,Ujan, Rabail
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- Experimental and theoretical investigation of N-(4-Nitrobenzoyl)-S-(2-hydroxyethyl)-carbamodithioate
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The title molecule, N-(4-Nitrobenzoyl)-S-(2-hydroxyethyl)-carbamodithioate, (C10H10N2O4S2), was synthesized and its structure verified by single crystal X-ray diffraction and FT-IR, 1H-NMR,
- Arslan, N. Burcu,Ayd?n, Fatma,Kazak, Canan
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p. 1084 - 1092
(2021/08/31)
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- Analysis of the structural, spectroscopic, and molecular electrostatic potential (MESP) of (amino)carbonothionyl (nitro)benzamide derivatives
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This study examined the structural and spectroscopic properties of ten synthesized derivatives of carbonothionylbenzamide. These nitro group based molecules are five meta- (named M) and five para- (named P) compounds. These compounds showed no significant
- Fayomi, Omotola M.,Adeniyi, Adebayo A.,Sha’Ato
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p. 690 - 701
(2021/05/11)
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- Synthesis and Spectral Characterization of New 2-(5-Aryl-4H-1,2,4-triazol-3-yl)-1H-isoindole-1,3(2H)-dione Derivatives
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Abstract: A series of novel 2-(5-aryl-4H-1,2,4-triazol-3-yl)-1H-isoindole-1,3(2H)-diones were synthesized in three steps. In the first step, treatment of substituted benzoyl chlorides with ammonium thiocyanate gave the corresponding benzoyl isothiocyanate
- Alimi,Hatamjafari,Shiroudi,Pourshamsian,Oliaey
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p. 631 - 637
(2021/06/02)
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- Novel N-Acyl-1H-imidazole-1-carbothioamides: Design, Synthesis, Biological and Computational Studies
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The present study reports the convenient synthesis, spectroscopic characterization, bio-assays and computational evaluation of a novel series of N-acyl-1H-imidazole-1-carbothioamides. The screened derivatives displayed excellent antioxidant activity, moderate antibacterial and antifungal potential. The screened derivatives were found to be highly biocompatible against hRBCs. Molecular docking ascertained the mechanism and mode of action towards the molecular target delineating that ligands and complexes were stabilized at the active site by electrostatic and hydrophobic forces in accordance to the corresponding experimental results. Docking simulation provided additional information about the possibilities of inhibitory potential of the compounds against RNA. Computational evaluation predicted that N-acyl-1H-imidazole-1-carbothioamides 5c and 5g can serve as potential surrogates for hit to lead generation and design of novel antioxidant and antibacterial agents.
- Aziz, Hamid,Saeed, Aamer,Khan, Muhammad Aslam,Afridi, Shakeeb,Jabeen, Farukh,Ashfaq-ur-Rehman,Hashim, Muhammad
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- 4-aminocoumarin based aroylthioureas as potential jack bean urease inhibitors; synthesis, enzyme inhibitory kinetics and docking studies
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Background: Urease enzyme catalyzes the hydrolysis of urea into ammonia and CO2, excess ammonia causes global warming and crop reduction. Ureases are also responsible for certain human diseases such as stomach cancer, peptic ulceration, pyelone
- Abbas, Qamar,Ashraf, Zaman,Channar, Pervaiz A.,Fattah, Tanzeela A.,Hassan, Mubashir,Larik, Fayaz A.,Saeed, Aamer
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p. 229 - 243
(2020/03/06)
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- Benzoylthioureas: Design, synthesis and antimycobacterial evaluation
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Background: New drugs and strategies to treat tuberculosis (TB) are urgently needed. In this context, thiourea derivatives have a wide range of biological activities, including anti-TB. This fact can be illustrated with the structure of isoxyl, an old anti-TB drug, which has a thiourea as a pharmacophore group. Objective: The aim of this study is to describe the synthesis and the antimycobacterial activity of fifty-nine benzoylthioureas derivatives. Methods: Benzoylthiourea derivatives have been synthesized and evaluated for their activity against Mycobacterium tuberculosis using the MABA assay. After that, a structure-activity relationship study of this series of compounds has been performed. Results and Discussion: Nineteen compounds exhibited antimycobacterial activity between 423.1 and 9.6 μM. In general, we observed that the presence of bromine, chlorine and t-Bu group at the para-position in benzene ring plays an important role in the antitubercular activity of Series A. These substituents were fixed at this position in benzene ring and other groups such as Cl, Br, NO2 and OMe were introduced in the benzoyl ring, leading to the derivatives of Series B. In general, Series B was less cytotoxic than Series A, which indicates that the presence of a substituent at benzoyl ring contributes to an improvement in both antimycobacterial activity and toxicity profiles. Conclusion: Compound 4c could be considered a good prototype to be submitted to further structural modifications in the search for new anti-TB drugs, since it is 1.8 times more active than the first line anti-TB drug ethambutol and 0.65 times less active than isoxyl.
- Abreu, Lethícia O.,Bispo, Marcelle L. F.,Brito, Tiago O.,Gomes, Karen M.,Louren?o, Maria C. S.,Macedo, Fernando,Pereira, Patricia M. L.,Tisher, Cesar A.,Yamada-Ogatta, Sueli F.,de Fátima, ?ngelo
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- Synthesis, characterization and biological activity of some dithiourea derivatives
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Novel dithiourea derivatives have been designed as HIV-1 protease inhibitors using Autodock 4.2, synthesized and characterized by spectroscopic methods and microanalysis. 1-(3-Bromobenzoyl)-3-[2-({[(3-bromophenyl)formami-do]methanethioyl}amino)phenyl]thio
- Frost, Carminita,Hoppe, Heinrich,Hosten, Eric,Isaacs, Michelle,Khanye, Setshaba D.,Krause, Jason,Lobb, Kevin,Odame, Felix,Sayed, Yasien,Tshentu, Zenixole
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p. 764 - 777
(2020/10/02)
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- Copper promoted C-S and C-N cross-coupling Reactions:The synthesis of 2-(N-Aryolamino)benzothiazoles and 2-(N-Aryolamino)benzimidazoles
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The synthesis of 2-(N-aryolamino)benzothiazoles and 2-(N-aryolamino)benzimidazoles has been accomplished in the presence of copper catalyst. These reactions involve C-S and C-N cross-coupling reaction. All electron donating and withdrawing substituent's readily underwent the reaction to give target products in good to excellent yield. In addition, the reaction also gave target product in high yield with bulk scale.
- Shaik, Baji vali,Seelam, Mohan,Tamminana, Ramana,Kammela, Prasad Rao
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p. 3865 - 3874
(2019/06/20)
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- Design, synthesis and algicides activities of thiourea derivatives as the novel scaffold aldolase inhibitors
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By using a new Fragment-Based Virtual Screen strategy, two series of novel FBA-II inhibitors (thiourea derivatives) were de novo discovered based on the active site of fructose-1, 6-bisphosphate aldolase from Cyanobacterial (CyFBA). In comparison, most of the N-(2-benzoylhydrazine-1-carbonothioyl) benzamide derivatives (L14～L22) exhibit higher CyFBA-II inhibitory activities compared to N-(phenylcarbamothioyl) benzamide derivatives (L1～L13). Especially, compound L14 not only shows higher CyFBA-II activity (Ki = 0.65 μM), but also exhibits most potent in vivo activity against Synechocystis sp. PCC 6803 (EC50 = 0.09 ppm), higher (7-fold) than that of our previous inhibitor (EC50 = 0.6 ppm). The binding modes of compound L14 and CyFBA-II were further elucidated by jointly using DOX computational protocol, MM-PBSA and site-directed mutagenesis assays. The positive results suggest that strategy adopted in this study was promising to rapidly discovery the potent inhibitors with novel scaffolds. The satisfactory algicide activities suggest that the thiourea derivatives is very likely to be a promising lead for the development of novel specific algicides to solve Cyanobacterial harmful algal blooms (CHABs).
- Xiao, Shan,Wei, Lin,Hong, Zongqin,Rao, Li,Ren, Yanliang,Wan, Jian,Feng, Lingling
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p. 805 - 812
(2019/02/03)
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- A useful synthesis of 2-acylamino-1,3,4-oxadiazoles from acylthiosemicarbazides using potassium iodate and the discovery of new antibacterial compounds
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A useful method for the synthesis of 2-acylamino-1,3,4-oxadiazoles was developed. By using potassium iodate as an oxidant in water at 60 ?C, a wide range of 2-acylamino-1,3,4-oxadiazoles were afforded in moderate to excellent yields within two
- Li, Tianlei,Wen, Gang,Li, Jishun,Zhang, Wenxuan,Wu, Song
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supporting information
(2019/05/02)
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- Synthesis of New N-Benzoyl-N'-Triazine Thiourea Derivatives and Their Antibacterial Activity
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Abstract: A series of new N-benzoyl-N'-triazine thiourea derivatives have been synthesized via the reaction of 4-amino-6-methyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one with benzoyl chloride derivatives and ammonium thiocyanate in acetone under reflux conditions. 4-Amino-6-methyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one was prepared from the reaction of two equivalents of hydrazine hydrate with carbon disulfide and sodium pyruvate. The chemical structure of thioureas was confirmed using FT-IR, 1H NMR, 13C NMR, and high-resolution mass spectrometry, and elemental analysis. The synthesized thioureas were assayed for their antibacterial activity against both gram-positive (Micrococcusluteus and Bacilluscereus) and gram-negative (Pseudomonasaeruginosa and Escherichiacoli) bacteria using the agar well diffusion method.
- Marzi,Pourshamsian,Hatamjafari,Shiroudi,Oliaey
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p. 391 - 397
(2019/10/28)
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- Synthesis of Novel Triazolyl Thiourea Derivatives and Their Antibacterial Activity
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4-Amino-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione was synthesized in three steps from carbon disulfide, hydrazine hydrate, and acetic acid. Its reaction with benzoyl isothiocyanates prepared from substituted benzoyl chlorides and ammonium thiocyanate afforded the corresponding N-benzoyl-N′-triazolyl-thioureas. The obtained compounds were screened for antibacterial activity against Staphylococcus aureus (ATCC 25923), Staphylococcus epidermidis (ATCC 12228), Enterococcus faecalis (ATCC 29212), Escherichia coli (ATCC 25922), and Pseudomonas aeruginosa (ATCC 27853). Their antibacterial activity against gram-positive bacteria was higher than against gram-negative bacteria, and derivatives containing electron-withdrawing groups were more active than those with electron-donating substituents.
- Kazeminejad,Pourshamsian,Hatamjafari,Shiroudi,Oliaey
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p. 1609 - 1615
(2019/12/28)
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- Chalcone-Thiazole Hybrids: Rational Design, Synthesis, and Lead Identification against 5-Lipoxygenase
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A hybrid pharmacophore approach is used to design and synthesize novel chalcone-thiazole hybrid molecules. Herein, thiazole has been hybridized with chalcone to obtain a new class of 5-LOX inhibitors. In vitro biological evaluation showed that most of the compounds were better 5-LOX inhibitors than the positive control, Zileuton (IC50 = 1.05 ± 0.03 μM). The best compounds in the series, namely, 4k, 4n, and 4v (4k: IC50 = 0.07 ± 0.02 μM, 4n: IC50 = 0.08 ± 0.05 μM, 4v: 0.12 ± 0.04 μM) are found to be 10 times more active than previously reported 2-amino thiazole (2m: IC50 = 0.9 ± 0.1 μM) by us. Further, 4k has redox (noncompetitive) while 4n and 4v act through a competitive inhibition mechanism. SAR indicated that the presence of methoxy/methyl either in the vicinity of chalcone or both thiazole and chalcone contributed to the synergistic inhibitory effect.
- Doble, Mukesh,Manju, S. L.,Sinha, Shweta
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supporting information
(2019/10/08)
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- Phosphine-free direct conversion of carboxylic acids into acyl isothiocyanates using various electrophilic halogenation reagents
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In this study, the efficiency of some electrophilic halogen reagents including 2,4,6-trichloro-1,3,5-triazine, 2,4,4,6-tetrabromo-2,5-cyclohexadienone, 2-chloro-1-methylpyridinium iodide, N-bromosuccinimide, trichloroisocyanuric acid, and 1,3-dibromo-5,5-
- Khaje-Kolaki, Aslan,Mokhtari, Babak
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p. 805 - 808
(2018/09/26)
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- Synthesis and enzyme inhibitory kinetics of some novel 3-(substituted benzoyl)-2-thioxoimidazolidin-4-one derivatives as α-glucosidase/α-amylase inhibitors
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The present work describes an efficient and convenient synthesis of a library of novel 3-(substituted benzoyl)-2-thioxoimidazolidin-4-ones (3a–j). The benzoyl isothiocyanates were treated with glycine in the presence of pyridine, the reactants got consumed giving a variety of thioxoimidazolidin-4-ones derivatives under mild reaction conditions. The structures of the compounds were determined by elemental analysis, FTIR, 1H, 13C NMR and mass spectral data. The title compounds were tested for their potential to inhibit the activity of enzymes α-glucosidase and α-amylase. It was found that most of the derivatives showed good enzyme inhibitory activity while compound 3j exhibited excellent activity with IC50 values 0.051 and 0.0082 mM for α-glucosidase and α-amylase, respectively. The presence of 3,5-di-NO2 functional groups at aromatic ring in compound 3j play important role in enzyme inhibitory activity. The enzyme inhibitory kinetic analysis of the most potent derivative 3j revealed that it is a mixed type inhibitor of α-glucosidase with Ki and Ki? values 0.0339 and 0.1562 mM, respectively. It was further investigated that compound 3j formed reversible enzyme inhibitor complex with α-glucosidase. The cytotoxicity of all the synthesized compounds was also evaluated and results showed that none of these compounds displayed toxicity against brine shrimps. Based upon results, it is suggested that compound 3j may act as a lead structure for the development of most potent α-glucosidase inhibitors.
- Qamar, Rabia,Saeed, Aamer,Saeed, Maria,Shah, Babar Hussain,Ashraf, Zaman,Abbas, Qamar,Seo, Sung Yum
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p. 1528 - 1537
(2018/04/02)
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- Design, synthesis and identification of novel substituted 2-amino thiazole analogues as potential anti-inflammatory agents targeting 5-lipoxygenase
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Human 5-Lipoxygenase (5-LOX) is a key enzyme targeted for asthma and inflammation. Zileuton, the only drug against 5-LOX, was withdrawn from the market due to several problems. In the present study, the performance of rationally designed conjugates of thi
- Sinha, Shweta,Doble, Mukesh,Manju
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- Synthesis, carbonic anhydrase inhibitory activity and antioxidant activity of some 1,3-oxazine derivatives
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(Table presented.). A series of 1-(6-methyl-2-substituted phenyl-4-thioxo-4H-1,3-oxazin-5-yl)ethanones (3a-n) were synthesized by the reaction of benzoyl isothiocyanates with active methylene compound acetylacetone in the presence of triethyl amine in a one-pot process. The structures of the products were elucidated by elemental analyses, FT-IR, 1H NMR, 13C NMR, and mass spectroscopy. These new 1,3-oxazine derivatives were evaluated for their inhibitory activity against carbonic anhydrase II. Results for in vitro assay revealed that compound 3b having 4-methoxy phenyl moiety was the most potent inhibitor with IC50 value of 0.144 ± 0.008 μM. It exhibited higher enzyme inhibitory activity as compared to the standard acetazolamide (IC50 = 0.997 ± 0.061 μM). The compounds 3c, 3h, and 3n also displayed superior inhibitory activities compared to the rest of the synthesized oxazine derivatives. The radical scavenging activity of oxazine derivatives was also performed and it was found that compounds showed moderate antioxidant activity. Lipinski rule confirmed the therapeutic potential of the synthesized compounds. Molecular docking studies were also performed to further understand the binding affinity of these compounds with PDBID 1V9E which confirmed that the synthesized derivatives bind in the active binding site of the target protein. Based upon our results, it is proposed that compound 3b may serve as a lead structure to design more potent carbonic anhydrase inhibitors.
- Qamar, Rabia,Saeed, Aamer,Saeed, Maria,Ashraf, Zaman,Abbas, Qamar,Hassan, Mubashir,Albericio, Fernando
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p. 352 - 361
(2018/10/20)
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- A cascade synthesis of: S -allyl benzoylcarbamothioates via Mumm-type rearrangement
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A catalyst and solvent free synthesis of S-allyl benzoylcarbamothioates has been achieved from the in situ generated benzoylcarbonimidothioates obtained by reacting MBH alcohols with aroyl isothiocyanates. An intramolecular thia-Michael addition of the in
- Dahiya, Anjali,Ali, Wajid,Alam, Tipu,Patel, Bhisma K.
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supporting information
p. 7787 - 7791
(2018/11/21)
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- One-pot solvent-free synthesis of novel functionalized ethyl 2-(alkylimino)-4-methyl-3-(alkanoyl)-2,3-dihydrothiazole-5-carboxylates
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A green and efficient one-pot two-step synthesis of ethyl 2-(alkylimino)-4-methyl-3-(alkanoyl)-2,3-dihydrothiazole-5-carboxylates from the reaction between acyl chlorides, ammonium thiocyanate, primary alkylamines, and ethyl 2-chloroacetoacetae under mild
- Iravani, Nasir,Keshavarz, Mosadegh,Hosseini, Fatemeh
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p. 1098 - 1103
(2018/04/19)
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- Caffeine catalyzed green synthesis of novel benzo[a][1,3]oxazino[6,5-c]phenazines via a one-pot multi-component sequential protocol in a basic ionic liquid
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Caffeine was applied as a green and natural catalyst for the one-pot, four-component sequential condensation between 2-hydroxy-1,4-naphthoquinone, aromatic 1,2-diamines, ammonium thiocyanate and acid chlorides in the presence of a basic ionic liquid (1-butyl-3-methylimidazolium hydroxide) to afford the corresponding benzo[a][1,3]oxazino[6,5-c]phenazine derivatives. In this one-pot transformation, five bonds and two new rings are efficiently formed. This protocol has the advantages of operational simplicity, high yields, easy workup, avoidance of hazardous or toxic catalysts and organic solvents and high chemo- and regioselectivities.
- Mohebat, Razieh,Yazdani-Elah-Abadi, Afshin
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p. 1340 - 1344
(2017/06/19)
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- Solvent-free synthesis of functionalised indenothiazoles using four-component reactions of ninhydrin
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A one-pot synthesis of indenothiazole derivatives via four-component reactions of ninhydrin, acid chlorides, ammonium thiocyanate and primary amines at 70 °C is described. The method offers several advantages including high yields of products and an easy experimental work-up procedure.
- Moradi, Ali Varasteh
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p. 403 - 405
(2017/08/04)
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- Synthesis, characterization, and in?vitro evaluation and in silico molecular docking of thiourea derivatives incorporating 4-(trifluoromethyl)phenyl moiety
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A series of acyl thiourea derivatives bearing 4-(trifluoromethyl)phenyl moiety (7 compounds) has been synthesized and characterized by FT-IR, 1H and 13C NMR spectroscopy and elemental analyses. The molecular structure of five compounds (2, 4, 5, 6 and 7) was determined by single crystal X-ray diffraction analysis. The crystal structures revealed that the carbonyl thiourea units in all determined compounds are mostly planar due in part to the formation of intramolecular N[sbnd]H?O[dbnd]C and C[sbnd]H?S[dbnd]C hydrogen bonds that form two S (6) rings. The intermolecular contacts of five crystal structures have been preformed based on the Hirshfeld surface and their associated 2D fingerprint plots. All the synthesized compounds were preliminarily screened for their in?vitro anti-fungal activity. Especially, compounds 4, 5 and 6 showed a good anti-fungal activity for four different kinds of fungi. Furthermore, all prepared thiourea derivatives were screened for antioxidant potential activity by DPPH free radical scavenging and the excellent activity were found compounds 5 and 6 with the IC50value of 191.75?μg/mL and 189.75?μg/mL, respectively. In silico molecular docking studies were performed to screen the thiourea derivatives against heat shock protein HSP90.
- Qiao, Lei,Huang, Jie,Hu, Wei,Zhang, Yu,Guo, Jiajia,Cao, Wenli,Miao, Kanghua,Qin, Baofu,Song, Jirong
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p. 149 - 159
(2017/03/22)
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- Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea against Meloidogyne incognita
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Two series of novel 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea were designed and synthesized. The bioassay results showed that most of the test compounds showed good nematicidal activity against M. incognita at the concentration of 10.0?mg?L?1 in vivo. The compounds A13, A17 and B3 showed excellent nematicidal activity on the second stage juveniles of the root-knot nematode with the inhibition rate of 51.3%, 58.3% and 51.3% at the concentration of 1.0?mg?L?1 respectively. It suggested that the structure of 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea could be optimized further.
- Chang, Yaning,Zhang, Jingwei,Chen, Xiulei,Li, Zhong,Xu, Xiaoyong
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supporting information
p. 2641 - 2644
(2017/05/10)
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- Synthesis of novel derivatives of chromenone bearing an N-carbamothioyl moiety as soybean 15-LOX inhibitors
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Novel derivatives of chromenone bearing an N-carbamothioyl moiety were synthesized and evaluated for their soybean 15-LOX inhibitory activity. Synthesis of the target compounds was started from 7-hydroxy-2H-chromen-2-one. It was reacted with 1-fluoro-2(4)
- Kaviani, Robabeh,Saeedi, Mina,Mahdavi, Mohammad,Nadri, Hamid,Moradi, Alireza,Shafiee, Abbas,Akbarzadeh, Tahmineh
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p. 335 - 344
(2017/07/04)
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- Identification of acylthiourea derivatives as potent Plk1 PBD inhibitors
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Thiourea derivatives have drawn much attention for their latent capacities of biological activities. In this study, we designed acylthiourea compounds as polo-like kinase 1 (Plk1) polo-box domain (PBD) inhibitors. A series of acylthiourea derivatives without pan assay interference structure (PAINS) were synthesized. Four compounds with halogen substituents exhibited binding affinities to Plk1 PBD in low micromole range. The most potent compound (3v) showed selectivity over other subtypes of Plk PBDs and inhibited the kinase activity of full-length Plk1.
- Yun, Taikangxiang,Qin, Tan,Liu, Ying,Lai, Luhua
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p. 229 - 236
(2016/09/09)
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- Scanning electrochemical microscopy for the investigation of corrosion inhibition of triazino-benzimidazole-2-thiones in hydrochloric acid solution
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Aryl-triazino-benzimidazole-2-thiones were synthesized via three-component reaction between ammonium thiocyanate, benzoyl chlorides, and 2-aminobenzimidazole in acetone. The structure of the products was confirmed by NMR, FT‐IR, and mass spectrometer. The
- Esmaeili,Neshati,Yavari
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p. 5339 - 5351
(2016/06/01)
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- Acylthiourea derivatives as colorimetric sensors for anions: Synthesis, characterization and spectral behaviors
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Several acylthioureas have been synthesized to develop colorimetric sensors for detection of biologically important anions. UV-vis titration experiments indicated that the absorbance values have a good linear relationship with concentration of anions when
- Liu, Shuangshuang,Kang, Jing,Cao, Xiufang,Yue, Xiali
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p. 471 - 477
(2015/09/22)
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- Synthesis and antitumor activity of novel N-benzoyl-N'-substituted pyrimidinyl (thio)semicarbazide derivatives
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A series of substituted pyrimidinyl (thio)semicarbazide derivatives were designed and synthesized. The antitumor results showed that the activity of thiosemicarbazide compounds (series II) was generally higher than that of the corresponding semicarbazide derivatives (series I). Among them, IIk displayed higher cytotoxicity against HL-60, BGC-823 and Bel-7402 than that of adriamycin and exhibited broad in vitro cytotoxicity against 13 human tumor cell lines. Meanwhile, the cytotoxic selectivity and anti-multidrug resistance were evaluated, and IIk exhibited selective cytotoxicity against cancer cells in comparison to human normal cells and had significant anti-multidrug resistance capability. The bioassay results showed that IIk showed great promise as a potent lead compound for further antitumor discovery.
- Song, Gaopeng,Li, Jianzuo,Tian, Hao,Li, Yasheng,Hu, Dekun,Li, Ying,Cui, Zining
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p. 329 - 334
(2016/04/04)
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- Design, syntheses and evaluation of benzoylthioureas as urease inhibitors of agricultural interest
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Urea is one of the most used nitrogen fertilizers worldwide. However, occurrence of urea hydrolysis to ammonia and carbon dioxide on soil surface, catalyzed by soil ureases, considerably reduces nitrogen availability to crops. In this study, we describe the design, synthesis and screening of sixty five benzoylthioureas (BTUs) for their ability to inhibit purified jack bean and soil ureases. BTUs were readily obtained in one pot, two steps synthesis with no need of cumbersome procedures for product purification. In vitro assays revealed BTUs 11, 12, 14, 19-22 and 37 as the most active jack bean urease inhibitors. Such BTUs were found to be able to bind to both catalytic and allosteric sites of urease, acting therefore as mixed-type inhibitors. Out of 28 compounds that effectively inhibited soil ureases activity, BTUs 3, 6, 10, 12, 16, 19 and 22 were determined to be more potent than the reference inhibitor N-(butyl) thiophosphoric triamide (NBPT; 40%). The other 22 BTUs were as potent as NBPT on soil ureases. The temperature-tolerance of BTUs, along with their ability to inhibit soil ureases, makes of this class of compounds potential additive for urea-based fertilizers.
- Brito, Tiago O.,Souza, Aline X.,Mota, Yane C. C.,Morais, Vinicius S. S.,De Souza, Leandro T.,De Fátima, ?ngelo,Macedo, Fernando,Modolo, Luzia V.
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p. 44507 - 44515
(2015/06/02)
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- Straightforward Approach Toward Dihydrothiazoles via Intramolecular Bromocyclization
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An intramolecular bromonium ion-assisted cyclization with sulfur as an internal nucleophile is described. Starting from benzoyl chlorides, this method provides an easy procedure for the synthesis of dihydrothiazole derivatives in moderate to good yields.
- Sadat-Ebrahimi, Seyed Esmail,Ganjizadeh Zarj, Marzieh,Moghimi, Setareh,Yahya-Meymandi, Azadeh,Mahdavi, Mohammad,Arab, Saman,Shafiee, Abbas,Foroumadi, Alireza
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p. 2142 - 2147
(2015/09/01)
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- Synthesis of 2-aryl-7-methyl-4-thioxo-4H-pyrano[3,4-e][1,3]oxazin-5-one by three-component condensation
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A novel method for oxazine ring formation is established though the reaction of ammonium thiocyanate and aroyl chlorides with 4-hydroxy-6-methyl-2H-pyran-2-one in the presence of N-methylimidazole to afford 2-aryl-7-methyl-4-thioxo-4H-pyrano[3,4-e][1,3]ox
- Khazaeian, Ali,Hassanabadi, Alireza
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p. 492 - 493
(2015/11/03)
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- A facile one-pot synthesis and heterocyclisation of (R)-2-amino-3- ((aroylcarbamothioyl)thio)propanoic acids
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A series of (R)-2-amino-3-((aroylcarbamothioyl)thio)propanoic acid derivatives have been synthesised by a one-pot, threecomponent reaction of L-cysteine with ammonium thiocyanate in the presence of various acid chlorides under solvent-free conditions in excellent yields. These compounds were converted to (R)-2-thioxothiazolidine-4-carboxylic acid in water under reflux conditions.
- Mohebat, Razieh,Kafrizi, Elahe
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p. 172 - 174
(2014/04/17)
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- Synthesis, biological evaluation and docking study of 3-aroyl-1-(4- sulfamoylphenyl)thiourea derivatives as 15-lipoxygenase inhibitors
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A series of 3-aroyl-1-(4-sulfamoylphenyl)thiourea derivatives containing sulfonamide moiety were designed and synthesized as 15-lipoxygenase (15-LOX) inhibitors. Most synthesized compounds showed potent activity against soybean 15-LOX with IC50
- Mahdavi, Mohammad,Shirazi, Maryam Shahzad,Taherkhani, Raana,Saeedi, Mina,Alipour, Eskandar,Moghadam, Farshad Homayouni,Moradi, Alireza,Nadri, Hamid,Emami, Saeed,Firoozpour, Loghman,Shafiee, Abbas,Foroumadi, Alireza
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p. 308 - 313
(2014/06/24)
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- Direct and facile synthesis of acyl isothiocyanates from carboxylic acids using trichloroisocyanuric acid/triphenylphosphine system
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A mild, efficient, and practical method for one-step synthesis of alkanoyl and aroyl isothiocyanates from carboxylic acids using a safe and inexpensive mixed reagent, trichloroisocyanuric acid/triphenyl-phosphine is described at room temperature. Availability of the reagents and easy workup of the reaction make this method attractive for organic chemists.
- Entezari, Najmeh,Akhlaghinia, Batool,Rouhi-Saadabad, Hamed
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p. 201 - 206
(2015/02/05)
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- Deposition and characterization of Cu9S5 nanocrystals from unsymmetrical [(Hex)(Me)NC(S)NC(O)C6H3(NO 2)2 -3,5]2Cu(II) and [(Et)(Bu)NC(S)NC(O)C 6H4-4-NO
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Cu9 S5 nanocrystals were synthesized from unsymmetrical [(Hex)(Me)NC(S)NC(O)C6H3 (NO 2)2 -3,5]2 Cu(II) and [(Et)(Bu)NC(S)NC(O)C 6H4 -4-NO2 ]
- Saeed, Sohail,Hussain, Rizwan
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p. 413 - 422
(2014/06/09)
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- Synthesis and metal complexes of thiourea ligands containing carbohydrate-derived substituents
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Two glucose-derived thiourea derivatives, 2a and 2b, were prepared by addition of the corresponding amino sugars to a solution of 4-nitrobenzoyl isothiocyanate (Scheme 1). The thioureas were isolated as colorless solids in good yields and were fully characterized by NMR spectroscopy, optical rotation, elemental analysis, and also by single-crystal X-ray diffraction. Attempts to obtain CuII and NiII bis(chelate) complexes with these thioureas failed. However, the C(1)-protected thiourea derivative 2a reacted with orthopalladated acetato-bridged dimers to afford the corresponding monomeric PdII complexes 3 and 4 (Scheme 2). In these compounds, the thiourea coordinates to the metal as monoanionic O,S chelate ligand, which was confirmed by X-ray crystallography. Copyright
- Sternberg, Michelle,Rust, J?rg,Lehmann, Christian W.,Mohr, Fabian
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p. 280 - 288
(2013/03/28)
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- Naked eye sensing of anions using thiourea based chemosensors with real time application
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Novel chromogenic sensors with thiourea moiety as receptor unit were synthesized and characterized using IR and NMR spectroscopic techniques. The receptors 1 and 2 bearing hydrogen bonding site demonstrate visually striking color change, UV-vis, and fluor
- Vinithra,Suganya,Velmathi
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supporting information
p. 5612 - 5615
(2013/09/23)
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- Synthesis, characterization and antibacterial activity of new 1,2- and 1,4-bis(n'-substituted thioureido)benzene derivatives
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Synthesis of two series of 1,2- and 1,4-bis(thioureido)benzene derivatives was accomplished by the treatment of corresponding alkanoyl/aroyl chlorides with potassium thiocyanate in dry acetone to afford the respective isothiocyanates as intermediates. The
- Saeed, Aamer,Abbas, Naeem,Ashraf, Zaman,Bolte, Michael
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p. 273 - 278
(2013/12/04)
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- Antituberculosis and antifungal activities of synthesized, benzoylthiourea derivatives
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A series of benzoylthiourea derivatives have been synthesized from benzoyl isothiocyanate and phenyleneamine in CH2Cl2 medium under solid-liquid phase transfer catalysis conditions. Structures of these compounds have been characterized by elemental analyses as well as IR and 1H NMR spectroscopy. All the compounds were tested for their antibacterial and antifungal activities, the results indicated that most of the compounds have antibacterial and antifungal activities close to the standard drugs, especially they were found to have remarkable antituberculosis and antifungal activities.
- Zhao, Meng-Meng,Dong, Xiu-Yan,Li, Gang,Yang, Yu-Hua,Zhang, Yu-Jie,Yang, Xiao-Qin
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p. 7548 - 7550
(2013/08/23)
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- Three-component and one-pot synthesis of 1,2,4-triazole-3-thione derivatives under solvent-free conditions
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A novel method for 1,2,4-triazole-3-thiones formation is established using the reaction of ammonium thiocyanate and aroyl chlorides with acylhydrazides under solvent-free conditions to afford triazole-3-thiones in good yields.
- Hassanabadi, Alireza
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p. 511 - 512
(2013/09/12)
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- Discovery of N-(4-sulfamoylphenyl)thioureas as Trypanosoma brucei leucyl-tRNA synthetase inhibitors
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Human African trypanosomiasis (HAT) is one of the most neglected diseases in the tropic regions, which is fatal if not treated in time. There is an urgent need for new therapeutics, especially those in new chemical classes. Leucyl-tRNA synthetase (LeuRS) has been paid much attention as a recently clinically validated antimicrobial target. Our group has previously reported T. brucei LeuRS (TbLeuRS) inhibitors, including benzoxaboroles targeting the editing site and pyrrolinones targeting the synthetic site. Here we report the discovery of N-(4-sulfamoylphenyl)thioureas as a new class of TbLeuRS inhibitors. The R1 and R2 groups, reminiscent of the leucyl and adenyl regions of aa-AMP and aa-AMS, were optimized to result in a significant 13-fold increase of inhibitory activity (compound 19, IC 50 = 13.7 μM). Aided by ligand-protein docking, the 1,3-substitution at the central phenyl ring was predicted and proved to give significantly improved activity (59, IC50 = 1.1 μM). This work provided a new scaffold for the exploration of novel inhibitors against TbLeuRS, which may become potential therapeutics for the treatment of HAT.
- Zhang, Fenglong,Du, Jin,Wang, Qing,Hu, Qinghua,Zhang, Jiong,Ding, Dazhong,Zhao, Yaxue,Yang, Fei,Wang, Enduo,Zhou, Huchen
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p. 5310 - 5324
(2013/08/23)
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