- Synthesis, crystal structure, spectral and electrochemical characterization, DNA binding and free radical scavenging studies of ferrocene-based thioureas
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Thioureas are important building blocks in medicinal chemistry; ferrocenes as highly hydrophobic moieties induce very interesting qualities in medicinal compounds. In this article, we have synthesized four ferrocene incorporated N,N′-disubstituted benzoyl
- Lal, Bhajan,Kanwal, Ammarah,Altaf, Ataf Ali,Badshah, Amin,Asghar, Faiza,Akhter, Sadia,Ullah, Shafiq,Khan, Syed Ishtiaq,Tahir, Muhammad Nawaz
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- Synthesis, molecular docking and kinetic studies of novel quinolinyl based acyl thioureas as mushroom tyrosinase inhibitors and free radical scavengers
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The enzyme tyrosinase plays a vital role in melanin biosynthesis and enzymatic browning of vegetables and fruits. A series of novel quinolinyl thiourea analogues (11a-j) were synthesized by reaction of 3-aminoquinoline and corresponding isothiocyanates, i
- Mustafa, Muhammad Naeem,Saeed, Aamer,Channar, Pervaiz Ali,Larik, Fayaz Ali,Zain-ul abideen, Muhammad,Shabir, Ghulam,Abbas, Qamar,Hassan, Mubashir,Raza, Hussain,Seo, Sung-Yum
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- Synthesis, structural characterization and quantum chemical calculations on 1-(isomeric methylbenzoyl)-3-(4-trifluoromethylphenyl)thioureas
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The 1-(isomeric methylbenzoyl)-3-(4-trifluoromethylphenyl)thioureas (1–3) have been synthesized using the reaction of 2-methylbenzoyl isothiocyanate, 3-methylbenzoyl isothiocyanate and 4-methylbenzoyl isothiocyanate with 4-aminotrifluorotoluene in dry tet
- Qiao, Lei,Zhang, Yu,Hu, Wei,Guo, Jiajia,Cao, Wenli,Ding, Zimei,Guo, Zhiwei,Fan, An,Song, Jirong,Huang, Jie
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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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- Synthesis, characterization, antimicrobial, antioxidant and computational evaluation of N-acyl-morpholine-4-carbothioamides
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Abstract: The present research paper reports the convenient synthesis, successful characterization, in vitro antibacterial, antifungal, antioxidant potency and biocompatibility of N-acyl-morpholine-4-carbothioamides (5a–5j). The biocompatible derivatives were found to be highly active against the tested bacterial and fungal strains. Moreover, some of the screened N-acyl-morpholine-4-carbothioamides exhibited excellent antioxidant potential. Docking simulation provided additional information about possibilities of their inhibitory potential against RNA. It has been predicted by in silico investigation of the binding pattern that compounds 5a and 5j can serve as the potential surrogate for design of novel and potent antibacterial agents. The results for the in vitro bioassays were promising with the identification of compounds 5a and 5j as the lead and selective candidate for RNA inhibition. Results of the docking computations further ascertained the inhibitory potential of compound 5a. Based on the in silico studies, it can be suggested that compounds 5a and 5j can serve as a structural model for the design of antibacterial agents with better inhibitory potential. Graphic abstract: Binding mode of compound 5j inside the active site of RNA in 3D space. 5j displayed highest antibacterial potential than the reference drug ampicillin with ZOI 10.50?mm against Staphylococcus aureus. 5j also displayed highest antifungal potential than the reference drug amphotericin B with ZOI 18.20?mm against Fusarium solani.[Figure not available: see fulltext.].
- Aziz, Hamid,Saeed, Aamer,Khan, Muhammad Aslam,Afridi, Shakeeb,Jabeen, Farukh
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p. 763 - 776
(2020/03/04)
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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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- 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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- Preparation, structure determination, and in silico and in vitro Elastase inhibitory properties of substituted N-([1,1′-Biphenyl]-2-ylcarbamothioyl)- Aryl/Alkyl benzamide Derivatives
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The preparation of a set of eight closely related biphenyl-thiourea conjugates with aromatic and aliphatic side chains (3a-3h) using a one-pot three-component strategy is reported. All the novel compounds were characterized by spectroscopic techniques (FT
- Abbas, Qamar,Channar, Pervaiz Ali,Echeverría, Gustavo A.,Erben, Mauricio F.,Hassan, Mubashir,Ilyas, Sara,Piro, Oscar E.,Raza, Hussain,Saeed, Aamer,Seo, Sung-Yum,Shaikh, Izhar Ahmed,Ujan, Rabail
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- Iodine-mediated multi-component reactions: Readily access to tetrazoles and guanidines
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Environmentally benign syntheses of One-pot sequential reactions of benzoyl chloride with amines followed by the treatment of molecular I2 reagent under basic conditions provide benzoyl tetrazoles and guanidines in moderate to excellent yields. This one-pot synthesis has several advantages such as mild reaction conditions, short reaction time, convenient workup, high yields, using cheap and readily available reagent molecular Iodine. In addition, functional group tolerance has been explored.
- Kammela, Prasad Rao,Seelam, Mohan,Shaik, Bajivali,Tamminana, Ramana
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supporting information
p. 382 - 388
(2021/09/07)
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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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- An intramolecular 1,5-chalcogen bond on the conformational preference of carbonyl thiocarbamate species
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Two closely related compounds, namely, O-methyl (4-fluorobenzoyl)carbamothioate (I) and O-methyl (4-methylbenzoyl)carbamothioate (II) were prepared in good yields by the reaction of the corresponding benzoyl isothiocyanates and methanol. The structural an
- Channar, Pervaiz Ali,Saeed, Aamer,Larik, Fayaz Ali,Fl?rke, Ulrich,El-Seedi, Hesham,Rodríguez Pirani, Lucas S.,Erben, Mauricio F.
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p. 5243 - 5253
(2020/04/17)
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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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- 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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- Supramolecular self-assembly of new thiourea derivatives directed by intermolecular hydrogen bonds and weak interactions: crystal structures and Hirshfeld surface analysis
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Abstract: We synthesized and characterized a series of four closely related thiourea derivatives (1–4) obtained by reaction of 4-R-benzoyl chloride (R: H, Cl, CH3, and OCH3) with equimolar amount of potassium thiocyanate and dibenzyl
- Gumus, Ilkay,Solmaz, Ummuhan,Binzet, Gun,Keskin, Ebru,Arslan, Birdal,Arslan, Hakan
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p. 169 - 198
(2018/09/25)
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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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- 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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- 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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- Synthesis, spectroscopic investigation, and DFT study of: N, N ′-disubstituted ferrocene-based thiourea complexes as potent anticancer agents
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In the present work, the synthesis, characterization (FT-IR, multinuclear (1H and 13C) NMR, AAS, Raman, and elemental analyses), DNA binding (cyclic voltammetry, UV-Vis spectroscopy), and in vitro biological screening of nine new fer
- Asghar, Faiza,Fatima, Saira,Rana, Sadaf,Badshah, Amin,Butler, Ian S.,Tahir, Muhammad Nawaz
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p. 1868 - 1878
(2018/02/17)
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- Novel guanidine compound against multidrug-resistant cystic fibrosis-associated bacterial species
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Chronic pulmonary infection is a hallmark of lung disease in cystic fibrosis (CF). Infections dominated by non-fermentative Gram-negative bacilli are particularly difficult to treat and highlight an urgent need for the development of new class of agents to combat these infections. In this work, a small library comprising thiourea and guanidine derivatives with low molecular weight was designed; these derivatives were studied as antimicrobial agents against Gram-positive, Gram-negative, and a panel of drug-resistant clinical isolates recovered from patients with CF. One novel compound, a guanidine derivative bearing adamantane-1-carbonyl and 2-bromo-4,6-difluouro-phenyl substituents (H-BDF), showed potent bactericidal activity against the strains tested, at levels generally higher than those exhibited by tobramycin, ceftazimide and meropenem. The role that different substituents exert in the antimicrobial activity has been determined, highlighting the importance of the halo-phenyl group in the guanidine moiety. The new compound displays low levels of cytotoxicity against THP-1 and A549 cells with a selective index (SI) > 8 (patent application PCT/IB2017/054870, August 2017). Taken together, our results indicate that H-BDF can be considered as a promising antimicrobial agent.
- Saeed, Aamer,Bosch, Alejandra,Bettiol, Marisa,Nossa González, Diana L,Erben, Mauricio Federico,Lamberti, Yanina
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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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- 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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- 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 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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- Synthesis and crystal structures of novel (4-phenylthiazol-2(3H)-ylidene) benzamide and ((benzoylimino)-3-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-4-oxothiazolidin-5-ylidene)acetate derivatives
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A new approach to the synthesis of new heterocyclic compounds with benzoylisothiocyanate, amines, and 2-bromoacetophenone (phenacyl bromide) fragments in one molecule has been developed. The synthesis method comprises condensation reaction for the prepara
- Hossaini, Mahshid,Heydari, Reza,Maghsoodlou, Malek Taher,Kolahdoozan, Majid,Graiff, Claudia
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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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- 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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- Synthesis, Characterization, and Structural Investigations of 1-(3-morpholinopropyl)-3-(4-chlorobenzoyl)thiourea monohydrate and 1-(3-morpholinopropyl)-3-(4-methylbenzoyl)thiourea monohydrate
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Two new compounds, 1-(3-morpholinopropyl)-3-(4-chlorobenzoyl)thiourea monohydrate (I) and 1-(3-morpholinopropyl)-3-(4-methylbenzoyl)thiourea monohydrate (II) have been synthesized and characterized by FT-IR, 1H NMR, 13C NMR, and Sing
- Razak, Ibrahim Abdul,Arshad, Suhana,Thanigaimani, Kaliyaperumal,Yusof, Mohd Sukeri Mohd,Abdullah, Sharifah Sakinah,Rahman, Azhar Abdul
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p. 151 - 175
(2015/10/05)
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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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- Design, synthesis, molecular docking studies and in vitro screening of ethyl 4-(3-benzoylthioureido) benzoates as urease inhibitors
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Thioureas are exceptionally versatile building blocks towards the synthesis of wide variety of heterocyclic systems, which also possess extensive range of pharmacological activities. The substituted benzoic acids were converted into corresponding acid chlorides, these acid chlorides were then treated with potassium thiocyanate in acetone and then the reaction mixture was refluxed for 1-2 h afford ethyl 4-(3-benzoylthioureido)benzoates thioureas in good yields. All the newly synthesized compounds were evaluated for their urease inhibitory activities and were found to be potent inhibitors of urease enzyme. Compounds 1f and 1g were identified as the most potent urease inhibitors (IC50 0.21 and 0.13 μM, respectively), and was 100-fold more potent than the standard inhibitors. Further molecular docking studies were carried out using the crystal structure of urease to find out the binding mode of the inhibitors with the enzyme.
- Saeed, Aamer,Khan, Muhammad Siraj,Rafique, Hummera,Shahid, Mohammad,Iqbal, Jamshed
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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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- 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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- Synthesis of new N-[3-(Benzo[d]thiazol-2-yl)-4-methylthiazol-2(3H)-ylidene] substituted benzamides
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A series of novel N -[3-(2-benzo[d]thiazol-2-yl)-4-methylthiazol-2(3H)- ylidene] substituted benzamides (2a-k) were efficiently synthesized by heterocyclization of the corresponding 1-(benzo[d]thiazol-2-yl)-3-aroylthioureas (1a{k). The cyclization was achieved by the reaction of α-bromoacteone produced in situ using bromine in dry acetone in the presence of triethylamine. TUeBITAK.
- Saeed, Aamer,Rafique, Hummera
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p. 909 - 916
(2013/12/04)
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- Study of new ferrocene incorporated N,N′-disubstituted thioureas as potential antitumour agents
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In this paper, we report the synthesis, structural characterisation, cytotoxicity against human ovarian tumour models (A2780, A2780cisR, and A2780ZD0473R), nature of interaction with calf-thymus (CT)-DNA and pBR322 plasmid DNA of new ferrocene based N,N′-
- Lal, Bhajan,Badshah, Amin,Altaf, Ataf Ali,Tahir, Muhammad Nawaz,Ullah, Shafiq,Huq, Fazlul
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p. 1352 - 1360
(2013/12/04)
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- Novel and efficient cyclization procedure for the synthesis of 2,5-disubstituted-1,3,4-thiadiazoles without using any ring-closing reagents
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A novel method for the synthesis of 2,5-disubstituted-1,3,4-thiadiazoles via direct ring closure of 1,6-disubstituted-2,5-dithioureas in dimethylformanide without using any ring-closing reagents has been accidentally discovered. Repeated and extended experiments confirmed that this is a very simple and efficient way to synthesize these kinds of fine chemicals. A series of novel 2,5-disubstituted-1,3,4-thiadiazoles have been synthesized via this method in good yields.
- Lin, Qi,Zhang, You-Ming,Li, Man-Lin,Wei, Tai-Bao
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p. 3251 - 3260
(2012/09/10)
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- SAR analysis of a series of acylthiourea derivatives possessing broad-spectrum antiviral activity
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A series of acylthiourea derivatives were designed, synthesized, and evaluated for broad-spectrum antiviral activity with selected viruses from Poxviridae (vaccinia virus) and two different genera of the family Bunyaviridae (Rift Valley fever and La Cross
- Burgeson, James R.,Moore, Amy L.,Boutilier, Jordan K.,Cerruti, Natasha R.,Gharaibeh, Dima N.,Lovejoy, Candace E.,Amberg, Sean M.,Hruby, Dennis E.,Tyavanagimatt, Shanthakumar R.,Allen III, Robert D.,Dai, Dongcheng
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scheme or table
p. 4263 - 4272
(2012/07/17)
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- One-pot synthesis and crystal structure of N-acyl-N′-[1-(2,6- dichloro-4-trifluoromethyl)phenyl-3-cyano-1H-pyrazol-5-yl]thioureas
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Nine novel thiourea derivatives containing pyrazole rings have been prepared in good yields by the reaction of 5-amino-3-cyano-1-(2,6-dichloro-4- trifluoromethylphenyl)pyrazole with acylisothiocyanates, which were generated in situ by potassium thiocyanate and different acyl chlorides in one pot. N-Benzoyl-N′-[1-(2,6-dichloro-4-trifluoromethyl)phenyl-3-cyano-1H-pyrazol- 5-yl]thiourea was characterised by a single crystal X-ray diffraction study.
- Zhang, Xiaohong,He, Hui,Xu, Mei,Zhong, Ping
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experimental part
p. 323 - 325
(2011/10/02)
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- Synthesis, characterization of some new 1-aroyl-3-(4-aminosulfonylphenyl) thioureas and crystal structure of 1-(3,4,5-trimethoxybenzoyl)- 3-(4-aminosulfonylphenyl)thiourea
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A small library of novel 1-aroyl-3-(4-aminosulfonylphenyl)thiourea derivatives was synthesized by the reaction of sulfanilamide with substituted aroyl isothiocyanates in dry acetonitrile. The scope of the reaction was indicated by the synthesis of 1-undecanoyl-3-(4-aminosulfonylphenyl)thiourea, an acyl derivative involving alkanoyl isothiocyanate. All the compounds have been characterized by analytical and spectroscopic methods and in one case by single-crystal X-ray diffraction data.
- Saeed, Aamer,Mumtaz, Amara,Ishida
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experimental part
p. 45 - 54
(2012/01/06)
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- Synthesis and pharmacological properties of N-substituted-N′-(4,6- dimethylpyrimidin-2-yl)-thiourea derivatives and related fused heterocyclic compounds
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A series of new N-Substituted-N′-(4,6-dimethylpyrimidin-2-yl)- thiourea derivatives (3a-d) and related fused heterocyclic compounds (4a-d) were synthesized using tetrabutylammonium bromide as phase transfer catalyst (PTC). N-[(2E)-5,7-dimethyl-2H-[1,2,4]
- Saeed, Sohail,Rashid, Naghmana,Jones, Peter G.,Tahir, Arifa
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experimental part
p. 74 - 82
(2011/04/16)
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- Three-component reaction between 4-hydroxycoumarin, ammonium thiocyanate and acid chlorides in the presence of N-methylimidazole under solvent-free conditions
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A novel method for oxazine ring formation is established using the reaction of ammonium thiocyanate and acid chlorides with 4-hydroxy coumarin in the presence of N-methylimidazole to afford oxazine derivatives in excellent yields.
- Hassanabadi, Alireza,Mosslemin, Mohammad H.,Tadayonfar, Seyd Ehsan
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experimental part
p. 29 - 31
(2011/04/26)
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- 2-substituted 4H-[1,3]thiazolo[3,2-a][1,3,5]triazine-4-thiones: Synthesis, crystal structure, and antifungal activity
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2-(4-Substituted aryl)-4H-[1,3]thiazolo[3,2-a][1,3,5]triazine-4-thiones (3a-3b) and 2-(2-thiophene)-4H-[1,3]thiazolo[3,2-a][1,3,5]triazine-4-thione (3d) were synthesized by the reaction of arylisothiocyanates/thiophene-2- isothiocyanate with 2-aminothiazo
- Saeed, Sohail,Rashid, Naghmana,Jones, Peter G.,Yunas, Uzma
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experimental part
p. 908 - 912
(2010/10/04)
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