- Bioactivity of new ferrocene incorporated N,N′-disubstituted ureas: Synthesis, structural elucidation and DFT study
-
We report here the synthesis, structural characterization and biological assessment of three new ferrocene incorporated ureas (1-3). The synthesis of these complexes was accomplished by the deprotection of ferrocene-based thioureas to the corresponding oxo analogues using NaOH(aq) and mercuric chloride. The new ferrocenyl ureas were characterized by FT-IR, multinuclear (1H and 13C) NMR, AAS and elemental analysis. Furthermore, the single-crystal X-ray structure of compound 2 was also determined. The DNA binding potency of these ureas was evaluated by UV-Vis spectroscopy and cyclic voltammetry (CV). The three complexes interact electrostatically with DNA and have impressive binding constants ranging from 3.42 × 104 to 8.15 × 104 M-1. The diffusion coefficients of the drug-DNA adducts are lower than is that for the free drug indicating the formation of a high molecular weight complex that diffuses slowly towards the electrode. The small binding site size of 0.509 (1), 0.528 (2) and 0.473 (3) base pairs is also indicative of an electrostatic mode of interaction. The DFT calculated HOMO and LUMO energies correlate well with the experimentally determined redox potential values. The synthesized ureas (1-3) were screened for their antibacterial, antifungal and protein kinase inhibition potency. These compounds play a significant role in arresting microbial growth and are potent protein kinase inhibitors.
- Asghar, Faiza,Badshah, Amin,Lal, Bhajan,Butler, Ian S.,Tabassum, Saira,Tahir, Muhammad Nawaz
-
-
Read Online
- Experimental and computational studies on ruthenium(ii) bis-diimine complexes of N, N ′-chelate ligands: The origin of changes in absorption spectra upon oxidation and reduction
-
This work presents an interpretation of the origin of changes in absorption spectra upon one-electron oxidation and reduction of two ruthenium polypyridyl complexes based on a combination of UV-Vis spectroelectrochemical experiments and theoretical calcul
- Tan, Siew San,Yanagisawa, Susumu,Inagaki, Kouji,Kassim, Mohammad B.,Morikawa, Yoshitada
-
-
Read Online
- Synthesis, kinetics and biological assay of some novel aryl bis-thioureas: A potential drug candidates for Alzheimer's disease
-
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
-
-
- Synthesis and Spectral Characterization of New 2-(5-Aryl-4H-1,2,4-triazol-3-yl)-1H-isoindole-1,3(2H)-dione Derivatives
-
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
-
p. 631 - 637
(2021/06/02)
-
- Benzoylthioureas: Design, synthesis and antimycobacterial evaluation
-
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
-
-
- Design, Synthesis, and Insecticidal Activity of Novel Doramectin Derivatives Containing Acylurea and Acylthiourea Based on Hydrogen Bonding
-
Our recent investigation on the insecticidal activities of several doramectin derivatives preliminarily revealed that the presence of hydrogen bonds at the C4″ position of the molecule with target protein γ-aminobutyric acid (GABA) receptor was crucial for retaining high insecticidal activity. As a continuation of our research work on the development of new insecticides, two series of novel acylurea and acylthiourea doramectin derivatives were designed and synthesized. The bioassay results indicated that the newly synthesized compounds (5o, 5t, and 6t) exhibited higher insecticidal activity against diamondback moth, oriental armyworm, and corn borer than the control compounds doramectin, commercial avermectins, chlorbenzuron, and lead compound 3g in our laboratory. Specifically, compound 5t was identified as the most promising insecticide against diamondback moth, with a final mortality rate of 80.00% at the low concentration of 12.50 mg/L, showing approximately 7.75-fold higher potency than the parent doramectin (LC50 value of 48.1547 mg/L), 6.52-fold higher potency than commercial avermectins (LC50 value of 40.5507 mg/L), and 3.98-fold higher potency than compound 3g (LC50 value of 24.7742 mg/L). Additionally, molecular docking simulations revealed that compound 5t (2.17, 2.20, 2.56, and 2.83 ?) displayed stronger hydrogen-bond action in binding with the GABA receptor, better than that of compound 5o (1.64 and 2.15 ?) and compound 6t (2.20 and 2.31 ?) at the C4″ position. This work demonstrated that these compounds containing hydrogen-bond groups might contribute to the improvement of insecticidal activity and supply certain hints toward structure optimization design for the development of new insecticides.
- Bai, Ping,Cheng, Yao,Lu, Xiaoxia,Yang, Jian,Zhang, Qi,Zheng, Cheng
-
p. 5806 - 5815
(2020/06/19)
-
- Synthesis, characterization and biological activity of some dithiourea derivatives
-
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
-
p. 764 - 777
(2020/10/02)
-
- Phosphine-free direct conversion of carboxylic acids into acyl isothiocyanates using various electrophilic halogenation reagents
-
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
-
p. 805 - 808
(2018/09/26)
-
- Thiosemicarbazones and thiadiazines derived from fluorinated benzoylthioureas: Synthesis, crystal structure and anti-Trypanosoma cruzi activity
-
A series of thiosemicarbazones was obtained by condensation of halogenated N-(diethylaminothiocarbonyl)benzimidoyl chlorides (3b–3h) with 4,4-dimethyl-3-thiosemicarbazide. The activity of the halogenated compounds against the parasite Trypanosoma cruzi was evaluated and compared to the previously reported activity of the corresponding non-substituted thiosemicarbazone. It was found that the halogen-substitution enhances in most cases the anti-parasitic activity. The meta-fluorinated compound (4g) was identified as the most potent one (IC50= 9.0 μM, CC50 > 200 μM), having a selectivity index (SI = IC50/CC50), which is 4-times higher than that of the non-substituted compound. Slight modification of the reaction conditions employed for the synthesis of some of the benzoylthioureas 3a–3g led to the unexpected formation of novel halogenated 6-amino-1,3,5-thiadiazine-2-thiones.
- Salsi, Federico,Bulh?es Portapilla, Gisele,Schutjajew, Konstantin,Carneiro, Zumira Aparecida,Hagenbach, Adelheid,de Albuquerque, Sérgio,da Silva Maia, Pedro Ivo,Abram, Ulrich
-
-
- Synthesis, spectroscopic investigation, and DFT study of: N, N ′-disubstituted ferrocene-based thiourea complexes as potent anticancer agents
-
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
-
p. 1868 - 1878
(2018/02/17)
-
- Biologically active: Halo -substituted ferrocenyl thioureas: Synthesis, spectroscopic characterization, and DFT calculations
-
In our search for new therapeutic agents, ferrocene-based thioureas (M1-M9) were successively synthesized and characterized by various analytical techniques like FT-IR, Raman, CHNS, AAS, and multinuclear (1H and 13C) NMR. The interac
- Asghar, Faiza,Rana, Sadaf,Fatima, Saira,Badshah, Amin,Lal, Bhajan,Butler, Ian S.
-
p. 7154 - 7165
(2018/05/04)
-
- 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
-
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
-
p. 1340 - 1344
(2017/06/19)
-
- Solvent-free synthesis of functionalised indenothiazoles using four-component reactions of ninhydrin
-
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
-
p. 403 - 405
(2017/08/04)
-
- Amino acid linked bromobenzoyl thiourea derivatives: Syntheses, characterization and antimicrobial activities
-
Five new bromobenzoyl thiourea derivatives (1-5) linked with different amino acids were synthesized via the reaction of bromobenzoyl chloride with potassium thiocyanide and the corresponding amines. The synthetic compounds were characterized by single cry
- Raheel, Ahmad,Imtiaz-Ud-Din,Badshah, Amin,Rauf, Muhammad Khawar,Tahir, Muhammad Nawaz,Khan, Khalid Mohammed,Hameed, Abdul,Andleeb, Sohaila
-
p. 959 - 964
(2016/11/22)
-
- Structure-Activity Relationships and Anti-inflammatory Activities of N-Carbamothioylformamide Analogues as MIF Tautomerase Inhibitors
-
Macrophage migration inhibitory factor (MIF), a proinflammatory cytokine, is an attractive therapeutic target for the treatment of inflammatory diseases. In our previous study, 3-[(biphenyl-4-ylcarbonyl)carbamothioyl]amino benzoic acid (compound 1) was discovered as a potent inhibitor of MIF by docking-based virtual screening and bioassays. Here, a series of analogues of compound 1 derived from similarity search and chemical synthesis were evaluated for their MIF tautomerase activities, and their structure-activity relationships were then analyzed. The most potent inhibitor (compound 5) with an IC50 of 370 nM strongly suppressed lipopolysaccharide (LPS)-induced production of TNF-α and IL-6 in a dose-dependent manner and significantly enhanced the survival rate of mice with LPS-induced endotoxic shock from 0 to 35% at 0.5 mg/kg and to 45% at 1 mg/kg, highlighting the therapeutic potential of the MIF tautomerase inhibition in inflammatory diseases.
- Zhang, Yu,Xu, Lei,Zhang, Zhiqiang,Zhang, Zhiyu,Zheng, Longtai,Li, Dan,Li, Youyong,Liu, Feng,Yu, Kunqian,Hou, Tingjun,Zhen, Xuechu
-
p. 1994 - 2004
(2015/10/06)
-
- Synthesis of 2-aryl-7-methyl-4-thioxo-4H-pyrano[3,4-e][1,3]oxazin-5-one by three-component condensation
-
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
-
p. 492 - 493
(2015/11/03)
-
- Direct and facile synthesis of acyl isothiocyanates from carboxylic acids using trichloroisocyanuric acid/triphenylphosphine system
-
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
-
p. 201 - 206
(2015/02/05)
-
- Synthesis and intramolecular cyclization of N-acyl- and N-allyl-N'-(2-oxo-1,2-dihydro-pyridin-3-yl)thiourea
-
The reaction of 3-amino-4,6-dimethylpyridin-2(1H)-one and 3-amino-4-phenylpyridin-2-one with acyl isothiocyanates (benzoyl-, 4-bromobenzoyl-, and methacryloyl isothiocyanates) and with allyl isothiocyanate has been studied. The N-carbamothioyl methacrylam
- Kulakov,Nikitina,Fisyuk,Goncharov,Shul'Gau,Gulyaev
-
p. 670 - 676
(2014/08/18)
-
- A facile one-pot synthesis and heterocyclisation of (R)-2-amino-3- ((aroylcarbamothioyl)thio)propanoic acids
-
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
-
p. 172 - 174
(2014/04/17)
-
- Synthesis of new 10,11-dihydrodibenzo[a,d]cycloheptene S-thiocarbamate derivatives via a benzylic Newman-Kwart rearrangement
-
New S-thiocarbamates possessing a 10,11-dihydro-5H-dibenzo[a,d]cycloheptene moiety were obtained unexpectedly in the process of preparing new O-thiocarbamates starting from 5-dibenzosuberol (10,11-dihydro-5H-dibenzo[a,d] cyclohepten-5-ol) and aroyl-isothi
- Cǎproiu, Miron Teodor,Dumitrascu, Florea,Shova, Sergiu,Chiritǎ, Ileana Cornelia,Missir, Alexandru Vasile,Cioroianu, Dana-Mihaela
-
supporting information
p. 4011 - 4013
(2014/07/08)
-
- Discovery of N-(4-sulfamoylphenyl)thioureas as Trypanosoma brucei leucyl-tRNA synthetase inhibitors
-
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
-
p. 5310 - 5324
(2013/08/23)
-
- Chemical transformations of N-morpholinylacetic acid hydrazide and steric structure of its derivatives
-
The reaction of N-morpholinylacetic acid hydrazide with various isothiocyanates and potassium thiocyanate resulted in the corresponding potentially biologically active thiosemicarbazide derivatives. Potassium N′-(2-morpholin-4-ylacetyl)hydrazinocarbothioate was synthesized and involved into heterocyclization in acidic environment to yield cyclic 5-(morpholinomethyl)-1,3,4-thiadiazole-2-thione. The structure of the synthesized compounds was established by IR, 1H NMR spectroscopy, mass spectrometry, and XRD analysis.
- Nurkenov,Fazylov,Satpaeva, Zh. B.,Kulakov,Turdybekov,Turdybekov,Talipov,Ibragimov
-
p. 520 - 525
(2013/08/23)
-
- Novel and efficient cyclization procedure for the synthesis of 2,5-disubstituted-1,3,4-thiadiazoles without using any ring-closing reagents
-
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
-
p. 3251 - 3260
(2012/09/10)
-
- IN VTRO ANTIBACTERIAL AND ANTIVIRAL ACTIVITIES OF SOME NOVEL 1,3,4-THIADIAZOLE DERIVATIVES
-
A series of new 2-(substituted benzoylthiocarbamido)-5-(phenyl/sulphonamido)-1,3,4-thiadiazoles 4(a-g) and 5(a-g) were synthesized as potential antibacterial and antiviral compounds. 1,3,4-Thiadiazole compounds were prepared by the reaction of 2-amino-1,3,4-thiadiazoles with a solution containing ammonium thiocyanae and substituted benzoyl chloride in acetone/tetrahydrofuran. The structures of the synthesized compounds were confirmed using the elemental analysis and spectroscopic techniques such as IR, 1H NMR and Mass. The newly synthesized compounds were evaluated for in vitro antimicrobial activities by broth micro dilution method. Evaluation of the antiviral activity of the compounds against HIV-1 strain IIIB and HIV-2 strain (ROD) in MT-4 cells was performed using the MTT assay method.
- Dixit, Sheshagiri,Gadaginamath, G. S.,Joshi, S. D.,Kulkarni, V. H.,More, Uttam A.
-
p. 109 - 114
(2020/12/09)
-
- Three-component reaction between 4-hydroxycoumarin, ammonium thiocyanate and acid chlorides in the presence of N-methylimidazole under solvent-free conditions
-
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
-
experimental part
p. 29 - 31
(2011/04/26)
-
- Facile synthesis of 3-aryl/alkylamino 5-aryl/alkyl 1,2,4-oxadiazoles from acylthiourea
-
Facile and selective synthesis of 3-aryl/alkylamino 5-aryl/alkyl 1,2,4-oxadiazoles starting from N-acylthioureas has been demonstrated. The regio-selectivity is achieved by simply selecting an appropriate base used for the generation of hydroxyl amine fro
- Chennakrishnareddy, Gundala,Debasis, Hazra,Jayan, Rapai,Manjunatha, Sulur G.
-
experimental part
p. 6170 - 6173
(2011/11/30)
-
- A rapid, four-component synthesis of functionalized thiazoles
-
An efficient synthesis of 2-(dialkylamino)-4-phenyl)-1,3-thiazol-5-yl) (phenyl)methanone using acid chlorides, secondary amines, 2-bromoacethophenone and ammonium thiocyanate is described.
- Sabbaghan, Maryam,Alidoust, Mostafa,Hossaini, Zinatossadat
-
experimental part
p. 824 - 828
(2012/04/23)
-
- Three-component reaction between 6-amino-N,N′ - Dimethyluracil and ammonium thiocyanate in the presence of aroyl chlorides under solvent-free conditions
-
A novel method for the pyrimidine ring formation is established using the reaction of ammonium thiocyanate and aroyl chlorides with 6-amino-N,N′ -dimethyluracil under solvent-free conditions to afford the functionalized pyrimido[4,5-d]pyrimidines in excel
- Mohebat, Razieh,Mosslemin, Mohammad H.,Dehghan-Darehshiri, Ali,Hassanabadi, Alireza
-
experimental part
p. 557 - 561
(2012/04/23)
-
- ARYL GUANIDINE F1F0-ATPASE INHIBITORS AND RELATED METHODS
-
The invention provides to a family of aryl guanidine-based F1F0-ATPase inhibitors, e.g., mitochondrial F1F0-ATPase inhibitors, methods for their discovery, and their use as therapeutic agents for treating certai
- -
-
Page/Page column 55-57
(2010/04/06)
-
- Design and synthesis of indole, 2,3-dihydro-indole, and 3,4-dihydro-2H-quinoline-1-carbothioic acid amide derivatives as novel HCV inhibitors
-
An efficient synthetic methodology to provide indole, 2,3-dihydro-indole, and 3,4-dihydro-2H-quinoline-1-carbothioic acid amide derivatives is described. These conformationally restricted heterobicyclic scaffolds were evaluated as a novel class of HCV inhibitors. Introduction of an acyl group at the NH2 of the thiourea moiety has been found to enhance inhibitory activity. The chain length and the position of the alkyl group on the indoline aromatic ring markedly influenced anti-HCV activity. The indoline scaffold was more potent than the corresponding indole and tetrahydroquinoline scaffolds and analogue 31 displayed excellent activity (EC50 = 510 nM) against HCV without significant cytotoxicity (CC50 >50 μM).
- Kang, Iou-Jiun,Wang, Li-Wen,Hsu, Sheng-Ju,Lee, Chung-Chi,Lee, Yen-Chun,Wu, Yen-Shian,Hsu, Tsu-An,Yueh, Andrew,Chao, Yu-Sheng,Chern, Jyh-Haur
-
scheme or table
p. 4134 - 4138
(2010/04/26)
-
- Synthesis and bioactivity study of 2,5-bismercapto-1,3,4-thiadiazole heterocyclic derivatives
-
A series of acylhydrazone compounds 3a-i and acylthiosemicarbazides 4a-h containing thiadiazole rings have been synthesized conveniently in high yields. Some heterocyclic derivatives 5 are prepared by the method of dehydration of compounds 4. Structure of all these compounds have been confirmed by elemental analysis, IR, 1H and 13C NMR. The bioassay result indicates that some compounds have relatively low antibacterial activity and other compounds have bioactivity for improving plant growth.
- Li, Man-Lin,Zhang, You-Ming,Wei, Tai-Bao
-
p. 544 - 549
(2008/09/18)
-
- 1-Phenacylmethyl-2-(acylaminothiocarbonylamino)pyridinium bromides as protectors of steel acid corrosion
-
Inhibiting effect of 1-phenacylmethylpyridinium bromides containing acylthiourea substituents in the pyridine ring on corrosion of mild steel in sulfuric acid (3 M) was studied.
- Yurchenko,Pogrebova,Pilipenko
-
p. 675 - 677
(2008/03/12)
-
- The synthesis of 1-(1-phenyl-1H-tetrazole-5-ylthiol)-acetyl-4-aroyl- thiosemicarbazides and 2-aroylamino-5-(1-phenyl-1H-tetrazole-5-ylthiolmethylene) - 1,3,4-thiadiazoles
-
A series of 1-(1-phenyl-1H-tetrazole-5-ylthiol)acetyl-4- aroylthiosemicarbazides were synthesized in good to excellent yields under phase transfer catalytic conditions. By the cyclization of compounds 3a-i in concentrated H2SO2 at 0°
- Wei, Tai-Bao,Li, Man-Lin,Lin, Qi,Liu, Hong,Zhang, You-Ming
-
p. 1583 - 1592
(2007/10/03)
-
- Synthesis of Thieno, Pyrazolo and Isothiazolopyrimidine Derivatives Based on o-Mercaptoacetylpyrimidine Derivative
-
Mercaptopyrimidine 4 was prepared and transformed into methylmercaptopyrimidine 5. Compound 5 was transformed into pyrazolopyrimidine 6, and cinnamoylpyrimidine 7. Compound 4 reacted with halomethylene to produce thienopyrimidines 9, 10. Pyrimidine 4 was converted into pyrimidine derivative 12a, b, upon treatment with H2O2 in acetic acid and NaOH, respectively. Oxidation of 4 leads to disulfide 13. Heterocyclization of 4 using NaOCl in the presence of NaOH/NH4OH afforded isothiazolopyrimidine 15. Heterocyclization of 4 using aromatic aldehydes gives thiopyranopyrimidines 17a, b. Chlorination of 4 afforded chloropyrimidine 18, which was transformed into pyrrolopyrimidine 20 and pyrimidine derivatives 21a, b, c, d.
- Ahmed, G. A.,Mostafa, H. Y.,Assy, M. G.,Mansor, Neven S.
-
-
- Synthesis of 2-(4-bromobenzoylamino)-5-aryloxymethyl-1,3,4-thiadiazoles
-
Reactions of 4-bromobenzoyl chloride with ammonium thiocyanate first, then with aryloxyacetic acid hydrazides under phase transfer catalysis give 1-aryloxyacety1-4-(4-bromobenzoyl)-thiosemicarbazides 3a-k. Compounds 3a-k on treatment with excess glacial a
- Wang,Li,Da,Chen
-
p. 422 - 425
(2007/10/03)
-
- Phase transfer catalyzed synthesis of 1,6- diaroyldithiohydrazodicarbonamide derivatives
-
Reaction of hydrazine hydrate with aroyl chloride and ammonium thiocyanate under the condition of solid-liquid phase transfer catalysis using polyethylene glycol-600 (PEG-600) as the catalyst yielded 1,5- diaroyldithiohydrazodicarbonamides 3a - 3h in good to excellent yield.
- Zhang, Youming,Wei, Taibao,Lu, Jinren
-
p. 3243 - 3248
(2007/10/03)
-
- Synthesis of n-aroyl-n'-hydroxyethyl (hydroxyphenyl)thiourea derivatives under the condition of phase transfer catalysis
-
Reaction of aminoethanol or aminophenol with aroyl chloride and ammonium thiocyanate under the condition of solid-liquid phase transfer catalysis using polyethylene glycol-600 (PEG-600) as the catalyst yielded N-aroyl-N'- hydroxyethyl(hydroxy phenyl)thiou
- Wei, Taibao,Zhang, Youming
-
p. 2851 - 2859
(2007/10/03)
-
- On the Preparation of Substituted 4H-1,3,4-Thiadiazolo[2,3-c]-1,2,4-triazin-4-ones and 1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazoles
-
The reaction of benzoyl isothiocyanates and methoxycarbonyl isothiocyanate with 4-amino-4,5-dihydro-3-(methylthio)-1,2,4-triazin-5-ones in acetonitrile gave several substituted 4H-1,3,4-thiadiazolo[2,3-c]-1,2,4-triazin-4-ones VIa-h instead of the expected
- Coppo, Frank T.,Fawzi, Maged M.
-
p. 1351 - 1354
(2007/10/03)
-