- Square planar Ni(II) complexes of pyridine-4-carbonyl-hydrazine carbodithioate, 1-phenyl-3-pyridin-2-yl-isothiourea and 4-(2-methoxyphenyl) piperazine-1-carbodithioate involving N-S bonding: An approach to DFT calculation and thermal studies
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Three new complexes [H2en][Ni(pchc)2] (1) (pchc = pyridine-4-carbonyl-hydrazine carbodithioate), [Ni(Hppith)2] (2) (H2ppith = 1-phenyl-3-pyridin-2-yl-isothiourea) and [Ni(mppcdt) 2] (3) {mppcdt = 4-(2-methoxyphenyl)piperazine-1-carbodithioate} have been synthesized and characterized by elemental analyses, IR and single crystal X-ray diffraction data. The ligand H2ppith and complexes [H 2en][Ni(pchc)2] (1) [Ni(Hppith)2] (2) and [Ni(mppcdt)2] (3) crystallize in monoclinic, orthorhombic, monoclinic and triclinic system with space group P21/n, Icab, C2/c and P1, respectively. The nitrogen and sulfur donor sites of the bidentate ligands chelate Ni(II) forming two five-membered CSN2M chelate rings in the complex 1, two six membered C2SN2M rings in complex 2 and the sulfur donor sites of the bidentate ligand chelate Ni(II) forming two four membered CS2M rings in complex 3. The Ni(II) complexes are diamagnetic and have distorted square planar geometry. The crystal structure of the complexes are stabilized by various types of inter and intramolecular extended hydrogen bonding providing supramolecular framework. Results obtained from quantum chemical calculations at the density functional theory level corroborate our experimental findings from IR and UV. The course of the thermal degradation of complexes 1,2 and 3 has been investigated by TG-DTA. Thermogravimetric analyses of the complexes indicate NIO/NIS as the end residue.
- Bharati,Bharti,Bharty,Maiti,Butcher,Singh
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- 3-Phenyl-1-(2-pyridyl)thiourea
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The title compound, C12H11N3S, contains an intramolecular N3 - H...Npy hydrogen bond, which stabilizes the coplanarity of the thiourea moiety and the pyridine (py) ring. The molecules form centrosymmetric hydrogen-bonded dimers, with the S atom forming bifurcated intermolecular hydrogen bonds involving the N2 - H group of the thiourea moiety and the C3 - H group of the pyridyl ring.
- West, Douglas X.,Hermetet, Anne K.,Ackerman, Lily J.,Valdes-Martinez, Jesus,Hernandez-Ortega, Simon
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- Synthesis and structures of two N,N′-bis(2-pyridinyl)thioureas and N-(2-pyridinyl)-N′-(benzoyl)thiourea
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N,N-′bis(4,6-lutidyl)thiourea, (4,6Lut)2Tu, triclinic, P-1, a = 7.4930(8), b = 8.7210(8), c = 12.6040(14) ?, α = 93.437(5), β = 94.919(5), γ = 110.246(5)°, V = 766.35(14) ?3 and Z = 2; N,N′-bis(5-picolyl)thiourea, (5Pic)2Tu, monoclinic, P21/c, a = 17.205(2), b = 4.4970(5), c = 17.425(2) ?, β = 117.763(5)°, V = 1272.6(3) ?3 and Z = 4 and N-(2-pyridyl)-N′-benzoylthiourea, PyTubenzo, monoclinic, P21/n, a = 5.345(3), b = 20.343(6), c = 11.808(2) ?, β = 90.23(3)°, V = 1290.8(1) ?3 and Z = 4. Intramolecular hydrogen bonding between N′H and the pyridyl nitrogen, intermolecular hydrogen bonding involving the thione sulfur and the NH hydrogen, and the planarity of the molecule is affected by substitution on the pyridine rings of the bis(2-pyridyl)thioureas. PyTubenzo has intramolecular hydrogen bonding to the carbonyl oxygen, intermolecular hydrogen bonding to a thione sulfur and is the least planar of the molecules under study. 1H NMR studies in CDCl3 show the NH′ hydrogen resonance considerably downfield from other resonances in the spectrum of the bis(2-pyridyl)thioureas.
- Kaminsky, Werner,Goldberg, Karen I.,West, Douglas X.
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- Diversity-Oriented Synthesis of Thiazolidine-2-imines via Microwave-Assisted One-Pot, Telescopic Approach and Its Interaction with Biomacromolecules
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In this work, a one-pot, telescopic approach is described for the combinatorial library of thiazolidine-2-imines. The synthetic manipulation proceeds smoothly via the reaction of 2-aminopyridine/pyrazine/pyrimidine with substituted isothiocyanates followed by base catalyzed ring closure with 1,2-dibromoethane to obtain thiazolidine-2-imines with broad substrate scope and high functional group tolerance. The synthetic strategy merges well with the thiourea formation followed by base catalyzed ring closure reaction for the thiazolidine-2-imine synthesis in a more modular and straightforward approach. The synthetic procedure reported herein represents a cleaner route toward thiazolidine-2-imines as compared to traditional methodologies. Moreover, the biological significance of combinatorially synthesized thiazolidin-2-imines has been investigated for their use as possible inhibitors for acetyl cholinesterase through molecular docking studies.
- Saikia, Ananya Anubhav,Rao, Ramdas Nishanth,Maiti, Barnali,Balamurali, Musuvathi Motilal,Chanda, Kaushik
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p. 630 - 640
(2020/12/15)
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- Copper-Catalyzed Aerobic Oxidative [3+2] Annulation for the Synthesis of 5-Amino/Imino-Substituted 1,2,4-Thiadiazoles through C-N/N-S Bond Formation
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A copper-catalyzed aerobic oxidative annulation reaction of 2-aminopyridine/amidine with isothiocyanate has been reported. This strategy involving C-N/N-S bond formations provides various 5-amino/imino-substituted 1,2,4-thiadiazole derivatives under a Cu/O2 catalytic system. This method has demonstrated high reactivity, mild reaction conditions, and a broad substrate scope. Furthermore, the synthetic utilities of the approach are demonstrated by further modifications.
- Yu, Wentao,Huang, Yubing,Li, Jianxiao,Tang, Xiaodong,Wu, Wanqing,Jiang, Huanfeng
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p. 9334 - 9343
(2018/07/30)
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- Nickle Catalysis Enables Access to Thiazolidines from Thioureas via Oxidative Double Isocyanide Insertion Reactions
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An efficient synthesis of thiazolidine-2,4,5-triimine derivatives was developed via Ni-catalyzed oxidative double isocyanide insertion to thioureas under air conditions, in which thioureas play three roles as a substrate, a ligand, and overcoming isocyanide polymerization. The reaction is featured by employing a low-cost and low loading Ni(acac)2 catalyst, without any additives, and high atom economy. This is the first example to directly apply a Ni(II) catalyst in oxidative double isocyanide insertion reactions.
- Yuan, Wen-Kui,Liu, Yan Fang,Lan, Zhenggang,Wen, Li-Rong,Li, Ming
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supporting information
p. 7158 - 7162
(2018/11/25)
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- Blue-light induced CO releasing properties of thiourea based manganese(I) carbonyl complexes
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A new class of blue-light triggered carbon monoxide releasing molecules based on Mn(CO)3Br(N,S) ((N,S)?=?N,S-bidentate thiourea ligands) has been reported in this work. The 1H and 13C NMR analysis indicated that the thioureas coordinate to Mn(I) in the thione form. The stability test and the ability to derive CO to DMSO and myoglobin solution upon the exposure to 468?nm light source have been investigated. The benzothiazole-thiourea-CORM released only one CO equivalent, while the pyridine-analogs offered two molecules at the same experimental conditions. Natural bond orbital analysis has been carried out to give details about the hybridization of Mn–C and C[tbnd]O bonds, natural charge, electronic arrangement of metal ion and strength of interaction between Mn(I) and the coordination sites. Both functional, B3LYP and CAM-B3LYP compare well with the experimental findings, where the longest wavelength band is assigned to MLCT.
- Mansour, Ahmed M.,Friedrich, Alexandra
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- ORGANIC MOLECULES FOR TERAHERTZ TAGGING APPLICATIONS
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The present invention discloses substituted heterocyclic compounds and /or aromatic compounds containing amide and/or urea groups exhibiting resonance in the range of 0.1- 10 THz. The invention also discloses binary molecular complexes based on the substituted heterocyclic compounds and/or aromatic compounds containing amide and/or urea groups of the present invention. The compounds and binary molecular complexes of the present invention have varying molecular mass and hydrogen bond strengths demonstrating several resonances below 10 THz. The compounds and binary molecular complexes of the present invention are customizable for various applications, such as authentication of a product.
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Page/Page column 16
(2015/07/23)
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- Synthesis and in vitro urease inhibitory activity of N,N′- disubstituted thioureas
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Thiourea derivatives (1-38) were synthesized and evaluated for their urease inhibition potential. The synthetic compounds showed a varying degree of in vitro urease inhibition with IC50 values 5.53 ± 0.02-91.50 ± 0.08 μM, most of which are superior to the standard thiourea (IC50 = 21.00 ± 0.11 μM). In order to ensure the mode of inhibition of these compounds, the kinetic study of the most active compounds has been carried out. Most of these inhibitors were found to be mixed-type of inhibitors, except compounds 13 and 30 which were competitive, while compound 19 was identified as non-competitive inhibitor with Ki values between 8.6 and 19.29 μM.
- Khan, Khalid Mohammed,Naz, Farzana,Taha, Muhammad,Khan, Ajmal,Perveen, Shahnaz,Choudhary,Voelter, Wolfgang
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p. 314 - 323
(2014/02/14)
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- Synthesis and quantum calculations of 1,3-thiazoles and 1,3,4-thiadiazole derivatives via pyridinylthioureas
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In this study, the reaction of 4- and 2-aminopyridines with phenyl isothiocyanate afforded the corresponding 1-phenyl-3-(pyridin-4-yl)thiourea 1 and its pyridin-2-yl analog 20. The reaction of 1 with ethyl chloroacetate gave 3-phenyl-2-(pyridin-4-ylimino)thiazolidin-4-one (3B), which upon a condensation reaction with aldehydes furnished 5-benzylidene derivatives 4a-c. Compounds 1 and 20 underwent heterocyclization upon their reaction with hydrazonoyl chloride 5 and gave the corresponding 1,3,4-thiadiazoles 8 and 22; however, the treatment of 1 and 20 with hydrazonoyl chloride 10 afforded the corresponding 1,3-thiazoles 14 and 25. The quantum calculations were studied using the density functional theory of the starting materials and some products.
- Dawood, Kamal M.,Mohamed, Adel A.,Alsenoussi, Mansour A.,Ibrahim, Ibrahim H.
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p. 383 - 394
(2013/09/23)
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- A selective, orally bioavailable 1,2,4-triazolo[1,5-a]pyridine-based inhibitor of janus kinase 2 for use in anticancer therapy: Discovery of CEP-33779
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Members of the JAK family of nonreceptor tyrosine kinases play a critical role in the growth and progression of many cancers and in inflammatory diseases. JAK2 has emerged as a leading therapeutic target for oncology, providing a rationale for the development of a selective JAK2 inhibitor. A program to optimize selective JAK2 inhibitors to combat cancer while reducing the risk of immune suppression associated with JAK3 inhibition was undertaken. The structure-activity relationships and biological evaluation of a novel series of compounds based on a 1,2,4-triazolo[1,5-a]pyridine scaffold are reported. Para substitution on the aryl at the C8 position of the core was optimum for JAK2 potency (17). Substitution at the C2 nitrogen position was required for cell potency (21). Interestingly, meta substitution of C2-NH-aryl moiety provided exceptional selectivity for JAK2 over JAK3 (23). These efforts led to the discovery of CEP-33779 (29), a novel, selective, and orally bioavailable inhibitor of JAK2.
- Dugan, Benjamin J.,Gingrich, Diane E.,Mesaros, Eugen F.,Milkiewicz, Karen L.,Curry, Matthew A.,Zulli, Allison L.,Dobrzanski, Pawel,Serdikoff, Cynthia,Jan, Mahfuza,Angeles, Thelma S.,Albom, Mark S.,Mason, Jennifer L.,Aimone, Lisa D.,Meyer, Sheryl L.,Huang, Zeqi,Wells-Knecht, Kevin J.,Ator, Mark A.,Ruggeri, Bruce A.,Dorsey, Bruce D.
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scheme or table
p. 5243 - 5254
(2012/09/21)
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- 2-aminothiazoles as therapeutic leads for prion diseases
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2-Aminothiazoles are a new class of small molecules with antiprion activity in prion-infected neuroblastoma cell lines (J. Virol. 2010, 84, 3408). We report here structure-activity studies undertaken to improve the potency and physiochemical properties of 2-aminothiazoles, with a particular emphasis on achieving and sustaining high drug concentrations in the brain. The results of this effort include the generation of informative structure-activity relationships (SAR) and the identification of lead compounds that are orally absorbed and achieve high brain concentrations in animals. The new aminothiazole analogue (5-methylpyridin-2-yl)-[4-(3-phenylisoxazol-5-yl)-thiazol-2-yl]-amine (27), for example, exhibited an EC50 of 0.94 μM in prion-infected neuroblastoma cells (ScN2a-cl3) and reached a concentration of ～25 μM in the brains of mice following three days of oral administration in a rodent liquid diet. The studies described herein suggest 2-aminothiazoles as promising new leads in the search for effective therapeutics for prion diseases.
- Gallardo-Godoy, Alejandra,Gever, Joel,Fife, Kimberly L.,Silber, B. Michael,Prusiner, Stanley B.,Renslo, Adam R.
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experimental part
p. 1010 - 1021
(2011/04/25)
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- Synthesis, phytotoxic, cytotoxic, acetylcholinesterase and butrylcholinesterase activities of N,N-diaryl unsymmetrically substituted thioureas
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Fourteen N,N-diaryl unsymmetrically substituted thioureas were synthesised and their cytotoxic (in vitro), phytotoxic (in vitro), acetylcholinesterase and butrylcholinesterase activities were determined. Thiourea 16 exhibited high, and 1 and 3 showed significant phytotoxic activity. Thioureas 1, 3, 4, 6 and 10 showed significant activity and 2, 6 and 7 indicated moderate cytotoxic activities. Compound 12 exhibited butrylcholinesterase activity higher than a standard reference.
- Begum, Saeedan,Choudhary, M. Iqbal,Khan, Khalid M.
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experimental part
p. 1719 - 1730
(2010/05/18)
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- Fused polycyclic nitrogen-containing heterocycles : 1117. 4-Hydroxy-3-phenyl-2-(2-pyridylimino)-and 4-hydroxy-2-phenyl-3-(2-pyridyl) thiazolidines and related thiazolo[3,4-a]quinoxalines
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The condensation of methyl phenylchloropyruvate with 1-phenyl-3-(2-pyridyl) thiourea and its 3-and 4-picolyl homologs affords the corresponding 4-hydroxythiazolidines, which react with o-phenylenediamine to give one of two possible thiazolo[3,4-a]quinoxalines containing the pyridyl-or picolylimine substituents at position 1. 3a-Hydroxy-3-phenylimino-1-(2-pyridyl)thiazolo[3,4- a]quinoxalin-4-(3H,5H)-one, which is a covalent hydrate of the final product, was isolated as an intermediate in this reaction.
- Mamedov,Zhukova,Beschastnova,Levin,Gubaidullin,Litvinov
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p. 2308 - 2314
(2008/09/18)
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- Antimicrobial activity and structural study of disubstituted Thiourea Derivatives
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The antimicrobial activity of six N-phenyl- and fourteen N-benzoylthiourea derivatives were evaluated from their Minimal Inhibitory Concentration (MIC) values using the microdilution procedure against ten microorganisms. Most of the compounds exhibited selective activity against fungi and Gram-positive bacteria, which were very effectively inhibited by some of the tested thioureas. Additionally, SAR considerations and four novel X-ray diffraction structures of N-benzoylthioureas are included. Springer-Verlag 2007.
- Cunha, Silvio,MacEdo Jr., Fernando C.,Costa, Giselle A. N.,Rodrigues Jr., Manoel T.,Verde, Rosival B. V.,De Souza Neta, Lourdes C.,Vencato, Ivo,Lariucci, Carlito,Sa, Fernando P.
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p. 511 - 516
(2008/02/03)
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- Corrosion-protective properties of 1-phenacylmethyl-2- arylcarbamido(arylthiocarbamido)pyridinium bromides
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Inhibiting effect of 1-phenacylmethylpyridinium bromides containing urea or thiourea substituents in the pyridinium ring on steel and zinc corrosion in sulfuric acid solutions was studied.
- Yurchenko,Pogrebova,Pilipenko,Shubina
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p. 1969 - 1972
(2008/02/09)
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- High-pressure-promoted condensation of isothiocyanates with aminopyridines: Efficient synthesis of pyridine-thiourea conjugates as building blocks for hydrogen-bonding receptors
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New N-pyridinothiourea derivatives have been prepared by the high-pressure-promoted condensation of isothiocyanates with aminopyridines under uncatalyzed conditions. Complexation of the prototype 3c with diphenyl hydrogen phosphate was investigated by 1H NMR, and the results suggest that it may be useful as a building block for hydrogen-bonding receptors.
- Kumamoto, Koji,Misawa, Yoshihiro,Tokita, Sumio,Kubo, Yuji,Kotsuki, Hiyoshizo
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p. 1035 - 1038
(2007/10/03)
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- Synthesis and antibacterial activity of pyridyl thioureas and arylthiosemicarbazones
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[N-(2-pyridyl)-N'-(4-(un) substituted] thioureas and (substitutedaryl)thiosemicarbazones were synthesised and evaluated for their antibacterial activity. All aryl thiosemicarbazones showed good activity against Aeromonas hydrophilia and Salmonella typhimuriurn. But none of the pyridyl thioureas showed any prominent activity against tested bacteria.
- Kumar,Singh,Pandeya
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p. 238 - 242
(2007/10/03)
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- 1-(Methyldithiocarbonyl)imidazole: A useful thiocarbonyl transfer reagent for synthesis of substituted thioureas
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1-(Methyldithiocarbonyl)imidazole 1 and its N-methyl quaternary salt 2 have been shown to be efficient methyldithiocarbonyl and thiocarbonyl transfer reagents for the synthesis of dithiocarbamates, symmetrical and unsymmetrical mono-, di- and tri-substituted thioureas in high yields under mild and simple non-hazardous reaction conditions. (C) 2000 Elsevier Science Ltd.
- Mohanta, Pramod K.,Dhar, Sanchita,Samal,Ila,Junjappa
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p. 629 - 637
(2007/10/03)
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- CHARGE-TRANSFER COMPLEXES OF SOME HETEROARYLTHIOUREA DERIVATIVES WITH ?-ACCEPTORS
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Spectral charcteristics and thermodynamic properties of charge-transfer molecular complexes of some heteroarylthioureas with ?-acceptors DDQ, TCNE and CHL are investigated and discussed.It is deduced that the formed CT complexes are of n-? kind.Moreover, 1:1 solid CT complexes are synthesized and characterized.Keywords: Charge-transfer complexes; solvent effects, stability; solid CT complex; heteroarylthioureas.
- Hamed, M. M. A.,Salman, H. M. A.,Abd-Alla, E. M.,Mahmoud, M. R.
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p. 127 - 134
(2007/10/02)
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- CHARGE-TRANSFER COMPLEXES OF SOME HETEROARYLTHIOUREA DERIVATIVES WITH ?-ACCEPTORS
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Charge-transfer complexes of some heteroarylthiourea derivatives with ?-acceptors have been studied spectrophotometrically in CH2Cl2.Spectral data, stability constants and enthalpies of complexation are reported.From the enrgies of the CT transition, ionization potentials of the donors have been obtained.Effects of donor molecular structure, ?-acceptor electron affinity and nature of solvent on KCT of complexes are investigated and discussed.It is deduced that the formed CT complexes are of n-? kind and of 1:1 stoichiometry.
- Hamed, Maher M. A.,Salman, Hassan M. A.,Abd-Alla, Elham M.,Mahmoud, Mohamed R.
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p. 2846 - 2852
(2007/10/02)
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- Interactions between substituted thioureas and π-acceptors
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Charge-transfer (CT) interactions between some N-aryl-N'-heterocyclic thioureas and both tetracyanoethylene (TCNE) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) were investigated spectroscopically. The formed CT complexes and the solvent effect on CT complexation are discussed. N-Aryl-N'-(2-pyridyl)-thioureas 1 a-d reacted with TCNE to give cyanothiourea derivatives 6, however in case of DDQ, the adducts 7 were obtained.
- Mohamed,Hassan,Ibrahim,Semida,Mourad
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p. 592 - 595
(2007/10/02)
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- 1H and 13C Nuclear Magnetic Resonance Study of 1,3-Dipyridylthioureas for Chemical Shift Assignments and Conformational Analysis
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A study of molecular conformation by 1H and 13C NMR methods of three 1,3-dipyridyl thioureas namely, 1,3-di(2-pyridyl)thiourea (1), 1,3-di(3-pyridyl)thiourea (2), 1-(2-pyridyl)-3-(3-pyridyl)thiourea (3), and also of 1-phenyl-3-(2-pyridyl)thiourea (4) and 1,3-diphenylthiourea (5), included for the sake of coparison, was carried out.Evidence was obtained that 3 and 4 exist in solution solely in one form, in an internally hydrogen bonded E,Z conformation, whereas 1, 2 and 5 exist in two (or more) rotamer forms.The data reveal an interesting dynamic exchange phenomenon occuring in 1 between two intramolecularly hydrogen bonded conformers.The 1H and 13C chemical shifts, 1H,1H and 13C,1H coupling constants are reported.The 13C and 1H chemical shifts are correlated with the electron densities calculated by the CNDO method. KEY WORDS 1H NMR 13C NMR 1,3-Dipyridylthioureas Conformation.
- Sudha, L. V.,Sathyanarayana, D. N.,Bharati, S. Narasimha
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p. 474 - 479
(2007/10/02)
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- Molecular Conformation of N,N'-Diarylthioureas: an Assessment by 1H NMR and Infrared Spectroscopy
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Several N,N'-dipyridyl- and N-phenyl-N'-pyridyl-thioureas were examined in different solvents at various temperatures by 1H NMR in order to study their conformational properties.The influence of concentration and the methyl substituent in the pyridine ring on the chemical shifts of the NH and pyridine groups was investigated.The observed chemical shifts are analysed in terms of the conformational properties of the molecules.Free energy barriers to the internal rotation about the C-N bonds have been determined.Infrared spectra have been measured to supplement the NMR studies.Intramolecular hydrogen bonding played a major role in the preferred conformation of pyridylthioureas.The data further revealed an interesting dynamic exchange phenomenon occuring in symmetric N,N'-dipyridylthioureas between two intramolecularly hydrogen bonded conformers.
- Sudha, L. V.,Manogaran, S.,Sathyanarayana, D. N.
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p. 591 - 596
(2007/10/02)
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- SYNTHESIS OF PYRIDO-1,3,5-TRIAZINES. REACTIONS OF 2-PYRIDYL ISOTHIOCYANATE WITH COMPOUNDS CONTAINING A C=N BOND
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New pyrido-1,3,5-triazine derivatives were prepared by the cycloaddition reaction of 2-pyridyl isothiocyanates with isocyanate, aldimines, and N,N'-diphenylcarbodiimide.On the other hand, reaction of 2-pyridyl isothiocyanate with aliphatic carbodiimides afforded cycloaddition products, 1,3-thiazetidines.
- Marchalin, Miroslav,Svetlik, Jan,Martvon, Augustin
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p. 2557 - 2563
(2007/10/02)
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- Anticonvulsant activity and succinate dehydrogenase inhibitory property of new substituted thiobarbiturates
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Eight 1-aryl-3-(2-pyridyl)thiobarbiturates were synthesized and evaluated for their anticonvulsant property and their ability to inhibit succinate dehydrogenase activity of rat brain homogenates. These substituted thiobarbiturates (100 mg./kg., i.p.) provided 20-60% protection against pentylenetetrazol-induced convulsions in albino mice. Low toxicity of these compounds was reflected by their high approximate LD50 values which were found to range from 500-1000 mg/kg. All substituted thiobarbiturates (1mM) inhibited in vitro succinate dehydrogenase activity and the degree of inhibition ranged from 10-72%.
- Dhasmana,Barthwal,Pandey,et al.
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p. 635 - 637
(2007/10/02)
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