4949-94-4Relevant academic research and scientific papers
Synthesis, structure and spectroscopic properties of cobalt(III) complexes with 1-benzoyl-(3,3-disubstituted)thiourea
Tan, Siew San,Al-Abbasi, Aisha A.,Mohamed Tahir, Mohamed Ibrahim,Kassim, Mohammad B.
, p. 287 - 294 (2014)
Reactions of Co(II) acetate with 1-benzoyl-(3-methyl-3-R)thiourea (R = ethyl, propyl, cyclohexyl and phenyl) and 1-benzoyl-(3-ethyl-3-benzyl)thiourea ligands, herein refer to as 1-benzoyl-(3,3-disubstituted)thiourea, derived from secondary alkyl- and arylamines gave [tris(1-benzoyl-(3,3-disubstituted) thiourea)cobalt(III)] complexes. The neutral cobalt(III) complexes were afforded through a one-pot reaction between a deprotonated 1-benzoyl-(3,3-disubstituted) thiourea ligands with cobalt(II) acetate with a 1:3 ratio in methanol. These complexes were characterized on the basis of elemental analysis, mass spectrometry, magnetic susceptibility measurement, X-ray crystallography and spectroscopic techniques namely infrared, UV-Vis and nuclear magnetic resonance. Based on the magnetic susceptibility and spectroscopic data as well as X-ray crystallographic structure of the octahedron [tris(1-benzoyl-(3-methyl-3-phenyl) thiourea)cobalt(III)] complex, it can be concluded that the ligands behave as bidentate O,S chelate.
Design, synthesis and identification of novel substituted 2-amino thiazole analogues as potential anti-inflammatory agents targeting 5-lipoxygenase
Sinha, Shweta,Doble, Mukesh,Manju
, p. 34 - 50 (2018/09/13)
Human 5-Lipoxygenase (5-LOX) is a key enzyme targeted for asthma and inflammation. Zileuton, the only drug against 5-LOX, was withdrawn from the market due to several problems. In the present study, the performance of rationally designed conjugates of thi
Bis- and tris-chelates of NiII, CuII, CoII and FeIII bound to N,N-dialkyl/alkyl aryl-N′-benzoylthiourea ligands
Mandal, Haridas,Ray, Debashis
, p. 127 - 133 (2014/03/21)
Bis- and tris-chelates (1-5) of Ni(II), Cu(II), Fe(III) and Co(II) with two O,S donor substituted benzoylthiourea based ligands 3,3-diethyl-1- benzoylthiourea (HL1) and 3-methyl-3-phenyl-1-benzoylthiourea (HL2) have been synthesized
Synthesis of a few novel bioactive 2-substituted amino-5-indol-3-oyl-4- phenylthiazoles
Thomas,Reshmy,Ushadevi
, p. 1016 - 1019 (2008/09/19)
The 2-amino-4-arylthiazole motif is an important structural element in a variety of bioactive molecules. The (4+1) thiazole construction strategy adopted involves the synthesis of the [C-N-C-S] precursors, namely 1-aryl-3-(N- phenylbenzimidoyl) thiourea or 1-alkyl-3-(N-phenylbenzimidoyl) thiourea and the preparation of the C5 synthone, the halo acetylhetaroyl derivative. The optimized reaction conditions developed have thus lead to the preparation of five 2-(N-arylamino)-5-(indol-3-oyl)-4-phenylthiazoles and three 2-(N,N-dialkylamino)-5-(indol-3-oyl)-4-phenylthiazoles. The structure of these new compounds were assigned on the basis of elemental analysis, FTIR, 1H NMR and 13C NMR and screened for their antimicrobial activity.
N-H...S hydrogen bonding in N-benzoyl-N'-methyl-N'-phenylthiourea and N-benzoyl-N'-(3,4-dimethylphenyl)thiourea
Shanmuga Sundara Raj,Puviarasan,Velmurugan,Jayanthi,Fun, Hoong-Kun
, p. 1318 - 1320 (2007/10/03)
In the title compounds, C15H14N2OS and C16H16N2OS, the C=S bond distances are 1.670 (2) and 1.667 (2) A, respectively. The molecules are packed in a centrosymmetric manner by forming a two-dimensional array through N-H...S hydrogen bonding.
An efficient synthesis of 1,2,4-oxathiazoles from N-acylthiourea derivatives
Chan, Chung Woo,Ng, Chun Ming Dominic,Ho, Joyce,Tin, Kam Chung
, p. 216 - 219 (2007/10/03)
l,2,4-Oxathiazoles have been synthesized from their precursors, the N-acylthioureas by oxidative cyclization reaction. Ring structure and the charge distribution above the ring have also been studied.
Substituted N-phenylisothioureas: Potent inhibitors of human nitric oxide synthase with neuronal isoform selectivity
Shearer, Barry G.,Lee, Shuliang,Oplinger, Jeffrey A.,Frick, Lloyd W.,Garvey, Edward P.,Furfine, Eric S.
, p. 1901 - 1905 (2007/10/03)
S-Ethyl N-phenylisothiourea (4) has been found to be a potent inhibitor of both the human constitutive and inducible isoforms of nitric oxide synthase. A series of substituted N-phenylisothiourea analogues was synthesized to investigate the structure-activity relationship of this class of inhibitor. Each analogue was evaluated for human isoform selectivity. One analogue, S-ethyl N-[4-(trifluoromethyl)phenyl]isothiourea (39), exhibited 115-fold and 29-fold selectivity for the neuronal isoform versus the inducible and endothelial derived constitutive isoforms, respectively. Studies have shown the substituted N-phenylisothiourea 39 binds competitively with L,-arginine.
SYNTHESIS AND STUDY OF NEW N-BENZOYLTHIOUREA DERIVATIVES
Mukmeneva, N. A.,Khabikher, V. Kh.,Cherkasova, O. A.,Cherezova, E. N.,Tuzova, N. G.
, p. 925 - 927 (2007/10/02)
A series of new derivatives of N-benzoylthiourea were synthesized and characterized, and the kinetics of their reactions with cumene hydroperoxide was studied.
N'-Substituted N-Acyl- and N-Imidoyl-thioureas: Preparation and Conversion of N',N'-Disubstituted Compounds into 2-(N,N-Disubstituted Amino)thiazol-5-yl Ketones
Brindley, Jocelyn C.,Caldwell, Jennifer M.,Meakins, G. Denis,Plackett, Simon J.,Price, Susan J.
, p. 1153 - 1158 (2007/10/02)
Known methods were developed to give convenient general procedures for preparing N-acyl-N'-mono- and -N',N'-disubstituted thioureas from acid chlorides, and related N-imidoyl thioureas from imidoyl chlorides.In the products from three acid chlorides and ammonium thiocyanate the acyl isothiocyanates did not appear to be accompained by the isomeric thiocyanates.Treatment of N-(anilino)benzylidene-N',N'-disubstituted thioures with chloroacetone in the presence of triethylamine leads to 5-acetyl-4-phenyl-2-(N,N-disubstituted amino)thiazoles.In contrast, the corresponding N-benzoyl thioureas form only small amounts of these compounds; the main products are the 5-benzoyl-4-methyl isomers, and this unexpected outcome requires a revision of the literature.It is thought that formation of the 5-benzoyl-4-methylthiazoles involves N-C(4) fission of a cyclic intermediate to give an open-chain intermediate in which nucleophilic attack can occur at either the acetyl or the benzoyl group.One of the latter intermediates was generated directly from 2-acetyl-2-bromoacetophenone and N-methyl-N-phenylthiourea, and found to give the 5-benzoyl-4-methyl- and 5-acetyl-4-phenyl-thiazoles as the major and minor products, respectively.
KINETICS AND MECHANISM OF REARRANGEMENT AND METHANOLYSIS OF ACYLPHENYLTHIOUREAS
Kavalek, Jaromir,Jirman, Josef,Sterba, Vojeslav
, p. 766 - 778 (2007/10/02)
S-Acyl-1-phenylthioureas and their 3-methyl derivatives are rearranged to 1-acyl derivatives of thiourea in methanolic solution.The rearrangement of the 1-acyl-1-phenyl derivative to the thermodynamically more stable 3-acyl derivative is subject to specific base catalysis.The rearrangement of acetyl group is about 2 orders of magnitude slower than that of benzoyl group. 1-Acetyl-1-phenylthiourea undergoes base-catalyzed methanolysis (giving phenylthiourea and methyl acetate) instead of the rearrangement.The methanolysis rates of 1-acyl-3-phenylthioureas and their N-methyl derivatives have been measured.The acetylthioureas react at most 3 x faster than the benzoyl derivatives.The methyl group at the nitrogen adjacent to acyl group accelerates the solvolysis by almost 2 orders of magnitude; the methyl group at the other nitrogen atom retards the solvolysis by almost 1 order of magnitude.Replacement of hydrogen atom by methyl group at the phenyl-substituted nitrogen increases acidity of the phenylacetylthiourea by 2 orders of magnitude.The same replacement at the benzoyl-substituted nitrogen increases the acidity by 3 orders of magnitude, the increase in the case of the acetyl derivative being as large as 4 orders of magnitude.
