532-55-8Relevant articles and documents
Structural, spectral, optical and antimicrobial properties of synthesized 1-benzoyl-3-furan-2-ylmethyl-thiourea
Karipcin, Fatma,Atis, Murat,Sariboga, Bahtiyar,Celik, Hasan,Tas, Murat
, p. 69 - 77 (2013)
The 1-benzoyl-3-furan-2-ylmethyl-thiourea (bftu) was synthesized and its structure was determined by elemental analyses, IR spectroscopy, 1H and 13C NMR spectroscopy and single crystal X-ray diffraction analysis. Also its antimicrobi
Syntheses based on 3,4-dimethyl-2-thioxothiazoline-5-carboxylic acid hydrazide and azide
Dovlatyan,Eliazyan,Pivazyan,Yengoyan
, p. 383 - 388 (2006)
Treatment of 3,4-dimethyl-2-thioxothiazoline-5-carboxylic acid hydrazide with NH4SCN and PhCONCS gave the corresponding thiosemicarbazides, arylsulfochlorides yielded the arylsulfonylhydrazides, and diazotization conditions gave the correspondi
Synthesis, spectral and single-crystal analyses of new derivatives of 4-amino-N-benzylpiperidine
Hassan, Ibrahim N.,Tarawneh, Mou'ad A.,Yamin, Bohari M.
, p. 4457 - 4460 (2015)
Two new compounds of thiourea derivatives of cinnamoyl and benzoylisothiocyanate with 4-amino-N-benzylpiperidine have been successfully synthesized. The new molecules, 1-(1-benzylpiperidine-4-yl)-3-benzoyl thiourea (I) (yield 83 %) and 1-(1-benzylpiperidi
Design, synthesis, and anticancer activity of novel 4-thiazolidinone-phenylaminopyrimidine hybrids
Türe, Asl?,Ergül, Mustafa,Ergül, Merve,Altun, Ahmet,Kü?ükgüzel, ?lkay
, p. 1025 - 1050 (2021)
Abstract: 4-Thiazolidinones and phenylaminopyrimidines are known as anticancer agents. Imatinib is the pioneer phenylaminopyrimidine derivative kinase inhibitor, which is used for the treatment of chronic myeloid leukemia. With a hybrid approach, a novel series of 5-benzylidene-2-arylimino-4-thiazolidinone derivatives containing phenylaminopyrimidine core were designed, synthesized, and tested for their anticancer activity on K562 (chronic myeloid leukemia), PC3 (prostat cancer), and SHSY-5Y (neuroblastoma) cells. Since superior anticancer activity was observed on K562 cells, further biological studies of selected compounds (8, 15, and 34) were performed on K562 cells. For the synthesis of designed compounds, thiourea compounds were converted to 2-imino-1,3-thiazolidin-4-ones with α-chloroacetic acid in the presence of sodium acetate. 5-Benzylidene-2-imino-1,3-thiazolidin-4-one derivatives were obtained by Knoevenagel condensation of 2-imino-1,3-thiazolidin-4-ones with related aldehydes. Compounds 8, 15, and 34 were evaluated for cell viability, apoptosis studies, cell cycle experiments, and DNA damage assays. IC50 values of compounds 8, 15, and 34 were found as 5.26 ± 1.03, 3.52 ± 0.91, and 8.16 ± 1.27?μM, respectively, in K562 cells. Preferably, these compounds showed less toxicity towards L929 cells compared to imatinib. Furthermore, compounds 8 and 15 significantly induced early and late apoptosis in a time-dependent manner. Compounds 15 and 34 induced cell cycle arrest at G0/G1 phase and compound 8 caused cell cycle arrest at G2/M phase. Based on DNA damage assay, compounds 8 and 15 were found to be more genotoxic than imatinib towards K562 cells. To put more molecular insight, possible Abl inhibition mechanisms of most active compounds were predicted by molecular docking studies. In conclusion, a novel series of 5-benzylidene-2-arylimino-4-thiazolidinone derivatives and their promising anticancer activities were reported herein. Graphic abstract: [Figure not available: see fulltext.]
Antihyperglycemic activity of chalcone based novel 1-{3-[3-(substituted phenyl) prop-2-enoyl] phenyl} thioureas
Acharjee, Satarupa,Maity, Tapan Kumar,Samanta, Subir,Mana, Supriya,Chakraborty, Tania,Singha, Tanushree,Mondal, Arijit
, p. 3015 - 3024 (2018)
The present study describes the synthesis of novel chalcone based 1-{3-[3-(substituted phenyl) prop-2-enoyl] phenyl} thioureas (4a-c) using Claisen Schmidt condensation and investigates their protective role in diabetic conditions and associated oxidative
Characterization and Computational Studies of 2-(Benzamido)Thiazol-5-yl Benzoate
Odame,Hosten,Betz,Lobb,Tshentu
, p. 136 - 142 (2019)
2-(Benzamido)thiazolylbenzoate is synthesized via a novel method. It is characterized by spectroscopy, micranalysis, and GC-MS. It crystallizes in the monoclinic space group P21/n with a = 19.8990(5), b = 7.3680(2), c = 22.3845(6) ?, β = 113.799(1)°, V = 3002.85(14) ?3Z = 8. The HOMO-LUMO of the reactants and products are considered.
The synthesis of triazolothiadiazines and thiadiazoles from 1,2-bis-(4-amino-5-mercapto-1,2,4-triazol-3-yl)-ethanol and ethane
Moustafa,Haggam,Younes,El Ashry
, p. 2361 - 2371 (2006)
The reaction of DL-malic and succinic acids with thiocarbohydrazide afforded 1,2-bis[4-amino-5-mercapto-1,2,4-triazol-3-yl]-ethane derivatives 3a and 3b. The reaction of 3a,b with phenacyl bromide and benzoin afforded 1,2-bis-1,2,4-triazolo [3,4-b][1,3,4]thiadiazine derivatives 4 and 5. The carboethoxymethylation of 3a and 3b gave 6a and 6b, respectively, and their reactions with carbon disulfide and benzoylisothiocyanate gave the 1,2-bis-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole 7 and 9, and with p-nitrobenzaldehyde gave a Schiff's base and dihydrothiadiazole 8. The structures were confirmed by using 1H and 13C NMR spectra. Selected members of these compounds were screened for antimicrobial activity. Copyright Taylor & Francis Group, LLC.
Synthesis and intramolecular cyclization of N-acyl- and N-allyl-N'-(2-oxo-1,2-dihydro-pyridin-3-yl)thiourea
Kulakov,Nikitina,Fisyuk,Goncharov,Shul'Gau,Gulyaev
, p. 670 - 676 (2014)
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
Gold(I), silver(I) and copper(I) complexes of 2,4,6-trimethylphenyl-3-benzoylthiourea; synthesis and biological applications
Khan, Umar Ali,Badshah, Amin,Tahir, Muhammad Nawaz,Khan, Ezzat
, (2020)
2,4,6-Trimethylphenyl-3-benzoylthiourea (L) and its gold(I), silver(I) and copper(I) complexes were synthesized. Treatment of L with HAuCl4, AgNO3 and CuI in CH3CN afforded complexes of general representation, M(L)X, where
Guanidinyl benzothiazole derivatives: Synthesis and structure activity relationship studies of a novel series of potential antimicrobial and antioxidants
Bhat, Mahesh,Belagali
, p. 6195 - 6208 (2016)
Abstract: A series of N-phenyl-substituted and disubstituted guanidinyl benzothiazole derivatives 4a–4m were synthesized and characterized as novel antimicrobial and antioxidant agents. The in-vitro antioxidant activities of these compounds were evaluated and compared with commercial antioxidants, using ascorbic acid (AA) and employing 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay and 2,2′-azino-bis (3-ethylbenzthiazoline-6-sulphonic acid (ABTS) assay. The results showed that IC50 values of compounds 4a and 4m were similar to the IC50 values of the standard. This assay indicates the good activities of these compounds. In addition, the in-vitro antimicrobial activities of these compounds were evaluated and the results demonstrated that the compounds 4i and 4l exhibited excellent antimicrobial activities. Compounds 4c and 4i having electron withdrawing groups at p-position and compound 4l and 4m having electron donating groups at o-position showed better antimicrobial activities compared to the standard. Graphical Abstract: [Figure not available: see fulltext.]
DNA binding, DNA cleavage and HSA interaction of several metal complexes containing N-(2-hydroxyethyl)-N′-benzoylthiourea and 1,10-phenanthroline ligands
Peng, Bo,Gao, Zhuantao,Li, Xibo,Li, Tingting,Chen, Guorong,Zhou, Min,Zhang, Ji
, p. 903 - 916 (2016)
Abstract: Four novel ternary metal complexes of the type [M(Phen)(L1)2)] [phen?=?1,10-phenanthroline, L1?=?N-(2-hydroxyethyl)-N′-benzoylthiourea, M?=?Ni(II)(1), Co(II) (2), Cu(II) (3), Pd(II) (4)] were synthesized. The org
Synthesis of acyl thiourea derivatives of chitosan and their antimicrobial activities in vitro
Zhong, Zhimei,Xing, Ronge,Liu, Song,Wang, Lin,Cai, Shengbao,Li, Pengcheng
, p. 566 - 570 (2008)
Three different acyl thiourea derivatives of chitosan (CS) were synthesized and their structures were characterized by FT-IR spectroscopy and elemental analysis. The antimicrobial behaviors of CS and its derivatives against four species of bacteria (Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Sarcina) and four crop-threatening pathogenic fungi (Alternaria solani, Fusarium oxysporum f. sp. vasinfectum, Colletotrichum gloeosporioides (Penz.) Saec, and Phyllisticta zingiberi) were investigated. The results indicated that the antimicrobial activities of the acyl thiourea derivatives are much better than that of the parent CS. The minimum value of MIC and MBC of the derivatives against E. coli was 15.62 and 62.49 μg/mL, respectively. All of the acyl thiourea derivatives had a significant inhibitory effect on the fungi in concentrations of 50-500 μg/mL; the maximum inhibitory index was 66.67%. The antifungal activities of the chloracetyl thiourea derivatives of CS are noticeably higher than the acetyl and benzoyl thiourea derivatives. The degree of grafting of the acyl thiourea group in the derivatives was related to antifungal activity; higher substitution resulted in stronger antifungal activity.
1-Benzoyl-3-[(2-benzylsulfanyl)phenyl]thiourea
Bhattacharjee, Tirtha,Gogoi, Prasanta,Puranik, Vedavati G.,Gawade, Rupesh L.,Barman, Pranjit
, p. o485-o487 (2012)
In the title compound, C21H18N2OS2, a strong intramolecular N-H?O hydrogen bond [N?O = 2.642(3)?] between the amide N atom and the benzoyl O atom forms an almost planar six-membered ring in the central part of the molecule. In the crystal, molecules are p
Cu(II)-N-benzyl-amino-1H-tetrazole complex immobilized on magnetic chitosan as a highly effective nanocatalyst for C-N coupling reactions
Ghafuri, Hossein,Nasrollahzadeh, Mahmoud,Sajjadi, Mohaddeseh
, (2021/07/24)
Herein, the synthesis of a novel catalytic nanosystem with high activity and easy recoverability through immobilization of Cu(II)-N-benzyl-amino-1H-tetrazole complex on magnetic chitosan (MCS-BAT-Cu(II)) is reported. The catalytic potential of MCS-BAT-Cu(II) catalyst has been assessed in C-N coupling reaction of 5-amino-1H-tetrazole with aryl halides. Various aryl iodides/bromides were successfully coupled using MCS-BAT-Cu(II) catalyst for the synthesis of 1-aryl-5-amino-1H-tetrazoles with excellent reaction yields. In addition, the magnetic catalyst was easily and effectively separated from the reaction mixture using an external magnet and reused five times without notable loss of catalytic activity.
Synthesis and evaluation of the anticancer activity of [Pt(diimine)(N,N-dibutyl-N′-acylthiourea)]+complexes
Harmse, Leonie,Kotzé, Izak A.,Magwaza, Rachael N.,Peega, Tebogo
, p. 11742 - 11762 (2021/09/06)
Despite the concerted efforts to develop targeted cancer treatments, these therapies are plagued by the rapid development of resistance and serious adverse drug reactions. Based on the wide clinical use and successes of the platinum drugs like cisplatin and oxaliplatin, we investigated the synthesis and potential anticancer efficacy of alternative platinum complexes. A series of nine cationic square planar platinum(ii) complexes were synthesized and characterized and then evaluated for their anticancer activity. The complexes were of the type [Pt(diimine)(Ln-κO,S)]+where diimine is either 1,10-phenanthroline (phen), 5,6-dimethyl-1,10-phenanthroline (dmp) or dipyrido[3,2-f:2′,3′-h]quinoxaline (dpq) and Ln-κO,Srepresenting variousN,N-dibutyl-N′-acylthiourea ligands. The anticancer activity of the synthesised complexes was evaluated against two lung cancer cell lines (A549 and H1975) and a colorectal cancer cell line, HT-29. The 50% inhibitory concentrations (IC50) for the most cytotoxic compounds were determined and the mode of cell death evaluated. The structure-activity relationships indicated that complexes with the 5,6-dimethyl-1,10-phenanthroline variation of the diimine ligand were the most active against the cell lines tested, while the activity of complexes based on the acylthiourea ligand varied between the cell lines. IC50values for the three active platinum complexes were in the low micromolar range for the three cell lines and ranged between 0.68 μM and 2.28 μM. Changes to cell morphology indicate that the active platinum complexes induce cell death by both apoptosis and paraptosis. The complexes were able to induce the nuclear expression of the cyclin-dependent kinase inhibitor, p21, which is an indicator of DNA damage. The collective data indicate that these platinum complexes are valuable lead compounds for further analysis and cancer drug discovery.
