- Reaction of functionally 4-substituted hexahydropyrimidine-2-thiones with sodium tetrahydroborate. Synthesis of six-membered cyclic thioureas
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A new method was developed for the production of six-membered cyclic ureas based on the reaction of readily obtainable 4-azido-, 4-acetoxy-, or 4-phenylsulfonylhexahydropyrimidine-2-thiones with sodium tetrahydroborate. 1998 Plenum Publishing Corporation.
- Shutalev
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- Reduction Of 4-Hydroxy(Alkoxy)Hexahydropyrimidine-2-Thiones And 1,2,3,6-tetrahydropyrimidine-2-Thiones, By The NaBH4-CF3COOH System. Synthesis Of Hexahydropyrimidine-2-Thiones
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A convenient method for the synthesis of hexahydropyrimidine-2-thiones by the reduction of the readily accesible 4-hydroxy(alkoxy)hexahydropyrimidine-2-thiones and 1,2,3,6-tetrahydropyrimidine-2-thiones by the NaBH4-CF3COOH system was proposed.
- Shutalev, A. D.,Komarova, E. N.,Ignatova, L. A.
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Read Online
- Synthesis Of di- and tri-substituted thiourea derivatives in water using choline chloride–urea catalyst
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In this work, di- and tri-substituted thiourea derivatives have been synthesized via a one-pot, three-component reaction from carbon disulfide and aliphatic or aromatic amines using choline chloride-urea deep eutectic solvent as a catalyst in water. Both cyclic and acyclic thiourea derivatives with two or three substituents were synthesized successfully. The reactions were done at 25–100°C, using 5–20 mol% catalyst, in 3–5 h and the GC-Mass yields were between 60% and 95%. All products were characterized using FT-IR, 1H-NMR, 13C-NMR, GC-MS and melting point analyses. The results showed that both water and the DES have important effects on the yield and the rate of this reaction and both of them are necessary to obtain higher yields in less time. The extra experiment, which was designed to study the mechanism of the reaction, showed that an isothiocyanate intermediate was formed in the reaction. Finally, the results showed that by the increase of the amine's nucleophilicity, the reaction occurs faster and gives higher yield.
- Tavakol, Hossein,Mahmoudi, Amir,Ranjbari, Mohammad-Amin
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p. 113 - 123
(2018/10/24)
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- Bis-(triethylphosphine)platinum(II) complexes with thiones as anti cancer agents
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Platinum(II) complexes having mixed ligands as anticancer agents. The central platinum atom is coordinated by two phosphine ligands and two heterocyclic thione ligands. Each heterocyclic thione ligand has a five-, six- or seven-membered heterocyclic ring with two nitrogen atoms at positions 1 and 3 of the ring and a thiocarbonyl group at position 2. Pharmaceutical compositions incorporated the platinum(II) complexes, methods of synthesizing the complexes and methods of treating cancers with the complexes or pharmaceutical compositions thereof are also described.
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Page/Page column 20
(2017/02/28)
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- Synthesis of five- and six-membered cyclic guanidines by guanylation with isothiouronium iodides and amines under mild conditions
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Cyclic guanidine hydroiodides were obtained in one step by the reactions of isothiouronium iodides with an equimolar amount of various amines in tetrahydrofuran. The obtained hydroiodides were neutralized with sodium hydroxide or anionic exchange resin to afford the corresponding substituted cyclic guanidines in quantitative yields.
- Aoyagi, Naoto,Endo, Takeshi
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supporting information
p. 442 - 448
(2017/02/24)
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- Synthesis, spectroscopic characterization and in vitro anticancer activity of new platinum(II) complexes with some thione ligands?in the presence of triethylphosphine
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Seven new platinum(II) complexes (1–7) of triethylphosphine (Et3P) and thiones (L) with general formula, cis-[Pt(Et3P)2(L)2]Cl2 were prepared and characterized by elemental analysis, FTIR and NMR (1H, 13C & 31P) measurements. The analytical and spectroscopic data suggested the formation of the desired complexes. The complexes were tested for in vitro cytotoxicity against four cell lines: Hela (human cervical adenocarcinoma), MCF-7 (human breast carcinoma), A549 (human lung carcinoma), and HTC15 (human colon carcinoma). The anticancer activity values of compounds 1–6 are much better than cisplatin and carboplatin as indicated by their IC50 values.
- Jomaa, Mohammed Yagoub,Altaf, Muhammed,Ahmad, Saeed,Bhatia, Gaurav,Singh, Jatinder,Altuwaijri, Saleh,Isab, Anvarhusein A.
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p. 787 - 795
(2017/10/13)
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- Thiocarbonyl Surrogate via Combination of Sulfur and Chloroform for Thiocarbamide and Oxazolidinethione Construction
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An efficient and practical thiocarbonyl surrogate via combination of sulfur and chloroform has been developed. A variety of thiocarbamides and oxazolidinethiones have been established, including chiral thiourea catalysts and chiral oxazolidinethione auxiliaries with high selectivity. Meanwhile, pesticides Diafenthiuron (an acaricide), ANTU (a rodenticide), and Chloromethiuron (an insecticide) were practically synthesized through this method in gram scale. Dicholorocarbene, as the key intermediate, was further confirmed via a carbene-trapping control experiment.
- Tan, Wei,Wei, Jianpeng,Jiang, Xuefeng
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supporting information
p. 2166 - 2169
(2017/04/27)
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- Heterocyclic substituted styrene compound and use thereof
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The invention relates to a heterocyclic substituted styrene compound and its use. The invention discloses a heterocyclic radical, alkoxy and halogen modified styrene compound. Results of inhibition activity of the compound against Syk (spleen tyrosine kinase) show that the compound has inhibition activity against the Syk (spleen tyrosine kinase), and part of the compound has stronger inhibition activity against the Syk, and a structure foundation for further design and development of new Syk inhibitor-class rheumatoid arthritis (RA) therapy drugs is laid.
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Paragraph 0056; 0057; 0058; 0059
(2016/10/07)
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- Discovery of Benzylidene Derivatives as Potent Syk Inhibitors: Synthesis, SAR Analysis, and Biological Evaluation
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Four scaffolds of varied benzylidene derivatives were synthesized and evaluated as Syk inhibitors for the treatment of rheumatoid arthritis (RA). Among these 31 compounds, 3-benzylidene pyrrolidine-2,5-dione derivatives (including 12k) universally showed good Syk inhibitory activities in the low micromolar to submicromolar range. In the cellular profiling, compound 12k, the most efficient compound, showed excellent antiproliferative activity against fibroblast-like synoviocytes (FLS)-RA, and demonstrated potencies for suppression of IL-6 and MMP-3 secretion almost equal to R406 (positive control). The oral efficacy of 12k in the murine collagen-induced arthritis model was significant, despite being weaker than R406. Taken together, all preliminary pharmacological results supported 12k as a potential small-molecule inhibitor targeting Syk for the treatment of RA.
- Zhang, Lingling,Liu, Wei,Mao, Fei,Zhu, Jin,Dong, Guoqiang,Jiang, Hualiang,Sheng, Chunquan,Miao, Liyan,Huang, Lixin,Li, Jian
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p. 463 - 474
(2015/07/07)
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- A Concise and Convenient Method for the Synthesis of Pure Substituted Thioureas
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Zinc dialkyldithiocarbamates offer excellent substrates for pure thioureas required for the ntifungal and X-ray crystallographic studies.
- Ramadas, K.,Janarthanan, N.
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p. 1101 - 1108
(2007/10/03)
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- Lac sulfur assisted synthesis of symmetrical thioureas
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This work presents a short and attractive method to synthesise a variety of 1,3-disubstituted symmetrical thioureas in high yields.
- Ramadas,Janarthanan,Velmathi
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p. 2255 - 2260
(2007/10/03)
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- Process for preparation of enantiomerically pure polysubstituted 1,4-dihydropyridines
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A process for the optical resolution of racemic 1,4-dihydropyridines, containing isothioureido groups. Salification of racemic isothioureas with optically active acids produces diasteroisomeric mixtures of isothiouronium salts, that, using conventional techniques, are separated in the individual components to give optically pure isothioureides of 1,4-dihydropyridines and salts thereof with conventional acids. Said optically pure 1,4-dihydropyridines can then be subjected to desulphuration and to different transformations to give to other enantiomerically pure and therapeutically useful 1,4-dihydropyridines.
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- N,N-connected heterobicycles from cyclic hydrazine derivatives. Part 5: Reaction of N-nucleophilic derivatives on pyrazolo heterocycles from pyrazolo and carbon disulphide
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The reaction of pyrazolidine and cahbon disulphide forms 1,3-dithioxo-5,6-dihydro-5 H-pyrazolo[1,2-c][1,3,4]thiadiazole or 5,11-dithioxo-2,3,8,9-tetrahydro-1 H,7 H-pyrazolo[1',2' : 2,3]pyrazolo[1,2-a][1,2,4,6]tetrazine depending on the conditions of the reaction. The S/N exchange at the first is successful with alkylamines under formation of analogous 2-substituted 1,3-dithioxopyrazolo[1,2-a][1,2,4]triazoles. If ethylen diamine is used a imidazo[2',3' : 1,2]pyrazolo[1,2-a][1,2,4]triazole derivative was obtained.
- Morgenstern,Klemann,Richter
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p. 416 - 418
(2007/10/02)
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- Stereospecific Synthesis of Some Novel cis-1-Aza Analogs of Cepham
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Annelation of N-acyl-2-thiomethyltetrahydropyrimidines (VII) with appropriate acid chlorides results in the formation of the corresponding β-methylthio-β-lactam (VIII) as single stereoisomer in each case.Treatment of these β-methylthio-β-lactams (VIII) with Ni in acetone yields stereospecifically the cis-1-azacepham analogs (IX).Application of a similar sequence of reactions on VIIf furnishes the novel 1-azacepham analog (XI) through a single step removal of the thiomethyl as well as the benzyloxycarbonyl groups from the intermediate β-lactam (X).Potassium carbethoxyacetonylglycinate (B) on treatment with the schiff base VIIa using POCl3/Et3N in CH2Cl2 gives the enamino-β-lactam (XII) which on exposure to HCl in ethanol yields the α-amino-β-lactam (XIV).Acylation of XIV with phenoxyacetyl chloride provides the α-amido-β-methylthio-β-lactam (XV).Raney-Ni desulphurisation of XII and XV affords ths cis-azacephams XIII and XVI respectively.
- Sharma, S. D.,Arora, S. K.,Mehra, Usha
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p. 895 - 901
(2007/10/02)
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- REACTION OF CYCLIC THIOUREAS WITH CHLOROACYLPIPERAZINES
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S-Alkylation products are formed in the reaction of tetrahydropyrimidine-2-thione and hexahydro-1,3-diazepine-2-thione with chloroacylpiperazines in dimethylformamide at room temperature; dihydrothiazolopyrimidine and tetrahydrothiazolo-diazepine systems are obtained in refluxing ethanol.It is shown that the S-alkyl derivatives are very readily converted to condensed systems.
- Groszkowski, S.,Krezhel, I.,Kozycka, L.
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p. 672 - 675
(2007/10/02)
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- Reactions of Cyanodithioformates with Primary Amines
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N-alkyldithiooxamides 3 and N,N-dialkyldithiooxamides 4 were synthesized in good yields by reaction of cyanodithioformates 1 with primary aliphatic amines.N-alkylcyanodithioformamides 2, intermediates in these reactions were obtained in very low yields only.The reaction of 1 and diaminoethane or 1,3-diaminopropane afforded imidazolidine-2-thione 5a respectively perhydropyrimidine-2-thione 5b.The reaction of 1 with 1-chloro-2-aminoethane did gave 2-thiocarbamoylthiazoline 7.
- Kibbel, H. U.,Kuecken, M.,Peters, E.,Weber, H.
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- Macroheterocycles. III. Synthesis, properties, and tautomeric transformations of macrocyclic thioureas
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Macrocyclic thioureas of the and types, where R=CH2(CH2OCH2)nCH2 and (CH2)m (n=1, 2, 3, m=8), were obtained for the first time by the reaction of diamines with carbon bisulfide.The UV, IR, and PMR spectra of the compounds were studied.It was shown that they exist in the thione form in the crystalline state and in protic solvents.Thione - thiol isomerization is observed in nonpolar solvents.
- Bogatskii, A.V.,Luk'yanenko, N. G.,Kirichenko, T. I.
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p. 1124 - 1129
(2007/10/02)
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