共查询到20条相似文献,搜索用时 11 毫秒
1.
A new route to the imidazole-2-thiones from 2-thiohydantoins. Implications in the study of ergothioneine 总被引:1,自引:0,他引:1
下载免费PDF全文
![点击此处可从《The Biochemical journal》网站下载免费的PDF全文](/ch/ext_images/free.gif)
1. 2-Thiohydantoins are reduced by borohydrides to 4(5)-hydroxyimidazolidine-2-thiones, which eliminate water in acid to form imidazole-2-thiones. Both steps take place in mild conditions, in high yield. A number of imidazole-2-thiones have been synthesized by this sequence of steps, with one, two or three substituents in the 1-, 3- and 4(5)-positions. 2. 4(5)-Hydroxyimidazolidine-2-thiones are ammonium pseudo-bases, giving rise to an equilibrium mixture of amino aldehyde, carbinolamine and mesomeric ammonium cationic forms. The elimination of water is suggested to be a property of the mesomeric ammonium cation. 3. The mild conditions in which imidazole-2-thiones are formed from 4(5)-hydroxyimidazolidine-2-thiones are similar to those in which ergothioneine, a naturally occurring imidazole-2-thione of uncertain function, is normally released and measured. It is suggested that the occurrence in vivo of a precursor to ergothioneine, in the form of a 4(5)-hydroxyimidazolidine-2-thione, would explain many otherwise conflicting published data. 相似文献
2.
Adel M. Attla Hanaa A. Mansour Ahmed A. Almehdi Mohammed M. Abbasi 《Nucleosides, nucleotides & nucleic acids》2013,32(10):2301-2306
Abstract A synthesis of 1-(β-D-ribofuranosyl)-pyridin-2-thiones via reaction of 3-cyanopyridin-2(H)-thiones with 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide under basic conditions, followed by hydrolysis with methanolic ammonia is reported. 相似文献
3.
Ibrahim O. F. Bakhite E. A. Metwally S. A. M. El-Ossaily Y. A. Abdu-Allah H. H. M. Al-Taifi E. A. Kandel M. 《Russian Journal of Bioorganic Chemistry》2021,47(4):918-928
Russian Journal of Bioorganic Chemistry - Reaction of 4,6-dimethyl-3-cyanopyridine-2(1H)-thione (IIIa) or 4,5,6-trisubstituted-3-cyanopyridine-2(1H)-thiones (IIIb–d) with... 相似文献
4.
Synthesis and structure determination of some oxadiazole-2-thione and triazole-3-thione galactosides
Ahmad R Iqbal R Akhtar H Zia-ul-Haq Duddeck H Stefaniak L Sitkowski J 《Nucleosides, nucleotides & nucleic acids》2001,20(9):1671-1682
The syntheses of 5-pyridyl-3(beta-D-galactopyranosyl)-1,3,4-oxadiazole-2-thiones 3a-3c and 5-pyridyl-2(beta-D-galactopyranosyl)-4-benzyl-1,2, 4-triazole-3-thiones 6a-6c are reported. The existence of N-galactosides--not S-galactosides--was proven by IR and 15N NMR spectroscopy. The structures of the final products and the intermediates were elucidated by IR, 1H, 13C and 15N NMR spectroscopy and mass spectrometry. 相似文献
5.
Pillaiyar Thanigaimalai Vinay K. Sharma Ki-Cheul Lee Cheong-Yong Yun Youngsoo Kim Sang-Hun Jung 《Bioorganic & medicinal chemistry letters》2010,20(16):4771-4773
In order to define the structural requirements of quinazoline-2(1H)-thiones 1 for their inhibitory activity on melanogenesis, a novel series of 3,4-dihydroquinazoline-2(1H)-thiones (3a–h) were prepared and screened for their melanogenesis inhibition on melanoma B16 cell line under the stimulant of α-MSH. The anti-melanogenesis activity of 3 is mainly mediated by the hydrogen bonding ability of thioamide unit in addition to complexation ability of thione and the hydrophobic binding power of side chain substitutions at 3-position. Thus, the pharmacophore of 3,4-dihydroquinazoline-2(1H)-thiones for their anti-melanogenesis activity could be refined as 3-hydrophobic substituted quinazolinethione. 相似文献
6.
A novel synthesis of a new class of 2-(beta-D-ribofuranosylthio)pyridine glycosides utilizing the reactions of substituted pyridine-2(1H)-thiones and 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose as starting components is described. 相似文献
7.
A novel synthesis of condensed bicyclic thiopyrimidine glycosides utilising 1H-cyclopentapyrimidine-2(3H)-thiones and alpha-bromoglucose or alpha-bromogalactose tetraacetate as starting components is described. 相似文献
8.
The reaction of 5-(1-adamantyl)-1,3,4-oxadiazoline-2-thione 2 with iodoethane, 2-dimethylaminoethyl chloride hydrochloride or 2-piperidinoethyl chloride hydrochloride in ethanolic potassium hydroxide yielded the corresponding 5-(1-adamantyl)-2-ethyl or substituted ethylthio-1,3,4-oxadiazoles 3a-c. Interaction of 2 with formaldehyde solution and primary aromatic amines or 1-substituted piperazines, in ethanol at room temperature yielded the corresponding 5-(1-adamantyl)-3-arylaminomethyl-1,3,4-oxadiazoline-2-thiones 4a-m or 5-(1-adamantyl)-3-(4-substituted-1-piperazinylmethyl)-1,3,4-oxadiazoline-2-thiones 5a-h, respectively. All the synthesized compounds were tested for in vitro activities against certain strains of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 2, 5a, and 5e were found as the most active derivatives, particularly against the Gram-positive bacteria. In addition, the antiviral activity of compounds 2, 4a-m, and 5a-h against HIV-1 using the XTT assay was carried out. Compound 2 produced 100%, 43%, and 37% reduction of viral replication at 50, 10, and 2microg/mL concentrations, respectively. 相似文献
9.
J. Fuentes Mota J. I. Fernández García-Hierro P. Areces Bravo F. Rebolledo Vicente J. A. Galbis Pérez 《Nucleosides, nucleotides & nucleic acids》2013,32(4):457-477
Abstract 1-Methyl- and 1-aryl-(1,2-dideoxy-D-glyofurano)[2,1-d]-imidazolidine-2-thiones having the configurations β-D-glycero-L-gluco (4), β-D-glycero-D-ido (5—8), α-D glycerol-D-galacto (9—10) and β-D-glycero-D-talo (11, 12) are prepared by reaction of 2-amino-2-deoxy-aldoses with methyl and aryl isothiocyanates. 1-Aryl-(1,2-dideoxy–β-D-glycero-L-gluco-heptofurano)[2,1-d]imidazolidine-2-thiones (1—3) have been converted into 1-aryl-4-(D-galacto-pentitol-1-yl)-4-imidazo-line-2-thiones (24—26) by acid catalysed isomerization. 相似文献
10.
Elgemeie GH El-Enany MM Ismail MM Ahmed EK 《Nucleosides, nucleotides & nucleic acids》2002,21(6-7):477-493
A novel synthesis of a new class of bipyridyl and biheterocyclic-nitrogen thioglycosides utilizing the reactions of heterocyclic substituted pyridine-2(1H)-thiones and alpha-bromoglucose or alpha-bromogalactose tetraacetate as starting components is described. 相似文献
11.
Galal E. H. Elgemeie Adel M. E. Attia Sherifa S. Alkabai 《Nucleosides, nucleotides & nucleic acids》2013,32(4):723-733
Abstract A novel synthesis of condensed bicyclic thiopyrimidine glycosides utilising 1H-cyclopentapyrimidine-2(3H)-thiones and α-bromoglucose or α-bromogalactose tetraacetate as starting components is described. 相似文献
12.
A. I. El-Shenawy 《Russian Journal of Bioorganic Chemistry》2016,42(1):100-105
5-Phenyl-2-[(3,4,5-trimethoxybenzylidene)hydrazino]-thiazole and 3-[(3,4,5-trimethoxybenzylidene)amino]-4-oxoimidazolidin-2-thione were prepared by cyclization of 1-[(3,4,5-trimethoxybenzyliden)amino]-thiourea with phenacyl bromide and ethyl chloroacetate in the presence of fused sodium acetate. Acetylation of the synthesized compounds with acetic anhydride gave corresponding N-acetyl derivatives. Condensation of the synthesized thione with aromatic aldehydes yielded two 3-substituted 5-arylidene-4oxo-imidazolidin-2-thiones. Acetylation of the latter compounds with acetic anhydride afforded the corresponding N-acetyl-4-oxo-imidazolidin-2-thiones. Some of the synthesized compounds exhibited antimicrobial activity. The cytotoxic activity of the prepared thiazole and imidazolidin-2-thione derivatives was studied on several tumor cell lines. 相似文献
13.
14.
Galal E. H. EIgemeie Adel M. E. Attia Badria A. W. Hussain 《Nucleosides, nucleotides & nucleic acids》2013,32(5):855-868
Abstract Condensation of cyanothioacetamide or cyanoacetamide with sodium salts of 2-formyl-l-cycloalkanones afforded the corresponding cycloalkane ring fused pyridine-2(1H)-thiones and -2-pyridones. The latter compounds served as a key intermediates for the synthesis of a new class of cycloalkane ring fused pyridine glycosides. 相似文献
15.
Amtul Z Rasheed M Choudhary MI Supino R Khan KM Atta-Ur-Rahman Rosanna S 《Biochemical and biophysical research communications》2004,319(3):1053-1063
Based on structure of the substrate of urease and for the purpose of designing pharmacophore models for urease inhibitors, which could be effective in physiological and pharmacological studies, a series of twenty-five 1,3,4-diazole-2(3H)-thiones-2(3H)-thiones, 1,3,4-diazoles-2(3H)-thiones, and 1,2,4-tri-3-thiones (OSNs) were designed, synthesized, and evaluated for various kinetic parameters of urease inhibition. OSNs inhibited the activity of urease(s) in a concentration dependent fashion. Dixon as well as Lineweaver-Burk plots and their secondary replots indicated that the nature of inhibition was of pure competitive type for all the 25 compounds. 5-[4-(hydroxy)phenyl]-1,3,4-thiadiazole-2(3H)-thione was found to be the most active one with a Ki value of 2 microM. The Ki values were increased with an increase in substrate concentrations. Apparently, OSNs employ a homologous mechanism of action by exploiting a common transition catalysis state and acting as ligand chelators to form octahedral complexes with the urease enzymes in an orientation-specific mode. The inhibition was slightly potentiated by lower pH and not abolished in the presence of NH2OH (a scavenger of histidine residue). Because of their safe profile in the genotoxic assay, they may be pursued in the near future for human testing 相似文献
16.
Kaplancikli ZA Altintop MD Turan-Zitouni G Ozdemir A Ozic R Akalin G 《Journal of enzyme inhibition and medicinal chemistry》2012,27(1):51-57
In the present study, 5-substituted-1,3,4-oxadiazolin-2-thiones (1a-b) were synthesized via the ring closure reactions of appropriate acid hydrazides with carbon disulphide. N-(Benzothiazol-2-yl)-2-[[5-substituted-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide derivatives (3a-j) were obtained by the nucleophilic substitution reactions of 5-substituted-1,3,4-oxadiazolin-2-thiones (1a-b) with N-(benzothiazol-2-yl)-2-chloroacetamides. The chemical structures of the compounds were elucidated by IR, (1)H NMR, (13)C NMR and FAB(+)-MS spectral data and elemental analyses. The synthesized compounds were screened for their antimicrobial activities against Micrococcus luteus, Bacillus subtilis, Pseudomonas aeruginosa, Staphylococcus aureus, Escherichia coli, Listeria monocytogenes and Candida albicans. All compounds except compound 3h exhibited the highest antibacterial activity against P. aeruginosa. Among all compounds (3a-j), the compounds bearing 4-methoxyphenoxymethyl moiety on oxadiazole ring (3a-e) exhibited the highest inhibitory activity against C. albicans. Although compound 3j did not possess 4-methoxyphenoxymethyl moiety on oxadiazole ring, this derivative also exhibited the same level of anti-candidal activity. The compounds were also investigated for their cytotoxic effects using MTT (3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Compound 3a exhibited the highest cytotoxic activity, whereas compound 3g possessed the lowest cytotoxic activity against NIH/3T3 cells. 相似文献
17.
Nabih Ghal Barbara Johnston Lilia Beauchamp Taj Naseree Tracy Scott Roy Flanagan 《Nucleosides, nucleotides & nucleic acids》2013,32(7):1591-1600
Abstract A novel synthesis of 1-(β-D-pentopyranosyl)pyridinethione nucleosides utilizing pyridine-2(1H)-thiones and α-bromoxylose or β-bromoarabinose triacetate as starting components is described. The free nucleosides were tested for their potential activity against HIV and different types of tumor virus. 相似文献
18.
Adel M. E. M. Attia Elsayed I. Ibrahim Fouad E. A. Hay Mohammed M. A. Abbasi Hanaa A. E. Mansour 《Nucleosides, nucleotides & nucleic acids》2013,32(7):1581-1590
Abstract A novel synthesis of 1-(β-D-pentopyranosyl)pyridinethione nucleosides utilizing pyridine-2(1H)-thiones and α-bromoxylose or β-bromoarabinose triacetate as starting components is described. The free nucleosides were tested for their potential activity against HIV and different types of tumor virus. 相似文献
19.
Girniene J Tatibouët A Sackus A Yang J Holman GD Rollin P 《Carbohydrate research》2003,338(8):711-719
The glucose transporter 5 (GLUT5)-a specific D-fructose transporter-belongs to a family of facilitating sugar transporters recently enlarged by the human genome sequencing. Prompted by the need to develop specific photolabels of these isoforms, we have studied the interaction of conformationally locked D-fructose and L-sorbose derived 1,3-oxazolidin-2-thiones and 1,3-oxazolidin-2-ones to provide a rational basis for an interaction model. The inhibition properties of the D-fructose transporter GLUT5 by glyco-1,3-oxazolidin-2-thiones and glyco-1,3-oxazolidin-2-ones is now reported. In vitro, the fused-rings systems tested showed an efficient inhibition of GLUT5, thus bringing new insights on the interaction of D-fructose with GLUT5. 相似文献
20.
《Nucleosides, nucleotides & nucleic acids》2013,32(6-7):477-493
ABSTRACT A novel synthesis of a new class of bipyridyl and biheterocyclic-nitrogen thioglycosides utilizing the reactions of heterocyclic substituted pyridine-2(1H)-thiones and α-bromoglucose or α-bromogalactose tetraacetate as starting components is described. 相似文献