苯并噻唑偶氮吡唑和苯并噻唑偶氮嘧啶的合成

2-氨基苯并噻唑重氮盐与丙二腈偶联, 生成2-(苯并噻唑腙基)-丙二腈, 然后分别与水合肼, 苯肼和硝酸胍反应, 形成相应的4'-(苯并噻唑-2-偶氮)-3',5'-二氨基吡唑, 4'-(苯并噻唑-2-偶氮)-3',5'-二氨基-2'-苯并吡唑和5'-(苯并噻唑-2-偶氮)-2',4',6'-三氨基嘧啶.     

6-取代苯并噻唑-2-氨基硫代磷酸二烷基酯的合成

用6-位取代的2-氨基苯并噻唑与三氯硫磷反应,合成了3个苯并噻唑-2-氨基硫代磷酰二氯,并由此合成了9个苯并噻唑-2-氨基硫代磷酸二烷基酯.讨论了苯并噻唑环上取代基对反应的影响和产物中硫代磷酸酯的烷基的空间效应对反应的影响.所合成的部分化合物对人喉鳞状细胞癌(Hep-2)具有一定的抑制能力.     

苯并噻唑-2-甲醛合成方法的改进

以邻氨基苯硫酚为原料,先与羟基乙酸反应合成2-羟甲基苯并噻唑,然后通过氧化反应生成苯并噻唑-2-甲醛。对比了几种氧化剂的效果,发现二氧化锰氧化的效果最好。优化的反应条件为,2-羟甲基苯并噻唑与二氧化锰的摩尔比为1∶8,回流反应8h,产率可达90.2%。该方法适合苯并噻唑-2-甲醛及其衍生物的大规模生产。     

磺胺苯并噻唑IV.具有羧基的磺胺苯并噻唑

1.自对位和间位氨基苯甲酸综合了相应的具有羧基的磺胺苯并噻唑。它们的钠盐在水中溶解度极大,溶液呈中性。2.白间-硫脲基苯甲酸导出的苯并噻唑,其环化并合地位没有确定。3.自邻-氨基苯甲酸或它的乙酯依同样途径综合,得不到相应的苯并噻唑,产物是苯并嘧啶类型化合物。     

新型苯并噁唑(噻唑)衍生物的合成与表征

通过N-氯乙酰或N、N＇-二氯乙酰取代的含氮杂环中间体，4，5-二氯-2-苯基-3-哒嗪酮分别与2-巯基苯并噁唑和2-巯基苯并噻唑反应，合成了8个未见文献报道的苯并噁唑和苯并噻唑衍生物，其结构经^1H NMR，IR，MS及元素分析确认。     

微波辐射法合成2-(4-取代苯乙烯基)苯并噻唑

甲基苯并噻唑;芳香醛;微波辐射法合成2-(4-取代苯乙烯基)苯并噻唑     

新型2-苯并噻唑磺酰脲氨基酸及其甲酯衍生物的合成与抗肿瘤活性

以2-巯基苯并噻唑为原料,经弱氧化和氨化制得2-苯并噻唑次磺酰胺（2）; 2经高锰酸钾氧化制得2-苯并噻唑磺酰胺（3）; 3与氯甲酸乙酯反应制得2-苯并噻唑磺酰胺甲酸乙酯（4）; 4与L-氨基酸甲酯反应制得一系列2-苯并噻唑磺酰脲氨基酸甲酯（6a~6j）; 6经水解合成了10个新型的2-苯并噻唑磺酰脲氨基酸（7a~7j）,其结构经¹H NMR, IR和ESI-MS表征。并研究了6和7对Cdc25B的抑制活性。结果表明:在用药浓度为20 μg·mL^-1时,6c, 6j, 7d, 7h和7j对Cdc25B抑制活性较好,抑制率分别为78.1%, 71.2%, 65.6%, 57.2%和65.9%。     

2-[1-芳酰基-1-(芳基偶氮) 亚甲基] 苯并噻唑啉的合成

本实验通过2-(1-芳甲酰基亚甲基)苯并噻唑啉和芳基重氮盐反应, 高产率地制得一系列2-[1-芳酰基-1-(芳基偶氮)亚甲基]苯并噻唑啉。     

含硅二烃基锡(Ⅳ)的2-巯基苯并噻唑配合物的合成、结构及抗癌活性

合成了6个含硅二烃基锡(IV)的2-巯基苯并噻唑配合物R1R2Sn L2(R1=Me3Si CH2,R2=Me3Si CH2或Ph,Cy;R1=Et Me2Si CH2,R2=Et Me2Si CH2或Ph,Cy.LH=2-硫基苯并噻唑),并通过IR、1H NMR、13C NMR、元素分析和X射线单晶衍射对目标化合物进行结构表征.结果表明,配体L以硫醇互变异构体形式与锡原子配位,形成了以锡为中心的六配位扭曲八面体结构;生物活性试验的初步结果显示,含硅二烃基锡(IV)-2-巯基苯并噻唑对肺腺癌细胞(A549)具有较强的体外抗癌活性.     

2-位官能团化合成2-取代苯并噻唑的研究进展

2-取代苯并噻唑类衍生物在化工、医药、农业等领域具有广泛的应用价值.2-位官能团化是合成2-取代苯并噻唑化合物的一种便捷、有效的合成方法.综述了苯并噻唑2-位的烷基化、酰基化、芳基化、胺基化以及磷酸化等产物的合成方法并进行了归类和分析,同时对其发展进行了展望.     

Pyrazolobenzothiazoles and their conversion to cyanine dyes

Thiocyanatlon of 5- and 6-aminoindazoles gives 5-amino-4-thiocyanoindazole and 6-amino-7-thiocyanoindazole. Sodium sulfide reduction of these amlnothiocyano derivatives, followed by cyclization with acetic anhydride gives 2-methylpyrazolo[5, 4-g] benzothiazole and 2-methylpyrazolo[4, 5-g]benzothiazole. Dimethyl sulfate alkylation in alkaline solution gives 2, 6-dimethylpyrazolo[5, 4-g]benzothiazole and 2, 8-dimethylpyrazolo[4, 5-g]benzothiazole. Quaternary salts of the latter were used to synthesize symmetrical and unsymmetrical trimethinecyanines, monomethinecyanines, and dimethinemerocyanines containing the thiocyano group, as well as styryl dyes. It is found that 2-methylpyrazolo[4, 5-g]benzothiazole is less basic than 2-methylpyrazolo[5,4-g]benzothiazole and more basic than unsubstituted benzothiazole.     

An efficient and facile synthesis of Zn(II) complexes with 2-substituted benzothiazoles and glycine- and alanine-based ligands having antifungal and antibacterial activities

We carried out an efficient and facile synthesis of Zn(II) complexes with heterocyclic ligands based on 2-substituted benzothiazole moieties, 2-(2′-hydroxynaphthyl)benzothiazole, 2-(2′-hydroxyphenyl)benzothiazole, and 2-(2′-merceptophenyl)benzothiazole, and amino acids, glycine and alanine, are reported and also examined for antifungal and antibacterial activities. Ligands and complexes were characterized by FTIR, ¹H NMR, and elemental analysis.     

苯并噻唑类化合物在银上的吸附机理研究

本文利用线性电势扫描的方法研究了几种苯并噻唑类化合物及巯基苯基四氮唑在银上的吸附机理。结果表明:2.巯基苯并噻唑和巯基苯基四氮唑以化学吸附方式,通过分子上巯基与银表面的作用形成分子紧密排列的吸附层。25℃下,PMT可以在银表面形成紧密单层。这种吸附在较高吸附温度下可以转化为多层,且完全覆盖银表面。在含Br^-的溶液中,它可以阻碍Br^-与表面的接触。在较大的浓度下,2-甲基苯并噻唑和苯并噻唑也可以在银表面的某些位置,通过杂环上的S原子(或N原子)形成松散的吸附,但这种吸附层不能完全覆盖银表面。电镜实验也表明以上物质在银表面发生了作用。     

Interactions entre les seringues non réutilisables et les médicaments: Migration d'un Accélérateur de Vulcanisation Benzothiazolique et de Composés Apparentés

Interactions between disposable syringes and drugs. Leaching of a benzothiazole vulcanization accelerator and related compounds)Disposable syringes (three brands) filled with water very quickly yielded one or more compounds with u.v. absorption peaks. The rubber plunger seals were identified as the source of contaminant. Their analysis by t.l.c. showed the presence of 2-mercaptobenzothiazole, used as vulcanization accelerator. The compounds extracted into water were identified by mass spectrometry (electron impact and methane chemical ionization) as 2-mercaptobenzothiazole, 2-methylthiobenzothiazole, 2-hydroxybenzothiazole, 2-(2-hydroxyethylthio)benzothiazole and 2-(2-hydroxyethoxy)benzothiazole. The last three compounds were formed during sterilization of the syringes with ethylene oxide. The role of the precise nature of the vulcanization accelerator in this reaction is briefly described (zinc ions seem to be necessary), as are the analytical interferences resulting from the observed phenomena.     

Oxorhenium(V) and oxotechnetium(V) [NN][S]3 complexes of 2-phenylbenzothiazole derivatives

The reaction of 2-(2'-pyridyl)benzothiazole, [NN], with the ReO(V)(3+) and TcO(V)(3+) cores in the presence of thiophenols, [S] (RC(6)H(4)SH, R = H, 4-CH(3), 4-OCH(3)), as coligands led to the isolation of hexacoordinated complexes of the MO[NN][S](3) type (M = Re, Tc). In all cases, two geometric mer isomers were formed, as evidenced by NMR spectroscopy and confirmed by X-ray crystallography. In both isomers, the coordination geometry about the metal ion is a distorted octahedral defined by the two nitrogen atoms of the bidentate ligand, the three sulfur atoms of the monodentate thiols, and the oxygen atom of the oxo group. The apical positions of the octahedron are occupied by the oxygen of the oxo group and, in one of the isomers, the nitrogen of the pyridyl moiety of 2-(2'-pyridyl)benzothiazole, while, in the second isomer, the imine nitrogen of 2-(2'-pyridyl)benzothiazole. The complexes are stable, neutral, and lipophilic. Complete (1)H and (13)C NMR assignments are reported for all complexes. The synthetic reaction was also successfully transferred at the technetium-99m tracer level by ligand exchange reaction using (99m)Tc-glucoheptonate as precursor in the presence of 2-(2'-pyridyl)benzothiazole and 4-CH(3)C(6)H(4)SH. The structure of the technetium-99m complex was established by high-performance liquid chromatographic comparison with the analogous oxotechnetium and oxorhenium complexes. The 2-(2'-pyridyl)benzothiazole ligand serves as a preliminary model for 2-(4-aminophenyl)benzothiazole, which possesses interesting properties for the development of technetium and rhenium radiopharmaceuticals for tumor imaging and/or radiotherapy as well as in vivo diagnosis of Alzheimer's disease.     

Liquid crystalline properties of new unsymmetrical compounds with benzothiazole core detected by TG/DSC-POM-XRD

Thermal properties of two azomethine liquid crystals with a benzothiazole core were synthesized and investigated by applied Mettler-Toledo AG equipment (TG/DSC). Azomethines with benzothiazole core was obtained by nucleophilic addition of benzothiazole-2-carboxaldehyde in N,N-dimethylacetamide (DMA) solution with 4-(heptadecafluoroctyl)aniline (BTA1) or 4-hexadecylaniline (BTA2). The differential scanning calorimetry (DSC) was employed to evaluate their phase transitional behavior. Variable heating and cooling rates were used to study liquid crystalline properties of azomethines with benzothiazole core. Compound BTA1 exhibited liquid crystalline properties, while BTA2 is non-mesogenic. Three or four endothermic DSC peaks were observed for both compounds during heating process with the rate 0.5?°C/min. The mesophase was identified and confirmed by XRD study and polarized optical microscopy (POM) too. The thermal stability was determined by thermogravimetric analysis (TG). The temperatures of 5% mass loss (T _5%) of BTA1 and BTA2 range from 212 to 317?°C in nitrogen.     

Unexpectedly ligand-free copper-catalyzed C–S cross-coupling of benzothiazole with aryl iodides in aqueous solution

A novel synthetic protocol for 2-aminophenyl sulfide derivatives via the reactions of benzothiazole with aryl iodides was reported for the first time. The reactions were catalyzed by CuCl with tetrabutylammonium hydroxide as the base and water as the solvent without ligand at 50 °C or room temperature. A variety of aryl iodides underwent the C–S cross-coupling reaction with benzothiazole to afford smoothly the corresponding products in excellent yield.     

Microwave assisted one pot synthesis of 2-ethylamino benzimidazole,benzoxazole and benzothiazole derivatives

A rapid and efficient one-pot method for the synthesis of 2-ethylamino benzimidazole, benzoxazole, and benzothiazole derivatives has been described. The reaction of o-phenylenediamines or o-aminophenols or 2-mercaptoanilines with EDC.HCl under microwave irradiation afforded the corresponding 2-ethylamino benzimidazole, benzoxazole and benzothiazole derivatives in excellent yields.     

A structure-activity relationship study of compounds with antihistamine activity

A structure-activity relationship (SAR) analysis of H(1)-, H(2)- and H(3)-antihistamine activity was carried out and chromatographic data of 2-[2-(phenylamino)thiazol-4-yl]ethanamine, 2-(2-benzyl-4-thiazolyl)ethanamine, 2-(2-benzhydrylthiazol4-yl)ethanamine, 2-(1-piperazinyl- and 2-(hexahydro-1H-1,4-diazepin-1-yl)benzothiazole, 2-(1-piperazinyl)benzothiazole, 2-[4-(1-alkyl)piperidinyl]benzothiazole, 2-(N,N',N'-dimethylalkyl-1,2-ethanediamino)benzothiazole, 2[1-(4-aminopiperidinyl)]benzothiazole, 2-[2-phenyl-4-thiazolyl]ethanamine derivatives and selected H(1)- and H(2)-antihistamine drugs were obtained. NP TLC and RP2 TLC plates (silica gel NP 60F(254) and silica gel RP2 60F(254) silanized precoated), impregnated with a solution of aspartic acid (L-Asp) and a solution of an analogue of aspartic acid (propionic acid), were used in two developing solvents as H(1)-, H(2)- and H(3)-antihistaminic interaction models. The lipophilicity data of the examined compounds were obtained and used in the SAR assay. Biochromatographic tests using TLC plates impregnated with solutions of asparic acid or propionic acid were found to be a source of useful data for the qualitative analysis of compounds with different structures, demonstrating activity to histamine H(1)-, H(2)- and H(3)-receptors. The four presented discriminant models based on biochromatographic studies are an efficient tool in the SAR analysis for initial prediction of compound activity direction within histamine receptors.     

Synthesis and Mechanistic Study of Triheterocyclic 4H‐Pyrimido[2,1‐b]benzothiazole derivatives,One‐Pot Three‐component Reaction under Solvent‐Free Conditions

An efficient method has been developed for the preparation of 4H‐pyrimido[2,1‐b]benzothiazole derivatives by the condensation of aldehydes, β‐ketoester, and 2‐amino benzothiazole under solvent and solvent‐free conditions using various catalysts. The reaction uses benzothiazole as a new component, and good yield is obtained at 60–65°C under solvent‐free conditions. Atom economies, good yield, environmentally benign, and easy to work‐up are some of the important features of this protocol. The present study suggests that acetic acid and metal catalysts follow different mechanism. In acetic acid, 2‐amino benzothiazole reacts with benzaldehyde, and resultant intermediate reacts with ethyl acetoacetate to give final product, whereas in the presence of metal catalysts, 2‐amino benzothiazole first reacts with ethyl acetoacetate, and resultant intermediate reacts with benzaldehyde to give pyrimido[2,1‐b]benzothiazole.