新型含2-取代-1,3-噻唑烷环的噻唑酰胺类化合物的合成与生物活性研究

为了寻找新的含噻唑杂环的先导化合物,利用¨(2-氰基亚胺基-1,3-噻唑烷-3-基)甲基]-2-氨基噻唑与取代苯甲酰氯(或乙酰氯)在吡啶存在下发生缩合反应,合成了19个新型含2-取代-1,3-噻唑烷环的噻唑酰胺类化合物4.经1HNMR和元素分析对目标化合物的结构进行了表征,经MS进一步证实了化合物4s的结构,并通过X射线单晶衍射分析测定了化合物4a的晶体结构.对所合成的目标化合物进行了生物活性测试,部分化合物表现出一定的杀菌和植物生长调节活性.     

新型含2-取代-1,3-噻唑烷和噻唑环的亚胺类化合物的合成及生物活性

通过4-[(2-氰基亚胺基-1,3-噻唑烷-3-基)甲基]-2-氨基噻唑与取代苯甲醛的缩合反应, 合成了14个新型含2-取代- 1,3-噻唑烷和噻唑环的亚胺类化合物5. 所有化合物的结构均经1H NMR和元素分析确证, 并通过X射线单晶衍射分析测定了化合物5a的晶体结构. 初步生物活性试验结果表明, 部分目标化合物具有一定的杀菌活性和植物生长调节活性.     

噻唑啉-2-硫酮衍生物的合成与生物活性

根据活性亚结构拼接原理,将3-芳基-4-氨基-5-乙氧羰基(氰基)-3H-噻唑啉-2-硫酮与酰氯反应得到目标化合物3-芳基-4-取代苯氧乙酰氨基-5-乙氧羰基(氰基)-3H-噻唑啉-2-硫酮.再以3-苯基-4-氨基-5-乙氧羰基-3H-噻唑啉-2-硫酮为合成原料,经过Aza-Wittig反应得到目标化合物5-芳氧基-3,6-二芳基-2-硫代噻唑并[4,5-d]嘧啶-7-酮.通过IR,1H NMR,EI-MS,元素分析等方法对所合成的化合物进行了结构表征.代表化合物5-对氯苯氧基-3,6-二苯基-2-硫代-2,3-二氢噻唑并[4,5-d]嘧啶-7(6H)-酮(C1)经单晶X衍射证实了结构.除草活性测试结果表明:部分噻唑啉-2-酮类衍生物对稗草和油菜都表现出了较好的抑制活性.     

2,6,6-三甲基-双环[3,1,1]庚基-3-(4-芳基-2-噻唑)腙类化合物的合成及其抑菌和抗肿瘤活性研究

以α-蒎烯为起始原料,经加成、氧化、缩合制得中间体,继而与α-溴代芳基乙酮在常温下反应合成12个新型2,6,6-三甲基-双环[3,1,1]庚基-3-(4-芳基-2-噻唑)腙类化合物,产率达52.4%~88.9%.其结构经1H NMR,13C NMR,IR,LC/MS和元素分析进行了确证.初步生物活性测试结果表明:部分目标化合物具有较好的抑菌活性和一定的抗肿瘤活性.     

四种α,α′-二氧代烯酮环二硫代缩酮类化合物的电化学性质及光谱研究

α-羰基二硫缩烯酮也可称为α-羰基烯酮二硫代缩醛,它是一类具有多官能团的有机合成中间体.有关这类化合物的研究已有许多报道[1~3],是目前有机合成化学的一个研究热点.α-羰基二硫缩烯酮类化合物有望成为制备自组装膜修饰电极的新材料[4].本文应用循环伏安法(CV)、UV-V is、交     

3-取代苯甲酰氨基-2-硫代-2,4-噻唑烷二酮类衍生物的新合成法

通过简便的路线合成了8个3-取代苯甲酰氨基-2-硫代-2,4-噻唑烷二酮衍生物,并对其反应机理进行了讨论.所有化合物的结构均经元素分析、₁HNMR、IR和MS谱确认.初步的生物活性测试结果表明,代表化合物表现出良好的抗菌活性和植物生长调节活性.     

α,α''-二氧代烯酮环二硫代缩酮类化合物的晶体结构研究

α,α-二氧代烯酮环二硫代缩酮类化合物是一类多官能团化合物。由于其结构上的特性,近年来,已成为有机合成研究的热点之一[1~3]。多年来,我合成了一系列的α,α-二氧代烯酮环二硫代缩酮类化合物,对于这类特殊结构化合物的谱学性质研究,我们也曾有过详尽的报道[1~6]。为了进一步     

超声辐射下含1,2,3-三唑噻唑烷酮衍生物的合成

采用超声辐射法,以2-苯基-1,2,3-三唑-4-甲酰肼为原料,合成了3-(2-苯基-1,2,3-三唑-4-基)-5H-4-氧代噻唑[2,3-c].1,2,4-三唑,再与各种芳香醛进行Knoevenagel缩合反应,合成了一系列噻唑烷酮衍生物.所有目标化合物结构经元素分析,IR,1H NMR确证.     

咪唑[2，1-b]噻唑多胺缀合物的合成与表征

以2-氨基噻唑和溴乙酰基吡啶为原料合成了二个咪唑[2,1-b]噻唑的甲酰基化合物3,4,然后与N1-氨基丁基-N1,N4-二叔丁氧羰基-1,4-丁二胺经缩合后用NaBH4还原,产物提纯后脱保护得目标产物7、8,并通过IR,^1H NMR,^13C NMR,ESI-MS对目标化合物的结构进行了表征．     

6-烷基-7-亚胺基-2-硫代-2,3,6,7-四氢噻唑并[4,5-d]嘧啶的合成、晶体结构与生物活性

通过3-苯基-5-氰基-2-硫代-2,3-二氢-4-乙氧亚甲胺基噻唑(5)与伯胺反应, 经中间体甲脒关环, 合成了10种新的噻唑并[4,5-d]嘧啶类化合物6a～6j. 所有化合物的结构均经1H NMR, IR和元素分析进行了表征, 并且采用X射线单晶衍射分析方法进一步测定了化合物6i的结构. 初步的生物活性试验表明, 部分标题化合物具有一定的杀菌或除草活性.     

Thiazolecarboxylic Acid Derivatives. 1. N-Substituted 2-Amino-4-methylthiazole-5-carboxylic Acid Derivatives

Acylation of the ethyl ester and anilide of 2-amino-4-methylthiazole-5-carboxylic acid gave 2-acetyl(arylsulfonyl)amino derivatives. Methylation of acetylaminothiazole and subsequent deacetylation gave 2-methylamino-4-methylthiazole-5-carboxylic acid, which was then converted into esters. The ethyl ester and anilide of thiazole-2-carboxylic acid were used as starting compounds for the synthesis of 2-dimethylaminoformimino- and 2-chlorobenzenesulfonylureido derivatives.     

One-dimensional Infinite Chain Organotin Compounds: Synthesis and Structural Characterization of Triphenyltin Thiazole-2-carboxylate and Triphenyltin 3-Pyridinylcarboxylate

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A convenient synthesis of 5-fluorofuran-2-carboxylic acid

A convenient synthesis of 5-fluorofuran-2-carboxylic acid has been achieved in two steps and 56% total yield. Fluorodenitration of commercially available benzyl 5-nitrofuran-2-carboxylate utilizing potassium fluoride and catalytic tetraphenylphosphonium bromide in sulfolane at 140 °C for 2 h furnished benzyl 5-fluorofuran-2-carboxylate. Hydrogenolysis of benzyl 5-fluorofuran-2-carboxylate gave the title compound.     

Effect of Different Substituents on Amine-imine Tautomerism of 2-Amino-4-methylthiazole Derivatives

We have used ¹H NMR to study the amine-imine tautomerism of some esters and amides of 2-N-labeled 4-methylthiazole-5-carboxylic acids and 5-carbamic acids. We have shown that the nature of the substituents of the 2-NHR¹, 5-COR², or 5-NHCOR² groups affects that position of the tautomeric equilibrium. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1240–1243, August, 2005.     

An Assay for Pyrroline 5-Carboxylate Based on its Interaction with Cysteine

Abstract

Pyrroline 5-carboxylate, a potent effector of redox dependent pathways, is a nutritionally responsive plasma constituent and is present in tissue culture medium conditioned by a variety of cells. Studies of P5C production and release both in vivo and in vitro have become increasingly important. To date, the assay used is a specific, sensitive radioenzymatic method. Unfortunately, the necessary materials (purified P5C reductase and NADP[3H], labeled in the transferable position) are not readily available. We now describe a method using commercially available reactants. This new method, based on the interaction of P5C with cysteine, is sensitive and specific; the presence of a wide variety of compounds only minimally affected the assay. [S³⁵] Cysteine at a defined specific activity is reacted with P5C and the P5C-CYS adduct can be separated from the reactants by cation exchange column chromatography. To optimize the assay conditions, we characterized the time course, pH dependence and cysteine concentrations for adduct formation. Studies showed that the sulfhydryl group of cysteine is critical in the formation of the P5C-CYS adduct. Comparison of this new method to the previously published radioenzymatic method showed close correlation over a wide range of P5C concentrations in conditioned media.     

Synthesis of azinylthioureas and their heterocyclization using α-chloroacetoacetic ester

Treatment of aminopyrimidines with a mixture of PhCOCl and NH₄SCN and subsequent debenzoylation of the N-benzoyl-N′-(4,6-substituted pyrimidin-2-yl)thioureas obtained gave pyrimidinyl-2-thioureas. The heterocyclization of the azinyl-2-thioureas with α-chloroacetoacetic ester gave ethyl 2-(4,6-substituted azin-2-yl)aminothiazole-5-carboxylates. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 437–440, March, 2006.     

Synthesis and Crystal Structure of a Novel Ethyl 5-（4-（2-Phenylacetamido）phenyl）-lH-pyrazole- 3-carboxylate as an Acrosin Inhibitor

The title compound （ethyl5-（4-（2-phenylacetamido）phenyl）-lH-pyrazole-3-carboxylate, C20H19N3O3） was synthesized by the reaction of Claisen condensation, cyclization, reduction and acylation. The struct...     

Synthesis and Crystal Structure of a Novel Ethyl 5-(4-(2-Phenylacetamido)phenyl)-1H-pyrazole-3-carboxylate as an Acrosin Inhibitor

The title compound (ethyl5-(4-(2-phenylacetamido)phenyl)-1H-pyrazole-3-carboxy- late, C20H19N3O3) was synthesized by the reaction of Claisen condensation, cyclization, reduction and acylation. The structure was characterized by X-ray diffraction, MS, NMR and IR. It belongs to the monoclinic system, space group C2/c with a = 22.723(9), b = 9.324(4), c = 18.890(8) , β = 114.259(6)°, V = 3649(3) 3, Dc = 1.272 Mg·m-3, Z = 8, Mr = 349.38, μ = 0.087 mm-1, F(000) = 1472, the final R = 0.0615 and wR = 0.1643. The biological test shows that the title compound has a moderate acrosin inhibition activity.     

Multicomponent synthesis and anticancer activity studies of novel 6-(Trifluoromethyl)-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylate derivatives

A series of novel 6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate derivatives were obtained in good yields from ethyl 4,4,4-trifluoro-3-oxobutanoate, urea, and aryl aldehyde via Biginelli multicomponent reaction. All the corresponding products 4a–4p were examined against four human cancer cell lines (A549, HepG2, COLO205 and DU145) and compounds 4e, 4i, and 4?m which showed promising anticancer activity have been identified.