Design,Synthesis and Anticancer Activity of New Polycyclic: Imidazole,Thiazine, Oxathiine,Pyrrolo-Quinoxaline and Thienotriazolopyrimidine Derivatives

In this article, we showed the synthesis of new polycyclic aromatic compounds, such as thienotriazolopyrimidinones, N-(thienotriazolopyrimidine) acetamide, 2-mercapto-thienotriazolo-pyrimidinones, 2-(((thieno-triazolopyrimidine) methyl) thio) thieno-triazolopyrimidines, thieno-pyrimidotriazolo-thiazines, pyrrolo-triazolo-thienopyrimidines, thienopyrimido-triazolopyrrolo-quinoxalines, thienopyrimido-triazolo-pyrrolo-oxathiino-quinoxalinones, 1,4-oxathiino-pyrrolo- triazolothienopyrimidinones, imidazopyrrolotriazolothienopyrimidines and 1,2,4-triazoloimidazo- pyrrolotriazolothienopyrimidindiones, based on the starting material 2,3-diamino-6-benzoyl-5- methylthieno[2,3-d]pyrimidin-4(3H)-one (3). The chemical structures were confirmed using many spectroscopic ways (IR, ¹H, ¹³C, −NMR and MS) and elemental analyses. A series of thiazine, imidazole, pyrrole, thienotriazolopyrimidine derivatives were synthesized and evaluated for their antiproliferative activity against four human cancer cell lines, i.e., CNE2 (nasopharyngeal), KB (oral), MCF-7 (breast) and MGC-803 (gastric) carcinoma cells. The compounds 20, 19, 17, 16 and 11 showed significant cytotoxicity against types of human cancer cell lines.     

偶氮芳基水杨醛缩氨基硫脲衍生物的合成及其生物活性研究

在室温下, 以酸作催化剂, 通过简单的方法合成了9个未见文献报道的偶氮芳基水杨醛缩氨基硫脲类化合物, 并通过元素分析、红外光谱及核磁共振谱确证了其结构. 初步的生长调节活性实验结果表明, 该类化合物在不同的浓度下对植物的生长调节表现出一定的规律性.     

A Facile and Rapid Method for Preparation of Thiazine and Thiadiazine Derivatives by Sonication Technique

Ultrasound accelerated synthesis of 2,3-(substituted)benzo-1,4-thiazino[5,6-b]-4H-9H-7- methyl-10-oxoquinolines (4), 7-substituted-2,2-dimethyl-2,3-dihydro-1H,10H-phenothiazin- 4-one (5), 4-substituted-3,9, 10-trihydro-11-oxo-quinolino[2,3-b]-1,3,4-thiadiazino[2,3-d]- 1,2,4-triazole (6), and 7,7-dimethyl-7,8-dihydro-3H,5H,6H-1,2,4-triazolo[3,4-b][1,3,4] benzothiadiazin-9-one (7) from carbostyril and dimedone using sulfur powder and iodine as a catalyst in THF is reported. The structures of the compounds have been elucidated on the basis of spectral and elemental analysis.     

新型紫罗兰酮基双查尔酮缩氨基硫脲的合成及抗肿瘤活性

根据活性亚结构拼接原理,通过紫罗兰酮与(取代)苯甲醛反应合成了紫罗兰酮基双查尔酮,然后经与氨基硫脲缩合得到一系列未见报道的新型含紫罗兰酮、查尔酮及氨基硫脲3种优势结构单元的杂化体,它们的化学结构经傅里叶变换红外光谱(FT-IR)、核磁共振波谱(~1H NMR、~(13)C NMR)、元素分析及质谱(MS)等测试技术所证实。采用溴化噻唑蓝四氮唑(MTT)法初步测定其体外抗肿瘤活性(乳腺癌细胞(MCF-7),肝癌细胞(Hep G2),肺癌细胞(A549)),结果表明,对于不同类型的肿瘤细胞,化合物展现较好的增殖抑制活性。尤其是化合物3a与3b对MCF-7细胞展现较强的抗增殖活性,半数致死量(IC_(50))值分别为10.83和7.62μmol/L,化合物3e对A549细胞显示一定的增殖抑制活性效果(IC_(50)值为13.36μmol/L),化合物3f对Hep G2细胞表现了高效的抗增殖活性(IC_(50)值为8.55μmol/L)。目标物的抗增殖活性与紫罗兰酮结构及查尔酮环上不同电子效应的取代基有关。     

芴三偶氮基水杨醛缩氨基芳基硫脲合成及其植物生长调节作用

以芴、水杨醛和氨基芳基硫脲为原料合成了一系列新型芴三偶氮基水杨醛缩氨基芳基硫脲衍生物,其结构经IR、1H NMR、MS和元素分析测试技术确证。经平皿油菜生根实验表明,该类化合物在低浓度下对油菜生根显示促进作用,高浓度下促进作用小或显示抑制作用,对油菜生根的调节作用与硫脲的苯取代基上的取代基性质有关。     

N^4—取代缩氨基硫脲衍生物的合成

以Ｎ４－取代氨基硫脲与尿嘧啶－１－乙醛反应，合成了６种Ｎ４－取代氨基硫脲衍生物，并进行了抗菌活性测试。结果表明，当Ｎ４－取代基为对氯苯基（Ⅲ６）时，具有较高的抑制枯草杆菌活性，对八叠球菌、白色念珠菌、黄曲霉菌亦有一定活性。     

新型硫脲化合物的合成与生物活性研究

以异硫氰酸酯为原料合成了5种新化合物，这些化合物结构均经1H NMR，元素分析确定，经生物活性测试，部分化合物具有良好抗烟草花叶病毒活性。     

芳香噻嗪类衍生物作为选择性醛糖还原酶抑制剂的分子对接和基于受体的三维定量构效关系研究

芳香噻嗪类衍生物被证明是一类选择性较好的高活性醛糖还原酶抑制剂(ARIs).本文对44个芳香噻嗪类化合物进行了分子对接(docking)和三维定量构效关系(3D-QSAR)研究,并探索了此类化合物与醛糖还原酶(ALr²)的作用机理.醛糖还原酶与醛还原酶(ALR1)活性位点的叠加结果显示, ALr²中残基Leu 300和Cys298的存在是化合物1m具有高选择性的原因.分别建立了比较分子场分析方法(CoMFA, q² = 0.649, r² =0.934; q²:交叉验证相关系数, r²:非交叉验证相关系数)和比较分子相似性指数分析方法(CoMSIA, q² = 0.746, r² = 0.971)模型,并对影响此类化合物生物活性的结构进行了鉴定.结果显示,两个模型均具有较高预测能力,并通过测试集中的7个化合物进行了验证,其中CoMFA模型和CoMSIA模型的预测相关系数(r_Pred²)分别为0.748和0.828. 3D-QSAR模型中的三维等值线图表明,在化合物1m的苄基环上C3和C4位置以及苯并噻嗪母核上C5和C7位置进行改进可能对生物活性的提高有利,此预测与我们前期报道的苯并噻嗪母核C7位改进结果一致.本文所建3D-QSAR模型能够在理性设计具有更高生物活性的新型ARIs中发挥重要作用.     

缩氨基硫脲衍生物的合成及抗菌活性研究

以邻甲苯胺、苯胺或乙醇胺和二硫化碳为原料,经与氨水、氯乙酸钠和水合肼反应,合成了N(4)取代氨基硫脲,再与取代水杨醛或2-乙酰基吡啶进行缩合反应,得到6个缩氨基硫脲化合物3a~3f。抗菌实验结果表明:当质量浓度为1 mg/mL时,化合物3d对革兰氏阳性菌—金黄色葡萄球菌和枯草芽孢杆菌有很强的抑菌活性,对革兰氏阴性菌-大肠杆菌有一定的抑菌活性。      

Tandem One‐pot Synthesis of Polysubstituted 1,3‐Thiazine Derivatives

A tandem one‐pot synthesis of polysubstituted 1,3‐thiazines has been developed by reacting with cyanoacetamide and isothiocyanate derivatives to give rise to 2‐cyano‐3‐mercaptoacrylamides, which are trapped in situ by various aldehydes or diversely substituted ketones through intermolecular cyclization, providing polysubstituted 1,3‐thiazine derivatives in short reaction times with good to excellent yields. The salient features of this novel protocol are operational simplicity, accessing the desired products from the readily available starting materials and easy of product isolation and may find wide spread applications in medicinal chemistry.     

一锅煮法合成苯基苄基酮缩氨基硫脲

以天然产物异黄酮与氨基硫脲为原料, 在碱性条件下乙醇为溶剂, 合成了10种苯基苄基酮缩氨基硫脲化合物. 此方法操作简便、条件温和、且产率较高, 是合成苯基苄基缩氨基硫脲的一种简便实用的方法. 采用IR, ¹H NMR, ¹³C NMR和元素分析对这10种化合物结构进行了表征.     

锡（Ⅳ）的某些噻嗪染料络合吸附波研究和分析应用

研究表明噻嗪染料中新亚甲蓝或甲苯胺蓝在硫酸－草酸介质中与Ｓｎ（Ⅳ）在－０．６０Ｖ（ｖｓ．ＳＣＥ）处出现一高灵敏的络合吸附电流，比无上述染料时电流增高约１６倍。检出限０．８ｎｇ／ｍＬ（相当６．７×１０＾－９ｍｏｌ／Ｌ）Ｓｎ（Ⅳ）．ＮＭＢ和ＴＢ在酸性介质中被质子化，可用Ｒ＾＋表示，与Ｓｎ（ＧＮ     

A New Route for the Synthesis of N-Substituted Diketopiperazine Derivatives

Eight N-substituted diketopiperazines (DKPs) were synthesized by solid-phase protocols. The introduction of iminodiacetic acid (Ida) and followed another α-amino acid residue as the precursor of DKP framework made the present synthesis to be very facile and efficient.     

缩氨基硫脲及其环化产物噻二唑的合成及其活性

合成了两个缩氨基硫脲及其两个环化产物———１,３,４－噻二唑,考察了噻二唑杂环的闭合条件,测定了产物的部分物理常数及红外光谱,对化合物作了初步抑菌活性筛选。为含有碳氮硫活性中心的金属螯合配体的研究提供了基础     

The Syntheses of New Cyclopenta[d][1,3]thiazine Derivatives and Their Use as Antimicrobial Agents

Cyclopentanone (1) was exploited as a starting material for the syntheses of hitherto unknown cyclopenta[d][1,3]thiazine derivatives.     

Polymer Supported Synthesis of Multi-substituted Pyrimidine-4-one Derivatives via Pb f-activated Thiourea

Efficient polymer supported synthesis of multi-substituted pyrimidine-4-one derivatives was described. Target products were produced from fluorenylmethoxycarbonyl(Fmoc) protected β-amino acid loaded on hydro- xymethyl resin through deprotection, N-alkylation, guanidine formation, and cleavage of 2,2,4,6,7-pentamethyl dihy-drobenzofuran-sulfonyl(Pbf) by trifluoracetic acid(TFA) followed with cyclization. The procedure has the advantages of easy operation, mild reaction conditions, and forming multiple substi...     

Synthesis and Crystal Structural Characterization of a Thiosemicarbazone Derived from 4-Acylpyrazolone

1 INTRODUCTION Pyrazol-5-one derivatives form an important class of organic compounds due to their structural che- mistry and biological activities as analgesic, antipy- retic, anti-inflammatory and hyperglycemic agents[1～4]. Even the simplest pyrazol-5-one derivatives like antipyrine and amidopyrine are widely used in anal- gesic medicine[5, 6]. On the other hand, thiosemicar- bazones, especially heterocyclic thiosemicarbazones, have been the subject of extensive investigations be- cause…     

Synthesis of Novel Cyclic Benzenesulfonylurea and Thiourea Derivatives

Treatment of the pyrazoline derivatives (1-6) with isocyanates or isothiocyanates afforded ureas (7-18) and thioureas (19-32) in a good yield. Subsequent treatment of the benzenesulfonylthioureas (19-32) with f - and g -halogenocarbonyl compounds gave the corresponding thiazolidines (33-41) and 1,3-thiazinones (42-46) respectively. When urea derivatives (7-18) were reacted with dimethyl malonate in sodium ethoxide, they gave the corresponding pyrazolebarbiturate derivatives (53-56) . The structure of the isolated product were determined by the spectral methods.     

新型苯并噻吩七元稠环芳烃衍生物的合成

以2,3,4,5-四碘代噻吩为起始原料,经Suzuki偶联反应和三氯化铁氧化成环反应,合成了三个新型的苯并噻吩七元稠环芳烃衍生物,其结构经1H NMR,13C NMR,MS,IR和元素分析表征。