三组分“一锅煮”合成4,5-二氢吡唑并[1,5-a]嘧啶

以芳香醛、5-氨基-1H-吡唑和丙二腈为原料, 三组分“一锅煮”合成4,5-二氢吡唑并[1,5-a]嘧啶类化合物. 所有化合物均经IR, ¹H NMR和元素分析检测. 该法是一种操作简单, 产率较高的方法.     

Microwave assisted synthesis of novel Hantzsch 1,4-dihydropyridines, acridine-1,8-diones and polyhydroquinolines bearing the tetrazolo[1,5-a]quinoline moiety and their antimicrobial activity assess

Microwave assisted efficient Hantzsch reaction via four-component coupling reactions of tetrazolo[1,5-α]quinoline-4-carbal-dehyde, dimedone/cyclohexane-1,3-dione,ethyl/methyl acetoacetate and ammonium acetate was described as the preparation of tetrazolo[1,5-α]quinoline based 1,4-dihydropyridines,acridine-1,8-diones and polyhydroquinolines.The process presented here is simple,rapid,environmentally welcoming and high yielding.All the derivatives were subjected to an in vitro antimicrobial screening against a representative panel of bacteria and fungi and results worth further investigations.     

微波辐射促进的3-烷基取代咪唑并[1,5-a]吡啶合成

分别在常规加热和微波辐射条件下, 由双(2-吡啶甲酰)、二(2-吡啶)甲酮与脂肪醛及醋酸铵在醋酸溶剂中反应成功地制备了3-烷基取代的咪唑并[1,5-a]吡啶. 实验结果表明: 微波法比传统的合成方法产率高、反应时间短. 产物的结构经过¹H NMR, MS和元素分析表征.     

Design, synthesis, and antimicrobial activity of fused triheterocyclic nitrogen systems involving tetrazolo[1,5-b][1,2,4]triazines [1]

Dehydrogenative cyclization of the 6-substituted 7-arylidenehydrazinotetrazolo[1,5-b][1,2,4]triazines derived from 6-methyl and 6-phenyl derivatives of 7-hydrazinotetrazolo[1,5-b][1,2,4]triazines and aromatic aldehydes gave the corresponding 6-substituted 9-aryl-[1,2,4]triazolo[4,3-d]tetrazolo-[1,5-b][1,2,4]triazines. The latter compounds were also obtained by an alternative route involving dehydrative cyclization of 6-methyl and 6-phenyl derivatives of 7-chlorotetrazolo[1,5-b][1,2,4]triazines with aromatic hydrazides through the isolable aroylhydrazino intermediates. Also, the triazolotetrazolotriazine rings were accomplished by one-pot cyclization of cyclic amidrazones with aromatic acid chlorides. The ditetrazolo[1,5-b:1′,5′-d][1,2,4]triazine systems were synthesized by cyclization of the former cyclic amidrazones with nitrous acid, or cyclic imidoyl chlorides with sodium azide. The bis-triazolotetrazolotriazine derivatives were synthesized by cyclization of two equivalents of each cyclic imidoyl chloride with acid dihydrazides through the isolable bis-hydrazide products. The antimicrobial activity of representative compounds was studied.     

Synthesis of imidazo[4,5-a]acridones and imidazo[4,5-a]acridines as potential antibacterial agents

Abstract  

New imidazo[4,5-a]acridone derivatives were synthesized from the rearrangement of 3H-imidazo[4′,5′:3,4]benzo[c]isoxazoles. New imidazo[4,5-a]acridines were obtained from the reaction of imidazo[4,5-a]acridones in boiling POCl₃. All of these compounds exhibited antimicrobial activities comparable to streptomycin as reference drug.     

Synthesis and cytotoxicity studies of quinoline-3-carbonitrile derivatives

<正>A series of quinoline-3-carbonitrile derivatives were designed and synthesized.Their cytotoxicity in vitro against four cancer cell lines(A549,HT-29,MDA-MB-231 and SMMC-7721) were evaluated by standard MTT assay.The pharmacological results showed that most of the prepared compounds displayed excellent selective cytotoxicity toward SMMC-7721 cell line.Among them, compounds 7c,7e,11b,11f and 11g were more active than Gefitinb against SMMC-7721 cell line.     

5,7-二甲基-1,2,4-三唑并[1,5-a]嘧啶-2-甲酰腙类化合物的合成与生物活性

以5-氨基-1H-1,2,4-三唑-3-羧酸为起始原料, 设计合成了13个新型的5,7-二甲基-1,2,4-三唑并[1,5-a]嘧啶-2-甲酰腙类化合物, 通过¹H NMR, MS和元素分析对所合成的化合物进行了结构表征. 初步的生物活性测试结果表明, 所合成的化合物均表现出不同程度的除草及杀菌活性, 其中化合物4b, 4h和5m的活性较好, 在50 mg/L浓度下对水稻纹枯病菌的抑制率达90 %以上.     

Efficient multicomponent synthesis of highly substituted [1,2,3]triazolo[1,5-a]pyrimidines

Abstract  

An efficient and facile multicomponent procedure for the synthesis of highly substituted [1,2,3]triazolo[1,5-a]pyrimidines by reaction of equimolar amounts of aromatic aldehyde, CH-acid, and 5-amino-1,2,3-triazole in refluxing dimethylformamide is described.     

Synthesis and hydrolytic cleavage of tetrazolo[1,5-c]quinazolines

A series of tetrazolo[1,5-c]quinazolines were synthesized by [4 + 1]-cyclocondensation of 4-hydrazinoquinazolines with sodium nitrite with good yields. Peculiarities of this reaction were discussed, namely, the influence of halogen on the reaction yield. Hydrolytic cleavage of tetrazolo[1,5-c]quinozoline cycle was studied in order to obtain 2-(1H-tetrazolo-5-yl)anilines. The structures of the compounds were elucidated by ¹H NMR, ¹³C NMR, infrared, mass spectrometry, and elemental analysis.     

Synthesis and biological activity of fluorinated 7-aryl-2-pyridyl-6,7-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-amines

In our lead finding program, 12 new fluorinated 7-aryl-2-pyridyl-6,7-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-amines were prepared via a practical three-step procedure starting from (iso)nicotinic hydrazides. The fluorine substituted aryl fragment was introduced in the last step through cyclocondensation of N-(3-pyridyl-1,2,4-triazol-5-yl)guanidines and fluoro/trifluoromethyl substituted benzaldehydes. The structures of the compounds were confirmed by ¹H and ¹³C NMR spectral data. The tautomeric preferences for the compounds were established using 2D NOESY experiments. The antiproliferative activity of the synthesized 1,2,4-triazolo[1,5-a][1,3,5]triazines was evaluated against breast, colon and lung cancer cell lines. The highest antiproliferative activity in the series was found for 2-(pyridine-3-yl)-7-(4-trifluoromethylphenyl)-6,7-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-amine. The lack of inhibitory activity against bovine dihydrofolate reductase (DHFR) indicated that the antiproliferative activity was realized via other mechanisms.     

含噁二唑杂环取代的新型三唑并嘧啶衍生物的合成及其生物活性

2-肼羰基亚甲硫基-5,7-二甲基-1,2,4-三唑并[1,5-a]嘧啶与二硫化碳在乙醇溶液中回流制得化合物2-(5-巯基-1,3,4-噁二唑-2-亚甲硫基)-5,7-二甲基-1,2,4-三唑并[1,5-a]嘧啶, 后者在碱性环境中与卤化苄反应得到17种新型双杂环化合物. 对所得化合物结构均经元素分析, ¹H NMR和MS确认. 初步生物活性测试表明这些化合物具有一定的杀菌活性.     

咪唑[1,5-a]吡啶鎓盐的合成、表征及生物活性测定

通过三组份串联反应合成一系列咪唑[1,5-a]吡啶鎓盐,利用1H NMR、13C NMR、MS以及X射线单晶衍射确定其结构,其中以二乙烯三胺与三乙烯四胺为原料获得预期外的结构。以青霉素作为对照,研究了化合物的抗菌性。结果表明,所合成的化合物对溶壁微球菌和乙型链球菌均有抗菌效果,化合物2的抗菌效果最好;含有杂原子O的化合物3对嗜麦芽单胞菌和肺炎克雷伯氏菌的抗菌能力优于青霉素;联苯桥联的刚性双齿咪唑[1,5-a]吡啶鎓(5)比乙基桥联的柔性双齿咪唑[1,5-a]吡啶鎓(4)的抗菌性更强;化合物6为单齿大π体系芳香环,其抗菌效果较好,而化合物7和8为双齿的大π体系芳香环,其抗菌效果较弱。     

Solvent-free combinatorial synthesis of tetrazolo[1,5-a]thiopyrano[3,4-d]pyrimidine derivatives

A series of novel tetrazolo[1,5-a]thiopyrano[3,4-d]pyrimidine derivatives were synthesized by reaction of aryl aldehyde, 2H-thiopyran-3,5(4H,6H)-dione, and 5-aminotetrazole under solvent-free conditions. The features of this procedure are mild reaction conditions, high yields, and operational simplicity.     

new simple and one-pot synthetic routes to polyfunctionally substituted imidazo-[1,2-a]pyridines, pyrido[1,2-a]pyrimidines, pyrido-[1,2-a]-1,3-diazepines, and imidazo[1,2-a]pyrimidines

Reactions of arylidenemalononitriles with 2-nitromethylene-substituted imidazolidine, hexahydropyrimidine, and hexahydro-1,3-diazepine afforded the title derivatives. Reaction of 2-nitromethylenehexahydropyrimidine with benzylamine or n-butylamine and formalin in a molar ratio of 1:1:2 gave the hexahydro-1H-imidazo[1,2-c]pyrimidine derivatives. Treatment of 2-nitromethyleneimidazolidine and hexahydropyrimidine with secondary aliphatic amines and formalin in a molar ratio of 1:1:1 afforded the corresponding methylene bis-compounds. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1850–1853, December, 2005.     

新型环烷烯并嘧啶并噻唑-3-酮类化合物的合成

以环戊酮、环庚酮为起始原料合成的环烷烯并[1,2-d]嘧啶-2-硫酮(2)与氯乙酸、芳香醛反应, 合成具有潜在抗癌活性的稠合杂环化合物5-芳基-2,8-二芳亚甲基-2,3,6,7-四氢-5H,8H-环戊烯并[1,2-d]噻唑并[3,2-a]嘧啶-3-酮(3)以及5-芳基-2,10-二芳亚甲基-2,3,6,7,8,9-六氢-5H,10H-环庚烯并[1,2-d]噻唑并[3,2-a]嘧啶-3-酮(4). 3和4的结构经¹H NMR, IR, MS分析确认.     

Synthesis of [1,5]benzothiazepine derivatives

Various derivatives of 2,3-dihydro[1,5]benzothiazepin-4(5H)-ones were synthesized. Alternative route for the synthesis of 5-dimethylaminoethyl-2,3-dihydro[1,5]benzothiazepin-4(5H)-ones and 4-dimethylaminopro-poxy-(2H,5H)-[1,5]benzothiazepines are described.