Synthesis of Benzazolyl Pyrimidines Under Ultrasonication and Their Antimicrobial Activity

(1) The benzoxazolyl/benzothiazolyl/benzimidazolyl pyrimidines were prepared under ultrasonication in the presence of pyridine/dimethylaminopyridine and triethylamine. (2) Better yields were recorded in 4‐(N,N‐dimethylamino)pyridine and Et₃N. (3) The presence of electron withdrawing chloro, bromo, and nitro substituents enhanced antimicrobial activity ( 13c , 13e , 14e : minimum inhibitory concentration = 6.25 μg/well against Bacillus subtilis; 13e , 14e : minimum inhibitory concentration = 6.25 μg/well against Aspergillus niger).     

Synthesis and Antibacterial Activity of Benzazolyl Azolyl Sulfamoyl Acetamides

A new class of benzazolyl azolyl sulfamoyl acetamides was prepared from azolyl sulfamoyl acetates and benzazolyl amines in the presence of KO^tBu in tetrahydrofuran. Compounds with benzothiazole‐thiazole, benzimidazole‐thiazole, benzothiazole‐imidazole, and benzimidazole‐imidazole moieties exhibited excellent antibacterial activity against Bacillus subtilis.     

含嘧啶环的噻吩磺酰脲的合成和除草活性测定

从噻吩出发经4步反应合成了15种含嘧啶的噻吩磺酰脲N’-(4,6-二取代嘧啶-2-基)-2-噻吩磺酰脲,其中11种为未见文献报道的新化合物.其结构经红外光谱、~1H NMR谱和元素分析证实.初步生物活性试验表明,这类化合物具有较好的除草活性.     

含唑基的1，4－戊二烯－3－酮类的合成及生物活性研究

由简单的芳醛经３步反应合成了３６种未见报道的含唑基的１，４－戊二烯－３－酮类化合物，经ＩＲ、１ＨＮＭＲ、ＭＳ测定和元素分析证实了其结构．生物活性试验表明，该类化合物具有不同程度的杀菌活性．     

Synthesis and Antiinflammatoryand Anticancer Activity Evaluation of Some Condensed Pyrimidines

Summary.  Upon condensation with 4-isothiocyanato-4-methyl-2-pentanone, 2,3-diaminonaphthalene and N-aminoethyladenosine gave in good yields substituted pyrimidonaphthoimidazole and imidazopyrimidine thione. Refluxing pyrimidobenzthiazole with methanol H₂SO₄ at pH∼1 resulted in S-methyl pyrimidobenzthiazole in moderate yield. Pyrimidobenzimidazole derivatives could be reacted to S-alkylated and N-acylated derivatives by refluxing with ethyl bromoacetate in the presence of anhydrous potassium carbonate in THF and by heating in an acetic acid/acetic anhydride mixture. Heating of pyrimidobenzimidazole with 75% aqueous H₂SO₄ on a water bath ended up in a rearranged product. All compounds gave correct ¹H NMR, IR, and HR mass spectra. Results of antiinflammatory, analgesic, and anticancer activity screening of the new compounds are described. Received October 29, 1999. Accepted (revised) January 13, 2000     

One‐pot Synthesis of Fully Substituted Pyrimidines Using Amidine and Ketene Dithioacetals as Synthons and Their Antimicrobial Activity

A simple, convenient, and efficient one‐pot synthesis of fully substituted pyrimidines was developed by cyclocondensation of α‐oxo ketene dithioacetals with amidine in the presence of potassium carbonate in good yield. Structures of all the newly synthesized compounds were elucidated by elemental analysis and spectral analysis. All the newly synthesized compounds are tested toward different microorganisms.     

含嘧啶环的新拟除虫菊酯的合成及其生物活性的研究

拟除虫菊酯是一类高效、低毒、广谱性杀虫剂。嘧啶环是生物分子和医药中有较好活性的基团。本文拟在菊酯分子中引入嘧啶杂环,并测试其生物活性。我们以β-二酮为起始原料,分别与尿素、甲酰胺和脒缩合关环形成嘧啶,并进一步合成含嘧啶环的新拟除虫菊酯。所合成化合物的生物试验表明其中一些化合物对家蝇具有较好的击倒效应和杀虫效能。     

Synthesis,Characterization, and Antioxidant Activity of a New Class of Amido linked Azolyl Thiophenes

A new class of amido linked azolyl thiophenes was prepared from the synthetic intermediates azolyl amines and 5‐chlorothiophene‐2‐carbonyl chloride adopting conventional and ultrasonication methodologies. It was observed that the reaction took place in shorter reaction times with higher yields under ultrasonication. The structures of the synthesized compounds were characterized by spectral parameters and also tested for antioxidant activity. Among all the tested compounds, methoxy substituted oxazolyl thiophene carboxamide ( 8c ) displayed promising antioxidant activity. Besides, the electron donating groups on the phenyl ring enhanced the antioxidant activity when compared with the electron withdrawing groups.     

Synthesis and Antimicrobial Activity of Substituted Phenophosphazines

Several Schiff base derivatives of phenophosphazines were synthesized by the reaction of amino phenophosphazines and aromatic aldehydes in equimolar ratio, using methanol as solvent. Possible structures have been proposed on the basis of elemental analysis, IR, and ¹H NMR spectral studies. The antibacterial and antifungal activities of the above mentioned Schiff base derivatives have been evaluated against pathogens E. coli, S. typhi, S. aureus, B. subtilis, A. niger, and C. Albicans.     

Synthesis of Steroidal Pyrimidines

Selected aryl aldehydes were treated with 17-oxo-5-androsten-3β-yl acetate (I) to give the corresponding 16-arylidene 17-oxo-5-androsten-3β-yl acetates(IIa-e). Condensation of these chalcones with urea revealed the formation of the corresponding substituted pyrimidin-2′-ones (IIIa-e) respectively.     

键合胍盐低聚物的抗菌聚苯乙烯的制备及其抗菌活性

在Haake转矩流变仪中,将盐酸胍与己二胺的低聚物(PHMG)与末端带环氧基的遥爪型聚苯乙烯(PS)进行熔融反应,得到具有抗菌性能的聚苯乙烯(PS-PHMG)。红外(FT-IR)光谱证明胍盐低聚物是以化学键的形式键合到PS分子链上的。分别用扩散法和振荡瓶法测试了抗菌聚苯乙烯对大肠杆菌和金黄色葡萄球菌的抗菌性能。扩散法实验表明,经提纯后的PS-PHMG不存在胍盐低聚物的溶出,但对大肠杆菌和金黄色葡萄球菌均有明显的抑菌圈。振荡瓶法结果表明:当PS中w(PS-PHMG)=0.2%(即w(PHMG)=0.069%)时,与大肠杆菌接触30 mi m后,抑菌率达100%;当w(PS-PHMG)=0.1%(即w(PHMG)=0.035%)时,30 min内对金黄色葡萄球菌的抑菌率也能够达到100%,具有较好的抗菌速效性,杀灭细菌的时间小于30 min。     

Synthesis and Biological Activity of Some New Diaryl Sulphones Containing Fused Thiazolo Pyrimidines

This paper describes the synthesis of some pyrimido[2,1‐b]benzothiazol‐8‐yl sulphones ( 7, 9, 11, 13, 14, 16 ) starting from bis[2‐aminobenzothiazol‐6‐yl)sulphone 1. Reaction of 1 with acetic anhydride and/or benzoyl chloride gave substituted amino derivatives 2a,b , whereas its reaction with phenacyl bromide and/or p‐chlorophenacyl bromide gave imidazo benzothiazol‐7‐yl sulphones 4a,b .     

抗菌聚合物合成及其抑菌性能的研究进展

抗菌聚合物作为新型的抗菌剂,其可控的结构和多样化的合成方式使其有很好的抗菌活性和应用前景。介绍了抗菌聚合物的合成方法及影响抗菌活性的主要因素、抗菌聚合物抗菌效果与聚合物结构的关系,为制备高活性的抗菌聚合物提供有益的参考,综述了新型抗菌材料的研究现状和发展趋势。     

Synthesis and Antimicrobial Activity of Novel Quinoxaline Derivatives

In this study, certain 3‐substituted styrylquinoxalin‐2(1H)‐ones ( 2a‐d ) and their 2‐chloro ( 3a‐d ) and 2‐piperazinyl derivatives ( 4a‐g ) were synthesized from 3‐methylquinoxalin‐2(1H)‐one ( 1 ). In addition, a series of 1‐alkyl‐3‐substituted styrylquinoxalin‐2(1H)‐ones ( 5a‐d ) was also prepared. Moreover, 3‐(N²‐arylidenehydrazinocarbonyl)quinoxalin‐2(1H)‐ones ( 8a‐c ) as well as their cyclized oxadiazolinyl derivatives ( 9a‐c ) were prepared from 3‐hydrazinocarbonylquinoxalin‐2(1H)‐one ( 7 ). Furthermore, 3‐(5‐substituted thio‐1,3,4‐oxadiazol‐2‐yl)quinoxalin‐2(1H)‐ones ( 11a‐c ) and ( 12a‐c ) were obtained from the intermediate compound ( 10 ) ‐ previously obtained via cyclization of ( 7 ) with CS₂. Likewise, 3‐(5‐oxo‐4,5‐dihydro‐(1,3,4‐oxadiazol‐2‐yl)quinoxalin‐2(1H)‐one ( 13 ), 3‐[5‐(4‐nitrophenyl)‐1,3,4‐oxadiazol‐2‐yl]‐quinoxalin‐2(1H)‐one ( 14 ) and its 2‐chloro derivative ( 15 ) were prepared from 3‐hydrazinocarbonylquinoxalin‐2(1H)‐one ( 7 ). Some of these derivatives were evaluated for antimicrobial activity in vitro and some of the tested compounds showed antibacterial or antifungal activity.     

Synthesis and Antimicrobial Activity of Novel Iminophosphocin Derivatives

Iminophosphocins 8a – 8e and 9a – 9e were synthesized in four‐step reactions via Staudinger reaction. 3‐(Bromomethyl)‐1,2,3,4,5‐pentahydro‐3λ⁵‐naphtho[1,8‐f,g][1,5,3]diazaphosphocin‐3‐one ( 3 ) was prepared by reacting tris(bromomethyl)phosphineoxide ( 1 ) with 1,8‐diaminonaphthalene ( 2 ) in the presence of triethylamine (TEA) in dry tetrahydrofuran (THF), and treated with L‐valine methyl ester ( 4 ) and bis(2‐chloroethyl)amine ( 5 ) in the presence of TEA in dry THF to get 3‐methyl‐2‐[(3‐oxo‐1,2,3,4,5‐pentahydro‐3λ⁵‐naphtho[1,8‐f,g][1,5,3]diazaphosphocin‐3‐yl)methylamino]butanoate ( 6 ) and 3‐[di(2‐chloroethyl)aminomethyl]‐1,2,3,4,5‐pentahydro‐3λ⁵‐ naphtho[1,8‐f,g][1,5,3]diazaphosphocin‐3‐one ( 7 ). The compounds 6 and 7 were treated with trichlorosilane (SiCl₃H) in dry tetrahydrofuran (THF) to form the trivalent P(III) intermediates 8 and 9 , which were further treated with various alkyl azides in dry THF in 55–60°C to afford the title compounds 8a – 8e and 9a – 9e . Their structures were established by multi‐nuclear NMR and mass spectra. All the newly synthesized compounds were found to possess moderate anti‐microbial activity.     

Synthesis and Antimicrobial Activity of New Pyridothienopyrimidines and Pyridothienotriazines

5‐Acetyl‐3‐amino‐4‐aryl‐6‐methylthieno[2,3‐b]pyridine‐2‐carboxamides ( 5a,b ) were reacted with triethyl orthoformate or nitrous acid to give the corresponding pyrimidinones 6a,b and triazinones 7a,b . The reaction of 5a,b with acetic anhydride was carried out and its products were identified as a mixture of 8‐acetyl‐9‐aryl‐2,7‐dimethylpyrido[3′,2′:4,5]thieno[3,2‐d]pyrimidine‐4(3H)‐one ( 9a,b ) and related 5‐acetyl‐4‐aryl‐3‐biacetylamino‐6‐methylthieno[2,3‐b]pyridine‐2‐carbonitrile ( 10a,b ). Reaction of 7a with some halocompounds afforded the N‐alkylated triazinones 8a‐c . Chlorination of 6a,b and 9a,b with phosphorus oxychloride produced 4‐chloropyrimidines 11a‐d which were used as precursors for the rest of the target heterocycles. Some of the prepared compounds were tested in vitro for their antimicrobial activities.     

Synthesis and Biological Activity of a Series of New Thieno[2,3-d]Pyrimidines

Ethyl 2-amino-5-ethylthiophene-3- carboxylate 1, obtained from the reaction of butyraldehyde, ethyl cyanoacetate, sulfur, and triethylamine, reacted with benzoylisothiocyanate to give the corresponding ureido derivatives 2 in a high yield. Further reactions of the compound 2 with an aqueous-alcohol solution of potassium hydroxide and then with hydrochloric acid gave the 2-thio-thieno[2,3-d]pyrimidine-4-ones 3, which were reacted with RX to give novel compounds 4a–4i. Treating the compound 3 with dibromoalkane led to the formation of triacylic compounds 5j–5m. Their structures were clearly verified by IR, ¹H NMR, EI-MS spectroscopy, and elemental analysis. The results of a preliminary bioassay indicated that some compounds possess excellent inhibitory activities against the root and the stalk of Brassica napus (rape) and Echinochloa crusgalli (barnyard grass) at a dosage of 100 mg/L.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.     

新型异噻唑啉酮化合物的合成和抑菌活性研究

合成了10个2-取代异噻唑啉酮化合物, 其中7个未见文献报道. 所有目标物的结构都经元素分析, ¹H NMR, MS及IR证实, 并将其中8个化合物对五种细菌进行了抑菌活性测试. 与市售农药20%三环唑、70%威尔达甲托以及三氯新的抑菌活性进行对比, 发现它们对五种有害菌种均有极强的杀菌活性.     

Synthesis and Antimicrobial Activity of Some Annelated Quinazoline Derivatives

A highly efficient and versatile synthetic approach to the synthesis of annelated quinazoline derivatives viz 1,2,4‐triazino[4,3‐c]quinazoline 5–7 , 11 , thiazolidinylquinazoline 9 , quinazolino[4,3‐b]quin‐azolin‐8‐one 12 and imidazoquinazolines 14a,b,15 is presented. Also, a variety of pyrazolylquinazolines 19–21 and pyrimidinylquinazolines 22a,b were obtained via a sequence of heterocyclization reactions of 4‐methyl‐N‐[4‐(4‐oxo‐3,4‐dihydroquinazolin‐2‐yl)phenyl]benzene‐sulfonamide ( 2 ) with different reagents. The new compounds were synthesized with the objective of studying their antimicrobial activity.