Synthesis and Antibacterial Activity of Novel Oxazolidinone Analogs Containing Substituted Thiazole/Fused-Bicyclic Groups

IntroductionOxazolidinones, exemplified by linezolid, are anovel class of totally synthetic antibacterial agents withactivities against a variety of clinically important sus-ceptible and resistant Gram-positive pathogenic bacteriasuch as methicillin-resis…     

Design,Synthesis and Antitumor Activity of Novel 6,7-Dimethoxyquinazoline Derivatives Containing Diaryl Urea Moiety

A series of 6,7-dimethoxyquinazoline derivatives connected by diaryl urea scaffolds was designed, synthesized and their in vitro antitumor activities were evaluated. Most of them showed an excellent potency against the four tested cancer cell lines as compared with sorafenib. Particularly, a promising compound 20 was identified, which showed the most potent antitumor activities with IC₅₀ values of 0.08, 0.09, 0.16 and 0.19 μmol/L against H460, HT-29, MKN-45 and MDA-MB-231 cell lines, respectively. The structure-activity relationship(SAR) analysis indicated that compounds with dimethylamino or diethylamino group at the C4 position of 6,7-dimethoxyquinazoline moiety exhibited superior activities than compounds bearing morpholino groups.     

含香豆素骨架的缩氨基硫脲化合物的合成和抑菌活性研究

由含不同取代基的水杨醛与乙酰乙酸乙酯在六氢吡啶存在下,得到一系列乙酰基香豆素中间体,然后进一步与氨基硫脲发生缩合反应,得到含有香豆素骨架的缩氨基硫脲化合物,目标化合物的结构均由IR、1H NMR 13C NMR和HRMS确证.它们对大肠杆菌和枯草杆菌具有优良的抑制效果,其中以二氯代的标题化合物的效果最佳.     

含哌嗪片段的噻吩查尔酮衍生物的合成及其抗菌活性

查尔酮是一类具有多种生物活性的1,3-二苯基丙烯酮化合物.以4-氟苯乙酮和2-噻吩甲醛为原料出发,经取代、Aldol反应和衍生化,合成得到16个未见文献报道的含哌嗪片段的噻吩查尔酮衍生物.以氧氟沙星、左氧氟沙星、莫西沙星作阳性对照,采用K-B纸片扩散法测试了目标化合物对金黄色葡萄球菌(Staphylococcus aureus Rosenbach)、大肠埃希菌(Escherichia coli)和枯草芽孢杆菌(Bacillus subtilis)的抑菌活性.结果表明,(E)-1-[4-(4-肉桂酸甲酯甲基哌嗪基)苯基]-3-(噻吩-2-基)丙-2-烯酮(4b)和(E)-1-{4-[4-(2-氧亚基苯乙基)哌嗪基]苯基}-3-(噻吩-2-基)丙-2-烯酮(4e)对枯草芽孢杆菌高度敏感,且最低抑菌浓度为4.0μg/m L.     

海洋来源真菌Penicillim grisefulvum中桔霉素类化合物的分离及抗菌活性

以海洋来源青霉真菌Penicillim grisefulvum为研究对象,采用硅胶、C18柱和Sephadex LH-20凝胶柱层析等手段,从中分离获得3个桔霉素类化合物:7-methyl-penicitrinone A(1),citrinin(2)和penicitrinone A(3),其中化合物1为新化合物.通过一维核磁共振谱(1D NMR)、二维核磁共振谱(2D NMR)和高分辨质谱(HR-ESI-MS)对化合物1的平面结构和相对构型进行确定,并运用电子圆二色光谱(ECD)和量子化学计算方法确定了其绝对构型.抗菌活性测试结果表明,化合物1对副溶血性弧菌(Vibrio parahemolyticus)表现出了较强的抑制活性(MIC=0.8μmol/L),高于阳性对照药物环丙沙星的活性(MIC=1.3μmol/L).     

Synthesis and Antitumor Activity of Sorafenib Analogs Containing a Tetrazole Moiety

A novel series of diaryl biuret derivatives containing a tetrazole moiety was designed and synthesized.All the target compounds were evaluated for their in vitro antitumor activity against HT-29,HepG2,MCF-7 and A549 cells by MTT assay.Most of them exhibited obvious antitumor activity,and four of them(4a,4c,4h and 7a)were superior to sorafenib in general.Among them,Compound 4h displayed more potent activity than sorafenib in all tested cancer cells.Compound 4c exhibited the most outstanding activity in inhibition of growth of HepG2 cells(IC50=0.55 μmol/L).Further,they both revealed favorable metabolic stability in in vitro assay.Compounds 4c and 4h are promising candidates for further development.     

Syntheses and Insecticidal Activity of Spirocyclic Tetronic Acid Derivatives Containing Oxime Ether Moiety

In order to develop novel spirocyclic tetronic acid lead compounds, a series of new spirocyclic tetronic acid derivatives containing oxime ether moiety was synthesized and bioassayed. The structures of 16 target compounds were characterized by ¹H NMR spectra, ¹³C NMR spectra and high-resolution mass spectrometer(HRMS). Preliminary bioassays indicated that most of the title compounds displayed excellent insecticidal activity against Aphis fabae and Nilaparvata lugens at 100 mg/L. In particular, compound 6k showed the similar activity(LC₅₀=6.87 mg/L) against A. fabae as the spirotetramat(LC₅₀=4.56 mg/L) and had better effects(LC₅₀=1.64 mg/L) against N. lugens in comparison with spirotetramat(LC₅₀=7.90 mg/L). The study showed that compound 6k exhibited more promising and broad-spectrum insecticide activity and may serve as a new insecticidal agent for sucking pests.     

Synthesis and Herbicidal Activity of Novel Sulfonylureas Containing 1,2,4-Triazolinone Moiety

A series of new sulfonylureas incorporating 1,2,4-triazolinone moiety was synthesized, which were further bio-assayed for the herbicidal activity against four herbs, representative of monocotyledons and dicotyledons. Some of them exhibited high potency to inhibit the growth of dicotyledons(Bassica napus and Amaranthus retroflexus) in the pot experiment. Compounds 9a and 9b also displayed an excellent herbicidal activity against Bassica napus at a concentration of 15 g/hectare, which were comparable with commercial triasulfuron.     

含4-氨基哌啶片段的6,7-二甲氧基喹啉衍生物的合成及抗肿瘤活性

以2-氨基-4,5-二甲氧基苯甲酸（2）和环酮（环戊酮、环己酮）为原料,在三氯氧磷作用下“一锅法”合成6,7-二甲氧基喹啉中间体（3）,再与4-氨基哌啶或4-异丙基-1-氨基环己烷（4）发生Buchwald-Hartwig偶联反应,得到含有4-氨基哌啶或4-异丙基-1-氨基环己烷片段的6,7-二甲氧基喹啉衍生物（1a～1f）,产物及中间体结构通过¹H NMR、¹³C NMR、MS及元素分析进行表征。初步抗肿瘤活性测试表明,所合成化合物对HepG2、MCF-7、PC3和HeLa均有明显的抑制活性,尤其是化合物1b展现出较强的MCF-7抑制活性(IC₅₀ =11.2μmol/L),甚至强于当前乳腺癌的一线治疗药物4-羟基他莫昔芬(IC₅₀ =15.1μmol/L);此外,标题化合物对正常的乳腺上皮细胞MCF-10A没有毒性。     

含喹唑啉硫醚的杨梅素衍生物的设计、合成及生物活性研究

以杨梅苷为原料,通过活性拼接,设计并合成一系列含喹唑啉硫醚的杨梅素衍生物,其结构通过1H NMR、13CNMR、19F NMR和HRMS进行确证.生物活性测试结果表明,该类化合物对水稻白叶枯病菌(X.Oryzae)、柑橘溃疡病菌(X.Citri)和烟草青枯病菌(R.Solanacearum)表现出一定的抑制活性.其中,...     

Synthesis,Characterization and Antibacterial Activity of New 5-Aryl Pyrazole Oxime Ester Derivatives

Eleven new 1-{5-[4-（benzyloxy）phenyl]-3-methyl-4,5-dihydropyrazol-l-yl} oxime ester dcrivatives were synthesized and characterized by elemental analysis, HRMS, ^1H NMR data. All the compounds were screened for their antibacterial potential in vitro against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. The results indicate that compounds 8c and 8f possess potent activity with the minimum inhibitory concentrations（MIC） of 1.562--3.125 ug/mL against all the four bacteria. Compounds 8c, 8e and 8f show moderate inhibition against the DNA gyrase（IC50=1.9--2.5 ug/mL）. On the basis of the biological activities, structure-activity relationship was discussed.     

Microwave-Assisted Solid-Phase Synthesis of Cephalosporin Derivatives with Antibacterial Activity

Summary.  The reaction of heterocyclic acids with 7-amino-cephalosporanic acid adsorbed on basic alumina under microwave irradiation afforded the N-acylated cephalosporin analogues in satisfactory yield. All compounds were tested for their antibacterial activity; some of them showed significant antibacterial properties. Cefotaxime and cephalothin were used as reference drugs. Received February 23, 2000. Accepted March 28, 2000     

取代噻吩双酰胺类化合物的设计、 合成及生物活性

利用中间体衍生化方法, 将噻吩环引入到双酰胺类化合物中, 合成了一系列取代噻吩双酰胺类化合物1~3; 目标化合物的结构经核磁共振波谱、 红外光谱及元素分析确认. 生物活性测试结果表明, 化合物1在600 mg/L剂量下对小菜蛾具有良好的杀虫效果, 致死率均为100%, 其中化合物1a和1e在20 mg/L剂量下对小菜蛾的致死率仍达到60%以上; 改变双酰胺结构中的吡唑环得到化合物2和3, 其杀虫活性消失, 说明该类化合物中吡唑环结构对杀虫活性具有关键作用.     

Synthesis, Characterization, and Evaluation of Antimicrobial Activity of Some 1,2,4-Triazole Derivatives Bearing an Antipyryl Moiety

Summary.  Some novel 4-[[2-[[5-(2-furanyl)-4-alkyl/aryl-4H-1,2,4-triazol-3-yl]thio]-acetyl/propionyl]-amino]-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazoles were synthesized and evaluated for in vitro antibacterial activity against Staphylococcus aureus ATCC 29213, Pseudomonas aeruginosa ATCC 27853, Escherichia coli ATCC 25922, and Enterococcus faecalis ATCC 29212 and antifungal activity against Candida albicans ATCC 10231, Candida parapsilosis ATCC 22019, Candida krusei ATCC 6258, Candida parapsilosis, Trichophyton mentagrophytes var. erinacei NCPF 375, Microsporum gypseum NCPF 580, and Trichophyton rubrum using the microbroth dilution method. All of the compounds were found to be ineffective against the above bacteria within the applied MIC ranges. On the other hand, they were effective against fungi to different degrees. Three compounds showed high activity against C. parapsilosis and T. mentagrophytes var. erinacei NCPF 375 (MIC = 8 μg cm⁻³). The in vitro antimycobacterial activity of the new compounds was also investigated against Mycobacterium tuberculosis H₃₇RV (ATCC 27294) in BACTEC 12B medium using a broth microdilution assay, the Microplate Alamar Blue Assay (MABA). Compounds exhibiting fluorescence were tested in the BACTEC 460 radiometric system. The most active compound was found with 66% inhibition at >6.25 μg cm⁻³. Corresponding author. E-mail: nurayulusoy@yahoo.com Received July 24, 2002; accepted August 26, 2002     

无溶剂研磨法合成3-取代色满-4-酮衍生物及其抑菌活性研究

以6-卤代或未取代色满-4-酮为原料,在碱催化的条件下采用无溶剂研磨法与醛发生缩合反应,合成一系列新型的3-取代色满-4-酮衍生物3a~3t,并通过IR、1H NMR、13C NMR、HRMS对所合成的化合物进行结构表征。抑菌活性测试结果表明,所合成的化合物对大肠杆菌、枯草杆菌、金黄色葡萄球菌均有不同程度的抑菌活性。     

含噻唑烷二酮-3-乙酸结构查尔酮衍生物的合成及抗菌活性的研究

合成了一系列含噻唑烷二酮-3-乙酸结构的新型查尔酮衍生物,并对化合物进行了抗菌活性测定.结果显示,一些化合物对4种多重耐药菌显示出较强的抗菌活性,其中化合物8g,8i,8l和8m在抗耐甲氧西林金黄色葡萄球菌的最小抑制浓度(MIC)达到4μg/mL,与对照药诺氟沙星(norfloxacin)相当.另外,在64μg/mL浓度下,所有化合物对大肠杆菌1356均无明显抑制活性.     

Synthesis and Fungicidal Activity of Thiazoline Derivatives Containing Halogenated Indolyl Moiety

Abstract

A series of novel 1,3-thiazoline derivatives containing a 5- or 6-position halogenated indole moiety were synthesized via a one-pot and three-step reaction. Their structures were confirmed by spectroscopic methods. The fungicidal activities of all the title compounds were evaluated. Most of them exhibited moderate to high activity against eight plant pathogens at the concentration of 50 ug/mL. Generally the fungicidal activity of fluorinated indolyl thiazolines was higher than that of chlorinated indolyl thiazoline derivatives.

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.

GRAPHICAL ABSTRACT      

Synthesis and Insecticidal Activity of New Quinoline Derivatives Containing Perfluoropropanyl Moiety

A series of new quinoline derivatives containing perfluoropropanyl moiety were designed and synthesized. Their structures were confirmed by ¹H‐NMR, MS, and elemental analysis. The bioassay results showed that compound 4e exhibited good insecticidal activity against Plutella xylostella and Mythimna separata at 100 mg/L.     

含吡唑环的1,3,4-噁二唑类衍生物的合成及杀菌活性研究

以乙酰丙酮、水合肼等为原料,通过多步反应制备了一系列新型含吡唑环的1,3,4-噁二唑类衍生物,并考察了微波辐射对反应的影响.产物结构均经过1H NMR,MS和元素分析确证;对所有化合物进行了活体杀菌活性测试,结果表明大部分化合物对黄瓜褐斑病、黄瓜核菌病、黄瓜霜霉病、黄瓜细菌性角斑病均具有较好的防效.