A facile one-pot three-component synthesis of benzylideneamino-3,5-dimethyl-1H-pyrazoles

A facile, one-pot three-component protocol for the synthesis of substituted 4-(benzylideneamino)-5-(3,5-dimethyl-1H-pyrazol-1-yl)-4H-1,2,4-triazole-3-thiols have been reported by the reaction of 4-amino-5-hydrazinyl-4H-1,2,4-triazole-3-thiol with acetyl acetone and various substituted benzaldehydes via multi component reaction. The newly synthesized derivatives were characterized by their elemental analysis and spectral data. The current strategy provides heterocyclic compounds in good yields with broad substrate scope.     

Synthesis of 4-amino-4,5-dihydro-1H-1,2,4-triazole-5-ones and their isatin-3-imine derivatives

Iminoester hydrochlorides 1 have been synthesized. These compounds were then converted into ester ethoxycarbonyl hydrazones 2, from which in turn a new series of substituted 4-amino-4,5-dihydro-1H-1,2,4-triazole-5-ones, 3, was then prepared.Finally a set of isatin imine derivatives 4 was obtained from the reaction of compounds 3 with isatin. The structures of all the new synthesized compounds were confirmed by elemental analyses, IR, (1)H-NMR and (13)C-NMR spectra.     

抗肿瘤氟喹诺酮C3等排衍生物——噁二唑曼尼希碱衍生物的合成和抗肿瘤活性

用噁二唑硫酮杂环作为培氟沙星(1)的C3羧基电子等排体,得中间体C3噁二唑硫酮4(5),再将其与仲胺或取代苯胺及甲醛通过氨甲基化反应形成系列氟喹诺酮C3噁二唑硫酮曼尼希碱(6a~6j)目标化合物。 用元素分析、1H NMR和MS测试技术确证了目标化合物的组成和结构。 采用MTT法评价了目标化合物对体外培养人肝癌Hep-3B细胞生长的抑制活性。 结果表明,10种目标化合物活性均显著高于对照化合物1的活性,并且脂肪胺曼尼希碱的活性高于芳香胺曼尼希碱的活性。     

5,6-2H-1,2,4-三唑[3,4-b][1,3,4]噻二嗪衍生物的合成及抗癌活性测定

取代苯甲醛与4-氨基-5-(3,4,5-三甲氧基苯基)-1,2,4-三唑-3-硫酮(2)缩合生成5-(3,4,5-三甲氧基苯基)-4-取代苯基亚胺基-1,2,4-三唑-3-硫酮(3),再烷基加成化为新型5,6-2H-1,2,4-三唑[3,4-b][1,3,4]噻二嗪衍生物4.化合物结构经1HNMR 13C NMR,IR以及元素分析确认.采用噻唑兰(MTT)比色法进行化合物抑制人体前列腺癌细胞(PC3)体外活性测试,结果表明所合成的化合物具有不同程度的抑制PC3活性,其中化合物4a在10μmol·L-1浓度下对PC3的抑制率为75.9%.     

Synthesis and NMR spectral studies of some 2,6-diarylpiperidin-4-one O-benzyloximes

Variously substituted 2,6-diarylpiperidin-4-one O-benzyloximes were synthesized by the direct condensation of the corresponding 2,6-diarylpiperidin-4-ones with O-benzylhydroxylamine hydrochloride. All the synthesized compounds are characterized by IR, Mass and NMR spectral studies. NMR spectral assignments are made unambiguously by their one-dimensional (1H NMR and 13C NMR) and two-dimensional (1H-1H COSY, NOESY, HSQC and HMBC) NMR spectra. All the synthesized compounds are resulted as single isomer, i.e., exclusively E isomer (9-14). The conformational preference of 2,6-diarylpiperidin-4-one oxime ethers with and without alkyl substituents at C-3 and C-5 has also been discussed using the spectral studies. The observed chemical shifts and coupling constants suggest that compounds 8-13 adopt normal chair conformation with equatorial orientation of all the substituents while compound 14 contributes significant boat conformation along with the predominant chair conformation in solution. The effect of oximination on ring carbons, their associated protons, alkyl substituents and ipso carbons are studied. Every proton in the piperidone ring of the oxime ether is observed as distinct signal due to oximination. The order of chemical shift magnitude in compound 8 is H-2a>H-6a>H-5e>H-3e>H-3a>H-5a. For 9-12, the order is H-6a>H-5e>H-2a>H-3a>H-5a, for 13, H-6a>H-2a>H-5e>H-3a>H-5a and for 14, the order is H-2a>H-6a>H-5e>H-3a>H-5a while the 13C chemical shift magnitude for 8-14 due to oximination is C-2>C-6>C-3>C-5.     

含1-[二-(4-氟苯)甲基]哌嗪均三氮唑环的Mannich碱的合成及表征

微波辐射下,在冰醋酸中,3-甲基-4-氨基-1,2,4-三氮唑-5-硫酮1与芳香醛经微波辐射制得相应的中间体Schiff碱2(a~j),然后中间体2与1-[二-(4-氟苯)甲基]哌嗪于室温反应制得10个新的Mannich碱3(a~j).合成的10个目标化合物通过熔点测定和质谱、红外光谱、核磁共振氢谱分析、元素分析对其结构进行确证。     

5-Furan-2yl[1,3,4]oxadiazole-2-thiol, 5-furan-2yl-4H [1,2,4] triazole-3-thiol and their thiol-thione tautomerism

5-Furan-2-yl[1,3,4]oxadiazole-2-thiol (Ia) and 5-furan-2-yl-4H-[1,2,4]-triazole-3-thiol (Ib) were synthesized from furan-2-carboxylic acid hydrazide. Mannich bases and methyl derivatives were then prepared. The structures of the synthesized compounds were confirmed by elemental analyses, IR and (1)H-NMR spectra. Their thiol-thione tautomeric equilibrium is described.     

新型含噻唑和三唑环的亚胺类化合物的合成及生物活性研究

设计合成了一系列新型含有噻唑和三唑环的亚胺类化合物, 其结构经元素分析、1H NMR和X射线晶体衍射确证. 生物活性测试结果表明, 部分化合物在50 μg/L浓度下对苹果轮纹菌具有一定的杀菌活性.     

噁唑酮类化合物的合成及其抗炎活性

以马尿酸为原料,与取代苯甲醛经Erlenmeyer环合反应合成了8个噁唑酮类化合物（3a~3h）,其结构经¹H NMR, FT-IR和HR-MS确证。二甲苯致小鼠耳肿胀实验结果表明：3f［4,3,5-二甲氧基甲撑基）-2-苯基-4H-5-噁唑酮］抗炎活性最好,其抑制率为50.3%,优于阿司匹林（41.5%）。     

三氮唑类席夫碱的合成及其荧光性能

近年来,Schiff碱因其结构的多样化以及具有光、电、磁等物理材料性能[1-3]的配位化学性能[4-5]等引起人们的关注,同时一些特殊结构的Schiff碱的合成和性质研究具有更为重要的理论意义和应用价值.     

Synthesis and antimicrobial activity of N-(substituted)-N'-(2,3-dihydro-2-oxido-5-benzoyl-1H-1,3,2-benzodiazaphosphol-2-yl) ureas

N-(substituted)-N'-(2,3-dihydro-5-benzoyl-2-oxido-1H-1,3,2-benzodiazaphosphol-2-yl) ureas were synthesized by reacting 3,4-diaminobenzophenone (4) with different chlorides of carbamidophosphoric acids (3) in the presence of triethylamine at 40-45 degrees C. Their 1H-, 13C- and 31P-NMR spectral data are discussed. The title compounds were screened for antifungal and antibacterial activity against the fungi Aspergillus niger and Fusarium solani and bacteria Escherichia coli and Staphylococcus aureus. These compounds showed higher antibacterial activity when compared with antifungal activity.     

Synthesis and antitubercular activity of substituted novel pyrazoline derivatives

A series of 2-2-methoxy-4-[5-(substituted phenyl)1-(4-pyridylcarbonyl)-4,5-dihydro-1H-3-pyrazolyl] phenoxyacetic acid were synthesized by the reaction between isoniazid (INH) and chalcones, and were tested for their antimycobacterial activity in vitro against Mycobacterium tuberculosis H37Rv and INH resistant M. tuberculosis using BACTEC-460 radiometric system and agar dilution method. Among the synthesized compounds, Compounds II 2-4-[5-(4-hydroxyphenyl)-1-(4-pyridylcarbonyl)-4,5-ihydro-1H-3-pyrazolyl]-2-methoxy phenoxy acetic acid was found to be most active agent against M. tuberculosis H37Rv (MTB) and INH resistant M. tuberculosis (INHR-MTB), with minimum inhibitory concentration of 0.12 microM, when compared to INH 5.6-fold more active against MTB and 78-fold more active against INHR-MTB, respectively.     

含吡唑1,2,4-三唑噻二嗪衍生物的合成及抑菌活性

1-苯基-3-甲基-5-氯-4-吡唑甲醛与4-氨基-5-取代苯基-1,2,4-三唑-3-硫酮缩合生成4-(1-苯基-3-甲基-5-氯吡唑次甲亚胺基)-5-(取代苯基)-2H-1,2,4-三唑-3(4H)-硫酮,再烷基加成化为新型含吡唑基5,6-2H-1,2,4-三唑[3,4-b][1,3,4]噻二嗪衍生物。 化合物结构经¹H NMR、IR以及元素分析确认。 初步生物活性测试结果表明,在100 mg/L浓度下,化合物8a(3-(2-甲基苯基)-6-(5-氯-2-甲基-4-苯基吡唑)-7-(4-硝基苯基)-5H-1,2,4-三唑[3,4-b][1,3,4]噻二嗪)对黄瓜炭疽病的抑制率达90%。     

3-取代苯氧甲基-4-氨基-1,2,4-三唑-5-硫酮席夫碱的合成、结构表征和生物活性研究

以醋酸为反应溶剂和催化剂,用自制的4-氨基-4,5-二氢-3-取代苯氧甲基-1,2,4-三唑-5-硫酮与4-氟苯甲醛反应合成了5个4-氨基-4,5-二氢-3-取代苯氧甲基-1,2,4-三唑-5-硫酮席夫碱化合物,通过1HNMR、IR和元素分析对所有化合物进行了结构表征.初步生物活性测试结果表明所有化合物具有优良的杀菌活性,并对席夫碱结构与活性的关系进行了探讨.     

Synthesis and plant-growth regulatory activities of novel imine derivatives containing 1H-1,2,4-triazole and thiazole rings

<正>Eleven new imine derivatives 6 containing 1H-1,2,4-triazole and thiazole rings were synthesized by the condensation of 5-((1H- 1,2,4-triazol-1-yl)methyl)-4-tert-butylthiazol-2-amine with various substituted benzaldehydes.The structures of the title compounds were characterized by ~1H NMR,MS and elemental analysis.The plant-growth regulatory activities of these compounds were evaluated.The primary bioassay results indicated that these target compounds exhibited promising plant-growth regulatory activities.     

水溶性稠杂环均三唑并噻二唑体系的合成及生物活性(II): 环丙氟喹诺酮哌嗪衍生物

为发现3-位稠杂环取代喹诺酮衍生物新的生物活性, 以环丙氟氯喹诺酮羧酸(1)为起始原料, 经3步反应得到3-(4-氨基-5-巯基-均-三唑)氟氯喹酮(4). 在常温加热和微波辐射条件下, 4与异烟酸缩环合反应得到中间体3-[6-吡啶-3- 均三唑[3,4-b][1,3,4]噻二唑]氟氯喹诺酮(5). 喹诺酮环上的氯原子与取代哌嗪在聚乙二醇和无机碱催化作用下发生选择性亲核取代反应, 形成相应的3-(6-吡啶-3-均三唑[3,4-b][1,3,4]噻二唑)氟喹诺酮哌嗪游离碱, 与盐酸反应得相应水溶性盐酸盐6. 同时也发现, 用1的酯化物却不能得到中间体2, 而仅得到环丙氟氯吡唑并喹啉酮(3). 新化合物的结构经元素分析和光谱数据表征, 用MTT和二倍试管稀释方法评价了它们体外对CHO, HL60和L1210 3种癌细胞株及S. aureus和E.coli 2种菌株的抑制活性. 结果表明, 在合成的9个新化合物中, 化合物3和 6具有潜在的体外抑制癌细胞生长活性, 其中6的IC50均在50 mmol/L以下, 尤其是化合物6a和6d对L1210的IC50值达到8.0×10－6 mol/L以下, 显示良好的选择性和体外活性; 目标化合物体外抑菌试验有意义的发现, 虽然抑菌活性不及对照环丙沙性, 但对革兰阳性菌活性显著高于对阴性菌的活性, 这与喹诺酮药物的抗菌活性相反. 以上结果表明, 氟喹诺酮类抗菌剂的3位稠杂环取代衍生物作为新结构抗肿瘤或抗菌先导物具有进一步研究和开发的价值.     

Microwave-assisted Synthesis of New 1,2,3-Triazoles Bearing an Isoxazole Ring by the Azide-alkyne Cycloaddition Click Chemistry

A comparison synthesis of 1,2,3-triazoles bearing isoxazole ether was developed between conventional and microwave-assisted heating. Single/double 1,2,3-triazoles bearing isoxazole ether were synthesized by click reaction starting from substituted isoxazolyl alkyne compounds and substituted benzyl azide compounds or neopentylglycol diazide in the presence of copper(I) that in-situ generated. Herein, the effect of different catalysts on the yield was researched by conventional method, and the optimal catalyst was selected. The structures of all the synthesized compounds were confirmed by MS, FTIR, ¹H and ¹³C NMR spectroscopies. Moreover, the crystal structure of 5-{[(1-benzyl-1H-1,2,3-triazol-4-yl)methoxy]methyl}-3-(4-fluorophenyl)isoxazole(2h) was determined.     

Novel 1,4-benzothiazine derivatives: synthesis,crystal structure,and anti-bacterial properties

In order to develop relatively small molecules as pharmacologically active molecules, novel 1,4-benzothiazine derivatives with triazole and oxazolidinone were synthesized. In this study, a series of 1,2,3-triazolylmethyl-1,4-benzothiazine derivatives were developed by exploiting a click chemistry reaction using a CuI-catalyzed Huisgen [3 + 2] cycloaddition. Starting from 2-(substituted)-3,4-dihydro-2H-1,4-benzothiazi-3-one, a number of 1,4-benzothiazine derivatives were also synthesized using different alkylating agents to give a 4-(substituted)-2-(substituted)-3,4-dihydro-2H-1,4-benzothiazi-3-one in good yields. The crystal and molecular structure of compound oxazolidin-2-one in basic benzothiazine was established by single-crystal X-ray diffraction. The newly synthesized products were subjected to in vitro biological evaluation. The result indicated that the compounds show convincing antibacterial activities against different microorganisms. All structures of the synthesized compounds were elucidated on the basis of spectral analyses and chemical reactions.     

3－嘧啶胺基或三嗪胺基甲酰基－4－羟基－2H－1，2－苯并噻嗪－1，1－二氧化物的合成及活性

通过３－乙氧甲酰基－４－羟基－２－氢（甲基）－２Ｈ－１，２－苯并噻嗪－１，１－二氧化物与取代嘧啶胺或均三嗪胺的胺解反应，合成了标题化合物。生物活性测定结果表明多数化合物具有较好的除草活性，部分化合物显示好的植物生长调节活性和抗炎免疫活性。     

含(1-芳乙酰胺基-2-叔胺基)乙烷结构的六氢-1H-1,4-二氮(艹卓)类化合物的合成与镇痛活性

2-或5-取代的六氢-1H-1,4-二氮(艹卓)类化合物(1～3)经单酰化及酰化反应后,合成了16个带有(1-芳乙酰胺基-2-叔氨基)乙烷结构的六氢-1H-1,4-二氮(艹卓)类目标化合物(5～9,11～13,15～17,19～23),经元素分析、IR、MS和¹H NMR确证了其组成和结构。对所有目标化合物都进行了豚鼠回肠试验,初步药理试验表明,16个化合物对受试标本显示不同程度的抑制作用,对抑制率较高的两个化合物5和7测试了IC₅₀值。对在豚鼠回肠试验中显示较强激动作用的4个化合物进行了小鼠扭体法镇痛活性试验,测得了其ED₅₀值。