含取代噁唑结构的新型吡唑肟衍生物的合成与生物活性

为了发现具有良好生物活性的吡唑肟化合物,以唑螨酯为先导化合物,在吡唑肟中引入取代噁唑结构,设计并制备了20个未见文献报道的新型吡唑肟衍生物,利用1H NMR,13C NMR和元素分析确证了目标产物的结构.生物活性测试结果显示,部分目标化合物在500和100μg/mL浓度下对粘虫或蚜虫表现出优良的杀虫活性,其中5-(3-氟苯氧基)-1,3-二甲基-1H-吡唑-4-甲酰基-O-{[5-(4-氯苯基)噁唑-2-基]甲基}肟(9j)、5-(4-氟苯氧基)-1,3-二甲基-1H-吡唑-4-甲酰基-O-{[5-(4-氯苯基)噁唑-2-基]甲基}肟(9k)、5-(4-叔丁基苯氧基)-1,3-二甲基-1H-吡唑-4-甲酰基-O-{[5-(4-氯苯基)噁唑-2-基]甲基}肟(9r)和5-(4-甲氧基苯氧基)-1,3-二甲基-1H-吡唑-4-甲酰基-O-{[5-(4-氯苯基)噁唑-2-基]甲基}肟(9s)在浓度为100μg/mL时对粘虫的防治效果均达100%,5-(4-溴苯氧基)-1,3-二甲基-1H-吡唑-4-甲酰基-O-{[5-(4-氟苯基)噁唑-2-基]甲基}肟(9g)和9s在浓度为100μg/mL时对蚜虫的杀灭活性均为100%.此外,化合物9s在500μg/mL时对朱砂叶螨的防治效果为70%.     

吡唑类化合物的合成研究进展

吡唑类化合物是一类重要的药物合成中间体,在抗肿瘤、抗病毒、抗抑郁等领域发挥着重要作用。本文综述了吡唑类衍生物的合成方法,包括1,3-亲电化合物与肼类的环化、1,3-偶极体系的环加成等。     

吡唑衍生物的合成及生物活性

以５－吡唑甲酰肼（７，８）为原料合成了４类共３０种新化合物，这些化合物的结构均经＾１Ｈ ＮＭＲ，元素分析证实，部分化合物还经过了ＭＳ、ＩＲ确证，对大部分化合物做了生物活性测试，结果表明均具有一定的杀菌和除草活性。     

Design,Synthesis, and Biological Evaluation of Novel Pyrazole,Oxazole, and Pyridine Derivatives as Potential Anticancer Agents Using Mixed Chalcone

New pyrazole, oxazole, and pyridine derivatives bearing naphthalene and furan moieties have been prepared by condensing 3‐(furan‐2‐yl)‐1‐(naphthalen‐2‐yl)prop‐2‐en‐1‐one 1 with different nitrogen and carbon nucleophiles such as hydrazine, hydroxylamine, cyclohexanone, cyclopentanone, ethyl cyanoacetate, and malononitrile, respectively. Cyclization of chalcone 1 with malononitrile in refluxing ethanol and ammonium acetate gave the corresponding dihydropyridine, which was condensed with different carbon electrophilic reagents such as ethyl cyanoacetate, ethyl acetoacetate, formamide, and acetic anhydride to yield the pyridine derivatives 13 – 16 . Elemental and spectroscopic evidences characterized all the newly synthesized compounds. All of the newly synthesized compounds were tested in vitro for their anti‐proliferative activities against HePG‐2 and MCF‐7 cell lines. Compounds 11 , 8 , and 15 displayed promising growth inhibitory effect toward the two cell lines compared with the standard drug doxorubicin.     

Design and Synthesis of Fused and Spiro Pyrazole Derivatives

Russian Journal of Organic Chemistry - Condensation of 5-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one with p-hydroxybenzaldehyde in alcoholic sodium hydroxide yielded...     

姜黄素-N-取代吡唑类衍生物合成及抑菌活性

为了寻求杀菌剂的新的先导化合物,用姜黄素与取代酰肼反应得到13个新的姜黄素-N-取代吡唑类衍生物,其结构经IR,1H NMR,13C NMR,MS和元素分析所表征,初步抑菌实验结果表明,在1×10-4mol/L浓度下,所有衍生物与姜黄素对比,对枯草杆菌、金黄色葡萄球菌、大肠杆菌、青霉、黑霉有较好的抑菌效果.其中,3,5-二(4-羟基-3-甲氧基苯基乙烯基)-N-脒基吡唑(3c),3,5-二(4-羟基-3-甲氧基苯基乙烯基)-N-(苯并噻唑-2-硫基乙酰基)吡唑(3k),3,5-二(4-羟基-3-甲氧基苯基乙烯基)-N-(香豆素-3-甲酰基)吡唑(3m)有优异的抑菌效果(抑菌圈16.34～23.81 mm).这些结果表明含有噻唑环、脒基、香豆素环取代基可能有助于提高姜黄素-N-取代吡唑类衍生物的活性.     

Synthesis of Novel Pyrazole Derivatives as Antineoplastic Agent

Anticancer evaluation of pyrazole 2 and Schiff base 5 is reported. Synthesis of some important heterocyclic compounds via 2,3‐diaryloxirane‐2,3‐dicarbonitrile 1 , pyrazole 2 , and Schiff base 5 with different nitrogen nucleophiles afforded new routes for synthesized fused heterocyclic derivatives. These compounds can be used as a key starting materials to synthesize some important imidazolo‐[4,5‐c ]pyrazole, pyrazolo[3,4‐e ]1,2,4‐triaging, imidazolo[3,2‐b ]pyrazole, and pyrazolo‐pyrazine, as anticancer reagents showed good results at optimum conditions (400–500 ppm), particularly the bridge head nitrogen compounds, and could be used to improve them. Electromeric effect of the halogen atom in the aryl moieties can be controlled upon the rate of reaction and the yield of the product. The structure of the synthesized new compounds would be characterized by elemental and spectral data.     

取代苯基吡唑类化合物的合成及其除草活性

以1′-(4-氯-2-氟-5-甲基苯基)-4′,4′,4′-三氟-1,3-丁二酮为原料,合成了一系列具有取代苯基吡唑结构的新化合物.化合物结构经¹HNMR,IR,CIMS和元素分析确认.初步生物活性测试表明,所合成的化合物对阔叶杂草具有较高的活性.     

Clean and Efficient Synthesis of Pyrazole Derivatives in Aqueous Media

A series of 5‐aryl‐1H‐pyrazole derivatives were synthesized via the reaction of 3‐(dimethylamino)‐1‐arylprop‐2‐en‐1‐one with hydrazine in aqueous media without using any catalyst. This method has the advantages of easier work‐up, mild reaction condition, high yields, and an environmentally benign procedure.     

Synthesis and Evaluation of Pyrazole Derivatives as Potent Antinemic Agents

Russian Journal of Organic Chemistry - Pyrazole derivatives were synthesized by bromination of pyrazole, followed by N-alkylation of 4-bromopyrazole. The synthesized derivatives were characterized...     

Synthesis and Antimicrobial Activity of Novel Thiazole Substituted Pyrazole Derivatives

A series of new 1‐[4‐(2,3,4‐substituted‐phenyl) thiazol‐2‐yl]‐3‐(2,3,4‐substituted‐phenyl)‐1H‐pyrazole‐4‐carbaldehyde ( 4a , 4b , 4c , 4d , 4e , 4f , 4g , 4h , 4i , 4j , 4k , 4l , 4m ), 4‐[4‐(4‐substituted‐phenyl) thiazol‐2‐yl]‐3‐(4‐substituted‐phenyl)‐1‐phenyl‐1H‐pyrazole ( 7a , 7b , 7c , 7d , 7e , 7f , 7g , 7h , 7i ), 4‐[4‐(4‐substituted phenyl)thiazol‐2‐yl]‐1‐phenyl‐1H‐pyrazol‐3‐amine ( 10a , 10b , 10c , 10d , 10e , 10f , 10g ) have been synthesized by using Vilsmeier Haack formylation and Hantzsch reaction in high yield. All the synthesized compounds were tested qualitative (Zone of inhibition) and quantitative antimicrobial activities (MIC). Most of the synthesized compounds showed potent antimicrobial activity against gram positive and gram negative bacteria as well as fungi species.     

新型含吡唑基异噁唑衍生物的合成与表征

以查尔酮4和取代的α-氯代吡唑甲醛肟3为原料,通过1,3-偶极环加成反应得到了16种新型的含吡唑基异噁唑衍生物,方法简单可行.化合物4,5-二氢-3-(1-苯基-3-甲基-5-取代-4-基)-5-芳基-4-芳酰基异噁唑啉(5)的结构经过IR,1HNMR,MS及元素分析确证.并利用单晶X射线衍射法测定了5g晶体结构.     

新型含吡唑基1,2,4-三唑衍生物的合成

以1-苯基-3-甲基-5-吡唑啉酮为起始原料,经氯甲酰化、氧化、酯化、肼解、成盐及闭环反应制得4-氨基-5-(1-苯基-3-甲基-5-氯吡唑)-1,2,4-三唑-3-硫酮(6);6与苯甲醛经缩合反应制得4-苯甲亚胺基-5-(5-氯-3-甲基-1-苯基)吡唑-4H-1,2,4-三唑-3-硫酮(7);7与对硝基苄氯反应合成了2个新型含吡唑基1,2,4-三唑化合物,其结构经1H NMR,IR和元素分析表征。     

新型含1,3,4-噁二唑的吡唑类化合物的合成及其抗肿瘤活性

以4-甲氧基苯乙酮为原料,设计并合成了7个新型的含1,3,4-噁二唑的吡唑类化合物(7a~7g),其结构经1H NMR,IR和ESI-MS表征。并用MTT法测定了7a~7g抑制人肝癌细胞Hep G2增殖的体外活性。结果表明,5-[3-(4-甲氧基苯基)-1-苯甲基吡唑-5-基]-2-[N-(4-溴苯基)乙酰胺-2-硫基]-1,3,4-噁二唑7g具有较好的抑制活性,其IC50为60.06μM。     

噻吩N-芳基吡唑类化合物的合成及光活化活性研究

以2,6-二氯-4-三氟甲基苯胺和溴代噻吩等为起始原料,设计并合成了12个未见报道的噻吩芳基吡唑类化合物5a～51,经1H NMR,13C NMR,ESI-MS和元素分析对化合物的结构进行了表征.初步生物活性测定结果表明,目标化合物均具有一定的光活化杀虫活性,其中51表现最为明显.在光照下对白纹伊蚊幼虫的LC50值为0.04 μg/mL,达到了商品化品种氟虫腈的水平.     

Novel and Efficient Synthesis of 4-Indazolyl-1,3,4-trisubstituted Pyrazole Derivatives

In the present study, 1-(4,5-dihydro-3,6-dimethyl-4-(1,3-diphenyl-1H-pyrazol-4-yl)-3aH-indazol-5-yl)methanone derivatives (9–12) and isoxazoleyl (13–16) have been synthesized by the condensation of 1,3-diphenyl-1H-pyrazole-4-carbaldehyde (1–4) with acetyl acetone via Knoevenagel/Michael/aldol reactions in a sequential manner to yield intermediate cyclohexanone (5–8). The intermediates (5–8) treated with NH₂NH₂ · H₂O/NH₂OH · HCl afforded 4-indazolyl-1,3,4-trisubstituted pyrazole and isoxazoleyl derivatives. All of these compounds are reported for the first time, and the structures of these compounds were confirmed by means of infrared, ¹H NMR, ¹³C NMR, and mass spectroscopy.     

新型含噻唑和吡唑环的醛腙类化合物的合成

1-苯基-3-甲基-吡唑-4.-甲醛与氨基硫脲缩合制得醛缩氨基硫脲(Ⅱf～Ⅱh);Ⅱ与α-溴代芳基乙酮反应合成了15个新型的含噻唑和吡唑环的醛腙类化合物(2a～4e),其结构经1 H NMR,IR和元素分析表征.X-射线单晶衍射测试结果表明,2c属斜方晶系,空间群Pbca,晶胞参数a=18.607 9(3)A,b=15...