Synthesis of Some Novel Class of Bis(isoxazoline) and Bis(aziridine) Derivatives

Synthesis of some new bis(isoxazoline) derivatives has been described from terepthaldehyde derived bis(nitrones) using microwave irradiation via 1,3‐dipolar cycloaddition reaction. Bis(isoxazoline) derivatives in turn successfully converted into new bis(aziridine) derivatives via Baldwin rearrangement. Simple reaction methodology, non involvement of catalysts, and good to excellent yields are the important features noticed in this synthesis.     

新型2-芳氨基嘧啶衍生物的合成

通过间羟基苯硼酸与2,4-二氯嘧啶的Suzuki反应及其后酚羟基的烷基化得到4-芳基-2-氯嘧啶衍生物. 然后, 采用Pd(PPh3)4/dppf催化剂, 在温和的条件下实现了4-芳基-2-氯嘧啶类化合物和芳香胺的偶联. 合成了3个结构新颖的2-芳氨基嘧啶类化合物. 中间体及产物的结构均经由IR, 1H NMR, 13C NMR, MS和元素分析表征而予以证实.     

Synthesis and Antibacterial Studies of Some Novel 2-(Coumarin-3-yl)-5-mercapto-1,3,4-oxadiazoles Containing 2,4,6-Trisubstituted s-Triazine Derivatives

A new series of 2-(coumarin-3-yl)-5-mercapto-1,3,4-oxadiazoles based on various aryl thiourea/ureas incorporating a 1,3,5-s-triazine moiety is reported. The components of this series have been obtained by the reaction of cyanuric chloride (1) with 2-(coumarin-3-yl)-5-mercapto-1,3,4-oxadiazole (2). The prepared 2-{(coumarin-3-yl-1,3,4-oxadiazolyl)-5-thio}-4,6-dichloro-s-triazine (3) was subsequently treated with morpholine (4) to form 2-{(coumarin-3-yl-1,3,4-oxadiazolyl)-5-thio}-4-(morpholino)-6-chloro-s-triazine (5). This was further treated with various substituted aryl urea/thioureas (6a–k/7a–k) to afford the title compounds 8a–k and 9a–k, which were and tested for their antibacterial activity (MIC) against different microorganisms. The structures of the novel synthesized compound have been established on the basis of ¹H NMR and FT-IR data together with elemental analysis.

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.     

Synthesis of Novel 3-(5-(Alkyl/arylthio)-1,3,4-Oxadiazol-2-yl)-8-Phenylquinolin-4(1H)-One Derivatives as Anti-HIV Agents

Novel quinolone derivatives featuring an 1,3,4-oxadiazole ring as a metal-chelating component and a benzyl group base on HIV-1 integrase inhibitors pharmacophore were designed and synthesized. An antiviral assay revealed that most analogues inhibited HIV-1 replication in the cell culture. Our results showed that compounds bearing small alkyl groups as R group were inactive in anti-HIV-1 assay, whereas compounds possessing benzyl or substituted benzyl at the same position showed good anti-HIV activity with the range of 20–57% at 100 μM concentration. Among them, 3-(5-((2-fluorobenzyl)thio)-1,3,4-oxadiazol-2-yl)-8-phenylquinolin-4-(1H)-one (compound 13) showed reasonable cell-based antiviral activity (EC₅₀ = 50 μM) with no considerable cytotoxicity (CC₅₀ > 100 μM) in the cell viability assay, suggesting that it may be amenable to further development for identifying new anti-HIV-1 agents. Docking studies using the later crystallographic data available for PFV integrase corroborate favorable binding to the active site of HIV integrase, providing a basis for the design of more potent analogues.     

One-Pot Synthesis of Novel 2-(Thiazol-2-yl)-4,5-dihydropyridazin-3(2H)-one Derivatives Catalyzed by Activated KSF

A series of 2-(thiazol-2-yl)-4,5-dihydropyridazin-3(2H)-one derivatives were synthesized by one-pot multicomponent cyclocondensation of ketoacid, thiosemicarbazide, and phenacyl bromide using catalytical amount of KSF in EtOH under reflux. The straightforward synthesis, presence of two important class of heterocyclic rings in the individual molecule, easy workup of the products, rapid reaction, mild conditions, and good to excellent yields are notable features of this protocol.

[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]     

二-(4-羟基丁基)四甲基二硅氧烷结构分析

以二甲基二氯硅烷、四氢呋喃和金属镁粉为原料，合成了二-(4-羟基丁基)四甲基二硅氧烷，其结构用高分辨率的质子核磁共振谱、碳核磁共振谱、硅核磁共振谱、红外光谱现代仪器技术进行了测试及确征。     

Synthesis of Novel Bis(mesocyclic) polyamines

介绍了带羟基桥连双－（中环多胺）的合成。首先利用Ｎ－对甲苯磺酰基－３－羟基－１，５－二氮杂环庚烷与５种双官能基化合物在Ｎ２气氛下于无水乙腈中反应，得到５种带对甲苯磺酰基的中环多胺，然后利用ＨＢｒ／ＨＯＡｃ脱去保护基团，得到桥连双－（中环多胺）的氢溴酸盐。所有新化合物的结构均经ＩＲ、１ＨＮＭＲ、ＭＳ或元素分析证实。     

Synthesis of bis(indole)-1,2,4-triazinones

A facile method for the synthesis of para- and meta-substituted bis(indole)-1,2,4-triazinones is presented. Our approach to access these triazinones involves a cyclocondensation reaction between amidrazone and ketoester functionalities. The structures of these interesting compounds were established unambiguously by X-ray crystallography.     

新型2-(吡咯烷-3-基)-噁唑衍生物的合成

根据亚结构链接法,以氯甲基三甲基硅烷和苄胺为原料,依次经酯化、缩合、环合、水解、成盐等12步反应制得5个新型的(4-甲基氨基甲酰基-2-吡咯烷-5-甲基噁唑) 胺基甲酸叔丁酯衍生物(15a~15e); 15a与醛(酮)或乙酰氯反应,合成了4个新型的5-胺基甲基-2-(1-甲基-吡咯烷)-噁唑-N-甲基甲酰胺盐酸盐衍生物,其结构经¹H NMR和ESI-MS表征。     

Synthesis and Biological Activities of Novel 1,4-Bridged Bis-1,2,4-Triazoles,Bis-1,3,4-Thiadiazoles and Bis-1,3,4-Oxadiazoles

Abstract

The terephthalic acid hydrazide(1) reacted with phenyl/benzyl isothiocyanate2a,bto yield the corresponding bis-thiosemicarbazides4a,b,viaacid hydrolysis of the intermediate 3whereas cyclization of4gave the bis-1,2,4-triazoles 5,6and bis-1,3,4-thiadiazoles7,8. Similarly, compound 1reacted with phenyl isocyanate9to give the bis-semicarbazide10, which was cyclized to the bis-oxadiazole 11and/or bis-1,2,4-triazole12in POCl_ti3and NaOH respectively.     

间二苄胍衍生物的合成

通过间二苄氯衍生物和二甲酰胺钠的亲核取代及水解方便地制备了相应的间二苄胺. 后者与甲基异硫脲作用生成间二苄胍硫酸盐,经离子交换得到相应的间二苄胍盐酸盐.     

邻羟基α-叠氮苯乙酮衍生物的合成

以邻羟基苯乙酮衍生物为原料,经溴化反应和叠氮化反应合成了一系列邻羟基α-叠氮苯乙酮衍生物,其结构经1H NMR,13C NMR,IR及HR-MS表征.     

Intramolecular Phototransfer of Protons and the Quenching of Fluorescence of Derivatives of 2-(Coumarinyl-3)-5-(ortho-hydroxyphenyl)-1,3,4-oxadiazole

The spectral-luminescence properties of ortho-hydroxy derivatives of 2-(coumarinyl-3)-5-phenyl-1,3,4-oxadiazole have been studied. It is shown that the basic reason for the decreased quantum yield of emission for the compounds studied is the high-speed phototransfer of a proton (estimated as 109 s^-1). Fluorescence of the products of this reaction (phototautomers) was not observed. It was confirmed by quantum-chemical calculations that the increase in efficiency of nonradiative dissipation of the electron excitation energy in phototautomeric forms of ortho-hydroxycoumarinyloxadiazoles is explained by an increase in intramolecular donor-acceptor interaction on introduction of the coumarin unit into the molecule. As a result of the high efficiency of nonradiative deactivation of the excited state, the ortho-hydroxyderivatives studied have promise as UV photostabilizers in polymeric materials.     

Synthesis of some N-(4,5,5-trisubstituted-Δ2-1,3,4-thiadiazolin-2-yl)-N,N′-dimethylureas

The synthesis of some N-(4,5,5-trisubstituted-Δ²-1,3,4-thiadiazolin-2-yl)-N,N′-dimethylureas is described.     

2-(1H-苯并咪唑-2-基)-5-取代-1,3,4-噁二唑化合物的合成及抑菌活性

以苯并咪唑-2-甲酸、水合肼、取代苯基异硫氰酸酯和取代苯甲酸等为原料,经多步反应合成了16种2-(苯并咪唑-2-基)-5-取代苯基-1,3,4-噁二唑和2-(苯并咪唑-2-基)-5-取代苯胺基-1,3,4-噁二唑新化合物,并考察了微波辐射对反应的影响.产物结构利用IR,1H NMR,13C NMR和元素分析确证.用生长速率法测试了目标化合物对番茄灰霉病菌和小麦菌核病菌的离体抑制活性,结果表明3种化合物对番茄灰霉病菌有很高的抑制活性,其EC50分别为2.55,6.34和5.12μg/mL,活性高于对照药剂多菌灵(EC50=7.40μg/mL).     

3-(P-氨基-P-乙氧基酰基)丙酸甲酯类化合物的合成

本文合成了两个未知氯代膦酰基丙酸甲酯和十四个新化合物,初步测定了这些化合物部分样品的生物活性。     

新型三氮唑席夫碱吡唑衍生物的合成

以乙醇为溶剂,乙酸为催化剂,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-硫酮于65℃反应4 h合成了7个新型的三氮唑席夫碱吡唑衍生物,收率74%~87%,其结构经1H NMR,IR和元素分析表征。     

The Reaction of 5-Aryl(hetaryl)-2-aroylmethylthio-1,3,4-oxadiazoles with Aryldiazonium Tetrafluoroborates

5-Aryl(hetaryl)-2-aroylmethylthio-1,3,4-oxadiazoles behave as CH acids and readily react with aryldiazonium tetrafluoroborates at the active methylene group to give azo coupling products. The spectroscopic properties of the compounds synthesized have been studied.     

Convenient Synthesis of Bis（oxazoline） Dicarboxylate Derivatives

The synthesis of bis(oxazoline) dicarboxylate derivatives was investigated.Diethyl-aminosulfur trifluoride (DAST) was used as a convenient cyclization reagent in the synthesis of bis(oxazoline) dicarboxylate derivatives,which can not be obtained by the general method using MsC1 and Et3N as dehydrating cyclization reagent.     

1-(2-苯并噻唑基)-3-苯基吡唑啉类化合物的合成

有机荧光化合物有多种结构类型,其中含氮唑系杂环类化合物可作为一些合成纤维和塑料制品的增白剂^[1～4]。据此,我们合成了一系列新的具有不同取代基的苯并噻唑基吡唑啉化合物,并观察了其荧光性质。