Synthesis and antitumor activity of 6- and 2-(1-acylsulfanylalkyl)-5,8-dimethoxy-1,4-naphthoquinones

Sixteen novel 6- and 2-（1-acylsulfanylalkyl）-5,8-dimethoxy-l,4-naphthoquinones were designed and synthesized. Their cytotoxicities were evaluated in vitro against BEL-7402, HT-29 and SPC-Al cell lines. The pharmacological results showed that most of the prepared compounds displayed the excellent selectivity for HT-29 cell line. Compound lab exhibited the most potent antitumor activity among the tested compounds.

Catalytic Oxidative Conversion from Naphthol to 2-Hydroxy-1, 4-naphthoquinone over Iron Porphyrin Catalysts by Molecular Oxygen in an Alkaline 2-Propanol Solution

In an alkaline 2-propanol solution with 5,10,15,20-tetra(4-methoxyl phenyl) porphyrin iron chloride(TOMPPFeCl) as a catalyst and oxygen as a cheap green oxidant, 2-naphthol was conversed to 2-hydroxy-\{1,4-naphthoquinone(HNQ)\} with a yield of 62.17% and a selectivity of 100%, and the conversion number of TMOPPFeCl catalyst was 8.32/min. The catalytic oxidation products were characterized by means of UV-Vis, IR, GC-MS, ~ 1H NMR and melting point determination. In this catalytic oxidation, the catalytic activity of TMOPPFeCl was researched in detail and the reacting conditions were optimized. A possible reaction mechanism is summarized based on in situ EPR determination.

Coordination Behavior and Biological Activity of Some Transition Metal Complexes with 2-Acetyl and 2-Formyl-3-Amino-1,4-Naphthoquinone Ligands

The aim of this work is to synthesize, characterize and evaluate the biological activity of 2-acetyl and 2-formyl-3-amino-1,4-naphthoquinone (L1 - L2) and their metal-Co(II), Ni(II) and Cu(II) chelates. The newly chelates were characterized by elemental analysis, IR, mass and 1HNMR spectra, thermogravimetric analysis (TGA) and biological activity. The antibacterial and antifungal activities of the ligands and its metal complexes were screened against bacterial species (Staphylococcus aureus, Bacillus subtilis and Escherichia coli) and fungi (Candida albicans). Ampicillin and amphotericin were used as references for antibacterial and antifungal studies. The activity data show that the metal complexes have a promising biological activity comparable with parent free ligand against bacterial and fungal species.

Synthesis, Characterization, Antibacterial, and Antifungal Activities of Cobalt(II), Nickel(II) and Copper(II) Complexes with 3-thioacetyl-2-amino-1,4-naphthoquinone and 2-benzoyl-3-amino-1,4-naphthoquinone Ligands

The aim of this work is to synthesize, characterize and evaluate the biological activity of 1,4-naphthoquinone derivatives ligands and their metal—Co(II), Ni(II) and Cu(II) chelates. Continuing our work with another derivatives of 1,4-naphthoquinone ligands, this work had been constructed for synthesis of new ligands derived from 1,4-naphthoquinone such as 3-thioacetyl-2-amino-1,4-naphthoquinone and 2-benzoyl-3-amino-1,4-naphthoquinone (L1-L2) which characterized on the basis of elemental analysis, electronic, IR, mass, 1H-NMR spectral data. The synthesized ligands have been carried out to achieve the coordination behavior towards bi-valent metal ions like cobalt, nickel and copper. The solid chelates of the different ligands were prepared and subjected to analytical techniques such as elemental analyses, spectroscopic techniques including mass, 1H-NMR, and IR spectroscopy, and thermal analyses techniques. The chelates were found to have octahedral geometry. The biological activity of the prepared ligands and their binary metals complexes were also screened against different antifungal and antibacterial organisms.

Evaluation of 1,4-naphthoquinone derivatives as antibacterial agents:activity and mechanistic studies

The diverse and large-scale application of disinfectants posed potential health risks and caused ecological damage during the 2019-nCoV pandemic,thereby increasing the demands for the development of disinfectants based on natural products,with low health risks and low aquatic toxicity.In the present study,a few natural naphthoquinones and their derivatives bearing the 1,4-naphthoquinone skeleton were synthesized,and their antibacterial activity against selected bacterial strains was evaluated.In vitro antibacterial activities of the compounds were investigated against Escherichia coli and Staphylococcus aureus.Under the minimum inhibitory concentration(MIC)of≤0.125μmol/L for juglone(1a),5,8-dimethoxy-1,4-naphthoquinone(1f),and 7-methyl-5-acetoxy-1,4-naphthoquinone(3),a strong antibacterial activity against S.aureus was observed.All 1,4-naphthoquinone derivatives exhibited a strong antibacterial activity,with MIC values ranging between 15.625 and 500μmol/Land ECso values rangingbetween10.56 and248.42μmol/L.Most of the synthesized compounds exhibited strong antibacterial activities against S.aureus.Among these compounds,juglone(la)showed the strongest antibacterial activity.The results from mechanistic investigations indicated that juglone,a natural naphthoquinone,caused cell death by inducing reactive oxygen species production in bacterial cells,leading to DNA damage.In addition,juglone could reduce the self-repair ability of bacterial DNA by inhibiting RecA expression.In addition to having a potent antibacterial activity,juglone exhibited low cytotoxicity in cell-based investigations.In conclusion,juglone is a strong antibacterial agent with low toxicity,indicating that its application as a bactericidal agent may be associated with low health risks and aquatic toxicity.

二和四叠氮化合物的合成

由一、二和三乙二醇二（２－氯乙酸酯），Ｎ，Ｎ’－１，２－亚苯基二（２－氯乙酰胺）和季戊四醇四（２－氯乙酸酯）分别与０．５ｍｏｌ／ＬＮａＮ３的二甲基亚Ｗ（ＤＭＳＯ）溶液于室温下反应１ｈ，可以高产率、高纯度地合成相应的二和四叠氮化合物。由二和三乙二醇二（对甲基苯磺酸酯）与０．５ｍｏｌ／ＬＮａＮ３的ＤＭＳＯ溶液于５０℃下反应３ｈ，几乎可以定量地得到相应的二叠氮化合物。产物纯度经１ＨＮＭＲ和１３ＣＮＭＲ测定，其结构经ＭＳ和ＩＲ证实。

2-甲基重氮萘醌在环醚中光解产物的2D NMR研究

应用二维核磁共振对２－甲基重氮萘醌在四氢呋喃和二氧六环中光解反应的产物：２－甲基－４－螺（２’－四氢吡喃）萘－１－酮（３）、２－甲基－４－（２’四氢呋喃基）－１－萘酚（４）、２－甲基－４－螺［７’－（１’，４’－二氧杂环庚烷）萘－１－酮（５）、２－甲基－４－［２’－（１’，４’－二氧杂环己基）］－１－萘酚（６）和二（２－甲基－萘－２２－冠－６）（７）的１Ｈ和１３Ｃ ＮＭＲ谱进行了全归属．

一株嗜碱放线菌发酵液 中的抗肿瘤活性成分(英文)

从嗜碱放线菌YIM80149的发酵液中分离得到4个抗肿瘤活性成分。根据波谱数据,鉴定为4′,7-dihydroxyisoflavone (1)、4′,5,7-trihydroxyflavone (2)、3-(4-hydroxy-3-methoxyphenyl)-2(E)-propenoic acid (3)、2-methoxy-1,4-naphthoquinone (4)。

含重氮萘醌化合物翻转成像体系的研究概述

本文对含重氮萘醌化合物的翻转成像体系作了详细的总结.所述翻转成像体系主要分为三类,其一主要是通过脱羧反应、酯化反应、酰胺化反应等化学反应生成碱难溶性化合物,使原本通过曝光、显影可获得的阳图图像翻转成负像;其二是以重氮萘醌化合物为产酸剂,通过酸的催化作用使交联剂与成膜树脂发生交联反应,或发生脱保护基的反应,实现翻转成像;还有一类是利用近紫外光和高能射线相结合实现翻转成像.第一类和第三类翻转成像体系在抗蚀剂方面可能有较大的应用价值,而第二类翻转成像体系可能在印刷版材方面有一定的应用前景.

1,3-二(炔丙基氧)苯与4,4'-二叠氮甲基联苯的聚合反应及聚合物性能的研究

研究了1,3-二(炔丙基氧)苯(BPOB)与4,4'-二叠氮甲基联苯(DAMBP)的本体聚合行为.核磁共振氢谱(1HNMR)表征了聚合物的结构,通过傅立叶红外技术(FT-IR)观察了反应过程中的基团变化情况,采用差示扫描量热技术(DSC)研究了聚合反应动力学,在较低温度(80℃)下二元叠氮与二元炔发生了1,3-偶极环加成聚合反应,生成了主链含三唑环的聚合物;利用Kissinger法和Crane法处理得到了反应的动力学参数:反应级数为0.92,反应活化能Ea为79.8kJ·mol-1,频率因子A为1.26×1010min-1.利用凝胶渗透色谱(GPC)、动态热机械分析(DMA)和热重分析方法(TGA)研究了聚合产物的性能.结果表明,聚合物的数均分子量达4.22×104,聚合物有较高的玻璃化转变温度和良好的热稳定性,玻璃化转变温度达到131℃,热分解温度(Td5)达355℃.

CL⁃20基爆炸网络装药的UV光辅助直写成型及性能

为了提高爆炸网络装药效率和成型效率、改善装药能量性能,以高能叠氮胶3,3-二叠氮甲基氧丁环-四氢呋喃共聚醚(PBT)和紫外光(UV)固化树脂为复合粘结剂、以CL-20为主体炸药,设计了一种UV光辅助固化的CL-20基含能油墨,并采用3D打印平台装置对油墨进行了直写成型。采用流变仪、扫描电子显微镜(SEM)、X射线衍射仪(XRD)、邵氏硬度仪等对成型复合物的流变性能、微观结构、晶型、硬度进行了表征和测试。结果表明,CL-20含量为82%时,油墨体系稳定性较好,采用UV光辅助固化的油墨固化速率快、成型样品表面平整,硬度为70 HA;撞击感度测试表明,复合物的特性落高比原料提高了20 cm;传爆性能测试表明,成型样品可实现90°拐角传爆,在1.2 mm装药宽度下,其传爆临界尺寸为0.387 mm。

Use of Ultrasound and Microwave Irradiation for Clean and Efficient Synthesis of 3,3’-(Arylmethylene)bis (2-hydroxynaphthalene-1,4-dione) Derivatives

Nine 3,3’-(arylmethylene)bis(2-hydroxynaphthalene-1,4-dione) derivatives were synthesized through the reaction between 2-hydroxy-1,4-naphthalen-1,4-dione and different aromatic alde-hydes in water applying ultrasonic irradiation for 5 min at room temperature and microwave irradiation for 15 min at 70°;C. Two of the nine derivatives, compounds 3-e and 3-i, obtained from 3-bromo-hydroxybenzaldehyde and 5-methylfuran-2-carbaldehyde, respectively, are previously unpublished. The structures of all compounds were established on the basis of their spectral data and mass analysis. The attractive features of this synthesis protocol include mild conditions, high atom-economy and excellent yields with the elimination of water as the only by-product.

Synthesis of Intermediate 2, 3-Dichloro-1,4-naphthoenone for Fungicide Dithianon

The synthetic method of dithianon intermediate 2,3-dichloro-1,4-naphthoquinone was introduced. Starting with raw material sodium 4-amino1-naphthalene sulfonate, 2,3-dichloro-1,4-naphthoquinone was synthesized through acidification, chlorination and oxidation. After filtration and recrystallization, more than 98% of 2,3-dichloro-1,4-naphthoquinone was obtained, and the yield reached 76%(measured by sodium 4-amino-1-naphthalene sulfonate).

Catalytic Conversion of 2-Naphthol to 2-Hydroxy-1,4-naphthoquinone Under Mild Conditions

2-Hydroxy-1,4-naphthaquinone (HNQ) was selectively synthesized from catalytic oxidation of 2-naphthol by molecular oxygen over tetra(4-methoxyl-phenyl)porphyrinate iron(III) chloride (TMOPPFeCl) catalyst in an alkali methanol solution under mild conditions. The influences of solvents, temperature, time, as well as amounts of cata-lysts and alkali were studied. The quantitative data show that 32.9% of 2-naphthol (0.093 mol/dm3) was catalyti-cally converted to HNQ with the selectivity of 100% at 323 K for 9 h over TMOPPFeCl catalyst (2.54×10-4 mol/dm3) in alkali media (30 mL of methanol containing 2.5 mol/dm3 of NaOH) by flowing molecular oxygen (flowing rate of 45 mL/min).

Magnetic Field Effects on Photoreduction Reaction of 2-Methyl-1,4-Naphthoquinone in Brij 35 Micellar Solution with Additional Radical

A study was made of magnetic field effects (MFEs) on the photoreduction reaction of 2-methyl-1,4-naphthoqui- none (MNQ) in Brij 35 micellar solution containing 4-lauroylamino-TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl) radical (L-R) under magnetic fields below 1.75 T by a nanosecond laser flash photolysis technique. The triplet MNQ mainly underwent the hydrogen abstraction from Brij 35 molecule to give a radical pair. The escaped radical yield increased with magnetic fields from 0 to 0.62 T and then saturated from 0.62 to 1.75 T. MFEs for both sys-tems can be explained by the relaxation mechanism. However, it was supposed that additional radical, L-R affected the MFEs mainly through enhancing the spin-spin interactions of radical pairs. The effect of the micelle size on MFEs of the studying system was also discussed.

Syntheses and Crystal Structures of Two One-dimensional Coordination Polymers Constructed from a Flexible Hinge-like Ligand

By using the flexible hinge-like ligand 2,2＇-bis（3-hydroxy-l,4-naphthoquinone） （H2bhnq）, two isomorphous one-dimensional zigzag chain coordination polymers have been obtained. Single-crystal X-ray analyses revealed that the metal centers in these two complexes are distorted octahedra involving four oxygen atoms of two bhnq2 anions, and two oxygen atoms of two DMF molecules situated in trans positions to one another. Crystal data for [Mn（bhnq）（DMF）2]n 1： C26H22MnN2O8, Mr = 545.40, monoclinic, space group C2/c, a = 14.936（3）, b = 10.362（2）, c = 15.901（3）A., β = 99.86（3）°, V = 2424.7（8）A3, Z = 4, Dc = 1.494 g/cm^3, F（000） = 1124,μ = 0.599 mm^-1, final GOOF = 1.025, R = 0.0654 and wR = 0.1537. Crystal data for [Cd（bhnq）（DMF）2]n 2： C26H22CdN2O8, Mr = 602.86, monoclinic, space group C2/c, a = 14.839（3）, b = 10.493（2）, c = 16.034（3）A, β = 99.40（3）°, V = 2463.1（9）A^3, Z = 4, Dc = 1.626 g/cm^3, F（000） = 1216,μ = 0.941 mm^-1, final GOOF = 1.069, R = 0.0358 and wR = 0.0944.

无水无氧条件下酚醛-邻重氮萘醌类感光性树脂的光交联行为

对无水无氧条件下酚醛-邻重氮萘醌类感光性树脂的光化学反应机理进行了探讨。发现在这种条件下,接在酚醛链上的邻-重氮萘醌光解后产生的烯酮,会和不同酚醛链上的羟基加成,使这类树脂发生光交联反应。