两种含杂环的氨基萘醌化合物的合成

以2,3-二氯-1,4-萘醌为主要原料,分别与吗啡啉和糠胺在一定条件下反应生成2种含杂环的氨基萘醌类化合物。2,3-二氯-1,4-萘醌与吗啡啉及2,3-二氯-1,4-萘醌与糠胺物质的量比均为1∶2,反应温度为60℃,溶剂为乙醇。2,3-二氯-1,4-萘醌与吗啡啉反应时间为1 h,产物2-氯-3-吗啡啉基萘-1,4-二酮(a)收率为93.5%;2,3-二氯-1,4-萘醌与糠胺反应时间为4 h,产物N~2,N~3-二(2-呋喃甲基)-1,4-二((2-呋喃甲基)亚胺)-1,4-二氢化萘-2,3-二氯化铵(d)收率为46.7%。对产物进行IR、Uv、MS和H-NMR等分析表征。     

1,2-和1,4-萘醌248 nm激光光解的瞬态吸收光谱研究

利用纳秒级激光光解动态吸收光谱装置,研究了1,2-和1,4-萘醌中性水溶液的瞬态吸收光谱.发现1,2-萘醌及1,4-萘醌被光电离后形成的阳离子自由基在380nm均有最大吸收,但1,4-萘醌阳离子自由基在衰变过程中又形成了两种新的活性粒子,它们的最大吸收分别位于410和580nm,分析表明:410nm属于1,4-萘醌脱氢自由基的吸收,而580nm很可能归属由于电子转移而形成的瞬态产物.进一步研究发现,1,2-萘醌在中性水溶液中能被248nm激光单光子电离.     

三种萘并萘醌酚醛树脂的合成与光致变色性质

通过酚醛树脂羟基活性基团与6-氯-5,12-萘并萘醌(1)接枝反应,制备了3种有光致变色性的酚醛树脂:萘并萘醌酚醛树脂(2),甲基萘并萘醌酚醛树脂(3)和氯代萘并萘醌酚醛树脂(4).在四氢呋喃(THF)溶液中,3种光致变色聚合物有与6-苯氧基-5,12-萘并萘醌相似的光致变色行为.同时,发现聚合物骨架上的取代基对聚合物的变色速度影响较小,聚合物的平均分子量影响聚合物的变色速度.     

2,3-二氯-1,4-萘醌在有机分析上的某些应用

2,3-二氯-1,4-萘醌(以下简称二氯萘醌)作为植物杀菌剂以及除草剂(2-氨基-3-氯-1,4-萘醌)的原料,国外已大量生产和应用。它在有机分析上的应用报导尚少,Abou-Ouf等人报导以二氯萘醌为显色剂测定某些药物中脂肪伯胺的分光光度法。Shishoo等人提出用二氯萘醒测4-乙酞胺基苯甲醛缩氨基硫脲(thioacetazone)分光光度法。Devani等人提出硫脲、缩氨基硫脲类的检出。Bartos等人以氨基硫脲与芳香醛反应     

铜（II）化合物作用下2-綦胺的氧化偶合反应

2-萘胺（1）在甲醇中与铜胺络合物[x(CuCl_2):x(苄胺或乙醇胺）=2：1]室温 下反应得到产率为74%的1,1'-联-2-萘胺（2）。在醋酸铜、硝酸铜或高氯酸铜的催 化下,1在甲醇中被氢气氧化为2-氨基-1,4-萘醌-4-2'-萘亚胺（3）,产率86%。 用X-ray单晶衍射证实3的乙酰化产物结构为2-乙酰氨基-1,4-萘醌-E-4-2'-萘亚胺 （4）。循环伏安研究表明,铜（II）化合物的氧化反应选择性与其还原峰电位有 关。电喷雾质谱的分析表明1,2-萘醌-2-亚胺（6）是生成3的中间体。     

3，3‘—二氯—4，4’—二氨基联苯的合成

从邻硝基氯苯合成3,3‘-二氯-4,4‘-二氨基联苯：邻硝基氯苯（a)在1,4-萘醌催化下与CH2O反应得到2,2‘-二氯氧化偶氮苯（b),产率91.0%;b在Al-Ni合金及1,4-萘醌催化下与水合肼反应得到2,2‘-二氯氢化偶氮苯（c),产率97.0%;c在盐酸中重排得到d,产率96.9%。d的总产率达85.5%,含量97.7%。     

新型含硫三唑类化合物的合成及生物活性研究

利用1,3-二芳基-2-[(¹H NMR-1,2,4-三唑-1-基)-甲基]-2-丙烯-1-酮与取代苯硫酚进行1,4-亲核加成反应,合成了一类新型含硫三唑类化合物,其结构经元素分析、核磁共振谱和红外光谱确证,并对其进行了生物活性的测试,发现它们具有中等程度的抑菌活性和较好的杀虫活性.     

苯氧基萘并萘醌衍生物的合成与光致变色性能研究

设计合成了16个新的具有不同迁移基团、不同取代基及双苯氧基萘的苯氧基并萘醌化合物; 通过红外光谱、核磁共振、质谱等方法对其结构进行了表征; 利用紫外-可见光谱研究化合物的光致变色性, 结果表明, 化合物的结构影响其变色性能, 当迁移基团为芳香基时, 其变色性较好; 主链醌环上有取代基时, 化合物成色体最大吸收波长红移; 双苯氧基萘并萘醌化合物较相应的单化合物有较大的摩尔吸光系数; 随着苯基上取代基增大, 其成色速率常数变小.     

芳香β-醛酮衍生物的合成及抗菌活性研究

鱼腥草素具有广谱的抗菌活性,其药效团为β-醛酮结构。本文以对羟基苯乙酮为原料,通过Claisen缩合、加成、缩合得到12个芳香β-醛酮衍生物,所合成化合物经过红外、核磁、质谱进行了结构表征。对所合成的化合物进行了抑菌活性测试,初步构效关系研究表明,烷氧基胺席夫碱可能是活性基团,酮羰基的存在对提高抗菌活性有利,苯环上取代基对抗菌活性有重要影响。     

微波辐射合成2-乙氧羰基甲硫基-4-取代苯基亚氨基-4H-1-萘酮类化合物

以对取代苯胺与2-乙氧羰基甲硫基-1,4-萘醌为底物,采用微波合成法合成了3个新型的蛋白酶体抑制剂的关键中间体——2-乙氧羰基甲硫基-4-苯基亚氨基-4H-1-萘酮类化合物(3a~3c),其结构经1H NMR和1D NOE表征。在最佳反应条件[THF为溶剂,TiCl4为催化剂,于60℃微波(240 W)反应15 min]下,2-乙氧羰基甲硫基-4-(4-硝基苯基)亚氨基-4H-1-萘酮(3a)的收率84.2%。     

Synthesis and Antimicrobial Evaluation of 1,4-Naphthoquinone Derivatives as Potential Antibacterial Agents

1,4-Naphthoquinones are an important class of compounds present in a number of natural products. In this study, a new series of 1,4-naphthoquinone derivatives were synthesized. All the synthesized compounds were tested for in vitro antimicrobial activity. In this present investigation, two Gram-positive and five Gram-negative bacterial strains and one pathogenic yeast strain were used to determine the antibacterial activity. Naphthoquinones tested for its antibacterial potencies, among seven of them displayed better antimicrobial activity against Staphylococcus aureus (S. aureus; 30–70 μg/mL). Some of the tested compounds showed moderate to low antimicrobial activity against Pseudomonas aeruginosa (P. aeruginosa) and Salmonella bongori (S. bongori; 70–150 μg/mL). In addition, most active compounds against S. aureus were evaluated for toxicity to human blood cells using a hemolysis assay. For better understanding, reactive oxygen species (ROS) generation, time-kill kinetic study, and apoptosis, necrosis responses were investigated for three representative compounds.     

Pterocaryquinone, a Novel Naphthoquinone Derivative from Pterocarya tonkinesis

Pterocaryquinone,a novel 1,4-naphthoquinone derivative,was isolated from Pterocarya tonkinesis and itsstructure was elucidated by spectroscopic methods.Pterocaryquinone is a new dimeric 1,4-naphthoquinone deriva-tive having a pentacyclic skeleton with two five-membered carbon rings,which provided a novel structural skeletonfor 1,4-naphthoquinone derivatives and showed apoptosis-inducing activity toward mouse cancer tsFT210 cells.     

Studies on topical antiinflammatory agents. II. Synthesis and vasoconstrictive activity of 21-substituted corticosteroids with sulfur-containing moieties

As part of the search for new topical antiinflammatory agents, various 21-substituted corticosteroids having sulfur-containing moieties were prepared and tested for vasoconstrictive activity in humans. A structure-activity relationship study revealed that substitution of the 21-hydroxy group with a lower alkyl-thio group enhanced the activity. The activities of the 21-methylthio (3Ad) and the 21-ethylthio (3Ae) compounds were more potent than that of 9 alpha-fluoro-11 beta,21-dihydroxy-16 beta-methyl-17 alpha-valeroyloxy-1,4- pregnadiene-3,20-dione (betamethasone 17-valerate, BV).     

Synthesis and Antibacterial and Antifungal Properties of Novel S-, N-, N,S-, and S,O-Substituted 1,4-Naphthoquinone Derivatives

Abstract

A novel series of substituted 1,4-naphthoquinone derivatives were synthesized and evaluated for their antibacterial and antifungal activity. The structures of the novel products were characterized by spectroscopic methods. Among the tested compounds, 2,2′,3,3′-alkoxy substituted naphthoquinones, S,O-substituted naphthoquinone, and N,S-substituted naphthoquinone derivatives are the most potent antifungals against C. tenuis. 2,3-Thio-2′,3′-alkoxy substituted naphthoquinones are the most effective antifungal compounds against A. niger.

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.     

Newbouldiaquinone and newbouldiamide: a new naphthoquinone-anthraquinone coupled pigment and a new ceramide from Newbouldia laevis

Newbouldiaquinone (1), a new naphthoquinone-anthraquinone coupled pigment and a new ceramide named newbouldiamide (2), have been isolated from Newbouldia laevis, besides the known compounds lapachol (3), canthic acid, oleanolic acid, 2-methyl-9,10-anthracenedione, 2-acetylfuro-1,4-naphthoquinone, 2,3-dimethoxy-1,4-benzoquinone, 2-(4-hydroxyphenyl)ethyl triacontanoate, beta-sitosterol and beta-sitosterol glucopyranoside. The structure elucidations of the isolated new compounds were performed on the basis of spectroscopic and chemical evidence. Preliminary studies showed that 1 is moderately antibacterial against Gram-positive Bacillus megaterium and that 3 has moderate herbicidal and antibacterial activities.     

Manganese(II) and palladium(II) complexes containing a new macrocyclic Schiff base ligand: antibacterial properties

Complexes of tetradentate macrocyclic Schiff base ligand, L, with Mn^II and Pd^II ions have been synthesized by the template condensation of 1,10-phenanthroline-2, 9-dicarboxaldehyde, 2,3-diamino-1,4-naphthoquinone and 1,2-dibromoethane in EtOH. The complexes were characterized by physicochemical and spectroscopic methods and an octahedral geometry is suggested for their structure. They have been screened for antibacterial activity against several bacteria, and the results are compared with the activity of penicillin.     

Reactions of Substituted Indoles with 2,3-Dichloro-1,4-naphthoquinone and Electrochemical Properties of Some 2,3-Substituted 1,4-Naphthoquinones

Russian Journal of Organic Chemistry - The reactions of 2,3-dichloro-1,4-naphthoquinone with some indoles and thiols were investigated. The resulting nucleophilic substitution products were...     

Silver Nanoparticle-Anchored Human Hair Kerateine/PEO/PVA Nanofibers for Antibacterial Application and Cell Proliferation

The main core of wound treatment is cell growth and anti-infection. To accelerate the proliferation of fibroblasts in the wound and prevent wound infections, various strategies have been tried. It remains a challenge to obtain good cell proliferation and antibacterial effects. Here, human hair kerateine (HHK)/poly(ethylene oxide) (PEO)/poly(vinyl alcohol) (PVA) nanofibers were prepared using cysteine-rich HHK, and then, silver nanoparticles (AgNPs) were in situ anchored in the sulfur-containing amino acid residues of HHK. After the ultrasonic degradation test, HHK/PEO/PVA nanofibrous mats treated with 0.005-M silver nitrate were selected due to their relatively complete structures. It was observed by TEM-EDS that the sulfur-containing amino acids in HHK were the main anchor points of AgNPs. The results of FTIR, XRD and the thermal analysis suggested that the hydrogen bonds between PEO and PVA were broken by HHK and, further, by AgNPs. AgNPs could act as a catalyst to promote the thermal degradation reaction of PVA, PEO and HHK, which was beneficial for silver recycling and medical waste treatment. The antibacterial properties of AgNP-HHK/PEO/PVA nanofibers were examined by the disk diffusion method, and it was observed that they had potential antibacterial capability against Gram-positive bacteria, Gram-negative bacteria and fungi. In addition, HHK in the nanofibrous mats significantly improved the cell proliferation of NIH3T3 cells. These results illustrated that the AgNP-HHK/PEO/PVA nanofibrous mats exhibited excellent antibacterial activity and the ability to promote the proliferation of fibroblasts, reaching our target applications.     

Chemistry of naphthazarin derivatives: XV. Bromination of naphthazarin and its derivatives

Bromination of a number of naphthazarin (5,8-dihydroxy-1,4-naphthoquinone) derivatives having different substituents in the aromatic ring with molecular bromine in carbon tetrachloride was studied. Preparative procedures for the synthesis of 2-bromo-5,8-dihydroxy-7-methoxy-1,4-naphthoquinone, 2-bromo-6,7-dichloro-5,8-dihydroxy-1,4-naphthoquinone, 2-bromo-3,5,8-trihydroxy-1,4-naphthoquinone, and 2-bromo-6,7-dichloro-3,5,8-trihydroxy-1,4-naphthoquinone were developed.     

Reaction of 2-chloro-3-(4-N,N-dimethylaminoanilino)-1,4-naphthoquinone with cyclic amines (piperidine,morpholine, and pyrrolidine)

It was shown that the reaction of 2-chloro-3-(4-N,N-dimethylaminoanilino)-1,4-naphthoquinone with piperidine in the absence of a solvent gives not only a product of replacement of the chlorine atom by a piperidino group, 3-(4-N,N-dimethylaminoanilino)-2-piperidino-1,4-naphthoquinone, but also 2-(4-N,N-dimethylaminoanilino)-1,4-naphthoquinone and 2-(4-N,N-dimethylaminoanilino-2-piperidino)-1,4-naphthoquinone. The latter compounds are the only reaction products formed in dimethyl sulfoxide. The reaction with morpholine occurs in a similar way, whereas that with pyrrolidine gives only a product of replacement of the chlorine atom by hydrogen.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2451–2454, December, 1995.