Synthesis and Cytotoxicity Evaluation of Some Isoquinoline Derivatives Related to 1-Arylnaphthalene Lignans

Two series of novel compounds designed as hybrids of 1-arylnaphthalene lignans with dihydroisoquinolines or isoquinolines were synthesized and evaluated for their cytotoxicities on human tumor cell lines, such as A549, Hela, PC-3 and KB. Some of the synthetic compounds exhibited their IC50 values on selected cell lines at μmol/L scale.     

Preparation of Substituted Quinolinyl and Isoquinolinyl Sulfonyl Chlorides for the Synthesis of Novel Sulfonamides

Abstract

Novel sulfonyl chlorides of quinolines and isoquinolines have successfully been prepared. This enabled the preparation of the corresponding sulfonamides via reaction with an amine using the “resin-capture and release” methodology.     

新型N-杂环取代苯乙酮衍生物的合成

以2-溴-4'-氟苯乙酮(1)为原料,在碳酸钾存在下分别与对甲酚(2a)和邻苯基苯酚(2d)反应制得2-芳氧基苯乙酮化合物(3a和3d);3a和3d分别与咪唑,N-甲基哌嗪和1-(2-嘧啶基)哌嗪经取代反应合成了6个新型的N-杂环取代苯乙酮衍生物,收率63%~81%,其结构经1H NMR,13C NMR,IR和HR-MS表征。     

Synthesis of New Functionally Substituted 1-R-tetrazoles and Their 5-Amino Derivatives

It has been shown that amino derivatives of sulfanilamide, and also some functionally substituted primary arylamines and cycloalkylamines, undergo heterocyclization with triethyl orthoformate and sodium azide with the formation of 1-monosubstituted tetrazoles. Primary amines of the azole series, 5-aminotetrazole, 5-amino-1-methyltetrazole, 4-amino-1,2,4-triazole, and also less basic arylamines (4-fluoro-3-nitroaniline, 2,6-dibromo-4-nitroaniline) did not react. An efficient method of introducing an amino group into position C₍₅₎ of the tetrazole ring of 1-aryltetrazoles is proposed, based on alkaline decomposition of the tetrazole ring and heterocyclization of the resulting N-arylcyanamides on interaction with ammonium azide generated in situ. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1174–1179, August, 2005.     

异喹啉吸附在银电极上的表面增强拉曼光谱研究

异喹啉吸附在银电极上的表面增强拉曼光谱研究陈建赵文涛，胡继明，徐知三，盛蓉生（中山大学测试中心，广州，５１０２７５）（武汉大学分析测试科学系，武汉，４３００７２）关键词异喹啉，ＳＥＲＳ，吸附，取向喹啉类和异喹啉类化合物在作为电解冶金、铜精炼和电镀的有...     

新型N-芳基哌嗪取代苯并呋喃衍生物的合成

以5-二甲氨基水杨醛和2-溴-4'-氟苯乙酮为原料,经缩合和取代反应制得中间体6-二乙氨基-2-[4'-(N-哌嗪基)苯甲酰基]苯并呋喃(2);2与卤代烃反应合成了6个新型的N-芳基哌嗪取代苯并呋喃衍生物(4a~4f),收率76%~93%,其结构经1H NMR,13C NMR和HR-MS(ESI-TOF)表征。     

Synthesis and Antibacterial Activity of Novel Substituted Purine Derivatives

A series of novel N‐substituted‐2‐(6‐morpholino‐9H‐purin‐9‐yl)acetamide and 4‐(9‐((5‐substituted‐1,3,4‐oxadiazole/thiadiazole‐2‐yl)methyl)‐9H‐purin‐6‐yl)‐morpholine derivatives were synthesized and evaluated their antibacterial activities against rice bacterial leaf blight and tobacco bacterial wilt caused by Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (R. solanacearum) via the turbidimeter test in vitro. Antibacterial bioassay indicated that most compounds demonstrated good inhibitory effect against Xoo and R. solanacearum. Especially, compound 6a demonstrated the best inhibitory effect against Xoo with half‐maximal effective concentration (EC₅₀) value of 8.39 μg/mL, which was even better than those of commercial agents Bismerthiazol and Thiodiazole copper. The synthesized purine derivatives containing amide and 1,3,4‐oxadiazole/thiadiazole moieties exhibited excellent antibacterial activities against Xanthomonas oryzae pv. oryzae and R. solanacearum in vitro.     

脉冲辐解研究喹啉和异喹啉与瞬态粒子的反应

通过合理控制反应条件, 使体系在电子束脉冲作用后只剩下所需要的一种瞬态粒子, 用脉冲辐解研究了喹啉、异喹啉分别与水合电子、羟基自由基、氢自由基等几种典型的氧化还原瞬态粒子的反应过程, 研究了各种瞬态产物的吸收光谱及其变化规律, 测定了相关反应的速率常数. 喹啉、异喹啉与水合电子的反应速率常数分别为7.1×10⁹和3.4×10⁹ mol^-1·L·s^-1, 与羟基自由基的反应速率常数分别为7.2×10⁹和3.4×10⁹ mol^-1·L·s^-1, 与氢自由基的反应速率常数分别为5.7×10⁹和3.6×10⁹ mol^-1·L·s^-1. 这一结果表明, 喹啉、异喹啉均能够非常迅速地与水合电子、羟基自由基、氢自由基发生反应, 喹啉比异喹啉的反应速率更快. 运用电子理论分析了瞬态反应产物结构的稳定性差异, 结果表明, 喹啉的反应产物比异喹啉的稳定, 从而揭示了喹啉比异喹啉反应速率快的原因.     

Synthesis,Structure, and Anti-Inflammatory Activity of Functionally Substituted Chalcones and Their Derivatives

Russian Journal of General Chemistry - Functionally substituted chalcones, pyrazolines, and flavonones have been synthesized. Their structure has been studied by means of 1H and 13C NMR...     

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.     

New Types of Functionally Substituted Methylphosphonites and Their Derivatives

Abstract

Organophosphorus compounds containing a functional group in the a-position of the alkyl radical are of great interest in both theoretical fundamental investigations and for practical applications. Functionally substituted methyl-phosphonites and their derivatives, belonging to this broad class of organophosphorus compounds, are convenient objects for investigating mutual effects of trivalent phosphorus and a heteroatom, or functional groups attached to it in the a-position. They have also become key substances in obtaining new organophosphorus compounds. Functionally sub-stituted compounds of tetracoordinated phosphorus have been intensively investigated in recent years; rather convenient methods of synthesis of these compounds have been proposed and their properties have been studied in detail¹. However, the corresponding compounds of tricoordinated phosphorus are not available or difficult to obtain. Recently we re-ported on the properties of halogen-substituted methylphos-phines and their derivatives². The present paper is devoted to the synthesis and investigation of the reactivity of alkoxy-, dialkylamino- and carbonyl substituted methylphos-phonites and their derivatives. In synthesis of alkoxymeth-ylphosphonites and their analogs we were the first to use labile alkoxymethylmagnesium chlorides in the reactions with tricoordinated phosphorus acid chlorides³. Previously unknown dialkoxymethylphosphonites and their analogs were obtained from hypophosphorous acid and trialkylorthofor-mates. The process of esterification and dialkoxymethylat-ion of hypophosphorous acid, being dependent on a catalyst, proceeds in different ways and results in the formation of dialkoxymethylphosphonite structures     

取代吡唑啉衍生物的合成与生物活性

采用α-三唑-β-烷氧基芳酮与肼关环,制备了1,3-二苯基-4-三唑基吡唑啉1a,1-苯基-3-对氯苯基-4-三唑基吡唑啉1b和3-取代苯基-4-三唑基吡唑啉(7),并研究了化合物7的成环优化条件.使用α,β-不饱和酮与肼关环合成了1,3,4,5-多取代吡唑啉衍生物1c-1h,并初步用质谱法确定了该反应产物的结构;同时,以3,5-二取代吡唑啉(6)和7作为中间体合成了1-,3-,4-或5-取代的化合物2a-2l.初步生物活性测定结果表明,所合成的化合物均有一定的杀菌、激素和除草效果.     

Novel Furochromone Derivatives: Synthesis and Anticancer Activity Studies

Medicinal plant extracts have been used for medical purposes throughout human history. In this study, khellin, having furochromone structure, which is obtained from a well‐known traditional medicinal plant, was selected. A series of furochromonyl compounds ( K1 – K14 ) were synthesized for their anticancer activities. Furochromonyl compounds ( K1 – K14 ) were synthesized by Knoevenagel reaction of substituted 2,4‐thiazolidinediones ( Ia – j )/rhodanines ( Ik – n ) with khellin‐2‐carboxaldehyde ( V ), and their cytotoxicity was investigated in 22 cancer cell lines, which were originated from tissues such as the liver, breast, colon, and cervix. As the first step, two hepatocellular carcinoma cell lines Huh7 and PLC/PRF/5 (Alexander cells) were treated with 10 μM of each compound for 72 h, and then sulforhodamine B assay was performed to analyze their anti‐growth activities. Ethyl 2‐(5‐((4,9‐dimethoxy‐5‐oxo‐5H‐furo[3,2‐g]chromen‐7‐yl)methylene)‐4‐oxo‐2‐thioxothiazolidin‐3‐yl)acetate ( K11 ) was found as the most cytotoxic compound of primary screening. Afterwards, 12 hepatocellular carcinoma, seven breast cancer, two colon cancer, and a cervical cancer cell lines were selected to test K11 for 72 h at multiple concentrations to determine 50% effective doses. Results showed that the 14 cell lines were affected by K11 quantities lower than 10 μM. The structure of K11 , which is particularly effective on breast cancers, can be used to slow down the progression of tumors. Furthermore, the discovery of more effective compounds can be carried out on the basis of this structure.     

Synthesis and Biological Activity of Novel Diphenyl N- Substituted Carbamimidoylphosphoramidate Derivatives

Abstract

An efficient synthesis of a series of novel diphenyl N-substituted carbamimidoyl phosphoramidate derivatives was accomplished in two steps. Diphenyl phosphorochloridate (1) was reacted with cyanamide (2) in the presence of 1,4–dimethylpiperazine as a base in THF at 50–55 °C to form an intermediate, diphenyl cyanophosphoramidate (3). Subsequently 3 was reacted with various aromatic/heterocyclic amines (4) in the presence of 1,4–dimethyl piperazine as a base at 55–60 °C to form the corresponding title compounds 5(a-k). The title compounds were tested for antiviral activity against Tobacco mosaic virus (TMV) in vitro, antibacterial and antifungal activities at two different concentrations of 50 and 100 μg/mL. The title compounds exhibited good antiviral and antimicrobial activities when compared to the standards.     

Synthesis and Spectral and Electrochemical Characterization of Novel Substituted 1,4-Naphthoquinone Derivatives

The novel substituted 2,3-dichloro-1,4-naphthoquinone derivatives were synthesized from the reactions of (1) and related nucleophilles in sodium carbonate (Na₂CO₃) solution of ethanol, chloroform with Et₃N, or potassium carbonate (K₂CO₃) solution of acetonitrile. The structures of novel compounds were characterized by using microanalysis, Fourier transform–infrared, ¹H NMR, ¹³C NMR, mass spectrometry, and cyclic voltammetry (CV).

[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.]     

新型三氟甲基吡啶类衍生物的合成及生物活性测试研究

新型三氟甲基吡啶类衍生物的合成及生物活性测试研究钱旭红，唐军，陈卫东，张荣，黄德音，倪长春，郭庆铭（华东理工大学农用化学品研究所，上海，２００２３７）（上海市农药研究所）关键词氟代物，吡啶，合成，生物活性，化学农药不少吡啶类化合物是有着广泛前途的生物...     

Synthesis and Properties of Functionally Substituted Unsaturated Polysulfones

High-temperature copolymerization of ethyl esters of vinyl- or isopropenylcyclopropanecarboxylic acids with SO₂ was studied as a route to functionally substituted unsaturated polysulfones. The composition, structure, and some properties of the polysulfones obtained were studied. The copolymerization mechanism was considered.     

Selective Synthesis of Functionally Substituted 1,2,3-Triazoles

Russian Journal of Organic Chemistry - Different conditions were used to achieve selective formation of 4.5-disubstituted 1-aryl(hetaryl)-1,2,3-triazoles via cycloaddition of the corresponding...     

New Derivatives of (Carbamoselenoyl)acetic Acid for the Synthesis of Functionally Substituted Selenazoles

Russian Journal of Organic Chemistry - New reagents for the synthesis of substituted selenazoles, 3-amino-N-cyclopropyl-3-selanylidenepropanamide and methyl 3-amino-3-selanylidenepropanoate, were...