N-苯基-N＇-（5-苯基-2-呋喃酰基）脲的合成与生物活性

为考察脲桥变化对活性的影响，通过异氰酸苯酯和取代苯基呋喃甲酰胺反应合成了8个未见报道的N-苯基-N‘-(5-苯基-2-呋喃酰基)脲化合物，其结构均经元素分析，IR和^1H NMR确证。测定了它们的生物活性,发现所合成的化合物对蚊幼虫有明显的几丁质抑制活性。     

新型4-(5-N-取代-1,3,4-噻二唑-2-巯基)-苯并[4,5]呋喃[3,2-d]嘧啶类衍生物的合成及其抗癌活性

将5-取代胺基-2-巯基-1,3,4-噻二唑引入苯并[4,5]呋喃[3,2-d]嘧啶中,设计并合成了10个新型的4-(5-N-取代-1,3,4-噻二唑-2-巯基)-苯并[4,5]呋喃[3,2-d]嘧啶类衍生物(3a～3j),其结构经1H NMR,13C NMR,IR和MS确认。用MTT法测定了3a～3j对人胃腺癌细胞体(MGC)的体外增殖活性。结果表明,3a～3j均具有不同程度的抑制MGC的活性,其中4-(5-N-2’-甲氧基苯基-1,3,4-噻二唑-2-巯基)-苯并[4,5]呋喃[3,2-d]嘧啶(3j)在10μmol·L-1的浓度下对MGC的抑制率为86.4%。     

立体选择性合成2-(a-噻吩甲酰基)-3-取代苯基-4-乙氧羰基-5-甲基-反式-2,3-二氢呋喃

溴化(a-噻吩甲酰基)甲基三苯鉮1与3-取代苯甲叉基-2,4-戊二酮 2以碳酸钾为碱,在苯中55℃条件下反应,可以较好的收率、高立体选择性地生成反-2-(a-噻吩甲酰基)-3-取代苯基-4-乙氧羰基-5-甲基-2,3-二氢呋喃3。产物结构均经波谱予以确定。本文还提出了生成产物的可能机理。     

4-(对取代苯基)-2-[2-(取代苯基)呋喃-4-甲酰胺]-1',3',4'-均三唑[1,2-d]-1,3,4-噻二唑类衍生物的合成和生物活性

以1-氨基-5-巯基-2-(对取代苯基)-1,3,4-均三唑和5-取代苯基-2-呋喃甲酰异硫氰酸酯为原料, 合成了10个未见文献报道的含苯环连呋喃的均三唑并噻二唑类衍生物, 通过元素分析, ¹H NMR, IR和MS确定化合物的结构, 初步生物活性测试表明标题化合物具有一定的除草活性.     

N-苯基-N''-(5-苯基-2-呋喃酰基)脲的合成与生物活性

为考察脲桥变化对活性的影响 ,通过异氰酸苯酯和取代苯基呋喃甲酰胺反应合成了 8个未见报道的N 苯基 N’ ( 5 苯基 2 呋喃酰基 )脲化合物 ,其结构均经元素分析 ,IR和1HNMR确证。测定了它们的生物活性 ,发现所合成的化合物对蚊幼虫有明显的几丁质抑制活性     

用NaBH4还原3-(3,4-二苄氧基苯基)-2-羟基丙烯酸甲酯

用NaBH4还原3-(3,4-二苄氧基苯基)-2-羟基丙烯酸甲酯得到3-(3,4-二苄氧基苯基)-乳酸甲酯和3,4-二苄氧基苯基-1,2-丙二醇(1)。1的结构经1HNMR,13CNMR和MS确定。     

(E)-3-(1-亚胺基乙基)-5,5-二取代-4-甲氨基呋喃-2(5H)-酮的合成及其意外的杀虫活性（英文）

为了提高化合物对植物病原菌的杀菌活性及扩大多样性导向合成策略建立的分子库,以甲氨基替换3-(1-亚胺基乙基)-5,5-二取代-4-苯基呋喃-2(5H)-酮的苯基,设计合成了18个新颖的(E)-3-(1-亚胺基乙基)-5,5-二取代-4-甲氨基呋喃-2(5H)-酮,结构经过~1H NMR, ~(13)C NMR, HR-ESI-MS表征.(E)-3-(1-(4-甲氧基苄氧亚胺基)乙基)-4-甲氨基-1-氧杂螺[4.5]癸-3-烯-2-酮(5O)还经过X射线衍射表征.生物活性测试结果表明,所有化合物对测试的四种植物病原菌均未显示明显的活体杀菌活性,但是意外地发现多个化合物在600μg/mL浓度时对桃蚜、粘虫和小菜蛾的致死率均为100%,显示出良好的杀虫活性.     

环戊二烯基二硫代氨基甲酸钛(Ⅳ), 锆(Ⅳ)配合物的合成及结构表征

(RCp)~2MCl~2, (RCp)TiCl~3分别与N-(4-苯基-2-噻唑基)二硫代氨基甲酸钾和3-苯基-5-(2-呋喃基)-吡唑啉-1-二硫代甲酸钠进行反应, 合成了三十二个未见报道的(RCp)M(S~2CNHR')~nCl~3~-~n,(RCp)~2M-(S~2CNHR')~nCl~2~-~n [R=H, Me; M=Ti, Zr; R'=4-苯基噻唑基(PTDTC), n=1,2,3] 以及(RCp)M(S~2CR^2)~nCl~3~-~n,(RCp)~2M(S~2CR^2)~nCl~2~n[R=H,Me;M=Ti,Zr,R^2=3-苯基-金-(呋喃-2)吡唑啉基(PFPDTC), n=1,2,3]型配合物。所有配合物经元素分析、UV、IR和^1H NMR谱证实, 二硫代氨基甲酸是以双齿配体键合的。     

1-[2′,4′-二氟-(1,1′-联苯)-4-基苯基甲基]-咪唑的合成

以2,4-二氟联苯为起始原料,经酰化反应制得2′,4′-二氟-(1,1′-联苯)-4-基苯基甲酮(2);2经NaBH4还原得2′,4′-二氟-(1,1′-联苯)-4-基苯基甲醇(3);3经氯代得2′,4′-二氟-(1,1′-联苯)-4-基苯基氯甲烷(4);4与咪唑发生亲核取代反应合成了1-[2′,4′-二氟-(1,1′-联苯)-4-基苯基甲基]-咪唑(5). 2～5为新化合物,其结构经1H NMR, IR, MS和元素分析确证.     

3-(2-苯并呋喃酰基)薁-1-羧酸甲酯的有效合成

以苯基三甲铵三溴盐(PTAB)为溴化试剂, 对3-乙酰基薁-1-羧酸甲酯进行了溴代反应研究, 将其单溴代产物与水杨醛在温和反应条件下进行缩合, 以极优的收率高选择性得到3-(2-苯并[b]呋喃酰基)薁-1-羧酸甲酯类衍生物, 其结构经¹H NMR, IR及元素分析等得以证实.     

Synthesis of some N-alkylated 1,2,4-triazoles, 1,3,4-oxadiazoles,and 1,3,4-thiadiazoles based on N-(furan-2-yl-methylidene)-4,6-dimethyl-1H-pyrazolo-[3,4-<Emphasis Type="Italic">b</Emphasis>]pyridine-3-amine

N-(Furan-2-ylmethylidene)-4,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-3-amine was prepared and alkyla- ted with the corresponding halo compounds to afford N-alkylated products. 2-[3-(Furan-2-ylmethy- lideneamino)-4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-1-yl]acetohydrazide was converted into the key intermediate thiosemicarbazide, which undergoes cyclization reactions under acidic and basic conditi- ons to give 1,2,4-triazole, 1,3,4-oxadiazole, and 1,3,4-thiadiazole derivatives. Condensation of the hyd- razide with monosaccharide aldoses gave the corresponding sugar hydrazones, which on treatment with acetic anhydride readily undergo cyclization reaction to afford oxadiazoline derivatives.     

Ethynylation of 2-(furan-2-yl)- and 2-(thiophen-2-yl)pyrroles with acylbromoacetylenes in the Al2O3 medium: relative reactivity of heterocycles

2-(Furan-2-yl)- and 2-(thiophen-2-yl)pyrroles are readily ethynylated with acylbromoacetylenes in the solid Al₂O₃ medium (no solvent, room temperature, 1 h) to afford 5-(furan-2-yl)- and 5-(thiophen-2-yl)-2-acylethynylpyrroles in 39–74% yields. In the case of 2-(furan-2-yl)pyrroles, an alternative ethynylation of the furan ring takes place, the ratio of the furan and pyrrole ring ethynylation products being 1:5–7. No ethynylation of the thiophene ring as well as ethynylation of both heterocycles in a one molecule has been detected. Thus the reactivity of the heterocycles towards the ethynylation system (acylbromoacetylenes/Al₂O₃) falls in the order: pyrrole>furan>thiophene.     

Mixed ligand complexes of tungsten(VI) containing aroyl hydrazones and isothiocyanate

Five complexes [WO(NCS)₄L–L] (where L–L = benzoic acid[1-(Furan-2-yl)methylene]hydrazide(BFMH), benzoic acid[(thiophen-2-yl)methylene]hydrazide(BTMH), benzoic acid[1-(thiophen-2-yl)ethylidene]hydrazide(BTEH), benzoic acid(phenylmethylene)hydrazide(BPMH) and benzoic acid[1-(anisol-3-yl) methylene]hydrazide(BAMH)) have been prepared by reaction of ammonium tetraisothiocyanatodioxotungstate(VI) with the corresponding ligand in aqueous medium in the presence of hydrochloric acid. The complexes have been characterized by elemental analysis, molar conductivity, magnetic moment measurements, IR, electronic spectra, thermogravimetric analysis TGA/DTA and ¹H NMR.     

Synthesis and Antimicrobial Study of New Fused Thiazolo[3,2-b]triazine,Triazolo[4,3-b]triazine,and 1,2,4-Triazinone Derivatives

Russian Journal of Organic Chemistry - 6-[2-(Furan-2-yl)ethyl]-3-sulfanylidene-3,4-dihydro-1,2,4-triazin-5(2H)-one (1) reacted with chloroacetone to give S-acetonyl derivative which cyclized in...     

Functionalized β-lactams based on (<Emphasis Type="Italic">E</Emphasis>)-1-(furan-2-yl)-<Emphasis Type="Italic">N</Emphasis>-[(4-methoxyphenyl)methyl]methanimine and its imine–imine rearrangement initiated by potassium hydride

Functionalized β-lactams were synthesized by reaction of (E)-1-(furan-2-yl)-N-[(4-methoxyphenyl)-methyl]methanimine with ketenes generated in situ from chloro- and dichloroacetic acids and 3-(methoxyimino) butanoic acid. (E)-1-(Furan-2-yl)-N-[(4-methoxyphenyl)methyl]methanimine underwent imine–imine rearrangement by the action of potassium hydride to give thermodynamically more stable (E)-N-[(furan-2-yl)-methyl]-1-(4-methoxyphenyl)methanimine.     

Corrosion inhibitive evaluation and DFT studies of 2-(Furan-2-yl)-4,5-diphenyl-1H-imidazole on mild steel at 1.0M HCl

A novel heterocyclic compound 2-(Furan-2-yl)-4,5-Diphenyl-1H-Imidazole (FDPI) was synthesized by a simple and cost effective one pot synthetic protocol and the structure of FDPI was confirmed by FT-IR, ¹H NMR and ¹³C NMR spectra. The corrosion inhibition activity of FDPI was investigated using gravimetric and electrochemical methods. It resulted a maximum inhibition efficiency of 95.84% at 10 mmolL⁻¹ concentrations of FDPI. The excellent inhibition efficiency is reasoned as the adsorption of FDPI on the mild steel surface as a protective layer immersed in the 1 ​M HCl. The adsorbed layer obeys Langmuir adsorption isotherm and the ΔG^o_ads values of FDPI suggested that process involves physisorption. The polarization curves showed that the FDPI behaves as a mixed type inhibitor. Surface morphology studied by SEM confirmed the formation of a protective film of FDPI on the mild steel surface. The computational studies using DFT have been analyzed for the FDPI to determine the HOMO-LUMO energy gap.     

Synthesis and incorporation of a furan-modified adenosine building block for DNA interstrand crosslinking

2'-O-(3-(Furan-2-yl)propyl)adenosine was synthesized and evaluated for interstrand crosslink (ICL) formation in DNA duplexes. In situ oxidation of the furan moiety with NIS showed rapid crosslink formation to dA and dC, while dT and dG were inactive.     

2-[4-(2,6-二氟苯基)噻唑-2-基]-3-羟基丙烯腈衍生物的合成及生物活性

为了寻找生物活性良好的噻唑基丙烯腈类化合物, 利用2-[4-(2,6-二氟苯基)噻唑-2-基]乙腈(3)分别与取代氯甲酸酯4和取代苯基异氰酸酯6在碱存在下反应, 合成了8个2-[4-(2,6-二氟苯基)噻唑-2-基]-3-羟基-3-烃氧基丙烯腈化合物5和7个2-[4-(2,6-二氟苯基)噻唑-2-基]-3-羟基-3-取代苯胺基丙烯腈化合物7, 均为首次报道的丙烯腈类化合物. 化合物结构经1H NMR, IR, MS和元素分析表征. 初步生物活性测定结果表明, 在试验浓度下, 目标化合物均具有一定的杀虫和抑菌活性, 其中化合物5f和5h在100 mg/L浓度下对炭疽病菌的抑制率达95%; 化合物5g和7d在250 mg/L浓度下对棉红蜘蛛的致死率达85%.     

Synthesis and antimicrobial activity of new 2-((1-furan-2-yl)ethylidene)hydrazono)-4-phenylthiazol-3(2H)-amine derivatives and their schiff bases with 4-nitrobenzaldehyde

Abstract

A new series of 2-((1-furan-2-yl)ethylidene)hydrazono)-4-substitutedphenylthiazol-3(2H)-amines (2a–2o) and their Schiff bases (3a–3o) from 4-nitrobenzaldehyde were synthesized. The chemical structures of all the synthesized compounds were confirmed by their IR, ¹H-NMR, ¹³C-NMR spectroscopy and mass spectrometry. They were screened for their antimicrobial and antifungal activities. Additionally, in vitro cytotoxic acivity of the most active antifungal compound (3o) and ketoconazole was determined in NIH/3T3 cells by MTT assay. Compound 2i (4-{3-Amino-2-[(1-(furan-2-yl)ethylidene)hydrazono]-2,3-dihydrothiazol-4-yl}phenol) showed the greatest antifungal activity among the newly synthesized derivatives. Schiff bases (3c-3n) displayed an undeniable fungicidal action against Candida parapsilosis ATCC 22019 as intense as the reference ketoconazole. In addition, the most active Schiff base 3o (2-[(1-(Furan-2-yl)ethylidene)hydrazono]-N-(4-nitrobenzylidene)-4-(2,3,4-trichloro phenyl)thiazol-3(2H)-amine) showed the highest antifungal activity against both Candida krusei ATCC 6258 and Candida parapsilosis ATCC 22019, and was as potent as ketoconazole. Moreover, compound 3o was found to be non-cytotoxic against NIH/3T3 cells.