N-[5-(1-邻(对)氯苯氧乙基)-1,3,4-噻二唑-2-基]-N'-芳酰基硫脲的合成与生物活性

为了寻找高活性的杂环农药, 通过2-氨基-5-(1-邻氯苯氧乙基)-1,3,4-噻二唑和2-氨基-5-(1-对氯苯氧乙基)-1,3,4-噻二唑与芳酰基异硫氰酸酯反应, 合成了26种新的芳酰基硫脲. 采用核磁共振氢谱、红外光谱及元素分析确证了它们的结构. 初步的生物活性测定试验表明, 部分目标化合物表现出良好的植物生长调节活性, 其中3c, 3d, 3e, 4b和4c具有优良的生长素活性.     

Synthesis and characterization of N′-(11H-indeno[1,2-b]quinoxalin-11-ylidene)benzohydrazonamides as potential antimicrobial agents

Abstract

A series of new N′-(11H-indeno[1,2-b]quinoxalin-11-ylidene)benzohydrazonamides 3a–3j was synthesized in excellent yields from the reaction of N³-substituted benzohydrazonamides 1 and 2-(11H-indeno[1,2-b]quinoxalin-11-ylidene)malononitrile 2 in dichloromethane or with 11H-indeno[1,2-b]quinoxalin-11-one 4 in ethyl acetate at ambient temperature. The new compounds have been characterized and screened for biological activity. Some of them showed significant antibacterial and antifungal activities. In particular, compounds 3c and 3e showed interesting activities as antibacterial agents while compounds 3a 3c, 3e, 3g, and 3i showed high antifungal activities.     

A Convenient One-Pot Synthesis of Some New 3-(2-Phenyl-6-(2-thienyl)-4-pyridyl)hydroquinolin-2-ones Under Microwave Irradiation and Their Antimicrobial Activities

A series of 3-(2-phenyl-6-(2-thienyl)-4-pyridyl)hydroquinolin-2-ones 4a–o were synthesized in high yields by a one–pot cyclocondensation reaction under Kröhnke's reaction conditions using 2-chloro-3-formyl quinoline 1a–c, 2-acetyl thiophene 2, and various N-phenacylpyridinium bromides 3a–e in a mixture of ammonium acetate and acetic acid by microwave irradiation. All the compounds have been characterized by elemental analysis, FT-IR, ¹H NMR, and ¹³C NMR spectral analysis. These compounds have been screened for their antimicrobial activities.

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 and Reactions of Some New Thieno[2,3-C]pyridazine Derivatives

The alkylation of 4-cyano-5,6-dimethylpyridazin-3(2H)-thione 3 with some halo compounds gave the S-alkylated products 4a–c , which upon treatment with ethanolic sodium ethoxide afforded the cyclized thienopyridazines 5a–c as products. Pyridazothienotriazines 6a–c were prepared by the treatment of compounds 5a–c with nitrous acid, while their reaction with triethyl orthoformate and with carbon disulfide gave the corresponding pyrimidothienopyridazines 7a–c , and 8a–c , respectively. S-alkylated products 9a–o were obtained by the reaction of 8a–c with some halo compounds.     

Studies on the synthesis of spiroheterocycles and their derivatives using dimedone as synthetic precursor

Diarylidene ketones 1a–c, formed by the condensation of acetone with diverse appropriate aryl aldehydes undergo Micheal reaction with dimedone to afford the desired spiro compounds 2a–c. The spirodiarylidene derivatives 3a–l on cyclisation with hydrazine, phenyl hydrazine, hydroxyl amine, urea, thiourea and guanidine carbonate furnish the respective insitu oxidized pyrazole 4a–l, phenylpyrazole 5a–l, isoxazole 6a–l, pyrimidine 7a–l, aminopyrimidine 8a–l. The antibacterial activities of the synthesized compounds have been investigated against the gram negative Escherichia coli and gram positive bacteria Staphylococcus aureus.     

New class of diethyl substituted phosphoramidimidates and phosphonimidates: synthesis,spectral characterization and antimicrobial activity

Abstract

A series of new class of diethyl N-2-hydroxyethyl-N'-substituted phosphoramidimidates 6(a–e) and diethyl P-morpholino-N-substituted phosphonimidates 6(f–j) was synthesized. The precursor intermediates, diethyl substituted phosphoramidites 3(a–b) were prepared initially by a reaction of various amines 1(a–b) and diethyl phosphorochloridite (2) and then they were treated by in situ with aromatic/alkyl azides through Staudinger reaction to accomplish title products. Structures of all the synthesized compounds were characterized by spectroscopic data such as IR, NMR (¹H, 13C, ³¹P), mass, and elemental analyses. The synthesized compounds were screened for their in vitro antimicrobial activity to understand their biological potency. The biological screening results disclosed that compounds 6b, 6c, 6e, 6g, 6h and 6j having potent antimicrobial activity against all the tested pathogens.     

Utilization of 2-substituted 3, 1-benzoxazin-4-ones in synthesis of some quinazoline annulated derivatives

Abstract

In this study, a new series of quinazoline and their annulated derivatives have been synthesized. A number of quiazolinone derivatives substituted at position-3 were prepared from 3, 1-benzoxazinone by the treatment of 3,1-benzoxazinone with different nitrogen nucleophiles such as, hydrazine hydrate, phenylhydrazine, ethanolamine, and cyano acetohydrazide afforded the quinazolinone derivatives 7–11. The reaction of hydrazide derivative 5 with aromatic aldehydes gave the Schiff’s bases derivative 16a–c. Some of the synthesized compounds were tested against the breast cancer cell line (MCF-7). The structures of all the newly synthesized compounds were established based on IR, ¹H, ¹³C NMR, mass spectral data, and elemental analyses.     

Convenient and efficient Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions catalyzed by 1,3,4-trisubstituted-1,2,3-triazolium iodide and palladium salt systems

A series of 1,3,4-trisubstituted-1,2,3-triazolium iodide salts (4a–c) were synthesized via a three-step reaction sequence. Corresponding anilines (1a–c) were converted to azides (2a–c) which were then treated with phenylacetylene with “Click” chemistry to access 1,4-disubstituted-1,2,3-triazoles (3a–c). Subsequent methylation of 1,4-disubstituted-1,2,3-triazoles (3a–c) yielded 1,3,4-trisubstituted-1,2,3-triazoliumiodide salts (4a–c) in appreciable yields. All the synthesized compounds were characterized by ¹H and ¹³C NMR, ATR–IR spectroscopic techniques and elemental analyses. Additionally, the structure of 1-(4-chlorophenyl)-4-phenyl-1,2,3-triazole (3b) was confirmed by single crystal X-ray diffraction analysis. The catalytic activity of 4a–c in a catalytic system consisting of 1,3,4-trisubstituted-1,2,3-triazoliumiodide salt/palladium(II) acetate/base were investigated toward Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions. The Suzuki–Miyaura cross-coupling reactions were carried out under mild reaction conditions with good to excellent yields, whereas Heck–Mizoroki cross-coupling reactions were performed at elevated temperature with moderate yields. Further, in situ method skips the synthetic procedure of preparing the palladium(II) complexes and hence is more economical and less tedious.     

Highly soluble Ni(II) vic-dioxime complexes containing branched thioether with alkyl chains of different lengths: synthesis and characterization

vic-Dioxime ligands (LH₂) containing branched alkylthioether chains of different length have been prepared from (E,E)-dichloroglyoxime and corresponding thiol derivatives. Mononuclear Ni(II) complexes (5a–5c) were synthesized in ethanol by reacting NiCl₂ · 6H₂O with new ligands (4a–4c) in the presence of KOH. Branched alkylthioether moieties appended at the periphery of the oxime provide solubility for the vic-dioxime complexes in common organic solvents. The compounds have been characterized by elemental analyses, FT-IR and UV-Vis spectroscopy, ¹H- and ¹³C-NMR, and ESI-Mass spectrometry. While 5a and 5b are solid at room temperature, 5c is obtained as an orange viscous liquid. The thermal stabilities of the complexes were determined by thermogravimetric analysis.     

Studies on Spiroheterocycles,Part II: Heterocyclization of the Spiro Compounds Containing Cyclohexanone and Thiobarbituric Acid with Different Bidentate Nucleophilic Reagents

The reaction of thiobarbituric acid with different diarylidene ketones 1a–c yields the spiro compounds 2a–c. The diarylidene derivatives 3a–c are synthesized by the condensation of spiro compounds 2a–c with different aldehydes. A series of spiro heterocycles compounds 4a–l, 5a–l, 6a–l, 7a–l, 8a–l, and 9a–l are synthesized from the diarylidene compounds. The structures of the compounds are ascertained from their analytical and spectral data. Some of the compounds are screened for their biological activities.     

One-pot synthesis of novel 1,2,3-triazole-pyrimido[4,5-c]isoquinoline hybrids and evaluation of their antioxidant activity

A series of novel pyrimido[4,5-c]isoquinolines (3a–3h) and 1,2,3-triazole-coupled pyrimido[4,5-c]isoquinolines (4a–4h) were synthesized in good to excellent yields in the one-pot method. The reaction of 6-amino-1,3-dimethyluracil with different 2-iodo benzoyl chlorides using Pd catalyst in dimethylformamide afforded corresponding pyrimido[4,5-c]isoquinolines (3a–3h). One-pot reaction of pyrimido[4,5-c]isoquinolines with propargyl bromide and benzyl azide in THF at room temperature furnished 1,2,3-triazole-coupled pyrimido[4,5-c]isoquinoline (4a–4h). In vitro antioxidant activity examination revealed that compounds 4d and 4c found to exhibit potent antioxidant activity as compared to the standard drug Trolox with IC₅₀ values 6.02?±?0.6 and 12.18?±?0.9?µM, respectively.     

Synthesis,characterization, and transfer hydrogenation of Ru(II)-N-heterocyclic carbene complexes

A new series of ruthenium(II) N-heterocyclic carbene complexes [RuL^1,2,3(p-cymene)Cl₂] (3a–c) (where L is a N-heterocyclic carbene), have been synthesized via transmetalation. The new ruthenium(II)-NHC complexes were applied to transfer hydrogenation of acetophenone derivatives and aldehydes using 2-propanol as a hydrogen source and KOH as a co-catalyst. The results show that the corresponding alcohols could be obtained in good yield with high catalyst activity (up to 100%) under mild conditions. [RuL¹(p-cymene)Cl₂] (3a) is much more active than the other complexes in transfer hydrogenation. Reactions, catalyzed by 3a–c, showed the highest reaction rates and yields of alcohol when the substrates bear more electron-withdrawing substituents. All new compounds were characterized by IR, elemental analysis, LC–MS (ESI), and NMR spectroscopy.     

Synthesis and Spectral Characterization of Some New 4-(2,6-Diarylpyridin-4-yl)-2H-chromen-2-ones

Some new 4-(2,6-diarylpyridin-4-yl)-2H-chromen-2-one derivatives 5a–l have been synthesized by reacting 4-(3-oxo-3-arylprop-1-enyl)-2H-chromen-2-ones 3a–c with appropriate 1-(2-oxo-2-arylethyl)pyridinium bromide salt 4a–d in the presence of ammonium acetate in refluxing glacial acetic acid. The newly synthesized compounds have been characterized by elemental and spectral analysis.     

Reaction of 2-imino-2H-chromene-3-carboxamide with some phosphorus esters: Synthesis of some novel chromenes containing phosphorus heterocycles and phosphonate groups and their antioxidant and cytotoxicity properties

Abstract

Novel chromenyl α-aminophosphonic acid 4 and dialkyl chromenyl phosphonate 6 have been obtained. In addition, some novel types of chromene fused with phosphorus heterocycles such as chromeno[4,3-c][1,2]azaphospholes 5 and 7, chromeno[2,3-d][1,3,2]diazaphosphinine 8 and 1,2-oxaphosphinino[3,4-c]pyridine 10 have been synthesized. The methodology depended on treatment of 2-imino-2H-chromene-3-carboxamide (1) with some phosphorus esters. The synthesized compounds were evaluated for antioxidant and cytotoxic activities. Among the synthesized compounds, compound 5 exhibited the most antioxidant activity with IC₅₀ = 2.8?μg/mL in comparison with ascorbic acid as standard antioxidant. Also, compound 5 had significant cytotoxic effects against four cancer cell lines. Its IC₅₀ values ranged between 4.96 and 7.44?μg/mL in comparison to doxorubicin (IC₅₀ = 0.426–0.493?μg/mL).     

SYNTHESIS AND REACTVITY OF N-[N-PHOSPHORAMIDO-1H-BENZIMIDAZOL-2-YL] IMIDATES

N-(-1H-Benzimidazol-2-yl) imidates 1a–c react with chlorophosphoramide to give the N-[-1-N,N,N′,N′-tetramethylphosphoramidoyl-1H-benzimidazol-2-yl]-imidates 2a–c or with dichlorophosphoramide to yield the bis[(N-1-benzimidazol-2-yl)-imidate] phosphoramide derivatives 3a–b. The reaction of compounds 2a–c toward primary amines is studied. The obtained amidine derivatives 4a–b were unambiguously characterized by different spectroscopic techniques (IR, ¹H, ¹³C, and ³¹P NMR, and in some cases MS).     

N-(5-三氟甲基-1,3,4-噻二唑-2-基)-N'-芳酰基脲的合成、晶体结构及生物活性

通过2-氨基-5-三氟甲基-1,3,4-噻二唑与芳酰基异氰酸酯反应, 合成了10种新的芳酰基脲．它们的结构经元素分析、红外光谱、核磁共振氢谱进行了表征．并用X射线单晶衍射法测定了化合物2j的晶体结构, 结果表明, 该化合物晶体属三斜晶系, 空间群为P-1, a＝0.54191(15) nm, b＝0.7766(2) nm, c＝1.7161(5) nm, α＝98.668(5)°, β＝95.103(5)°, γ＝101.070(5)°, V＝0.6955(3) nm³, Z＝2, D_c＝1.653 g/cm³, F(000)＝352, μ＝0.289 mm^–1．初步的生测试验结果表明一些目标化合物具有良好的植物生长调节活性．     

3-(4-β-D-吡喃阿洛糖苷-苯基)-4-芳基-5-芳基-1,2,4-噁二唑啉的合成及其镇静活性的研究

以豆腐果苷为原料, 与盐酸羟胺缩合反应生成4-β-D-吡喃阿洛糖苷-苯甲醛肟(2), 2与次氯酸叔丁酯发生取代反应生成4-β-D-吡喃阿洛糖苷-α-氯苯甲醛肟(3); 再将3与Schiff碱通过1,3-偶极环加成生成一系列3-(4-β-D-吡喃阿洛糖苷-苯基)-4-芳基-5-芳基-1,2,4-噁二唑啉(5a～5h). 3和 5a～5h共9个化合物均未见文献报道, 其结构经¹H NMR, IR和MS (HRMS)加以确认, 并对5a～5h进行了药理活性筛选. 结果表明, 部分化合物具有良好的镇静活性. 其中, 化合物5g (200, 100 mg•kg^－1)和5h (200, 100 mg•kg^－1)与豆腐果苷相比较具有更强的活性.     

A conventional and solid-state synthesis,biological activity,and molecular docking studies of 6-arylbenzo[4,5]imidazo[1,2-a] [1,8]naphthyridin-10-ols

An effective, practical, and simple approach toward the preparation of highly-substituted 6-arylbenzo[4, 5]imidazo[1,2-a][1,8]naphthyridin-10-ols 6(a-h) by the reaction of 3-aryl-1,8-naphthyridin-2-amines 3(a-h) with benzoquinone 4 in acid catalyzed cyclization under solid-state method, as well as conventional conditions, has been described. The products are obtained in good yields and in a solid of high purity. The major advantages of solid states are easy workup, low costs, short reaction time, good efficacy, and environment-friendly procedure. The newly synthesized compounds were thoroughly characterized using spectral data and elemental analyses. All compounds were screened for their biological evaluation. Predominantly 6b and 6c compounds showed the highest antibacterial activity. Moreover, all the synthesized compounds were docked against topoisomerase II DNA gyrase enzyme.     

Synthesis and Spectroscopic Properties of S-,O-Substituted Naphthoquinone Dyes

New S-,O-substituted naphthoquinone compounds (3a, 4b, 6, 7c, 9d, 10, 12, 13c, 14d, 15) were synthesized via vinilic substitution. 2,3-Dichloro-1,4-naphthoquinone gave 3a and 4b with 4,4′-thiobisbenzenethiol, respectively. Compounds 6 and 7c were obtained from the reaction of 2,3-dichloro-1,4-naphthoquinone with cyclohexylmercaptane. The compounds 9d and 10 were prepared from the reaction of 2,3-dichloro-1,4-naphthoquinone with 6-mercapto-1-hexanol. Compounds 12, 13c, 14d, and 15 were synthesized from the reaction of 2,3-dichloro-1,4-naphthoquinone with 1,6-hexanedithiol. Their structures were characterized by micro analysis, FT-IR, ¹H NMR, ¹³C NMR, MS, UV-Vis, and fluorescence spectroscopy.     

Iron(III), nickel(II) and zinc(II) complexes based on acetophenone-S-methyl-thiosemicarbazone: synthesis,characterization, thermogravimetry,and a structural study

New complexes, [Fe(L)Cl], [Ni(L)], and [Zn(L)C₂H₅OH] (1–3), were synthesized by template reaction of 2-hydroxy-acetophenone-S-methyl-thiosemicarbazone with 2-hydroxy-benzaldehyde. The compounds were characterized by elemental analysis, magnetic measurements, FT-IR, ¹H NMR, UV–visible, and ESI–MS spectra. In these complexes, the ligand is coordinated to the metal ion as dinegatively charged tetradentate chelating agents via the N₂O₂ donor set. The iron(III) and zinc(II) complexes exhibit square pyramidal geometry whereas the nickel(II) complex has a square planar geometry. The crystal structure of 1, determined by X-ray diffraction method, indicates that 1 crystallizes in the monoclinic space group P21/c with Z = 4. Thermal decompositions of the compounds have been investigated using TGA in air.