A new dimeric secoiridoids derivative,japonicaside E,from the flower buds of Lonicera japonica

A new dimeric secoiridoids derivative, named japonicaside E, together with six known compounds were isolated from the flower buds of Lonicera japonica. The structures of these compounds were elucidated by the analyses of mass spectrometry and NMR spectroscopy. All compounds were evaluated for anti-inflammatory activity in vitro.     

Design,Synthesis, and Biological Screening of Novel Anthranilic Diamides

Three series of new anthranilic diamide derivatives containing sulfide, N‐cyanomethylsulfilimine, and N‐cyanomethylsulfoximine groups were designed and synthesized by combining the active substructures of anthranilic diamides and sulfoxaflor. The structures of all newly synthesized compounds were confirmed by IR and ¹H/¹³C‐NMR, and some of them were confirmed by elemental analysis or HRMS too. The synthesized compounds were screened for their insecticidal and fungicidal activities. Bioasssay results indicated that some of the synthesized compounds possessed certain degrees of insecticidal activity against Mythimna separata. However, some compounds exhibited good fungicidal activity against Sclerotinia sclerotiorum.     

The Synthesis of Novel S-, S,S-, S,S,S-, and N,S-Substituted Nitrodienes from Polyhalonitrodienes and Thiols

Abstract

The novel S-, S,S-, and S,S,S-substituted nitrobutadienes were synthesized from the reactions of 2-nitrobutadiene compounds with some thiols. The new N,S-substituted nitrobutadienes were obtained from the reaction of the mono-thiosubstituted butadienes with morpholine, thiomorpholine, homopiperazine, and piperazine derivatives. The structures of new compounds were determined by spectroscopic techniques.

GRAPHICAL ABSTRACT      

Synthesis and Antioxidant Evaluation of Some Novel Thiophene,Pyrazole, Chromene,Pyrazolotriazine Derivatives Bearing Sulfonamide Moiety

As a part of ongoing studies in developing new potent antioxidant agents, N‐[4‐(aminosulfonyl)phenyl]‐2‐cyanoacetamide ( 3 ) was utilized as key intermediate for the synthesis of some new thiophene, chromene, and pyrazolotriazine pyridine derivatives. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, ¹H‐NMR, and mass spectral data. Representative compounds of the synthesized products were tested and evaluated as antioxidant. Compounds 7 and 30 are promising compounds.     

Design,synthesis, and anticancer activity evaluation of novel aziridine-1,2,3-triazole hybrid derivatives

Some new 1-aryl-4-[(aziridine-1-yl)diaryl-methyl]-5-methyl-1H-1,2,3-triazole derivatives 7j–s were synthesized by the one-pot reaction of diaryl-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)methanol compounds 6j–s formed from 1-aryl-5-methyl-1H-1,2,3-triazole-4-carboxylic acid derivatives. The new compounds 7j–s and 6j–s are investigated by ¹H and ¹³C NMR, MS, and IR. The anticancer activity of the synthesis target compounds was evaluated against human leukemia (HL-60) cells and human hepatoma G2 cells. Some of the compounds were highly efficient. The ¹H-NMR signals of the aziridine-ring cis-H/trans-H protons were found to be two group peaks at 1.800–1.884 and 1.183–1.327?ppm.     

Synthesis,Crystal Structure,and Biological Activity of Novel Anthranilic Diamide Insecticide Containing Propargyl Ether Group

In search of environmentally benign insecticides with high activity, low toxicity, and low residue, a series of novel anthranilic diamide containing propargyl ether were designed and synthesized. All compounds were characterized by ¹H NMR spectroscopy, high‐resolution mass spectrometry, or elemental analysis. The single crystal structure of 18g was determined by X‐ray diffraction. The insecticidal activities against Lepidoptera pests of the new compounds were evaluated. Their insecticidal activities against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that most of the compounds showed moderate to high activities at the tested concentration.     

Green synthesis,antibacterial, antiviral and molecular docking studies of α-aminophosphonates

Abstract

An efficient method for the synthesis of α-aminophosphonate derivatives has been developed with different functional groups under catalyst and solvent free conditions at room temperature in both conventional and ultrasonication methods. Ultrasonication method offers excellent yields within shorter reaction times. All the title compounds 4a–l were tested for their antibacterial, antiviral activity using Gram-positive bacteria (Staphylococcus aureus, and Bacillus subtilis), Gram-negative bacteria (Klebsiella pneumoniae and Escherichia coli) and NDV infected embryonated eggs (in ovo) and NDV infected BHK-21 cell lines (in vitro) respectively. Besides, molecular docking studies were also carried out to the title compounds against Hemagglutinin-neuramidase enzyme to determine the therapeutic binding efficacy of the ligands synthesized. The results indicated that, among the title compounds, compounds such as 4f, 4l, 4k, 4b, 4i and 4h have shown high content of antibacterial and antiviral activity than the rest of the compounds and the level activity was high when compared to the standard, ribavirin. Based on the results, it is concluded that, the reported α-aminophosphonates will open new vistas and stands as a new generation of antiviral and antibacterial drug candidates in future.     

Design,Synthesis, and Biological Evaluation of Novel 1,3,4‐Thiadiazolylpyrazolines Compounds Containing Ferrocene

The synthesis of 1,3,4‐thiadiazole skeleton compounds exhibiting high fungicidal activities has been demonstrated. Thirteen novel 1,3,4‐thiadiazolyl‐pyrazolines compounds containing ferrocene were designed and synthesized from the ferrocenylchalcones intermediates 3a – 3m and the 2‐hydrazino‐5‐phenyl‐1,3,4‐thiadiazole intermediate 8 . All compounds were characterized by ¹H NMR, ¹³C NMR, FT‐IR spectra, and HR‐MS, and the structure of one of the new compounds N‐(4‐phenyl‐1,3,4‐thiadiazol‐2‐yl)‐3‐ferrocenyl‐5‐phenyl‐pyrazoline 9a was further determined by X‐ray diffraction analysis. The preliminary results of a biological activity assay indicated that all the title compounds exhibited significant fungicidal activities against Pythium solani, Gibberella saubinetii, and Gibberella nicotiancola. Furthermore, compounds 9e and 9h displayed even higher fungicidal activities against the three fungal species compared with the control drug pyraclostrobin.     

Two new compounds,Talaromycin A and B,isolated from an endophytic fungus,Talaromyces aurantiacus

Abstract

Two new compounds Talaromycin A (1) and Talaromycin B (2) were isolated from a liquid culture of Talaromyces aurantiacus. The structures of 1 and 2 were elucidated by IR, MS, 1D and 2D NMR spectra and comparison of the experimental and calculated electronic circular dichroism spectra. Additional known compounds (3–6) were also isolated. These compounds were tested for monoamine oxidase, acetylcholinesterase and PI3K inhibitory activity, but showed only weak activity.     

Microwave assisted synthesis of 4-methyl-3-arylpyrano[2,3-f]chromen-2(8H)-one derivatives,evaluation of antiproliferative,and antimicrobial activities

A series of new 4-methyl-3-arylpyrano[2,3-f]chromen-2(8H)-one derivatives were designed and synthesized through an efficient, an eco-friendly manner under microwave irradiation and conventional heating methods. Structures of final compounds established based on IR, NMR and mass spectral analysis. The final target compounds were screened for their in vitro antiproliferative activity by taking cisplatin as a reference, Further, antibacterial activity by taking strains such as Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumonia and Escherichia coli. Furthermore, antifungal activity screened with Aspergillus niger, Aspergillus flavus and Fusarium oxysporum strains. Many compounds results good activity.     

Synthesis,design, and antimicrobial activity of pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidinones based on quinoline derivatives

The pyrido[2,3-d]pyrimidine moieties are one of the most biologically widespread heterocyclic compounds as antimicrobial, antioxidant, antitubercular, antiviral and anti-inflammatory. Hence, we synthesized an efficient new series of 2-thioxo-pyrido[2,3-d]pyrimidinone, 2-hydrazinyl-(quinolin-2-yl)pyrido[2,3-d]pyrimidinone,N′-(quinolin-2-yl)-pyrido[2,3-d]pyrimidine-(formo/aceto)-hydrazide and substituted-(quinolin-2-yl)pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidinone derivatives. The characterization of new compounds was corresponded by using spectroscopic techniques, IR, NMR and Mass spectra. In vitro, all compounds were evaluated as antimicrobial activity compared with cefotaxime sodium and nystatin as the standard drug. This work deals with the exploration of the new heterocyclic compounds and medicinal diversity of quinoline-pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives that might pave the way for long in the discovery of therapeutic medicine for future drug design.     

Synthesis,Crystal Structures,and in Silico Toxicity Prediction of Thienopyridine Phosphoramidates

New thieno[2,3-b]pyridine phosphoramidates compounds were synthesized and characterized by infrared; ¹H, ¹³C, and ³¹P NMR spectroscopy; and high-resolution mass spectrometry. The products were obtained in good yields (64–82%) under mild conditions by nucleophilic aromatic substitution reaction of aminoalkylphosphoramidates over 4-chlorothieno[2,3-b]pyridine-5-carbonitrile. The crystal structures of two compounds were solved by x-ray diffraction and showed a network of intermolecular interactions involving phosphoramidate groups. Druglike properties and toxicity of the new compounds were studied with the help of the software Molinspiration, Osiris, and Toxtree, and were compared with the standard drugs amphotericin B, miltefosine, benznidazole, and nifurtimox.

[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.]     

Synthesis and antimicrobial evaluation of some novel dithiolane,thiophene, coumarin,and 2-pyridone derivatives

Novel 2-cyano-N-[1-(naphtha-2-yl)ethylidene] acetohydrazide 1 was utilized as key intermediate for the synthesis of some new dithiolane, thiophene, coumarin, 2-pyridone, and other related products containing a hydrazide moiety. Newly synthesized compounds were characterized by elemental analyses and spectral data (IR, ¹H NMR and mass spectra). The antimicrobial activity of the synthesized compounds was evaluated.     

Two new polyhydroxysterols produced by Fusarium solani,an endophytic fungus from Chloranthus multistachys

A highly antagonistic endophytic fungus, designated strain CL39, was originated from the leaves of Chloranthus multistachys collected in Wulong of Chongqing municipality of China in November 2015. The strain was identified as Fusarium solani based on morphological characteristics, 5.8S gene and internal transcribed spacer sequence analysis. Two new compounds, 2β, 9α-dihydroxy-5α-methoxyergosta-7, 22-diene (1), 2β, 6β-dihydroxy-5α-methoxyergosta-7, 22-diene (2) have been isolated from the culture broth of the strain. Structures of the new compounds were elucidated by detailed analysis of their spectroscopic data aided by the comparison with reported data of related derivatives, and found to belong to the polyhydroxylated steroids with a hydroxyl at C-2 instead of C-3, a rare structure among the steroids. The extract of this strain and all isolated compounds were evaluated for their antagonistic activities.     

Two New Metabolites,Epoxydine A and B,from Phoma sp.

The new compounds, epoxydines A and B ( 1 and 2 , resp.), along with the known and related metabolites, 3 – 6 , were isolated from the fungal endophyte Phoma sp. The structures of the new compounds were elucidated by detailed spectroscopic analysis, and the relative configuration of 1 was confirmed by ROESY experiments. Preliminary studies indicated that compounds 2 – 5 possess good antibacterial, antifungal, and algicidal properties. Similarly, compound 1 showed antifungal and algicidal, and compound 6 antibacterial and algicidal properties.     

Synthesis,biological evaluation,and docking study of a series of 1,4-disubstituted 1,2,3-triazole derivatives with an indole-triazole-peptide conjugate

A series of new compounds containing an indole-triazole - peptide conjugate were designed as potential agents possessing the dual anti-bacterial and anticancer activities. Accordingly, 20 compounds were prepared via a multi-step synthesis involving the copper-catalyzed azide-alkyne cycloaddition (CuAAC) as a key step in moderate to high yield. All the synthesized compounds were purified by chromatographic techniques and characterized by IR, ¹H and ¹³C NMR and mass spectral data. The synthesized derivatives were screened for their antimicrobial activities against one gram-positive (Staphylococcus aureus) and three gram-negative (Escherichia coli, Klebsiella pneumonia, and Proteus vulgaris) bacteria using an agar-well diffusion method. Most of the compounds showed moderate to reasonable antibacterial activities especially the compound 9e that showed good activities against all the strains. The potential of DNA gyrase inhibitory activity of this compound was assessed by using molecular docking studies in silico carried out using Autodock Vina software. The low ΔG_bind value (−9.4 Kcal/mol) of compound 9e suggested its good interactions with the target protein in silico. The cytotoxic activities of some of the compounds synthesized were evaluated via a MTT assay using the human lung cancer cell line A549. Several compounds showed promising activities among which compound 9b , 9k, and 9e showed low IC₅₀ values.     

Design,Synthesis, and Antifungal Activities of New β‐Methoxyacrylate Analogues

Strobilurins have become one of the most important classes of agricultural fungicides. To search for new strobilurin derivatives with high activity against resistant pathogens, a series of new β‐methoxyacrylate analogues containing substituted pyrimidine in the side chain with strobilurin pharmacophore were synthesized and their biological activities were tested. The compounds were confirmed and characterized by ¹H‐NMR, elemental analysis and mass spectroscopy. The bioassays indicated that most of the compounds 1 exhibited potent antifungal activities against Colletotrichum orbiculare, Botrytis cinerea Pers and Phytophthora capsici Leonian at a concentration of 50 μg mL^?1. Notably, compound 1b (R = 2,5‐dimethylphenyl) showed better antifungal activity against all the tested fungi than the commercial strobilurin fungicide azoxystrobin.     

Two new compounds of Penicillium polonicum,an endophytic fungus from Camptotheca acuminata Decne

Abstract

To discover novel structural compounds which are producted by endophytic fungi, a primary chemical profiling of Camptotheca acuminata Decne derived endophytic fungus Penicillum polonicum had been taken. Two new compounds β-lactone polonicin A (1) and enoic acid polonicin B (2) together with seven known compounds 3-9 were isolated from Penicillum polonicum obtained from C. acuminata. The structures of the new compounds 1 and 2 were identified by modern spectrum technology including detailed 1D, 2D NMR and MS data analyses. When tested against HepG2 hepatocellular carcinoma (HCC) cell lines, compounds 4-8 showed moderate anti-HCC activity. In addition, compound 1-3 have effects on increasing GLUT4 translocation and glucose uptake in vitro. Compound 1 showed the strongest glucose uptake and GLUT4 translocation activities in rat skeleton (L6) myoblast cell line with enhancements of 1.8 and 2.1 folds respectively compared to the control.     

Antimicrobial activity of amino acid,imidazole, and sulfonamide derivatives of pyrazolo[3,4-d]pyrimidine

Derivatives of pyrazolo[3,4-d]pyrimidine with amino acid 3a–d , imidazole 4a–d , carbonyl 6–9 , pyrazole 10 , pyrazolone 11 , and sulfonamide 12–17 moieties were synthesized. Structure of the new compounds were established by their elemental analyses and spectral data. Some of the synthesized compounds were tested in vitro for their antimicrobial activity. Compounds 4b, 12 , and 16 were almost as potent as the standard antibiotic Chloramphenicol as positive control. Also, compounds 3b, 3c, 12 , and 16 were nearly as active as Terbinafine as positive control. © 2003 Wiley Periodicals, Inc. 15:57–62, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/.hc10212     

Synthesis,reactions, and biological study of some new thienopyrimidine derivatives as antimicrobial and anti‐inflammatory agents

Pyrimidine and thienopyrimidine derivatives play a very important role in organic chemistry because of their wide applications as bioactive compounds with multiple biological activities. However, a literature survey revealed that the merger of different groups in the thieno[2,3‐d]pyrimidine heterocyclic ring enhances its antibacterial, antifungal and anti‐inflammatory activities. This encouraged us to prepare a new series of thieno[2,3‐d]pyrimidine heterocyclic compounds and to test them as antimicrobial and anti‐inflammatory agents. These compounds have shown remarkable activity toward fungi, bacteria, and inflammation. Thus, these compounds have been prepared by the chloroacylation of 5‐amino‐4‐phenyl‐2‐(p‐tolylamino)thieno[2,3‐d] pyrimidine‐6‐carboxamide ( 4 ) using chloroacetyl chloride under neat condition to afford the target compound ( 6 ), which was used as precursor for the synthesis of a number of bioactive compounds. Thus reaction of the chloromethylpyrimidine derivative ( 6 ) with triphenylphosphine in dry benzene gave the corresponding ((4‐oxo‐9‐phenyl‐7‐(p‐tolylamino)‐3,4‐dihydropyrimido[4′,5′:4,5]thieno[2,3‐d]pyrimidin‐2‐yl)methyl) triphenylphosphonium chloride ( 7 ). Compounds 8a – 8c and 9a – 9c were obtained by the reaction of 7 with some selected aromatic aldehydes and ketones in methanol and sodium methoxide under Wittig reaction condition. The structures of the all new synthesized compounds were established on the basis of their analytical and spectral data (IR, ¹H NMR, ¹³C NMR, and MS).