Synthesis, structures and biological activity research of novel ferrocenyl-containing 1H-1,2,4-triazole derivatives

Novel ferrocene-containing propenones have been synthesized from acetylferrocene via a Mannich-type intermediate. Sequential condensation cyclization of these propenones with phenylhydrazine afforded highly substituted 4,5-dihydropyrazole derivatives, which structures have been characterized by spectra data and single crystal X-ray diffraction analysis. In addition, these new ferrocene-containing derivatives have been evaluated for in vitro fungicidal activities against five selected fungi.     

Synthesis and biological evaluation of novel 1,2,4-triazole containing 1,2,3-thiadiazole derivatives

A series of novel 1,2,4-triazoles containing 1,2,3-thiadiazole derivatives were designed and synthesized. Their structures were confirmed by melting points, IR, 1H NMR, and elemental analysis and ESI-MS or HRMS. Preliminary bioassays indicated that these compounds exhibited very good insecticidal activity against Aphis laburni at 100 μg/mL, with mortality no less than 95%. Compounds 6a, 6c, 6f, 61 showed higher curative activity against TMV and compound 6h showed a higher induction effects against TMV in vivo at 100 μg/mL. Collectively, our data demonstrate a new strategy for control of insects and viruses.     

Basicity and structure of 1, 2, 4-triazole derivatives

Basicity constants for a number of 1, 2, 4-triazole derivatives are determined. An assumed amine structure for 3-amino-1, 2, 4-triazoles in aqueous solution is demonstrated. It is assumed that protonization of 3- and 4-amino-1, 2, 4-triazoles occurs at the nitrogen in the heterocyclic ring, and not at the amino group.     

Microwave-assisted synthesis of novel fluorinated 1,2,4-triazole derivatives,and study of their biological activity

Microwave irradiation was used for synthesis of a series of novel fluorinated 1,2,4-triazole derivatives. The molecular structures of the compounds were determined by use of ¹H NMR and FTIR spectroscopy and MS and HRMS. Study of their biological activity showed most of the compounds had good herbicidal activity.     

Synthesis,biological evaluation,and molecular docking studies of novel 1,2,3-triazole derivatives as potent anti-inflammatory agents

In the present study, a novel series of 1,2,3-triazole derivatives have been synthesized using click chemistry approach. The structures were confirmed by spectroscopic methods. The products were screened for their in vivo anti-inflammatory activity. The tested compounds 6a, 6f, 6g, 6i, 6j, 6n, and 6p, demonstrated potent anti-inflammatory activity compared to the reference drug ibuprofen. Molecular docking studies of these 1,2,3-triazole derivatives into the active site of human cyclooxygenase-2 (COX-2) (PDB code 4PH9) demonstrated good affinity for the enzyme and suggested binding properties similar to ibuprofen.     

Synthesis of nitrogen-containing heterocycles. 4. A facile route to new 1, 2, 4-triazole derivatives

The reaction of amino-N(4),N(4)-dimethylaminornethylenehydrazones 1 of some aliphatic carbonyl compounds with ethyl ethoxymethylenecyanoacetate 2 gave directly symmetrical gem-bis(3-dimethylamino-1, 2, 4-triazol-1-yl)alkanes 4 and (3-dimethylamino-1, 2, 4-triazol-1-yl)alkenes 5 at room temperature, with the former being major product. On the other hand, the reaction of amino- N (4)-methylaminomethylenehydrazone homologue 1 of aliphatic ketone with 2 gave ethyl 2-alkyl-5-methylamino[1, 2, 4]triazolo[1, 5-c]pyrimidine-8-carboxylate 7 as the only product with elimination of alkane.     

Synthesis and anti-inflammatory properties of novel 1,2,4-triazole derivatives

This research is based on the pharmacological activity of the triazole ring. In the last decade much work has been conducted on the triazole ring. Scientists have developed many new compounds based on this structure and screened them to obtain molecules with good pharmacological activity. In this research starting from 4-amino-5-(4-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione, a series of new 1,2,4-triazole derivatives were prepared. Results revealed that two compounds had anti-inflammatory potency after 4 h greater than that of indomethacin whereas another derivative had less potency than indomethacin.     

Synthesis and biological activity of some novel derivatives of 4-amino-3-(D-galactopentitol-1-yl)-5-mercapto-1,2,4-triazole

To discover new 1,2,4-triazole derivatives which may possess significant biological activities, we synthesized a series of novel 6-aryl-3-(D-galactopentitol-1-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines and 4-(arylmethylidene)amino-5-(D-galactopentitol-1-yl)-3-mercapto-4H-1,2,4-triazoles from 4-amino-3-(D-galactopentitol-1-yl)-5-mercapto-1,2,4-triazole. All the title compounds were characterized by elemental analysis, IR, 1H- and 13C-NMR. Plant growth-regulating activity tests showed that these compounds have remarkable effects on the growth of radish and wheat.     

Synthesis and biological activity of novel 2-methyl-4-trifluoromethyl-thiazole-5-carboxamide derivatives

Nine novel 2-methyl-4-trifluoromethylthiazole-5-carboxamide derivatives were designed and synthesized utilizing ethyl 4,4,4-trifluoroacetoacetate as a starting material. Subsequently, the biological activity of the compounds was evaluated in the greenhouse. Results indicated that all of the compounds have some fungicidal and insecticidal activity but no herbicidal activity. Compound 1 has fungicidal activity with 90% control of tomato late blight at 375 g ai/ha, while two compounds 2F and 2H show insecticidal activity with 80 and 100% control, respectively, against potato leafhopper at 600 g ai/ha.     

The preparation of N- and C-halogen derivatives of 1, 2, 4-triazole

The action of halogens in an alkaline medium on 1, 2, 4-triazoles has given their N-chloro, N-bromo, and N-iodo derivatives. The formation of C-halogen derivatives of some 1, 2, 4-triazoles from their N-halogen derivatives has been studied, and also the action of halogens on 1, 2, 4-triazoles at elevated temperatures. It has been shown that N-bromo-1, 2, 4-triazoles very readily form 1, 2, 4-triazole and 3, 5-dibromo-1, 2, 4-triazole in approximately equimolar proportions. N-Chloro-1, 2, 4-triazole is more stable to the action of heat and forms 3-chloro-1, 2, 4-triazole with a yield of 40%. It was impossible to convert N-iodo-1, 2, 4-triazole into C-derivatives.     

Synthesis and biological evaluation of novel piperidin-4-ol derivatives

Abstract  

A series of novel piperidin-4-ol derivatives were designed, synthesized, and evaluated for potential treatment of HIV. The compounds were obtained via an efficient synthetic route in excellent yields and have been characterized by ¹H NMR, ¹³C NMR, MS, and elemental analysis. The CCR5 antagonistic activities of the compounds have also been evaluated.     

Infrared absorption spectra of some C-halogenated 1, 2, 4-triazole derivatives

The IR absorption spectra of 3(5)-halo and 3, 5-dihalo derivatives of 1, 2, 4-triazoles and of their potassium and silver salts as solids in the 3500-400 cm^–1 range were studied. The characteristic absorption bands of the triazole ring and the C-H and N-H bonds were established.     

Synthesis, reactivity and biological activity of novel bisbenzofuran-2-yl-methanone derivatives

Preparation of bisbenzofuran-2-yl-methanone (1), the corresponding ketoxime 4, semicarbazone and thiosemicarbazone 3a and 3b, ether derivatives of the ketoximes 5a-j and the alcohol 2 are described. These substances have been prepared in excellent yields. All the synthesized compounds except 5i have been tested against five different microorganisms and some of them were found to be active against some of the species studied.     

Synthesis,anticancer screening,and in silico ADME prediction of novel 2-pyridones as Pim inhibitors

A novel series of 26 substituted N-(2-ethylphenyl)-2-oxo-pyridine-3-carbonitriles have been designed and synthesized via one-pot synthesis of various aromatic aldehydes, different aromatic acetophenones, and 2-cyano-N-(2-ethylphenyl)acetamide 1 . Moreover, cytotoxicity of the target compounds was evaluated by NCI, which selected 14 compounds for one-dose screening. Among them, compound 21 was selected for five-dose screening, which confirmed its potency against most of cancer cell lines. This compound elicited selectivity profile against human cell line WI-38. Cell cycle analysis was carried out, revealed that compound 21 is an apoptosis inducer causing cell cycle arrest at G2/M. Further exploration on the mode of action by evaluating its effect against Pim-1, Pim-2, and Pim-3 demonstrated its inhibitory effect on Pim-1 and Pim-3 rather than Pim-2. Molecular docking showed that compound 21 binds with high affinity to the active site of Pim-1 enzyme through three hydrogen bonds and two arene-H bonds.     

Synthesis and antimicrobial activities of some novel 1,2,4-triazole derivatives

In the present investigation, a series of new Schiff bases 4a–f were synthesized by the condensation of N-[(4-amino-5-sulfanyl-4H-1,2,4-triazol-3-yl)methyl]-4-substituted-benzamides 3a–b with various substituted aromatic aldehydes in ethanol–dioxane mixture using catalytic amount of sulfuric acid. The starting materials 3a–b were in turn synthesized by the fusion of benzoyl glycine/substituted benzoylglycine with thiocarbohydrazide. Newly synthesized compounds were characterized by IR, NMR, mass spectra and elemental analyses. All the compounds were evaluated for their antibacterial and antifungal activity using the Minimum Inhibition Concentration (MIC) method by serial dilution technique. Few of the compounds were found to be biologically active.     

Synthesis and biological activities of novel 2-amino-1,3-thiazole-4-carboxylic acid derivatives

A series of novel 2-amino-1, 3-thiazole-4-carboxylic acid derivatives were designed and synthesized. Their structures were confirmed by melting points, IR, ¹H NMR, ¹³C NMR, and HRMS or elemental analysis. Biological activities of all title compounds including fungicidal activity and antivirus activity were evaluated systematically. Preliminary bioassays indicated that these compounds exhibited good fungicidal activity at 50 μg/mL, compounds 4b and 4i exhibited over 50% activity against six fungi tested. Most compounds showed good activity against TMV with different models in vivo at 100 μg/mL. Compounds 4c and 4e stood out with high effects against TMV in vivo in all models tested, including protective, inactivative, curative, and inductive activities. These data demonstrate a new strategy for fungi and virus control.     

Naproxen derivatives: Synthesis,reactions, and biological applications

This review describes the synthesis and reactions of naproxen derivatives and highlights the effects of compounds containing the naproxen moiety in important biological applications.