4-hydroxy-2H-1,2-benzothiazine-3-carbohydrazide 1,1-dioxide-oxalohydrazide (1:1): X-ray structure and DFT calculations

The title compound, 4-hydroxy-2H-1,2-benzothiazine-3-carbohydrazide 1,1-dioxide-oxalohydrazide (1:1), is determined using X-ray diffraction techniques and the molecular structure is also optimized at the B3LYP/6-31G(d,p) level using density functional theory (DFT). The asymmetric unit consists of four independent molecules. The oxalohydrazide molecules have the centre of symmetry at the mid-point of the central C-C bond. Each thiazine ring adopts a half-chair conformation. Intermolecular C-H...O, N-H...O and N-H...N hydrogen bonds produce R ₂ ² (10), R ₂ ² (13), R ₃ ³ (12) and R ₃ ³ (15) rings, which lead to one-dimensional polymeric chains. An extensive three-dimensional supramolecular network of N-H...N, N-H...O, C-H...O and O-H...O hydrogen bonds is responsible for crystal structure stabilization.     

Synthesis,anticancer, and computational studies of 1, 3, 4-oxadiazole-purine derivatives

Theophylline-7-acetic acid (acefylline) ( 3 ) and its derivatives are pharmacologically active compounds and generally recognized as bronchodilators for the treatment of respiratory diseases like acute asthma for over 70 years. In this article, synthesis of 2-((5-((1,3-dimethyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)methyl)-1,3,4-oxadiazol-2-yl)thio)-N-arylacetamides ( 10a-j ) has been reported. All the synthesized derivatives ( 10a-j) were structurally verified by FT-IR, ¹H NMR, ¹³C NMR and evaluated for their anti-cancer (using MTT assay), hemolytic and thrombolytic potential. N-(4-Chlorophenyl)-2-(5-((1,3-dimethyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)methyl)-1,3,4-oxadiazol-2-ylthio)acetamide ( 10g ) was found to be the most active against human liver cancer cell lines (Huh7) having cell viability 53.58 ± 1.28 using 100 μg/mL concentration of compound which was further in-silico modelled to describe the possible mechanistic insights for its anti-proliferative activity. The results of hemolytic and thrombolytic activities indicated that these derivatives were less toxic and hold considerable potential as a drug candidate. 2-(5-((1,3-Dimethyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)methyl)-1,3,4-oxadiazol-2-ylthio)-N-(2-fluorophenyl)acetamide ( 10c ) of the series was found to be least toxic with 0.1% hemolysis relative to ABTS (95.5%) as positive control. 2-(5-((1,3-Dimethyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)methyl)-1,3,4-oxadiazol-2-ylthio)-N-(tetrahydro-2H-pyran-4-yl)acetamide ( 10j ) exhibited potent clot lysis activity (90%) as compared to negative control DMSO (0.57%).     

Redox behavior of juglone in buffered aq.: Ethanol media

The present work reports the redox mechanism of 5-hydroxynaphthalene-1,4-dione (HND), commonly known as juglone, in buffered aqueous media having 50% of ethanol. HND followed different mechanistic routes depending upon the pH of the media and more than one pK_a were evaluated from the changes in the slope of the E_p vs. pH plot. The change of pH from acidic to neutral conditions was found to switch the mechanism from CEC to EE mechanism. Pulse techniques were utilized to determine the number of electrons involved in the oxidation and/or the reduction step and to ensure the nature of the redox process. Based upon the obtained results, an electrode reaction mechanism was proposed. Computational studies of HND supported the experimental results. UV-Visible spectroscopy was also employed for the detailed characterization of the compound in a wide range of pH and for the determination of its pK_a.     

New dimeric, trimeric and supramolecular organotin(IV) dithiocarboxylates: Synthesis, structural characterization and biocidal activities

Some new tri-, chlorodi- and diorganotin(IV) dithiocarboxylates (1–10) of 4-benzylpiperidine-1-carbodithioate ligand (L), with general formulae R₃SnL {R = n-C₄H₉ (1), C₆H₁₁ (2), CH₃ (3) and C₆H₅ (4)}, R₂SnClL {R = n-C₄H₉ (5), C₂H₅ (7), CH₃ (9)} and R₂SnL₂ {R = n-C₄H₉ (6), C₂H₅ (8), CH₃ (10)}, have been synthesized by the reaction of organotin(IV) chlorides with the ligand-salt in the appropriate molar ratio. Elemental analysis, Raman, IR, multinuclear NMR (¹H, ¹³C and ¹¹⁹Sn) and X-ray crystallographic studies have been undertaken to elucidate the structures of the complexes, both in solution and in solid state. Single-crystal X-ray diffraction study indicate trimeric, dimeric, supramolecular cyclic and supramolecular zig–zag chain structures for complexes 2, 4, 6 and 9, respectively. Square-pyramidal geometry is attributed to complex 9 on the basis of the τ value (0.4). A subsequent antimicrobial study indicates that the compounds are biologically active.     

Homobimetallic zinc(II) dithiocarbamates: synthesis,characterization and in vivo antihyperglycemic activity

This article presents structural characteristic and in vivo antihyperglycemic activities of three new homobimetallic Zn(II) dithiocarbamates (1–3) with general formula [ZnL₂]₂, where L is 4-(3-methoxyphenyl)piperazine-1-carbodithioate (1), 4-(4-methoxyphenyl)piperazine-1-carbodithioate (2) and 4-benzhydrylpiperazine-1-carbodithiaoate (3). These complexes have been characterized by elemental analysis, FT-IR, multinuclear NMR (¹H and ¹³C), and X-ray single crystal analysis. The latter technique has confirmed the homobimetallic nature of 1 and 2 in which Zn ions are linked via sulfurs to form a four-membered ring Zn₂S₂. Non-covalent intermolecular interactions give a supramolecular ladder-like zigzag chain (1) and layered structure (2). The antihyperglycemic activities revealed that the blood glucose lowering ability follows the trend: glibenclamide (83.0 mg dL^?1) > 3 (97.6 mg dL^?1) > 2 (100.4 mg dL^?1) > 1 (141.4 mg dL^?1).     

Synthesis of Novel N-Acylhydrazones and Their C-N/N-N Bond Conformational Characterization by NMR Spectroscopy

In this article, a synthesis of N’-(benzylidene)-2-(6-methyl-1H-pyrazolo[3,4-b]quinolin-1-yl)acetohydrazides and their structural interpretation by NMR experiments is described in an attempt to explain the duplication of some peaks in their ¹H- and ¹³C-NMR spectra. Twenty new 6-methyl-1H-pyrazolo[3,4-b]quinoline substituted N-acylhydrazones 6(a–t) were synthesized from 2-chloro-6-methylquinoline-3-carbaldehyde (1) in four steps. 2-Chloro-6-methylquinoline-3-carbaldehyde (1) afforded 6-methyl-1H-pyrazolo[3,4-b]quinoline (2), which upon N-alkylation yielded 2-(6-methyl-1H-pyrazolo[3,4-b]quinolin-1-yl)acetate (3). The hydrazinolysis of 3 followed by the condensation of resulting 2-(6-methyl-1H-pyrazolo[3,4-b]quinolin-1-yl)acetohydrazide (4) with aromatic aldehydes gave N-acylhydrazones 6(a–t). Structures of the synthesized compounds were established by readily available techniques such as FT-IR, NMR and mass spectral studies. The stereochemical behavior of 6(a–t) was studied in dimethyl sulfoxide-d₆ solvent by means of ¹H NMR and ¹³C NMR techniques at room temperature. NMR spectra revealed the presence of N’-(benzylidene)-2-(6-methyl-1H-pyrazolo[3,4-b]quinolin-1-yl)acetohydrazides as a mixture of two conformers, i.e., E_(C=N)(N-N) synperiplanar and E_(C=N)(N-N) antiperiplanar at room temperature in DMSO-d₆. The ratio of both conformers was also calculated and E_{(C=N) (N-N)} syn-periplanar conformer was established to be in higher percentage in equilibrium with the E_{(C=N) (N-N)} anti-periplanar form.     

Effect of Phytosynthesized Selenium and Cerium Oxide Nanoparticles on Wheat (Triticum aestivum L.) against Stripe Rust Disease

In this study, selenium nanoparticles (SeNPs) and cerium oxide nanoparticles (CeONPs) were synthesized by using the extract of Melia azedarach leaves, and Acorus calamusas rhizomes, respectively, and investigated for the biological and sustainable control of yellow, or stripe rust, disease in wheat. The green synthesized NPs were characterized by UV-Visible spectroscopy, scanning electron microscopy (SEM), energy-dispersive X-ray (EDX), and X-ray diffraction (XRD). The SeNPs and CeONPs, with different concentrations (i.e., 10, 20, 30, and 40 mg/L), were exogenously applied to wheat infected with Puccinia striformis. SeNPs and CeONPs, at a concentration of 30 mg/L, were found to be the most suitable concentrations, which reduced the disease severity and enhanced the morphological (plant height, root length, shoot length, leaf length, and ear length), physiological (chlorophyll and membrane stability index), biochemical (proline, phenolics and flavonoids) and antioxidant (SOD and POD) parameters. The antioxidant activity of SeNPs and CeONPs was also measured. For this purpose, different concentrations (50, 100, 150, 200 and 400 ppm) of both SeNPs and CeONPs were used. The concentration of 400 ppm most promoted the DPPH, ABTS and reducing power activity of both SeNPs and CeONPs. This study is considered the first biocompatible approach to evaluate the potential of green synthesized SeNPs and CeONPs to improve the health of yellow, or stripe rust, infected wheat plants and to provide an effective management strategy to inhibit the growth of Puccinia striformis.     

Synthesis of potential biologically active 1,2-benzothiazin-3-yl-quinazolin-4(3H)-ones

A series of potential biologically active 2-(4-hydroxy-1,1-dioxido-2H-1,2-benzothiazin-3-yl)quinazolin-4(3H)-ones was synthesized in a straight forward manner by condensation of respective 4-hydroxy-1,2-benzothiazine-1,1-dioxides with anthranilamide followed by simple and high throughput cyclization of N-[2-(aminocarbonyl)phenyl]-4-hydroxy-1,2-benzothiazine-3-carboxamide-1,1-dioxides. All the synthesized compounds were subjected to preliminary evaluation for their biological activity against Gram positive and Gram negative bacteria. Some of the assayed compounds showed marked activity against Bacillus subtilis.