Synthesis and Antioxidant Activity of Some Novel a Zino and Pyranopyrazole Derivative

Background: Pyranopyrazole derivatives has vital role in the class of organic compounds because of their broad spectrum of biological as well as pharmacological importance.Results: Our current goal is the [3+3] Cycloaddition of benzoyl isothiocyanate and pyrazolone 1 undergo oxidation cyclization producing pyrazoloxadiazine 3. The diol 5 was obtained as a condensation of two equivalent of 1 with thiopene-2-carboxaldhyde in acetic acid above sodium acetate mixture. When the condensation carried out in presence of piperidine under fusion the unsaturated ketone 4 was obtained. The cyclocondensation of pyrazolone 1 and pyruvic acid derivative in the presence of aminotive reagent resulted in pyrazolo pyrimidine 7. The pyrazolo pyran derivative 11 was resulted from the [3+3] cycloaddition of 1 and cinnamic acid. ᴽpyrone derivative was prepared by acylation of 12 with to equivalent of acetic anhydride. Phthalic anhydride undergoes arolyation using zinc chloride as a catalyst. The cyclic keto acid 23 was synthesized by the action of succinic anhydride on 12 in acetic medium. Cinnamic acid and 12 leads to pyrazole derivative 24 through Michael reaction. All of the tested compounds showed good microbial activity against pathogenic microorganisms. Newly synthesized compounds were screened for their antioxidant activity. Some of tested compounds exhibited promising activities.Conclusions: The newly synthesized compounds were found to be potent towards antioxidant activity. Moreover, the results showed that nearly a compound 5 was found to be the most potent levels of activity. Additionally, compounds 13, 14, 16, 22, 23 and 24 were found to have moderate activity. While compound 14 was found the lowest potent levels.

[2-Chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone: structural characterization of a side product in benzothiazinone synthesis

1,3-Benzothiazin-4-ones (BTZs) are a promising new class of anti-tuberculosis drug candidates, some of which have reached clinical trials. The title compound, the benzamide derivative [2-chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone, C13H12ClF3N2O3, occurs as a side product as a result of competitive reaction pathways in the nucleophilic attack during the synthesis of the BTZ 8-nitro-2-(piperidin-1-yl)-6-(trifluoromethyl)-1,3-benzothiazin-4-one, following the original synthetic route, whereby the corresponding benzoyl isothiocyanate is reacted with piperidine as secondary amine. In the title compound, the nitro group and the nearly planar amide group are significantly twisted out of the plane of the benzene ring. The piperidine ring adopts a chair conformation. The trifluoromethyl group exhibits slight rotational disorder with a refined ratio of occupancies of 0.972 (2):0.028 (2). There is structural evidence for intermolecular weak C—H...O hydrogen bonds.

Design, Synthesis and Characterization of Some Novel benzamide derivatives and it's Pharmacological Screening

The new series of substituted N-(phenylcarbamothioyl)benzamide derivatives (2a-2f) was designed, development and synthesized by using conventional and microwave method. In present work 6 different N-(phenylcarbamothioyl)benzamide were synthesized. Substituted benzoyl chloride is converted into benzoyl isothiocyanate by esterification. Benzoyl isothiocyanate is converted into Substituted (phenylcarbamothioyl)benzamide by treating with different types of substituted aniline. Confirmation of the chemical structure of the synthesized was substantiated by TLC, IR, 1H NMR, MS spectroscopy.Novel synthesized compounds screened for their in vivo and in-vitro anti-inflammatory studies and compound 2f shows promising anti-inflammatory activity.

Experimental results and computational insight into sequential reactions of β-(2-aminophenyl)-α,β-ynones with aryl isocyanates/benzoyl isothiocyanate

The selective formation of quinazoline vs. benzoxazine and benzothiazine derivatives from β-(2-aminophenyl)-α,β-ynones and aryl isocyanates/benzoyl isothiocyanate was explored. DFT calculations provide a plausible rationale.

Evaluation of Novel N-(Dibenzylcarbamothioyl)benzamide Derivatives as Antibacterial Agents by Using DFT and Drug-Likeness Assessment

Isomers of monothioureas, 2a–2d, derived from the reaction of disubstituted benzoyl isothiocyanate and dibenzylamine were synthesised and characterised by using elementary analysis CHNS and IR, 1H NMR, and 13C NMR spectroscopies. The compounds were screened for their in vitro antibacterial activity by using selected Gram-positive bacteria, and moderate inhibition activity was displayed for compound 2b with the value of inhibition zone 11 ± 0.8 mm at a concentration of 50 mg/ml. The outcomes of Lipinski’s rule of five assessment appeared to be in agreement with all compounds as they adhered to most of the rules, in which they can be preliminarily classified as active drug-like. The frontier molecular orbitals (HOMO and LUMO) for halogen-substituted 3,4-dichloro (2a) and 3,4-difluoro (2b) were also determined by applying the computational method of density functional theory (DFT) to determine their relationship as a molecular descriptor in antibacterial activities. The value of LUMO energy for compound 2b (1.8229 eV) is lower than that of compound 2a (1.8492 eV) which indicates higher antibacterial activities.

Metal-mediated reactions towards the synthesis of a novel deaminolysed bisurea, dicarbamolyamine

A new selective cobalt acetate tetrahydrate or cerium nitrate hexahydrate mediated cleavage of the C–N bond of a benzoyl isothiocyanate derivative to give (carbamoylamino)methanethioamide is presented. The cleavage of the C–N could not be achieved in the absence of thione. The novel silver-mediated conversion of a thione to the carbonyl was achieved on 1-((benzamido)formyl)urea and replicated on (carbamoylamino)methanethioamide to give the deaminolyzed bisurea (dicarbamolyamine). The compounds were characterized by IR, NMR, microanalysis and GC–MS. The single crystal X–ray diffraction studies of the crystal structures of compounds I, II, III and V is discussed.