Search

In an attempt to develop effective and safe antibacterial agents, thiazinanones bearing the quinolone scaffold were prepared by reaction of the corresponding (quinolinylmethylene)hydrazinecarbothioamides with 2,3-diphenylcycloprop-2-enone.

Herein, we reported on a new series of hydrazono bis-4-oxothiazolidines during the reaction of (hydrazinecarbonothioyl)hydrazinecarbothioamides with dimethyl acetylenedicarboxylate in ethanol as a solvent. The products were obtained in good yields. The structure assignment of obtained products was confirmed by NMR, mass and IR spectroscopy in addition to elemental analyses. The structure of the products was also confirmed by a single-crystal X-ray structure analysis. The possible mechanism for the reaction was also discussed.

Reaction of 2-((4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)methylene)hydrazinecarbothioamides with dimethyl acetylenedicarboxylate afforded, in good yields, the corresponding thiazoles derived from 2-quinolones. However, the reaction of N-ethyl-2-quinonylhydrazinecarbothioamide with 2-(bis(methylthio)methylene)malononitrile or its ester derivative gave the corresponding quinolin-3-yl-methylenehydrazono-1,3-thiazines. The proposed mechanism was discussed. The structure of the obtained products was elucidated via NMR, IR and mass spectra as well as elemental analysis.

During formylation of 2-quinolones by DMF/Et3N mixture, the unexpected 3,3′-methylenebis(4-hydroxyquinolin-2(1H)-ones) were formed. The discussed mechanism was proved as due to the formation of 4-formyl-2-quinolone as intermediate. Reaction of the latter compound with the parent quinolone under the same reaction condition gave also the same product. The structure of the obtained products was elucidated via NMR, IR and mass spectra. X-ray structure analysis proved the anti-form of the obtained compounds, which were stabilized by the formation hydrogen bond. Molecular docking calculations showed that most of the synthesized compounds possessed good binding affinity to the SARS-CoV-2 main protease (Mpro) in comparable to Darunavir. Graphic abstract Electronic supplementary material The online version of this article (10.1007/s11030-020-10140-z) contains supplementary material, which is available to authorized users.

Great attention has been paid to cyclopropenones as they are present in many natural sources. Various synthesized cyclopropenone derivatives also show a wide range of biological activities. The cyclopropenone derivatives undergo a variety of reactions such as ring-opening reactions, isomerization reactions, C-C coupling reactions, C-H activation, cycloaddition reactions, thermal and photo-irradiation reactions, and acid-base-catalyzed reactions under the influence of various chemical reagents (electrophiles, nucleophiles, radicals, and organometallics) and external forces (heat and light). Many previous reviews have dealt with the chemistry and reactions of cyclopropenones. However and to the best of our knowledge, the utility of cyclopropenones in the synthesis of heterocycles has not been reported before. Therefore, it would be interesting to shed light on this new topic. The present review article provides, for the first time, a comprehensive compilation of synthetic methods for the synthesis of various heterocyclic ring systems, as a significant family in the field of organic chemistry.

Quinoline-2,4-diones reacted with 2-[bis(methylthio)methylene]malononitrile in DMF/Et3N to produce 3-(methylthio)-4-oxo-4,5-dihydrofuro[3,2-c]quinolone-2-carbonitriles and 3-(methylthio)-4-oxo-4,5-dihydrofuro[3,2-c]quinolone-2-carboxamides in state of 2-imino-substituted 4-(methylthio)-5,6-dihydro-2H-pyrano[3,2-c]quinolone-3-carbonitriles. The structures of all new products were proved using NMR, IR, and mass spectral data. The possible mechanism for the reaction is also discussed.

The reactivity of 4-amino-5-hydrazineyl-4H-1,2,4-triazole-3-thiol (1) towards several carbonyl compounds was investigated. We have found that on treatment of 1 with isatoic anhydride (2), 1,8-naphthalic anhydride (4), diphenic anhydride (6), pyromellitic dianhydride (8), and tetrabromophthalic anhydride (10), the reaction proceeds to give triazolotetrazine- and triazolophthalazine derivatives in good yields using simple experimental procedures. The structure of the synthesized compounds was confirmed using different spectroscopic data (1H NMR, 13C NMR, mass spectrometry, and elemental analysis). The mechanism of the obtained products was also discussed.

Synthesis of novel tetrahydroquinazoline-2-carboxylate and arylaminoquinazoline-2-carboxylate in good yields has been established via the nucleophilic cycloaddition of 2-amino-N′-arylbenzimidamides on dimethyl acetylenedicarboxylate. Moreover, studying the reaction of 2-amino-N′-arylbenzimidamides with 2-(dicyanomethylene)indan-1,3-dione to give 3,4-dihydroquinazolin derivatives. The results obtained from IR, 1H NMR, and 13C NMR data as well as the mass spectra are in agreement with the assigned structures. A plausible mechanism for the formation of the products is presented.

The reactivity of N-2-(2-aminobenzoyl)-N-phenylhydrazinecarbothioamide (1) as an electron donor toward several electron-accepting compounds through electron donor-acceptor interaction has been studied. Thus, upon treatment of 1 with either 1,4-naphthoquinone, 2-dicyanomethyleneindan-1,3-dione, or 2,3-dichloro-1,4-naphthoquinone, the reaction proceeds to give thiadiazino[5,4-b]quinazoline, N-phenylcarbamohydrazonothioate, and thiadiazine-5,10-dione, respectively. Also, the reactivity of compound 1 toward some aldehydes and anhydrides was studied. The products were fully characterized by their spectral data. The mechanisms of formation of the products have been rationalized.

Background: Urinary bladder tumor is the seventh most common worldwide tumor . According to National Cancer Institute in Egypt , urinary bladder tumor constitutes 30% of all cancer cases with an incidence rate of 13.5/100,000 individuals. CD10 protein has been an immediate part in pathways of transduction that control cellular development , apoptosis , metastatic possibilities of cancer cells and influence on invasion .CD10 has prognostic incentive in bladder cancer. HER2/neu protein seems to assume a part in neoplastic cell and included in pathogenesis of urinary bladder carcinoma. Association of HER2 receptor in proliferation of invasive urothelial carcinomas has incited trials to HER2/neu targeted therapies in advanced diseases. Aim of work: To evaluate the immunohistochemical expression of CD10 and HER2/ neu with the pathological parameters of urothelial carcinoma of urinary bladder well as grade and stage versus chronic cystitis Methods: CD10 and HER2/neu expressions were retrospectively analysed by immunohistochemistry in 30 cases of chronic cystitis and 30 paraffin-embedded specimens of patients with primary urothelial carcinoma (UC).The expressions were related to clinicopathological parameters ,well as grade and pathological stage Results: The immunohistochemial expression of CD10 and HER2/neu were negative(score 0) in chronic cystitis cases than urothelial carcinoma and was significantly (p < 0.05). Nineteen cases (63%) of primary urothelial carcinomas were positive for CD10 expression and 17 cases (56.7%) were positive for HER2/neu compared to chronic cystitis . The high grade of urothelial carcinoma and the high pathological stage were significantly connected with the high CD10 and HER2/neu expression (p < 0.05). Conclusion : High CD10 and HER2/neu expression was related to high grade and pathological stage of urothelial carcinoma. Keywords: CD10 – HER2/neu – urothelial carcinoma of urinary bladder – Immunohistochemistry (IHC)

We direct for the synthesis of 1,6,7-trisubstituted-4-phenylthiazol-2(3H)-ylidene)hydrazono)methyl)quinolin-2-one derivatives by the reaction of corresponding thiosemicarbazone derived by 2-quinolone derivatives with 2-bromoacetophenones in presence of triethylamine at room temperature. The mechanism of the formed products was discussed. The structure of the obtained products was fully characterized using different spectral techniques including infrared (IR), nuclear magnetic resonance (NMR), and mass spectrometry (MS) together with elemental analyses. The new synthesized compounds showed a moderate colon anticancer activity.

Reaction of 3,6-dichlorocarbazole with propargyl bromide in the presence of a basic medium gave an N-propargylated carbazole. The latter compound was converted into molecular architectures containing 1,2,3-triazole moiety through Cu(I)-catalyzed 1,3-cycloaddition reaction with different azides. Similarly, 2-azidomethyl benzothiazole was cliched with N-Boc-protected N´-propargyl glutamate to give the biomolecule 2-triazolylmethyl product.

The reactivity of N-amidinothiourea (1) as an electron donor towards several electron-accepting functional groups via electron-donor-acceptor (EDA) interaction has been studied. Thus on treatment of 1 with either 1,1,2,2-tetracyanoethylene (TCNE, 2), 2,3-dicyano-1,4-naphthoquinone (DCNQ, 4), 2,3,5,6-tetrabromo-1,4-benzoquinone (BHL-p, 6), 2,3-dichloro-1,4-naphthoquinone (DCHNQ, 8), 2,3,5,6-tetrachloro-1,4-benzoquinone (CHL-p, 13), 2,3-dicyano-5,6-dichloro-1,4- benzoquinone (DDQ, 15), 2-dicyanomethyleneindan-1,3-dione (CNIND, 17), 2-(2-oxoindolin-3- ylidene)malononitrile (19), and/or dimethyl acetylenedicarboxylate (DMAD, 21), the reaction proceeds to give thiazole and thiazine derivatives, respectively. However, isoindole derivatives 24 and 26 were formed on heating of 1 with either tetrabromophthalic anhydride and=or o-phthalaldehyde, respectively. The products were fully characterized according to their spectral data. The mechanisms of formation of the products have been rationalized.

Technical iodine was found to catalyze the condensation between 2-aminobenzohydrazide (1) and some aldehydes and ketones in absolute ethanol under mild conditions to afford hydrazone and quinazoline derivatives, respectively. Condensation of 1with terephthalaldehyde (2) in 1 : 1 molar ratios afforded the hydrazone 3, while hydrazone 4was formed on using a double molar ratio of 1. On the other hand, compound 1condensed with 4-formyl [2.2]paracyclophane (5) to give the hydrazone 6. However, spiro-quinazolines 8, 10, 12, and 14 were formed when compound 1reacted with ketones such as N-benzylpiperidone (7), indane-1,2,3-trione (9), cyclohexane-1,2-dione (11), and dimedone (13), respectively. Treatment of 1with tetrabromophthalic anhydride (TBPA, 18) and pyromellitic dianhydride (PMDA, 20) furnished phthalazino-quinazoline 19 and 21, respectively. The products were fully characterized according to their spectral analyses. The mechanisms of formation of the products have been rationalized.

The formation of metal complexes with acid hydrazides plays an important role in the growth of their biological activity. A simple synthetic strategy is described for the synthesis of novel 1,2,4-tri-azepine and 1,2,5-triazocine derivatives via electron donor–acceptor interaction. Thus when 2-aminobenzohydrazide reacted with tetracyanoethylene (TCNE) and 2-dicyanomethylene-indan-1,3-dione (CNIND) afforded 1,2,4-triazepine derivatives. While on reacting 1 with 2,3-dicyano-5,6-dichloro-1,4-benzoquinone (DDQ), 2,3-dichloro-1,4-naphthoquinone (DCHNQ), 1,4-naphthoquinone and/or 2,3,5,6-tetrabromo-1,4-benzoquinone, 1,2,5-triazocine derivatives were formed.

Technical iodine was found to catalyze the condensation between 2-aminobenzohydrazide (1) and some aldehydes and ketones in absolute ethanol under mild conditions to afford hydrazone and quinazoline derivatives, respectively. Condensation of 1with terephthalaldehyde (2) in 1 : 1 molar ratios afforded the hydrazone 3, while hydrazone 4was formed on using a double molar ratio of 1. On the other hand, compound 1condensed with 4-formyl [2.2]paracyclophane (5) to give the hydrazone 6. However, spiro-quinazolines 8, 10, 12, and 14 were formed when compound 1reacted with ketones such as N-benzylpiperidone (7), indane-1,2,3-trione (9), cyclohexane-1,2-dione (11), and dimedone (13), respectively. Treatment of 1with tetrabromophthalic anhydride (TBPA, 18) and pyromellitic dianhydride (PMDA, 20) furnished phthalazino-quinazoline 19 and 21, respectively. The products were fully characterized according to their spectral analyses. The mechanisms of formation of the products have been rationalized.

A convenient, one-pot method for the preparation of 1,2,4-triazepine and 1,2,5-triazocine derivatives is described.

The tricyclic aromatic ring system of the title compound, C15H9Cl2N, is essentially planar (r.m.s. deviation = 0.002 Å). The two Cl atoms lie slightly out of the plane of the carbazole ring system, with the C—Cl bonds forming angles of 1.23 (8) and 1.14 (8)° with the plane. The acetylene group has a syn orientation with respect to the ring system. In the crystal, no weak hydrogen bonds nor any π–π stacking interactions are observed.