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A simple synthetic strategy to construction of novel 4-oxo-2-phenyl-4H-chromene-3-carbothioamides (2–6) was achieved. The synthetic strategy depended on the treatment of 1-(2-hydroxyphenyl)-3-phenylpropane-1,3-dione (1) with some examples of aryl, aralkyl, aroyl and phosphorus isothiocyanates with promotion of DBU. The interesting 4,6-diphenyl-5-(2-hydroxy-benzoyl)-2-thioxo-3,4-dihydro-2H-1,3,4-oxazaphosphinine (8) as a highly regioselective product was obtained through treatment of the substrate 1 with phenyl phosphonisothiocyanatidous chloride whereas the other novel 2-phenyl-3-(2-thioxo-2H-1,3,5,4-thiadiazaphosphinin-6-yl)-4-oxo-4H-chromenes (9 and 10) were formed by using phosphorous diisothiocyanate and triisothiocyanate, respectively, under the same basic reaction conditions. All the reaction mechanisms were discussed. Structures of all the synthesized products were established by elemental analysis and available spectral tools. [ABSTRACT FROM AUTHOR]

A novel series of coumarin‐pyrazole‐thiazoles hybrids was designed. The methodology depended on a simple condensation reaction of 3‐(2‐oxo‐2H‐chromen‐3‐yl)‐1‐phenyl‐1H‐pyrazole‐4‐carboxaldehyde with a variety of thiazole compounds having amino or active methylene groups. In addition, another series of 1‐(thiazol‐2‐yl)‐3‐(2‐oxo‐2H‐chromen‐3‐yl)‐1H‐pyrazole‐4‐carboxaldehydes was also achieved by applying Vilsmeier‐Haack formylation on 3‐[1‐(2‐(thiazol‐2‐yl)hydrazineylidene]ethyl)‐2H‐chromen‐2‐ones. The obtained products were verified by spectral techniques such as IR, NMR, and mass spectra. To screen their abilities to inhibit cancer cell growth, these compounds were investigated against three tumor cell lines (MCF‐7, HepG2, and HCT116) using a standard method called SRB. The products 3 e, 7 b, 12 c and 14 a have considerable cytotoxic effects comparable to Doxorubicin. These products caused significant cell death by late apoptosis in all tumor cell lines. Furthermore, they preferentially induced G2 cell cycle arrest in MCF‐7 and HepG2 cells, while causing G1 cell cycle arrest in HCT116 cells. The molecular docking of these bioactive products showed good binding affinities with Cyclin‐dependent kinase 8 (CDK‐8). The ADMET‐predicted drug‐likeness properties of these bioactive compounds enable them to can used as promising anticancer agents. [ABSTRACT FROM AUTHOR]

With the ultimate goal of discovering new anticancer agents, this study involved the design and synthesis of fifteen novel Schiff bases 4a,b, 5, 6a–d, 7a–e, and 8–10 which contain 3-(2-oxo-2H-chromen-3-yl)-1-(4-phenylthiazol-2-yl)-1H-pyrazole moiety. The synthetic method depended on reaction of 3-(2-oxo-2H-chromen-3-yl)-1-(4-phenylthiazol-2-yl)-1H-pyrazole-4-carboxaldehyde (3) with a series of aromatic and heteroaryl amines under ultrasound irradiation to explore the influence of aromatic and heteroaryl rings on biological activity. The chemical structures of these Schiff bases were fully elucidated using various spectral and elemental analyses. The antiproliferative activities of the Schiff bases were studied by the standard SRB method. Among the new 15 Schiff bases, derivatives 4a,b, 5, and 7b have significant cytotoxic effects against PC3, HepG2, and HCT116 cancer cell lines. These four bioactive Schiff bases significantly increased the late apoptosis of all studied tumor cells. Also, both products 4a and 4b arrested the cell cycle at the G1 phase, while both compounds 5 and 7b arrested the S and G2 phases against PC3 cells. In addition, the products 4a, 4b, 5, and 7b have promising high abilities to arrest the cell cycle at the G2 phase against HepG2 and HCT116 cells. The different substitutions on the aryl ring were the basis for the structure–activity relationship study. The molecular docking study confirmed good binding interactions of these compounds with Cyclin-dependent kinase 8 (CDK-8) receptor, while the absorption, distribution, metabolism, excretion, and toxicity (ADMET) prediction supported that these bioactive products can be promising anticancer agents. [ABSTRACT FROM AUTHOR]

A novel series of some 2-[(9-ethyl-9H-carbazol-3-yl)imino]thiazoles/thiazolidinones was synthesized and established by spectroscopic tools and elemental analysis. The synthetic strategy depended on cyclization of 1-(9-ethyl-9H-carbazol-3-yl)-3-phenylthiourea (2) with different α-halocarbonyl compounds and some carbon electrophiles under mild reaction conditions. All products were screened for their in vitro cytotoxic activities toward three human cancer cell lines (MCF-7, HepG-2 and HCT-116). Interestingly, the particular carbazolyl derivatives 7, 13, 14 and 16 exhibited promising cytotoxicity results against all the evaluated cell lines. Also, molecular docking studies for the highly bioactive compounds were achieved to investigate the binding mode toward (VEGFR-2-KDR) receptor. Moreover, anticancer results were validated computationally by applying SwissADME server. [ABSTRACT FROM AUTHOR]

We discovered a simple synthetic approach to the construction of novel 2-amino-5-mercapto-6-(mercaptomethyl)-4-aryl-4H-pyran-3-carbonitriles (3a-i) under metal-free conditions. The methodology depended on the treatment of 2-arylidenemalononitriles (2a-i) with 2-(5-oxo-1,3-dithian-2-ylidene)malononitrile (1) or 1,3-dimercaptopropan-2-one (5) in absolute ethanol using triethylamine as an effective catalyst. The reaction mechanism was discussed. Structures of all the synthesized products were established by elemental analysis and spectral tools. [ABSTRACT FROM AUTHOR]

The synthesis of some novel diethyl {(4-oxo-1,4-dihydroquinolin-3-yl)(aryl/heteroaryl-amino)methyl}phosphonates, was achieved. The methodology is based on one-pot three-component reaction of 4-oxo-1,4-dihydroquinoline-3-carboxaldehyde (1), amine, and diethyl phosphite in the presence of CdI2 nanoparticles as an efficient catalyst under conventional heating at 80 °C or ultrasound irradiation at 50 °C. The mild reaction conditions, operational simplicity, and excellent yields are the essential advantages of this protocol. Most of the products recorded inhibitory effects toward plant pathogenic fungi nearly to the standard control. The hybridization between diethyl α-aminophosphonate and quinolin-4-one moieties clubbed with sulfonamide, antipyrine, or 1,2,4-triazine in one molecular frame displayed good antifungal activities. [ABSTRACT FROM AUTHOR]

A series of novel 6-amino-4-thioxo-pyrano[2,3-c]pyrazole-5-carbonitriles, 7-amino-5-thioxo-pyrano[2,3-d]pyrimidine-6-carbonitriles and 4,7-diamino-5-thioxo-pyrido[2,3-d] pyrimidine-6-carbonitriles were achieved by facile green one-pot and three-component synthesis. The method depended on one-pot three-component reaction of readily available starting materials carbon disulfide, malononitrile and heterocyclic active methylene compounds catalyzed by triethylamine in water as solvent under ultra-sonication technique. The remarkable advantages of this method are the simple procedure; high yields, short rection time and environmentally benign method are the advantages of this protocol. There is no need for any additional chromatographic separation with this procedure. Analytical and spectroscopic methods were used to comprehensively characterize the structures of all newly products. [ABSTRACT FROM AUTHOR]

An efficient and practical method for the synthesis of novel fused phosphorus heterocycles incorporating diethyl phosphonate by the one-pot in the presence of Fe3O4 nanoparticles as a reusable catalyst was achieved. The four-component reactions of ortho-substituted anilines, namely 2-aminophenol, 2-aminothiophenol and 1,2-phenylenediamine with salicylaldehyde, diethyl phosphite and hexaethylphosphorus triamide in the presence of Fe3O4 nanoparticles as a catalyst at 80–90 °C afforded the corresponding 1,3,2-benzo(oxaza/thiaza/diaza)phospholo[2,3-b][1,3,2]benzoxazaphosphinines 1–3 in good yields (80-84%). When the same reactions were repeated by substitution of salicylaldehyde with benzaldehyde, the 1,2-benzazaphospholo[2,1-b][1,3,2]benzo(oxaza/thiaza)phospholes 4 and 5 and 1,3,2-benzodiazaphosphole 6 derivatives were isolated in 78–83% yields. The structures of the synthesized compounds were established by elemental analysis and spectroscopic techniques (IR, MS and NMR). [ABSTRACT FROM AUTHOR]

Synthesis of novel 4-(1,3,2-diazaphosphinin-5-yl)-1,2-dihydrothieno[3,2-d][1,2,3] diazaphosphinines 5-8 was achieved. The methodology depended on preparation of 5-[(2-thienyl)methyl]hydrazono-2-oxido-2-phenyl-4-(trifluoromethyl)-1H-1,3,2-diazaphosphinine (4) through the cyclization of 2-[(dimethylamino)methylene]-4,4,4-trifluoro-1-(2-thienyl)-butane-1,3-dione (2) with phenyl phosphonic diamide, followed by hydrazine hydrate. Cyclization of the hydrazone 4 with some phosphorus halides at refluxing pyridine gave the target products in acceptable yields. [ABSTRACT FROM AUTHOR]