Synthesis of novel amide‐crownophanes and Schiff base‐crownophanes based on <i>p</i>‐phenylene, 2,6‐naphthalene, and 9,10‐anthracene

Ghozlan

et al. 2018

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Section: Resultsmentioning

confidence: 99%

3‐Amino‐5‐cyanomethylpyrazole‐4‐carbonitrile: Versatile Reagent for Novel Bis(pyrazolo[1,5‐a]pyridine) Derivatives via a Multicomponent Reaction

Ghozlan

et al. 2018

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“…Subsequently, with optimal condition in hand, the generality and synthetic scope of this reaction were demonstrated by synthesizing a series of bis(4Hchromene-3-carbonitriles) 6a-l (linked to aliphatic or aromatic cores via ether linkage). Thus, different bisaldehydes 7a-f [42][43][44] were well tolerated under the optimized reaction conditions and furnished the corresponding bis(4H-chromene-3-carbonitriles) 6 in good yields (Scheme 5 and Table 2).…”

Section: Resultsmentioning

confidence: 99%

Novel bis(dihydropyrano[3,2‐c]chromenes): Synthesis, Antiproliferative Effect and Molecular Docking Simulation

Abdella

Mohamed

et al. 2017

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An efficient and convenient route for the synthesis of novel bis dihydropyrano[3,2‐c]chromenes is reported. The synthetic pathway involves one‐pot, multicomponent reaction of bis‐aldehydes, malononitrile, and 4‐hydroxycoumarin in the presence of pyridine or acetic acid/sodium acetate. A stepwise approach for the synthesis of the target compounds was also investigated. The anticancer activity of the synthesized products against MCF7, HEPG2, and A549 cell lines was assessed. Attempts to detect the molecular action of 6g, docking simulation was done using DHFR PDB:ID (1DLS). The study revealed that compound 6g was strongly fit into the active sites of the target protein through six bindings, and hence, it was considered as promising inhibitor for cancer proliferation.

“…In connection with these findings and in continuation of our interest in the synthesis of bis(hetrocycles) [38][39][40][41][42][43][44][45][46], we describe herein simple and efficient routes for the synthesis of novel bis(s-triazolo [3,4-b] [1,3,4]thiadiazines) in which the triazolothiadiazines are linked to arene core either directly or via alkyl, ether, thioether, or amine linkages.…”

Section: Introductionmentioning

confidence: 99%

Efficient Routes for the Synthesis of Novel Bis(s‐triazolo[3,4‐b][1,3,4]thiadiazines)

Sarhan

Badawy

Elwahy

2014

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Bis(triazolo[3,4‐b]thiadiazine) 4 in which the fused system is linked directly to the benzene core can be synthesized in 75% yield by, firstly, preparation of bis(s‐triazole) 2 followed by reaction with phenacyl bromide 3 in refluxing EtOH/DMF mixture containing piperidine. Bis(s‐triazolo[3,4‐b][1,3,4]thiadiazines) 8 and 11 in which the triazolothiadiazines are linked to benzene core via alkyl or ether linkage were synthesized in 70 and 72% yields, respectively, starting from dicarboxylic acids 5 and 9 upon treatment with two moles of thiocarbohydrazide 6 to give the corresponding bis(4‐amino‐5‐mercapto‐s‐triazolo‐3‐y1) derivatives 7 and 10 and subsequent reaction with two equivalents of phenacyl bromide. Bis(6‐phenyl‐7H‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazines) 15a, 15b, 15c, 15d, 15e, 15f, which are linked to arene cores via sulfanylmethylene spacers, were prepared by the reaction of 4‐amino‐4H‐1,2,4‐triazole‐3,5‐dithiol 12 with the appropriate bis(bromomethyl)benzenes 13a, 13b, 13c, 13d, 13e, 13f to give bis(4‐amino‐5‐mercapto‐4H‐3‐sulfanylmethyl)arenes 14a, 14b, 14c, 14d, 14e, 14f and subsequent reaction with phenacyl bromide. Compounds 15a, 15b, 15c, 15d, 15e, 15f were alternatively obtained in 60–70% yields by twofold substitution of 13a, 13b, 13c, 13d, 13e, 13f with two equivalents of 6‐phenyl‐7H‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazine‐3‐thiol 16 in refluxing EtOH/DMF mixture containing KOH. Bis(triazolothiadiazine) 22 attached to the benzene core through the thiadiazine ring via an amine linkage was prepared in 70% yield starting from p‐phenylenediamine 19 by, firstly, acylation with chloroacetyl chloride 18 followed by bis‐alkylation with 1,2,4‐triazole 20 and subsequent intramolecular ring closure upon treatment with phosphorus oxychloride.