Hantzsch-like synthesis of bis(sulfanediyl)bis(tetrahydropyrimido[4,5-b]quinoline-4,6-diones) linked to arene or heteroarene cores utilizing bis(sulfanediyl)bis(6-aminopyrimidin-4-ones) as precursors

Hantzsch‐Like Synthesis, DNA Photocleavage, DNA/BSA Binding, and Molecular Docking Studies of Bis(sulfanediyl)bis(tetrahydro‐5‐deazaflavin) Analogs Linked to Naphthalene Core

“…The fact that H5 and H10 are not coupled is evidence for the linear structure 2 and discard the angular 12a in which coupling between H6, and NH must be seen. Also, the 2D‐HMBC spectroscopy of some related compounds [72,86] confirmed that compounds 6 were formed.…”

“…By applying the same synthetic approach, varieties of bis (8,8- In order to achieve the molecular hybridization concept, [72,87] In continuation to our interest in the synthesis of spiro-heterocyclic compounds [71,88 -96] and in a trial to extend the scope of this reaction, the Hantzsch-like reaction of bis(6-aminopyrimidin-4-one) with both dimedone and indoline-2,3-dione was also conducted under the similar reaction conditions to employ the synthesis of compounds 16. Thus…”

“…In order to achieve the molecular hybridization concept, [72,87] in which two pharmacophoric moieties of different bioactive classes are combined to create new hybrid molecules aiming at enhancing biological efficacy and overcoming drug resistance, we extended the scope of this reaction to include the synthesis of 2,2′‐((naphthalene‐2,6‐diylbis(methylene))bis(sulfanediyl))bis(tetrahydropyrimido[4,5‐ b ]quinoline‐4,6‐dione) 14a – c , which are linked to thiophen‐2‐yl, pyridin‐3‐yl, or pyridin‐4‐yl at position‐5. Thus, the reaction of 7 with two equivalents of both dimedone and the heteroaldehydes (thiophene‐2‐carbaldehyde, nicotinaldehyde, or isonicotinaldehyde) 13a – c in the presence of acetic acid furnished 14a – c ( Scheme 5).…”

“…In light of these facts, and as a continuation of our previous work on bis‐heterocycles [70–74] and C−C bond formation reactions [75–79] such as Hantzsch [71–73,80–85] we planned to synthesize a novel series of bis‐pyrimido[4,5‐ b ]quinoline derivatives linked by naphthalene‐2,6‐diylbis(methylene))bis(sulfanediyl) linker and bearing aryl, heteroaryl, or N ‐aryl‐2‐phenoxyacetamide at position‐5. The affinity of the new compounds toward the supercoiled DNA was examined by gel electrophoresis.…”

New Azacycles by One‐Pot Three‐Component Hantzsch‐Like Synthesis of Tetra(hexa)azacyclopenta[a]anthracenes, Tetraazaindeno[5,4‐b]fluorenes, and Oxatetraazacyclopenta[m]tetraphenes

“…As a part of our sequential work on spirocyclic oxindoles,[ 39 , 40 , 41 , 42 , 43 , 44 , 45 ] we modified the structures by replacing the aldehydes with isatin 17 to achieve the concept of molecular hybridization [46] to improve their medicinal efficacy and overcome drug resistance. [ 47 , 48 , 49 , 50 ] Thus, the reaction of isatin 17 and 7‐amino‐2‐methyl‐3‐phenylpyrazolo[1,5‐ a ]pyrimidin‐5‐one 3 with either dimedone 5 or indan‐1,3‐dione 9 leads to the formation of the spirocyclic oxindoles of the respective tetraazacyclopenta[ a ]anthracene 18 or tetraazaindeno[5,4‐ b ]fluorene 19 (Scheme 7 ).…”