On the Fluorescence Reaction of Pharmaceutically Important 1,3‐Diamines and <i>o</i>‐Aminobenzenesulfonamides with Homophthalaldehyde

Troschütz, Reinhard; Heinemann, Oliver

doi:10.1002/ardp.19963290109

Cited by 5 publications

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“…The synthesis of isoquinolinobenzothiadiazine derivatives was reported previously by Troschü tz & Heinemann (1996), who investigated their fluorescence. These authors made tetracyclic isoquinolinobenzothiadiazines 1 (see Fig.…”

Section: Introductionmentioning

confidence: 99%

“…Notably, many heterocyclic DNA minor-groove binders (MGBs) are providing clinically useful drugs against diverse diseases and are finding extensive uses in technology Isoquinolinobenzothiadiazine derivatives (Troschü tz & Heinemann, 1996;Kisel & Kovtunenko, 2000;Kisel et al, 2002). (Nanjunda & Wilson, 2012;Paul et al, 2019;Rahman et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, crystal structure and docking studies of tetracyclic 10-iodo-1,2-dihydroisoquinolino[2,1-b][1,2,4]benzothiadiazine 12,12-dioxide and its precursors

et al. 2020

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The title compound, 10-iodo-1,2-dihydroisoquinolino[2,1-b][1,2,4]benzothiadiazine 12,12-dioxide, C15H11IN2O2S (8), was synthesized via the metal-free intramolecular N-iodosuccinimide (NIS)-mediated radical oxidative sp 3-C—H aminative cyclization of 2-(2′-aminobenzenesulfonyl)-1,3,4-trihydroisoquinoline, C15H16N2O2S (7). The amino adduct 7 was prepared via a two-step reaction, starting from the condensation of 2-nitrobenzenesulfonyl chloride (4) with 1,2,3,4-tetrahydroisoquinoline (5), to afford 2-(2′-nitrobenzenesulfonyl)-1,3,4-trihydroisoquinoline, C15H14N2O4S (6), in 82% yield. The catalytic hydrogenation of 6 with hydrogen gas, in the presence of 10% palladium-on-charcoal catalyst, furnished 7. Products 6–8 were characterized by their melting points, IR and NMR (1H and 13C) spectroscopy, and single-crystal X-ray diffraction. The three compounds crystallized in the monoclinic space group, with 7 exhibiting classical intramolecular hydrogen bonds of 2.16 and 2.26 Å. All three crystal structures exhibit centrosymmetric pairs of intermolecular C—H...π(ring) and/or π–π stacking interactions. The docking studies of molecules 6, 7 and 8 with deoxyribonucleic acid (PDB id: 1ZEW) revealed minor-groove binding behaviours without intercalation, with 7 presenting the most favourable global energy of the three molecules. Nonetheless, molecule 8 interacted strongly with the DNA macromolecule, with an attractive van der Waals energy of −15.53 kcal mol−1.

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Section: Introductionmentioning

confidence: 99%