Macrocycles embedding phenothiazine or similar nitrogen and/or sulphur containing heterocycles

Abstract

Macrocycles emerged as an important class of useful compounds with multiple applications ranging from selective complexation of different anions, cations or neutral molecules to the development of new sensors, materials with improved properties and biologically active compounds. In this review we focus our discussion on the synthesis and structural analysis of macrocycles containing dibenzoheterocycles with sulphur and/or nitrogen atoms in the central six-membered ring (i.e. 10H-phenothiazine, 9,10-dihydroacridine or acridane, acridone, thianthrene, phenoxathiine, acridine, phenazine). We further highlight selected application of these compounds as host molecules, DNA intercalating agents or enzyme inhibitors.

Enantioselective Rhodium‐Catalyzed Dimerization of ω‐Allenyl Carboxylic Acids: Straightforward Synthesis of C2‐Symmetric Macrodiolides

“…We also looked into the preparation of macrodiolides, functionalized with several different heterocyclic systems. Such heterocyclic diolides might serve as receptors for differently charged ions and neutral molecules . We were delighted to see that thiophene‐ and indole‐based substrates provided the corresponding diolides D10 – D12 with good yields (Table ).…”

New Polymerizable Tetraaza Macrocycle Containing Two Acridine Units for Selective Fluorescence Sensing of Metal Ions

“…Thus, signaling is induced by an indirect electron transfer mechanism. However, direct type acridino-sensor molecules containing a fluorophore as a part of the receptor unit have also been developed [13][14][15][16]. These acridino-crown ethers are most commonly used as organic-and heavy metal cation sensors [13][14][15][16].…”

“…However, direct type acridino-sensor molecules containing a fluorophore as a part of the receptor unit have also been developed [13][14][15][16]. These acridino-crown ethers are most commonly used as organic-and heavy metal cation sensors [13][14][15][16]. In the case of environmental analyzers it is sufficient to physically immobilize the ionophores.…”

Enantioselective Rhodium‐Catalyzed Dimerization of ω‐Allenyl Carboxylic Acids: Straightforward Synthesis of C2‐Symmetric Macrodiolides

“…[23] We were delighted to see that thiophene-and indole-based substrates provided the corresponding diolides D10-D12 with good yields (Table 4). Such heterocyclic diolides might serve as receptors for differently charged ions and neutral molecules.…”

“…Such heterocyclic diolides might serve as receptors for differently charged ions and neutral molecules. [23] We were delighted to see that thiophene-and indole-based substrates provided the corresponding diolides D10-D12 with good yields (Table 4). Even basic, potentially metal-coordinating pyridines (D13)w ere tolerated.…”