284685-12-7Relevant academic research and scientific papers
The photodecarboxylative addition of carboxylates to phthalimides as a key-step in the synthesis of biologically active 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones
Anamimoghadam, Ommid,Mumtaz, Saira,Nietsch, Anke,Saya, Gaetano,Motti, Cherie A.,Wang, Jun,Junk, Peter C.,Qureshi, Ashfaq Mahmood,Oelgem?ller, Michael
, p. 2833 - 2841 (2017)
The synthesis of various 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones was realized following a simple three-step process. The protocol utilized the photodecarboxylative addition of readily available carboxylates to N-(bromoalkyl)phthalimides as a versatile and efficient key step. The initially obtained hydroxyphthalimidines were readily converted to the desired N-diaminoalkylated 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones via acid-catalyzed dehydration and subsequent nucleophilic substitution with the corresponding secondary amines. The procedure was successfully applied to the synthesis of known local anesthetics (AL-12, AL-12B and AL-5) in their neutral forms.
Continuous flow photochemical and thermal multi-step synthesis of bioactive 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones
Mumtaz, Saira,Robertson, Mark J.,Oelgem?ller, Michael
, (2019/12/25)
An effective multi-step continuous flow approach towards N-diaminoalkylated 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones, including the local anesthetic compound AL-12, has been realized. Compared to the traditional decoupled batch processes, the combined photochemical–thermal–thermal flow setup rapidly provides the desired target compounds in superior yields and significantly shorter reaction times.
Structure-activity relationships in a series of bisquaternary bisphthalimidine derivatives modulating the muscarinic M2-receptor allosterically
Botero Cid, Hector M.,Tr?nkle, Christian,Baumann, Knut,Pick, Rainer,Mies-Klomfass, Elisabeth,Kostenis, Evi,Mohr, Klaus,Holzgrabe, Ulrike
, p. 2155 - 2164 (2007/10/03)
Hexane-bisammonium-type compounds containing lateral phthalimide moieties are well-established ligands of the common allosteric binding site of muscarinic M2 receptors. Previous structure-activity relationships (SAR) revealed two positively charged centers and two lateral phthalimide moieties in a defined arrangement to be essential of a high allosteric potency. The purpose of this study was to replace one carbonyl group of the phthalimides with hydrogens, hydroxy, alkoxy, phenyl, benzyl, and benzylidene groups in order to check the influence of these substituents on the allosteric activity in antagonist-linked receptors. The analysis of the quantitative SAR indicated that a high allosteric potency is related to a certain amount of rigidity as well as polarizibility and the ability to form hydrophobic interactions.
