Syntheses and structure–activity relationships of novel, potent, and selective trans-2-[3-oxospiro[isobenzofuran-1(3H),1′-cyclohexan]-4′-yl]benzimidazole NPY Y5 receptor antagonists

Discovery of Potent, Isoform-Selective Inhibitors of Histone Deacetylase Containing Chiral Heterocyclic Capping Groups and aN-(2-Aminophenyl)benzamide Binding Unit

“…The following compounds were prepared according to the literature: methyl 4-amino-3-nitrobenzoate ( 2a ); 2-nitro-4-phenylaniline ( 6 ); methyl 4-(guanidinomethyl)­benzoate; ( E )-3-(dimethylamino)-1-(pyridin-3-yl)­prop-2-en-1-one; methyl 4-((4-(pyridin-3-yl)­pyrimidin-2-ylamino)­methyl)­benzoate; 4-((4-(pyridin-3-yl)­pyrimidin-2-ylamino)­methyl)­benzoic acid ( 7 ); N -(2-aminophenyl)-4-({[4-(pyridin-3-yl)­pyrimidin-2-yl]­amino}­methyl)­benzamide (mocetinostat); (5 S )-1-acetyl-5-benzyl-2-thiohydantoin ( 10a ); (5 S )-1-acetyl-5-(1 H -indol-3-ylmethyl)-2-thiohydantoin ( 10b ); N -( tert- butoxycarbonyl)- l -phenylalanine ( 14a ), N -( tert- butoxycarbonyl)- l -tryptophan ( 14b ); N-(tert -butoxycarbonyl)- d -phenylglycine ( 14c ); (5 S )-1-( tert- butoxycarbonyl)-5-benzyl-2-thiohydantoin ( 15a ); 4-[(trifluoroacetamido)­methyl]­benzoic acid ( 20 ); tert -butyl (2-aminophenyl)­carbamate); tert -butyl N -(2-{4-[(trifluoroacetamido)­methyl]­benzamido}­phenyl)­carbamate ( 21a ); tert -butyl N -{2-[4-(aminomethyl)­benzamido]­phenyl}­carbamate ( 21b ); d -phenylalaninol; l -phenylalaninol ( 25a ); (2 R )-2-amino-2-phenylethan-1-ol; (2 S )-2-amino-2-phenylethan-1-ol ( 25c ); (4 S )-4-benzyl-1,3-thiazolidine-2-thione ( 26a ); (4 S )-4-phenyl-1,3-thiazolidine-2-thione ( 26c ) …”

Ninhydrin in synthesis of heterocyclic compounds

“…[304][305][306] In addition, isobenzofurans are an important class of natural products possessing significant biological properties. [307][308][309] Pramanik's group used 2-hydroxy-2,2'-biindan-1,1',3,3'-tetrone 254 in a condensation reaction with various phenols, polyhydroxy benzenes, and α-and β-naphthols 255 in an acid medium to produce 2-aryl/alkyl-2,2'-biindan-1,1',3,3'-tetrones 256. 1 H and 13 C NMR spectra from adducts of 256, in the case of substrates such as resorcinol, orcinol, 1,3,5-trihydroxybenzene and α-and β-naphthols, indicate that such derivatives prefer the intramolecular hemi-ketal form 257 (Scheme 78).…”

Asymmetric synthesis of spirocyclic isobenzofuranones via a squaramide-catalysed sulfa-Michael desymmetrisation reaction

“…7 The naturally occurring spirocyclohexane isobenzofuranone ansaspirolide ( G ) is a serotonin receptor (5-HT7) binding compound, and the synthetic spirocyclohexane isobenzofuranone ( H ) is a Y-5 receptor antagonist. 8 Due to these broad spectra of biological properties, the asymmetric synthesis of spirocyclic isobenzofuranone systems is highly desirable.…”