A New Glycociamidine Ring Precursor:  Syntheses of (Z)-Hymenialdisine, (Z)-2-Debromohymenialdisine, and (±)-endo-2-Debromohymenialdisine

Abstract

[chemical reaction: see text]. The synthesis of the C11H5 marine sponge alkaloids, (Z)-hymenialdisine and (Z)-2-debromohymenialdisine, is described. A key step was the condensation between aldisine or its monobromo derivative and a new, efficient imidazolinone-based glycociamidine precursor. In the first case, the main product turned out to be the unprecedented (+/-)-endo-2-debromohymenialdisine.

Experimental and computational energetic study of two halogenated 2-acetylpyrrole derivatives: 2-Trichloroacetylpyrrole and 2-trifluoroacetylpyrrole

“…Both halogenated title compounds are widely used in synthetic organic chemistry. The 2-trichloroacetylpyrrole is used in the synthesis of naturally occurring pyrrole alkaloids, extracted from marine sponges [4][5][6]; these alkaloids have found applications in the treatment of neurodegenerative disorders, diabetes, cancer, inflammatory pathologies, and ocular diseases. Furthermore, 2-trichloroacetylpyrrole is used as starting material in the preparation of antibacterial agents of potential interest in human chemotherapy [7].…”

Exploring the Synthesis of New 1-(4-Substitutedphenylamino) imidazo[1,5-a]indol-3-one Derivatives as Cyclized Analogs of Leucettines

“…GSK-3 (porcine brain, native) was assayed, as described for CDK5/p25 but in Buffer A and using a GSK-3 specific substrate (GS-1: YRRAAVPPSPSLSRHSSPHQSpEDEEE) (pS stands for phosphorylated serine) (Primot et al, 2000). GS-1 was synthesized by Millegen (Labege, France).…”

“…Several total synthesis of Leucettamine B have been reported (Molina et al, 1994, Roué et al, 1999, Chérouvrier et al, 2001and 2002, Debdab et al, 2009. Other marine natural products containing the 2-aminoimidazoline-4-one core, such as polyandrocarpamine A (Cimino et al, 1982), hymenialdisine (Meijer et al, 2000, Xu et al, 1997, and Papeo et al, 2005 and zorrimidazolone (Aiello et al, 2011), are subject to intensive research by organic chemists, biochemists and biologists.…”

A Submarine Journey: The Pyrrole-Imidazole Alkaloids

“…Synthetic approaches [74–78] towards ( Z )-HMD ( 17 ) and ( Z )-DBH ( 19 ) have been reported (Scheme 4). 1-Benzoyl-2-methylsulfanyl-1,5-dihydroimidazol-4-one ( 21 ) employed in Papeo’s approach was also useful in the first total synthesis of ( Z )-axinohydantoin (see Subsection 3.2).…”

“…Recently our group accomplished the first synthesis of ( Z )- and ( E )-axinohydantoins ( 22 ) and ( 23 ), along with a second generation synthesis of 24 and 25 [90]. To this purpose, the chemistry already optimized for HMD synthesis [78] was successfully employed.…”