4396-11-6Relevant academic research and scientific papers
The first isolation of unsubstituted porphyrinogen and unsubstituted 21-oxaporphyrinogen by the '3+1' approach from 2,5-bis(hydroxymethyl)pyrrole and tripyrrane derivatives
Taniguchi, Shozo,Hasegawa, Hikaru,Yanagiya, Shoko,Tabeta, Yusuke,Nakano, Yoshiharu,Takahashi, Masahiko
, p. 2103 - 2108 (2001)
The treatment of 2,5-bis(hydroxymethyl)pyrrole or 2,5-bis(hydroxymethyl)furan with pyrrole in the presence of hydrochloric acid gave tripyrrane and 2,5-bis(2-pyrrolylmethyl)furan in 58-61% yield, which afforded the simplest porphyrinogen (hexahydroporphine) and 21-oxaporphyrinogen by the '3+1' approach in 14 and 11% yields, respectively. 21-Oxaporphyrinogen has been shown to adopt a 1,2-alternated conformation in the solid state by X-ray crystallography.
Synthesis of bisindolylmethane, bispyrrolylmethane, and indolylpyrrolylmethane derivatives via reductive heteroarylation
Zhou, Hang,Huang, Zhuo,Huang, He,Song, Chuanjun,Chang, Junbiao
, (2021/07/25)
An efficient and general reductive heteroarylation approach toward the synthesis of bisindolylmethane, bispyrrolylmethane, and indolylpyrrolylmethane derivatives has been developed. Thus, treatment of acylpyrrole or acylindole derivatives with indoles or pyrroles in the presence of a combination of sodium borohydride and acetic acid resulted in the formation of the title compounds in moderate to excellent isolated yields.
Porphyrin synthesis in surfactant solution: Multicomponent assembly in micelles
Bonar-Law, Richard P.
, p. 3623 - 3634 (2007/10/03)
A synthesis of meso-substituted porphyrins in anionic sodium dodecyl sulfate micelles has been developed. Polar, functionalized aromatic aldehydes condense reversibly with pyrrole in the micellar phase. Oxidation of the porphyrinogen then provides functionalized porphyrins in yields of 10-48%. Hydrophobic aldehydes condense irreversibly to give low yields at practical substrate concentrations. Synthesis in D2O solution results in per-β-deuterated porphyrins. A two-phase model is used to rationalize the dependence of porphyrin yield on reactant and surfactant concentration. Micelles are viewed as potential wells which promote porphyrinogen assembly by binding products more tightly than reactants.
Synthetic drug molecules that mimic metalloenzymes
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, (2008/06/13)
Synthetic enzymes that mimic the catalytic activity of naturally occurring enzymes by providing catalytic sites enclosed in cages that protect the sites from undesirable molecules and attract and permit entry of the relevant substrates are disclosed. Mole
