915-74-2

Usage

Type of compound

Organic compound

Usage

Commonly used in pharmaceuticals and as an intermediate in the synthesis of various organic compounds

Potential applications

Anti-hypertensive agent, inhibiting cancer cell growth, development of drugs for treating cardiovascular diseases and cancer, and treatment of neurodegenerative diseases (however, further research is needed to fully understand its potential applications and effectiveness).

Upstream product

• 4424-76-4 2-((benzyloxy)carbonyl)-3,4,5-trimethylpyrrole 
• 92578-75-1 5-bromomethyl-3,4-dimethyl-pyrrole-2-carboxylic acid benzyl ester 
• 2199-49-7 ethyl 4-methylpyrrole-3-carboxylate 
• 65038-94-0 5-((acetoxy)methyl)-2-((benzyloxy)carbonyl)-3,4-dimethylpyrrole 
• 87462-15-5 benzyl 5-methylpyrrole-2-carboxylate 

Downstream Products

• 119695-11-3 C₂₉H₂₈N₂O₄ 
• 119695-13-5 C₂₉H₂₈N₂O₄*BrH 
• 27226-49-9 3,3',4,4'-tetramethyldipyrromethane-5,5'-dicarboxylic acid 

Relevant academic research and scientific papers

A meso-unsubstituted N-confused porphyrin prepared by rational synthesis

Condensation of a tetraalkyl-α,α-dipyrromethane dialdehyde in a MacDonald-type [2+2]-condensation with a trialkyl-α,β-dipyrromethane gives a heptaalkyl N-confused porphyrin.

CHARACTERIZATION OF DECAMETHYL AND ETHOXYCARBONYL PENTAPHYRINS

The syntheses of decamethyl- and ethoxycarbonyl pentaphyrins are described.Their spectroscopic characterizations are presented in comparison with the permethyl derivatives of porphiryn, sapphyrin and hexaphyrin.The ethoxycarbonyl containing pentaphyrins are the only examples, amongst the expanded polypyrrolic macrocycles, that have an electron withdrawing group directly attached to the macrocyclic ring system.Elimination of a pyrrole and methine carbon unit in the mass spectrometr has been observed as a common feature for the pentaphyrin free bases as well as their metal derivatives.

Tetrapyrrole products from electrochemical cyclization of 1′,8′-disubstituted-a,c-biladiene salts

Anodic oxidation of 1′,8′-dimethyl- and other 1′,8′-disubstituted a.c-biladiene salts affords novel cyclized products. In addition to porphyrin, an unconjugated macrocyclic intermediate product resulting from oxidadve cyclizatfon during porphyrin synthesis is isolated, structurally identified, and characterized with regard to its spectroscopy, electrochemical behavior and chemical reactivity. The formation of a novel homoporphyrin from a 1′-ethoxycarbonylmethy-8′-(2-methoxycarbonylethyl)-a,c-biladiene salt is also briefly discussed.

Synthetic and Biosynthetic Studies of Porphyrins.Part10.Syntheses of Porphyrins with Acetic,Propionic,and Butyric Acid Side-chains for Biosynthetic Syudies.

In connection with studies of substrate specificity of uroporphyrinogen decarboxylase and coproporphyrinogen oxidase, enzymes in the heme and chlorophyll biosynthetic pathways,and heme oxygenase,an enzyme involved in the catabolism of hemes,we have synthesized a number of new porphyrins substituted with acetic,propionic,and butyric side-chains,using the a,c-biladiene route;one porphyrin was also prepared by the MacDonald pyrromethane approach.In one of the a,c-biladiene cyclizations,meso-chlorinated porphyrins were formed as minor by products,but this side-reaction was suppressed by carefully drying the copper(II) chloride used in this stage, or by use of copper(II) acetate as an alternative oxidant.