3019-51-0

Usage

Uses

Used in Pharmaceutical Industry:
3-(carboxymethyl)-8,13,18-trimethyl-21H,23H-Porphine-2,7,12,17-tetrapropanoic acid is used as a pharmaceutical compound for its potential therapeutic applications. The presence of multiple functional groups in its structure allows for interactions with various biological targets, making it a promising candidate for the development of new drugs.
Used in Antimicrobial Applications:
In the field of antimicrobial research, 3-(carboxymethyl)-8,13,18-trimethyl-21H,23H-Porphine-2,7,12,17-tetrapropanoic acid is used as an antibacterial agent. Its unique chemical structure may provide new insights into the development of novel antibiotics, particularly against drug-resistant bacterial strains.
Used in Drug Delivery Systems:
3-(carboxymethyl)-8,13,18-trimethyl-21H,23H-Porphine-2,7,12,17-tetrapropanoic acid can be utilized in the development of drug delivery systems to improve the bioavailability and efficacy of various therapeutic agents. Its functional groups can be exploited to enhance the stability, solubility, and targeted delivery of drugs, potentially leading to more effective treatments for various diseases.
Used in Chemical Research:
As an aporphine alkaloid, 3-(carboxymethyl)-8,13,18-trimethyl-21H,23H-Porphine-2,7,12,17-tetrapropanoic acid is used in chemical research for the study of its structure, properties, and potential applications in various fields. This may include the development of new synthetic methods, the investigation of its biological activities, and the exploration of its potential use in other industries, such as agriculture or materials science.

References

Spath, Tharrer., Ber., 66,904 (1933) Schlittler., ibid, 66,988 (1933)

InChI:InChI=1/C19H21NO4/c1-20-5-4-10-8-16(24-3)19(22)18-12-9-15(23-2)14(21)7-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3/t13-/m0/s1

Upstream product

• 485-19-8 (R)-reticuline 
• 475-81-0 glaucine 
• 371196-16-6 (6aS)-4,5,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6H-dibenzo[de,g]quinoline-6-carbaldehyde 
• 5890-18-6 (+)-norboldine 
• 371196-15-5 N-formyl-laurolitsine 
• 485-19-8 (+)-(S)-reticuline 

Relevant academic research and scientific papers

Semisynthesis and myocardial activity of thaliporphine N-homologues

The N-homologues and optical isomers of thaliporphine (5a), a potent antiarrhythmic agent, were prepared starting from laurolitsine (1), an abundant aporphine present in Phoebe formosana. Treating N-propylnorglaucine with 90% H2SO4 yielded one additional product, an 11-sulfonyl-1,11-anhydroaporphine. Reaction of N-formylnorglaucine (3a) with 90% H2SO4, however, yielded the 9-sulfonyl-seco product as a major product. Treatment of 3a with 98% H2SO4 yielded pancordine (10), which, upon catalytic hydrogenation, yielded (±)-wilsonirine. 1H NMR spectroscopic analysis was applied successfully to monitor the optical purity of the crystalline salt while undertaking optical resolution. Thaliporphine (5a) was demonstrated to possess better positive inotropic and less negative chronotropic effects than the left-hand optical isomer and showed the best activity on rat cardiac tissue among the N-homologues prepared.

Rat CYP2D2, not 2D1, is functionally conserved with human CYP2D6 in endogenous morphine formation

The assumption that CYP2D1 is the corresponding rat cytochrome to human CYP2D6 has been revisited using recombinant proteins in direct enzyme assays. CYP2D1 and 2D2 were incubated with known CYP2D6 substrates, the three morphine precursors thebaine, codeine and (R)-reticuline. Mass spectrometric analysis showed that rat CYP2D2, not 2D1, catalyzed the 3-O-demethylation reaction of thebaine and codeine. In addition, CYP2D2 incubated with (R)-reticuline generated four products corytuberine, pallidine, salutaridine and isoboldine while rat CYP2D1 was completely inactive. This intramolecular phenol-coupling reaction follows the same mechanism as observed for CYP2D6. Michaelis-Menten kinetic parameters revealed high catalytic efficiencies for rat CYP2D2. These findings suggest a critical evaluation of other commonly accepted, however untested, CYP2D1 substrates.

BIOTRANSFORMATION OF ISOQUINOLINE ALKALOIDS WITH RAT LIVER MICROSOMES

Optically active (+)-reticuline (1) was biotransformed into (-)-coreximine (2), (-)-scoulerine (3), (+)-isoboldine (4) and (-)-pallidine (5) with retention of the chirality by the incubation with rat liver microsomes.On the other hand, the racemate of reticuline formed the racemates of the above alkaloids on the some treatment.The S-adenosylmethionine was partially incorporated into the berberine bridge during the biotransformation of reticuline into the protoberberines.