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Synthesis of type III isomers of diacetyldeutero-, hemato-, and protoporphyrins with the use of Knorr's pyrrole
- Source :
- Tetrahedron. 72:4022-4026
- Publication Year :
- 2016
- Publisher :
- Elsevier BV, 2016.
-
Abstract
- Derivation of the Knorr's pyrrole with 2-ethyl and 4-benzyl mixed-ester groups into 3,3′-diacetyl-5,5′-diiodo-4,4′-dimethyl-2,2′-dipyrromethane was developed. Coupling of the dipyrromethane with 5,5′-diformyl-3,3′-bis(2-methoxycarbonylethyl)-4,4′-dimethyl-2,2′-dipyrro-methane afforded in a reasonable yield diacetyldeuteroporphyin III with C2v symmetry. The porphyrin was further converted to protoporphyrin III through hematoporphyrin III. Utilization of readily available Knorr's pyrrole as the starting material much facilitates the access to symmetric iron porphyrins which are free from the orientational disorder in hemoprotein pocket.
- Subjects :
- Hematoporphyrin
Hemeprotein
010405 organic chemistry
Stereochemistry
Organic Chemistry
010402 general chemistry
01 natural sciences
Biochemistry
Porphyrin
Medicinal chemistry
0104 chemical sciences
chemistry.chemical_compound
chemistry
Yield (chemistry)
Drug Discovery
Protoporphyrins
Protoporphyrin
Pyrrole
Subjects
Details
- ISSN :
- 00404020
- Volume :
- 72
- Database :
- OpenAIRE
- Journal :
- Tetrahedron
- Accession number :
- edsair.doi...........28ce2fd7e41b81bdbf15e3b431ee7ff1