ChemInform Abstract: NEW EFFICIENT TOTAL SYNTHESES OF DERIVATIVES OF PROTOPORPHYRIN-IX BEARING DEUTERIATED METHYL GROUPS

Melicopine, melicopidine, and melicopicine are each oxidized by nitric acid to the same acid, C11H9O3N. Decarboxylation gives 1-methyl-4-quinolone (I) and the acid is shown to be 1-methyl-4-quinolone-3-carboxylic acid (II). The 3- and 6- mononitro-, 3,6-dinitro-, and 2-hydroxy-3,6-dinitro- derivatives of 1-methyl-4-quinolone have been prepared and the orientation of the substituents established by oxidation of the hydroxydinitro- compound to 5-nitro-N-methylanthranilic acid. 1-Methy1-4-quinolone-3-carboxylic acid is readily converted to a tetrahydro- derivative. The carboxyl groups in II and in the tetrahydro- acid are reduced by zinc and hydrochloric acid to methyl groups.

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Pyrazolinyl and cyclopropyl derivatives of protoporphyrin IX and chlorins related to chlorophyll a

Tetrahedron ◽

10.1016/s0040-4020(02)01525-9 ◽

2003 ◽

Vol 59 (4) ◽

pp. 499-504 ◽

Cited By ~ 18

Author(s):

Andrei N Kozyrev ◽

James L Alderfer ◽

Byron C Robinson

Keyword(s):

Chlorophyll A ◽

Protoporphyrin Ix ◽

Derivatives Of

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Molecular Aspects of Herbicide Action on Protoporphyrinogen Oxidase

Zeitschrift für Naturforschung C ◽

10.1515/znc-1993-3-434 ◽

1993 ◽

Vol 48 (3-4) ◽

pp. 326-333 ◽

Cited By ~ 5

Author(s):

Beate Nicolaus ◽

Gerhard Sandmann ◽

Peter Böger

Keyword(s):

Diphenyl Ether ◽

Protoporphyrin Ix ◽

Protoporphyrinogen Oxidase ◽

Relative Specificity ◽

Oxidase Inhibition ◽

Dilution Experiments ◽

Membrane Bound ◽

The Common ◽

Molecular Aspects ◽

Derivatives Of

Abstract Protoporphyrinogen oxidase, the last enzyme of the common tetrapyrrole biosynthetic pathway, is inhibited by several peroxidizing compounds resulting in accumulation of photodynamic tetrapyrroles, mainly protoporphyrin IX. The inhibition characteristics of two chemically unrelated compounds were studied using membrane bound protoporphyrinogen oxidase from corn etioplasts. As shown by Lineweaver-Burk-analysis, the inhibition of enzyme activity by the diphenyl ether oxyfluorfen and the cyclic imide MCI 15 are competitive with respect to the substrate. The competitive interaction of protoporphyrinogen and the two chemically unrelated inhibitors indicate a relative specificity of the binding site. The reversibility of oxyfluorfen inhibition was evaluated by dilution experiments and was shown to be independent of the presence of DTT. The analysis of structure-activity-relationship on protoporphyrinogen oxidase inhibition was investigated with para-substituted derivatives of phenyl-3,4,5,6-tetrahydro-phthalimides. The results obtained by QSAR -calculation yielded a good correlation of the inhibitory activity determined by the lipophilicity of the para-substituent. These data point to one binding region of the inhibitors within a lipophilic environment associated with the active center of the enzyme.

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The chemistry of pyrrolic compounds. XIV. meso-Hydroxyprotoporphyrin IX and its derivatives

Australian Journal of Chemistry ◽

10.1071/ch9702477 ◽

1970 ◽

Vol 23 (12) ◽

pp. 2477 ◽

Cited By ~ 13

Author(s):

PS Clezy ◽

AJ Liepa

Keyword(s):

Protoporphyrin Ix ◽

Bile Pigment ◽

General Properties ◽

Biliverdin Ix ◽

Hydrolysis Of ◽

Derivatives Of ◽

Benzoate Derivatives

The preparation of the acetate and benzoate derivatives of �-hydroxy-protoporphyrin IX is described and the hydrolysis of these enolic esters examined. The general properties of these porphyrins are discussed together with the oxidation of this system to a bile pigment identical with biliverdin IX�: with regard to spectroscopic and chromatographic characteristics.

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SYNTHESIS OF DERIVATIVES OF 1,2-DICHLORO-4-BENZENESULFONAMIDO-5-NITROBENZENE AND THEIR USE IN THE CHEMOTHERAPY OF SPONTANEOUS CANCERS

Canadian Journal of Chemistry ◽

10.1139/v65-196 ◽

1965 ◽

Vol 43 (5) ◽

pp. 1454-1459 ◽

Cited By ~ 1

Author(s):

D. W. Woolley ◽

T. Van Der Hoeven

Keyword(s):

Active Substance ◽

Quaternary Ammonium ◽

Water Solubility ◽

Parent Compound ◽

Para Position ◽

Methyl Groups ◽

Chlorine Atoms ◽

Derivatives Of ◽

Ionizable Groups

A series of compounds related to 1,2-dichloro-4-benzenesulfonamido-5-nitrobenzene has been synthesized. These included derivatives in which ionizable groups had been placed in the para position of the benzenesulfonamido portion to confer on the compounds water solubility at physiological pH. Thus, carboxyl and quaternary ammonium groupings were introduced in this position. Water solubility was also conferred by introduction at the same position of non-ionizable groups such as polyhydroxyalkylamido groups. Additional relatives of the parent compound in which the chlorine atoms were replaced by methyl groups, and in which para-substituted benzenesulfonamido groups replaced those in the 4 and 5 positions, were synthesized. These compounds were tested for their ability to cure permanently the spontaneous mammary cancers of two strains of mice. All compounds were tested in combination with 1,2-dimethyl-4-(p-carboxyphenylazo)-5-hydroxybenzene. The most active substance found was 1,2-dichloro-4-(p-carboxybenzenesulfonamido)-5-nitrobenzene.

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