54278-10-3Relevant articles and documents
(m.n)-Homorubins: Syntheses and structures
Pfeiffer, William P.,Lightner, David A.
, p. 1777 - 1801 (2015/02/19)
Five new homorubin analogs of bilirubin with their two dipyrrinone components conjoined to (CH2)2, (CH2)3, and (CH2)4 units were synthesized with propionic acid chains shortened to acetic and elongated to butyric, and examined by spectroscopy and molecular mechanics computations for an ability to form conformation-determining hydrogen bonds. With m designating the number of conjoining CH2 units and n indicating the number of CH2 units of the alkanoic acid chains of ( m.n)-homorubins, (2.1)-, (3.2)-, (4.2)-, and (4.3)-homorubins were prepared and compared with previously synthesized (2.2) and (2.3), which adopt intramolecularly hydrogen-bonded conformations in CHCl3.
Methods for treating diseases and disorders related to unregulated angiogenesis and/or vasculogenesis
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, (2008/06/13)
The present invention relates to methods for treating diseases and disorders related to unregulated angiogenesis and/or vasculogenesis. More specifically, this invention relates to methods for treating diseases and disorders, such as rheumatoid arthritis,
Pyrrole substituted 2-indolinone protein kinase inhibitors
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, (2008/06/13)
The present invention relates to novel pyrrole substituted 2-indolinone compounds and physiologically acceptable salts and prodrugs thereof which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.
SYNTHESIS AND UNUSUAL PROPERTIES OF C(10)-gem-DIMETHYL BILIRUBIN ANALOGS
Xie, Meiqiang,Lightner, David A.
, p. 2185 - 2200 (2007/10/02)
The characteristic thermodynamically-favored intramolecularly hydrogen-bonded conformation adopted by bilirubin pigments is destabilized by substituting methyl groups on the C(10) central methylene.These methyl groups impose conformation-destabilizing methyl-methylene non-bonded steric interactions with the propionic acid β-CH2 groups at C(8) and C(12) when the propionic acids are engaged in intramolecular hydrogen bonding with the opposing dipyrrinones.Amphiphilic 10,10-dimethylbilirubins (1) and (2) are found to be more polar, but also more soluble than the parents (3) and (4) in organic solvents; yet, 1H-NMR studies in non-polar solvents indicate that a deformed but folded, intramolecularly hydrogen-bonded conformation is retained.The dimethyl esters of 10,10-dimethylbilirubins 1 and 2 did not exhibit the typical strong tendency of bilirubin dimethyl esters to form intermolecular hydrogen bonds in non-polar solvents such as chloroform and benzene.
An efficient route to dipyrrinones: Synthesis of xanthobilirubic acid methyl ester
Shrout,Lightner
, p. 1062 - 1065 (2007/10/02)
Structurally interesting and complicated dipyrrinones, such as xanthobilirubic acid methyl ester (9), can be synthesized on a large scale from simple, inexpensive starting materials like ethyl acetoacetate, 2,4-pentanedione (1) and ethyl acrylate in 8 steps with an average yield of 80% at each step and an overall 17% yield.
Xanthobilirubic Acid and Its Amides. Synthesis, Spectroscopy, and Solution Structures
Lightner, D. A.,Ma, J.-S.,Adams, T. C.,Franklin, R. W.,Landen, G. L.
, p. 139 - 144 (2007/10/02)
Xanthobilirubic acid, 5--2,4-dimethyl-1H-pyrrol-3-propanoic acid, its methyl ester, amide, N-methylamide and dimethylamide, and kryptopyrromethenone have been synthesized and characterized spectroscopically.In d6-DMSO solution all pyrromethenones were monomeric, with lactam and pyrrole N-Hs H-bonded to solvent.In deuteriochloroform, the pyrromethenones preferred a dimeric form, with intramolecular H-bonding between the lactam C=O of one unit and the lactam and pyrrole N-Hs of the second.
