Synthesis of bilin-1,19-diones and biladiene-ac-1,19-diones with C(10) adamantyl and tert-butyl groups

被引：5

作者：

Kar, AK ^{[1
]}

Lightner, DA ^{[1
]}

机构：

[1] Univ Nevada, Dept Chem, Reno, NV 89557 USA

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1998年 / 35卷 / 04期

关键词：

D O I：

10.1002/jhet.5570350404

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bilirubin and biliverdin analogs bearing bulky adamantyl and tert-butyl groups at the central C(10) position were synthesized and their structures were analyzed by nmr and ultraviolet-visible spectroscopy and by molecular mechanics calculations, all of which collectively indicated a preference for helical conformations.

引用

收藏

页码：795 / 803

页数：9

相关论文

共 25 条

[1] Synthesis and stereochemistry of bilirubin analogs lacking carboxylic acids [J].

Boiadjiev, SE ;

Pfeiffer, WP ;

Lightner, DA .

TETRAHEDRON, 1997, 53 (43) :14547-14564

[2] SYNTHESIS AND STEREOCHEMISTRY OF OPTICALLY-ACTIVE BILIVERDIN CYCLIC ESTERS [J].

BOIADJIEV, SE ;

ANSTINE, DT ;

LIGHTNER, DA .

TETRAHEDRON-ASYMMETRY, 1995, 6 (04) :901-912

[3] STRUCTURE OF BILIRUBIN [J].

BONNETT, R ;

DAVIES, JE ;

HURSTHOUSE, MB ;

SHELDRICK, GM .

PROCEEDINGS OF THE ROYAL SOCIETY SERIES B-BIOLOGICAL SCIENCES, 1978, 202 (1147) :249-268

[4] CRYSTALLOGRAPHIC STUDIES IN PYRROLE SERIES .2. CRYSTAL AND MOLECULAR STRUCTURE OF 5,5'-DIETHOXYCARBONYL-3,3',4,4'-TETRAETHYLDIPYRROL-2-YLMETHANE [J].

BONNETT, R ;

NEIDLE, S ;

HURSTHOU.MB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1972, (10) :1335-&

[5] DEPOSITION OF BILIRUBIN ACID IN THE CENTRAL-NERVOUS-SYSTEM - A HYPOTHESIS FOR THE DEVELOPMENT OF KERNICTERUS [J].

BRODERSEN, R ;

STERN, L .

ACTA PAEDIATRICA SCANDINAVICA, 1990, 79 (01) :12-19

[6] HYPERBILIRUBINEMIA RESULTS IN REDUCED OXIDATIVE INJURY IN NEONATAL GUNN-RATS EXPOSED TO HYPEROXIA [J].

DENNERY, PA ;

MCDONAGH, AF ;

SPITZ, DR ;

RODGERS, PA ;

STEVENSON, DK .

FREE RADICAL BIOLOGY AND MEDICINE, 1995, 19 (04) :395-404

[7] ON THE CHEMISTRY OF PYRROLE PIGMENTS .79. THE STRUCTURAL INFLUENCE OF STRONGLY SPACE DEMANDING RESIDUES OF 10-SUBSTITUTED 1,19-BILINDIONES [J].

FALK, H ;

MULLER, N ;

WOSS, H .

MONATSHEFTE FUR CHEMIE, 1989, 120 (01) :35-43

[8]

Falk H., 1989, The Chemistry of Linear Oligopyrroles and Bile Pigments

[9]

Fischer H, 1937, H-S Z PHYSIOL CHEM, V245, P107

[10]

GOSSAUER A, 1994, CHIMIA, V48, P352