Synthesis and Absolute Configuration of Cis- and Trans-Opened Cyclopenta[cd]pyrene 3,4-OxideN2-Deoxyguanosine Adducts:  Conversion to Phosphoramidites for Oligonucleotide Synthesis

2007 ◽  
Vol 20 (4) ◽  
pp. 650-661 ◽  
Author(s):  
Haruhiko Yagi ◽  
Heinrich Frank ◽  
Albrecht Seidel ◽  
Donald M. Jerina
Keyword(s):  
Absolute Configuration ◽  
Oligonucleotide Synthesis ◽  
Cis And Trans

Molecular Structure of cis- and trans-Tergurides

1998 ◽  
Vol 63 (3) ◽  
pp. 425-433 ◽  
Author(s):  
Michal Hušák ◽  
Bohumil Kratochvíl ◽  
Petr Sedmera ◽  
Vladimír Havlíček ◽  
Hana Votavová ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Absolute Configuration ◽  
Catalytic Hydrogenation ◽  
Ergot Alkaloid ◽  
Cd Spectra ◽  
X Ray ◽  
Relative Stereochemistry ◽  
Cis And Trans

Four isomers of terguride, a semisynthetic ergot alkaloid derivative, have been prepared by catalytic hydrogenation of (5R,8S)- and (5S,8S)-lisuride [1,1-diethyl-3-(6-methyl-8-ergolenyl)urea]. Relative stereochemistry of the isomers is based on NMR and CD spectra. Absolute configuration of all the series has been confirmed by the X-ray crystal structure determination of (5R,8S,10S)-terguride 2-bromobenzoate [1,1-diethyl-3-(6-methyl-8-isoergolenyl)urea, cis-dihydrolisuride].

scholarly journals Synthesis and HPLC-ECD Study of Cytostatic Condensed O,N-Heterocycles Obtained from 3-Aminoflavanones

Biomolecules ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 1462
Author(s):  
Ádám Szappanos ◽  
Attila Mándi ◽  
Katalin Gulácsi ◽  
Erika Lisztes ◽  
Balázs István Tóth ◽  
...  
Keyword(s):  
Cell Lines ◽  
Absolute Configuration ◽  
Major Product ◽  
Acid Ceramidase ◽  
Substitution Pattern ◽  
Aryl Group ◽  
Ic50 Values ◽  
The Absolute ◽  
Cis And Trans ◽  
Condensed Heterocycles

Racemic chiral O,N-heterocycles containing 2-arylchroman or 2-aryl-2H-chromene subunit condensed with morpholine, thiazole, or pyrrole moieties at the C-3-C-4 bond were synthesized with various substitution patterns of the aryl group by the cyclization of cis- or trans-3-aminoflavanone analogues. The 3-aminoflavanone precursors were obtained in a Neber rearrangement of oxime tosylates of flavanones, which provided the trans diastereomer as the major product and enabled the isolation of both the cis- and trans-diastereomers. The cis- and trans-aminoflavanones were utilized to prepare three diastereomers of 5-aryl-chromeno[4,3-b][1,4]oxazines. Antiproliferative activity of the condensed heterocycles and precursors was evaluated against A2780 and WM35 cancer cell lines. For a 3-(N-chloroacetylamino)-flavan-4-ol derivative, showing structural analogy with acyclic acid ceramidase inhibitors, 0.15 μM, 3.50 μM, and 6.06 μM IC50 values were measured against A2780, WM35, and HaCat cell lines, and apoptotic mechanism was confirmed. Low micromolar IC50 values down to 2.14 μM were identified for the thiazole- and pyrrole-condensed 2H-chromene derivatives. Enantiomers of the condensed heterocycles were separated by HPLC using chiral stationary phase, HPLC-ECD spectra were recorded and TDDFT-ECD calculations were performed to determine the absolute configuration and solution conformation. Characteristic ECD transitions of the separated enantiomers were correlated with the absolute configuration and effect of substitution pattern on the HPLC elution order was determined.

Synthesis and Assignment of Absolute Configuration to the N6-Deoxyadenosine Adducts Resulting from Cis and Trans Ring-Opening of Phenanthrene 9,10-Oxide

1994 ◽  
Vol 59 (7) ◽  
pp. 1755-1760 ◽  
Author(s):  
Mahesh K. Lakshman ◽  
Wei Xiao ◽  
Jane M. Sayer ◽  
Albert M. Cheh ◽  
Donald M. Jerina
Keyword(s):  
Absolute Configuration ◽  
Ring Opening ◽  
Cis And Trans ◽  
Deoxyadenosine Adducts

Absolute configuration of cis- and trans-2-(o-bromophenyl)cyclohexylamine and related compounds

1976 ◽  
Vol 41 (9) ◽  
pp. 1640-1642 ◽  
Author(s):  
Todd G. Cochran ◽  
Allan. Weber ◽  
Alain C. Huitric ◽  
Arthur. Camerman ◽  
Lyle H. Jensen
Keyword(s):  
Absolute Configuration ◽  
Cis And Trans ◽  
Related Compounds

CYCLOPROPANES. VII. THE ABSOLUTE CONFIGURATION OF trans-CARONIC AND cis AND trans-UMBELLULARIC ACIDS1

1960 ◽  
Vol 82 (19) ◽  
pp. 5255-5256 ◽  
Author(s):  
H. M. Walborsky ◽  
T. Sugita ◽  
M. Ohno ◽  
Y. Inouye
Keyword(s):  
Absolute Configuration ◽  
The Absolute ◽  
Cis And Trans
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