Synthesis and Biological Evaluation of Some Enantiomerically Pure C8c - C15 Monoseco Analogues of the Phenanthroquinolizidine-Type Alkaloids Cryptopleurine and Julandine

2008 ◽  
Vol 61 (7) ◽  
pp. 506 ◽  
Author(s):  
Magne O. Sydnes ◽  
Anna Bezos ◽  
Christopher Burns ◽  
Irma Kruszelnicki ◽  
Christopher R. Parish ◽  
...  
Keyword(s):  
Single Crystal ◽  
Building Blocks ◽  
Biological Evaluation ◽  
Enantiomerically Pure ◽  
X Ray ◽  
System 1 ◽  
Synthesis And Biological Evaluation ◽  
Related Compounds

A series of enantiomerically pure C8c–C15 monoseco analogues, 23–30, of the alkaloids cryptopleurine (1) and julandine (2) have been prepared using cinnamyl chloride 37 and (S)- or (R)-2-methylpiperidine as key building blocks. Two related compounds, 31 and 32, have also been synthesized. Each of these analogues has been subjected to various biological evaluations and most of them show dramatically reduced cytotoxicity compared with parent system 1. Nevertheless, they are potent anti-angiogenic agents. The formation and single-crystal X-ray analysis of the spirocyclic dienone 54, a by-product arising from attempts to prepare analogue 32, is also described.

Competitive Intramolecular Diels - Alder Reactions of bis-α,β-Unsaturated Ester Derivatives of Enzymatically Derived and Enantiopure cis-1,2-Dihydrocatechols. Enantiodivergent Synthesis of Monochiral Bicyclo[2.2.2]oct-2-enes

2003 ◽  
Vol 56 (9) ◽  
pp. 861 ◽  
Author(s):  
Martin G. Banwell ◽  
Cai Chun ◽  
Alison J. Edwards ◽  
Markus M. Vögtle
Keyword(s):  
Natural Products ◽  
Single Crystal ◽  
Building Blocks ◽  
Diels Alder ◽  
Unsaturated Ester ◽  
Enantiomerically Pure ◽  
X Ray ◽  
Derivatives Of ◽  
Natural Products Synthesis

bis-Crotonate and related α,β-unsaturated ester derivatives of readily available and enantiomerically pure cis-1,2-dihydrocatechols engage, upon heating in refluxing toluene, in two competitive intramolecular Diels–Alder reactions to give varying mixtures of chromatographically separable and pseudo-enantiomeric bicyclo[2.2.2]oct-2-enes. Such adducts, many of which have been characterized by single-crystal X-ray analysis, are likely to serve as useful building blocks in natural products synthesis.

The Synthesis and Biological Evaluation of Two Analogues of the C-Riboside Showdomycin

2005 ◽  
Vol 58 (2) ◽  
pp. 86 ◽  
Author(s):  
Jens Renner ◽  
Irma Kruszelnicki ◽  
Beata Adamiak ◽  
Anthony C. Willis ◽  
Edward Hammond ◽  
...  
Keyword(s):  
Single Crystal ◽  
Biological Evaluation ◽  
X Ray ◽  
Synthetic Equivalent ◽  
Synthesis And Biological Evaluation

Two novel analogues, 2 and 3, of the C-riboside showdomycin (1) have been prepared by exploiting the N-TIPS-substituted pyrrole 7 as a synthetic equivalent for the maleimide C3 anion. The tetraacetate precursor, 12, of target 2 as well as target 3 itself were subjected to single-crystal X-ray analyses. Analogues 2 and 3 as well as showdomycin and its anomer (4) have each been evaluated in various assays for their cytotoxic, anti-bacterial, and anti-viral effects.

Harnessing the main event of drimentines biosynthesis: bio-inspired synthesis and biological evaluation of Δ8'-isodrimentine A and related compounds

Planta Medica ◽  
2016 ◽  
Vol 81 (S 01) ◽  
pp. S1-S381
Author(s):  
A Skiredj ◽  
MA Beniddir ◽  
L Evanno ◽  
E Poupon
Keyword(s):  
Biological Evaluation ◽  
Synthesis And Biological Evaluation ◽  
Related Compounds

scholarly journals Stereoselective Convergent Synthesis of Carbon Skeleton of Cotylenin A Aglycone

Synthesis ◽  
2021 ◽  
Author(s):  
Kazuyuki Sugita ◽  
Motoi Kuwabara ◽  
Ami Matsuo ◽  
Shogo Kamo ◽  
Akinobu Matsuzawa
Keyword(s):  
Single Crystal ◽  
Aldol Reaction ◽  
Coupling Reaction ◽  
Carbon Skeleton ◽  
Convergent Synthesis ◽  
X Ray ◽  
Related Compounds

AbstractIn this paper, the synthesis of the carbon skeleton of cotylenin A aglycone is described. The key reactions, including an intramolecular aldol reaction, an aldol coupling reaction, and a ring-closing meta­thesis, allow for the effective and stereoselective access to the carbon skeleton of cotylenin A aglycone. The stereochemistry was confirmed by single-crystal X-ray crystallographic analyses of related compounds.

ChemInform Abstract: Synthesis and Biological Evaluation of 4-(Hydroxyalkyl)estradiols and Related Compounds.

ChemInform ◽  
2010 ◽  
Vol 29 (8) ◽  
pp. no-no
Author(s):  
C. J. LOVELY ◽  
A. S. BHAT ◽  
H. D. COUGHENOUR ◽  
N. E. GILBERT ◽  
R. W. BRUEGGEMEIER
Keyword(s):  
Biological Evaluation ◽  
Synthesis And Biological Evaluation ◽  
Related Compounds

First practical synthesis of enantiomerically pure (R)- and (S)-desmethylsibutramine (DMS) and unambiguous determination of their absolute configuration by single-crystal X-ray analysis

2002 ◽  
Vol 13 (2) ◽  
pp. 107-109 ◽  
Author(s):  
Zhengxu Han ◽  
Dhileepkumar Krishnamurthy ◽  
Derek Pflum ◽  
Qun K. Fang ◽  
Hal Butler ◽  
...  
Keyword(s):  
Single Crystal ◽  
Absolute Configuration ◽  
Enantiomerically Pure ◽  
X Ray ◽  
Unambiguous Determination ◽  
Practical Synthesis

Design, synthesis and biological evaluation of novel human monoamine oxidase B inhibitors based on a fragment in an X-ray crystal structure

2019 ◽  
Vol 29 (8) ◽  
pp. 1012-1018 ◽  
Author(s):  
Kai Cheng ◽  
Shiyu Li ◽  
Xiao Lv ◽  
Yongbin Tian ◽  
Haiyan Kong ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Monoamine Oxidase ◽  
Biological Evaluation ◽  
Monoamine Oxidase B ◽  
Design Synthesis ◽  
X Ray ◽  
Synthesis And Biological Evaluation

Synthesis, single-crystal X-ray diffraction, and in vitro biological evaluation of sodium, cobalt, and tin complexes of o-nitro-/o-methoxyphenylacetic acid: experimental and theoretical investigation

2020 ◽  
Vol 151 (11) ◽  
pp. 1727-1736
Author(s):  
Muhammad Danish ◽  
Muhammad Asam Raza ◽  
Sana Iftikhar ◽  
Muhammad Waseem Mumtaz ◽  
Muhammad Nawaz Tahir ◽  
...  
Keyword(s):  
Single Crystal ◽  
Theoretical Investigation ◽  
Biological Evaluation ◽  
X Ray Diffraction ◽  
X Ray ◽  
Tin Complexes

scholarly journals Organometallic Nucleosides: Synthesis and Biological Evaluation of Substituted Dicobalt Hexacarbonyl Alkynyl Modified 2′-Deoxyuridines

Proceedings ◽  
2019 ◽  
Vol 22 (1) ◽  
pp. 62
Author(s):  
Roman Dembinski ◽  
Renata Kaczmarek ◽  
Dariusz Korczyński ◽  
Karolina Królewska-Golińska
Keyword(s):  
Cell Line ◽  
K562 Cells ◽  
Biological Evaluation ◽  
Oxygen Species ◽  
K562 Cell Line ◽  
Dicobalt Octacarbonyl ◽  
Cobalt Compounds ◽  
Dicobalt Hexacarbonyl ◽  
Synthesis And Biological Evaluation ◽  
Related Compounds

In continuation of synthetic pursuit of metallo-nucleosides, in particular dicobalt hexacarbonyl 5-alkynyl-2′-deoxyuridines, novel compounds with alkynyl groups were synthesized, starting from 5-iodo-2′-deoxyuridine. Reactions of dicobalt octacarbonyl [Co2(CO)8] with 2′-deoxy-5-oxopropynyluridines and related compounds gave dicobalt hexacarbonyl nucleoside complexes (83–31%). The growth inhibition of HeLa and K562 cancer cell lines by organometallic nucleosides was examined and compared to that by alkynyl nucleoside precursors. Coordination of the dicobalt carbonyl moiety to the 2′-deoxy-5-alkynyluridines led to a significant increase in its cytotoxic potency. The cobalt compounds antiproliferative activities against the HeLa cell line and the K562 cell line will be described. Coordination of an acetyl-substituted cobalt nucleoside was expanded using the 1,1-bis(diphenylphosphino)methane (dppm) ligand, resulting in cytotoxicity at comparable levels. The formation of reactive oxygen species in the presence of cobalt compounds was determined in K562 cells. The results indicate that the mechanism of action for most antiproliferative cobalt compounds may be related to the induction of oxidative stress.

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