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Related Concept Videos

Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
Stereoisomers02:32

Stereoisomers

On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to restricted...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...

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Trans-, cis-, and dihydro-resveratrol: a comparative study.

Natalia Yu Anisimova1, Mikhail V Kiselevsky, Andrey V Sosnov

  • 1National Institutes of Health, NIDDK, 8 Center Drive, Bethesda, MD 20892, USA. gakhaa@yahoo.com.

Chemistry Central Journal
|December 22, 2011
PubMed
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Dihydroresveratrol (dihydro-R) shows a complex role in prostate cancer cell proliferation, exhibiting proliferative effects at low concentrations and inhibitory effects at higher concentrations. Trans-resveratrol (trans-R) can reverse dihydro-R

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Area of Science:

  • Oncology
  • Pharmacology
  • Molecular Biology

Background:

  • Moderate wine consumption has differential effects on cancer risk.
  • Red wine's trans-resveratrol (trans-R) is linked to reduced prostate cancer rates.
  • Varied resveratrol (R) forms' roles in cancer require investigation.

Purpose of the Study:

  • To investigate the impact of different resveratrol (R) forms on cancer proliferation.
  • To compare the antiproliferative potency of trans-resveratrol (trans-R), cis-resveratrol (cis-R), and dihydroresveratrol (dihydro-R).

Main Methods:

  • In vitro assessment of resveratrol isomers and dihydroresveratrol on prostate cancer cell lines.
  • Evaluation of dose-dependent effects and cross-modulation between dihydro-R and trans-R.

Main Results:

  • Trans-resveratrol (trans-R) is the most potent antiproliferative agent.
  • Dihydroresveratrol (dihydro-R) exhibits proliferative effects on androgen-independent prostate cancer cells at low concentrations (picomolar).
  • At higher concentrations, dihydro-R inhibits proliferation; trans-R acts as a partial antagonist to dihydro-R's proliferative effects, showing complex cross-modulation.

Conclusions:

  • Dihydroresveratrol (dihydro-R) demonstrates a dual role in prostate cancer cell proliferation, with effects potentially mediated by hormone receptor modulation.
  • Complex cross-modulation observed between dihydro-R and trans-R at very low concentrations.
  • The precise role of dihydro-R in wine-associated cancer proliferation remains unclear due to its complex activity patterns.