138090-06-9 Usage
Description
(5R,11R)-5,11-DIETHYL-5,6,11,12-TETRAHYDRO-2,8-CHRYSENEDIOL, also known as cis-5,11-Diethyl-5,6,11,12-tetrahydro-2,8-chrysenediol, is a chemical compound that belongs to the tetrahydrochrysene family. It is characterized by its unique molecular structure, which includes two ethyl groups at the 5 and 11 positions, and a tetrahydro ring system. (5R,11R)-5,11-DIETHYL-5,6,11,12-TETRAHYDRO-2,8-CHRYSENEDIOL exhibits interesting biological activities and has been synthesized as a fluorescent ligand for the estrogen receptor.
Uses
Used in Pharmaceutical Research:
(5R,11R)-5,11-DIETHYL-5,6,11,12-TETRAHYDRO-2,8-CHRYSENEDIOL is used as a fluorescent ligand for the estrogen receptor. It serves as a valuable tool in the study of estrogen receptor interactions and signaling pathways, which are crucial for understanding various physiological processes and the development of hormone-related disorders.
Used in Drug Development:
(5R,11R)-5,11-DIETHYL-5,6,11,12-TETRAHYDRO-2,8-CHRYSENEDIOL is used as a selective ligand for estrogen receptors, specifically acting as an ERα agonist and an ERβ antagonist. This dual functionality makes it a promising candidate for the development of targeted therapies for hormone-related conditions, such as breast cancer and other estrogen receptor-positive diseases.
Used in Analytical Chemistry:
(5R,11R)-5,11-DIETHYL-5,6,11,12-TETRAHYDRO-2,8-CHRYSENEDIOL, due to its fluorescent properties, can be employed in the development of novel analytical methods for the detection and quantification of estrogen receptors in biological samples. This can aid in the diagnosis and monitoring of hormone-related disorders and the evaluation of the effectiveness of treatments.
Used in Material Science:
The unique molecular structure and properties of (5R,11R)-5,11-DIETHYL-5,6,11,12-TETRAHYDRO-2,8-CHRYSENEDIOL may also find applications in the development of new materials with specific optical, electronic, or sensing properties, particularly in the field of molecular recognition and detection.
Biological Activity
Non-steroidal, selective estrogen receptor ligand; agonist at ER α receptor (K i = 9.0 nM) and antagonist at ER β receptor (K i = 3.6 nM).
Check Digit Verification of cas no
The CAS Registry Mumber 138090-06-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,8,0,9 and 0 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 138090-06:
(8*1)+(7*3)+(6*8)+(5*0)+(4*9)+(3*0)+(2*0)+(1*6)=119
119 % 10 = 9
So 138090-06-9 is a valid CAS Registry Number.
InChI:InChI=1/C22H24O2/c1-3-13-9-15-11-17(23)6-8-20(15)22-14(4-2)10-16-12-18(24)5-7-19(16)21(13)22/h5-8,11-14,23-24H,3-4,9-10H2,1-2H3/t13-,14-/m1/s1
138090-06-9Relevant articles and documents
5,6,11,12-Tetrahydrochrysenes: Synthesis of Rigid Stilbene Systems Designed To Be Fluorescent Ligands for the Estrogen Receptor
Hwang, Kwang-Jin,O'Neil, James P.,Katzenellenbogen, John A.
, p. 1262 - 1271 (2007/10/02)
We have prepared a series of tetrahydrochrysenes as fluorescent ligands for the estrogen receptor.The stilbene chromophore in this tetracyclic system is held rigid and is adorned with an electron-donating hydroxyl group at C-8 that corresponds to the phenolic hydroxyl of estrogens and an electron acceptor at C-2 to give a donor-acceptor fluorophore.Additional substituents at C-5 and C-11 provide additional bulk that improves receptor binding affinity without distorting the planar conjugated system.The tetrahydrochrysene core was prepared by an acyloin condensation of α-alkyl m-methoxyhydrocinnamate esters, followed by a double dehydrative cyclization.The cis and trans isomers of the alkyl substituted systems could be separated and their stereochemistry ascertained by X-ray crystallographic analysis; the trans isomer has the higher receptor binding affinity, and the derivative with ethyl substituents at C-5 and C-11 has the best affinity.The donor-acceptor systems were prepared by functional group manipulations on one of the aromatic methoxy groups: conversion to the trifluoromethanesulfonate was followed by a palladium-mediated carbonylation to give the acetyl derivative and methoxycarbonylation to give the ester.The ester was further elaborated to the amide and nitrile.The nitro compound was prepared by nitration of protio system, itself prepared by hydrogenolysis of the trifluoromethanesulfonate.As will be described later, these tetrahydrochrysenes provide a favorable combination of estrogen receptor binding affinity and long wavelength, high quantum yield fluorescence to make them useful as fluorescent ligands for the estrogen receptor.
