cas 84449-65-0, 2-[4-[(Methylsulfonyl)oxy]phenyl]-Benzo[b]thiophene-6-ol 6-Methanesulfonate

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84449-65-0

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Antiestrogens. 2. Structure-Activity Studies in a Series of 3-Aroyl-2-arylbenzothiophene Derivatives Leading to thien-3-yl>phenyl>methanone Hydrochloride (LY156758), a Remarkably Effective Estrogen Antagonist with On...
In an effort to prepare nonsteroidal antiestrogens demonstrating greater antagonism and less intrinsic estrogenicity than those currently available, a series of 3-aroyl-2-arylbenzothiophene derivatives was synthesized.These compounds were prepared by Friedel-Crafts aroylation of appropriate O-protected 2-arylbenzothiophene nuclei with basic side-chain-bearing benzoyl chlorides followed by removal of the protective groups to provide the desired compounds containing both hydroxyl and basic side-chain functionality.A particularly useful method for the cleavage of aryl methoxy ethers without removal of (dialkylamino)ethoxy side chain functionality elsewhere in the molecule was found to be AlCl3/EtSH.The benzothiophene derivatives were tested for their ability to inhibit the growth-stimulating action of estradiol on the immature rat uterus.Seemingly minor changes in the side-chain amine moiety were found to have profound effects on the ability of the compounds to antagonize estradiol.Analogues having basic side chains containing cyclic (pyrrolidine, piperidine, and hexamethyleneamine) moieties were found to have less intrinsic estrogenicity and to antagonize estradiol action more completely than their noncyclic counterparts.The most effective antiestrogen in the series, compound 44, thien-3-yl>phenyl>methanone, elicited a modest uterotropic activity that did not increase with increasing dose.In antagonism of estradiol, 44 exhibited a degree of inhibition surpassing that of tamoxifen at any dose tested.The new benzothiophene antiestrogen was also shown to have high affinity for rat uterine cycloplasmic estrogen receptor and to be an inhibitor of the growth of DMBA-induced rat mammary tumors.
Jones, Charles D.,Jevnikar, Mary G.,Pike, Andrew J.,Peters, Mary K.,Black, Larry J.,at al.
p. 1057 - 1066
(2007/10/02)

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methanesulfonyl chloride

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84449-70-7
6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-pyrrolidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride

84449-75-2
3-[4-(2-diisopropylaminoethoxy)benzoyl]-6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)benzo[b]thiophene, hydrochloride

84449-85-4
<6-<(methylsulfonyl)oxy>-2-<4-<(methylsulfonyl)oxy>phenyl>benzothien-3-yl><4-<2-(1-pyrrolidinyl)ethoxy>phenyl>methanone hydrochloride

84449-72-9
6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-hexamethyleneiminoethoxy)benzoyl]benzo[b]thiophene, hydrochloride

166975-60-6
methanesulfonic acid 4-[3-(4-hydroxy-benzoyl)-6-methanesulfonyloxy-benzo[b]thiophen-2-yl]-phenyl ester

Chemical Properties

Boiling Point: 630.078 °C at 760 mmHg

Flash Point:334.859 °C

Density: 1.485 g/cm³

Storage Temp.:Sealed in dry,Room Temperature

PSA: 131.74000

LogP: 5.40670

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84449-65-0

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Chemical Properties

Boiling Point: 630.078 °C at 760 mmHg

Flash Point:334.859 °C

Density: 1.485 g/cm3

Storage Temp.:Sealed in dry,Room Temperature

PSA: 131.74000

LogP: 5.40670

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Density: 1.485 g/cm³