Category: 63675-74-1

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Nonsteroidal estrogens bearing acyl azide functions: potential electrophilic and photoaffinity labeling agents for the estrogen receptor

In an effort to develop novel affinity labeling agents for the estrogen receptor, we have synthesized two nonsteroidal ligands, a 1-aroyl-2-aryl tetralin system (1) and a 2-aryl-3-aroylbenzothiophene system (2).These agents, patterned after the Lilly antiestrogens trioxifene and LY 117018, respectively, embody acyl azide functions as part of a benzoyl chromophore.The acyl azide group has weak acylating activity, suitable for electrophilic affinity labeling,but this function is also photoreactive and, in its particular embodiment within these ligands, it could provide an efficient photochemical route to the highly reactive singlet acyl nitrene.The tetralin system (1) was prepared nine steps from 6-methoxy-1-tetralone, and the benzothiophene system (2) was prepared in four steps from a known substituted benzothiophene precursor.In competitive binding assays, both compounds show reasonable binding affinity for the rat and lamb uterine estrogen receptor : estradiol = 100percent, 1 = 3percent, and 2 = 12percent.When assayed by indirect receptor consumption assays, both compounds appear to have substantial capacity for irreversible binding (electrophilic reaction) with the receptor.This reactivity, which suggests that acylation of the receptor has occurred, is photoreversible.The nature of this ligand-receptor interaction is being investigated further. keywords: estrogen receptor, affinity labeling, photoaffinity labeling, nonsteroidal estrogens, antiestrogens, steroids

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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SUBSTITUTED BENZO(B)THIOPHENE COMPOUNDS HAVING ACTIVITY AS SELECTIVE ESTROGEN RECEPTOR MODULATORS

The present invention provides compounds with nitrogen, sulfur or carbon linked basic side chains of formula STR1 where R 1 and R. sup.2 are independently hydrogen, halo, hydroxy, alkoxy, alkylcarbonyloxy, alkoxycarbonyl, alkoxycarbonyloxy, arylcarbonyloxy, aryloxycarbonyloxy, or alkylsulfonyloxy; O–SO 2–(C 4-C 6 alkyl), chloro, fluoro, or bromo; W is CHOH, C(O), or CH 2 ; Y is–CH 2–,–NH–,–NMe–,–S–,–SO 2–; and R 3 and R. sup.4 are independently hydrogen, alkyl, alkylcarbonyl, alkylamino-carbonyl, or arylcarbonyl, or together with the nitrogen to which they are attached form 1-pyrrolidinyl, 1-piperidinyl, or a 5-or 6-membered imide or cyclic amide ring.

The present invention also provides pharmaceutical compositions containing the compounds optionally containing estrogen or progestin, and the use of such compounds, alone, or in combination with estrogen or progestin, for treating osteoporosis, aortal smooth muscle cell proliferation, (particularly restenosis), and estrogen-dependent cancer (particularly breast cancer).

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Processes for preparing benzothiophenes

The present invention relates to intermediates and processes for preparing benzothiophenes.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Process for the synthesis of benzo[b]thiophenes

The present invention is directed to new processes for the synthesis of 2-aryl benzo[b]thiophenes.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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A PROCESS FOR PREPARING BENZO[B]THIOPHENE DERIVATIVES

The present invention relates in general to the field of organic chemistry, and in particular to the preparation of benzo[b]thiophene derivatives. These benzo[b]thiophene derivatives are useful as intermediates in the synthesis of pharmaceutically active agents such as raloxifene or derivatives thereof.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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X-ray structures of two methoxybenzo[b]thiophenes

The crystal and molecular structures of two methoxybenzo[b]thiophenes have been determined by three-dimensional, single-crystal X-ray diffractometry. Both 3-(4?-hydroxy-3?,5?-dimethoxybenzoyl)-2-(4?- methoxyphenyl)-6-methoxybenzo[b]thiophene and 3-(2?,6?-dimethoxybenzoyl)-2-(4?-methoxyphenyl)-6- methoxybenzo[b]thiophene (hereafter referred to as I and II, respectively) crystallize in the monoclinic centrosymmetric space group P21/n (No. 14, C52h) with four formula units-per cell with a = 6.866(1), b = 28.638(2), c = 11.830(2) A, and beta = 105.52(1) and a = 9.328(1), b = 7.977(1), c = 29.650(4) A, and beta = 97.87(1), respectively. The phase problems were solved by direct methods and the respective final full-matrix least-squares refinements converged to R = 0.046 and 0.031. The structures differ in the positioning of the dimethoxy groups of the benzoyl ligands and the addition of a hydroxyl group in I. The molecules in the crystal lattice are held together by van der Waals forces plus the addition of hydrogen bonding in compound I. Selected bond distances and angles and torsion angles are tabularized.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Process for preparing benzothiophenes

The present invention relates to intermediates and processes for preparing benzothiophenes of the following formula: wherein Y is chloro, bromo, iodo or -SO2R9; and, R9is C1-C4alkyl, trifluoromethyl, trichloromethyl, phenyl, p-tolyl, p-anisyl, or mono- or di(halo or nitro)phenyl.

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Benzothiophene – Wikipedia,
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Synthesis of 3-[4-(2-aminoethoxy)-benzoyl]-2-aryl-6-hydroxy-benzo[B]thiophenes

The present invention is directed to chemical processes for preparing 2-aryl-6-hydroxy-3-[4-(2-aminoethoxyl)benzoyl]benzoyl]benzo[b]-thiophenes.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Process for preparing 3-(4-aminoethoxy-benzoyl) benzo B!-thiophenes

The invention provides a process for preparing 6-alkoxy-3-(4-alkoxyphenyl)benzo B!thiophenes in good yield on a manufacturing scale without generating a thick, potentially yield-reducing, paste. The invention also provides methods for converting a-(-alkoxyphenylthio)-4-alkoxyacetophenones into 6-hydroxy-2-(4-hydroxyphenyl)-3- 4-(2-aminoethoxy)benzoyl!benzo B!thiophenes via acylation of a dialkoxy benzo B!thiophene. Each of these preparations relies on an intramolecular cyclization of a dialkoxy acetophenone derivative to yield a benzo B!thiophene without generating a thick paste that lowers overall yields on a manufacturing scale.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Brief introduction of 6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophene

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TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS WITH SELECTIVE ESTROGEN RECEPTOR MODULATORS

The present invention provides a method of treating depression, mood swings, or Alzheimer’s disease in a patient in need of such treatment by administering a selective estrogen receptor modulating compound of the formula STR1 in which R 1 and R 2 are independently hydroxy and alkoxy of one to four carbon atoms; and R 3 and R 4 are independently methyl or ethyl, or R 3 and R 4, taken together with the nitrogen atom to which they are attached, form a pyrrolidino, methyl-pyrrolidino, dimethylpyrrolidino, piperidino, morpholino, or hexamethyleneimino ring.

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Reference£º
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem