- A new anti-tubulin agent containing the benzo[b]thiophene ring system
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A new type of inhibitor of tubulin polymerization was discovered based on the 3-aroyl-2-arylbenzo[b]thiophene molecular skeleton. The lead compound in this series, 2-(4'-methoxyphenyl)-3-(3',4',5'-trimethoxybenzoyl)-6- methoxybenzo[b]thiophene 1, inhibited tubulin polymerization, caused an increase in the mitotic index of CA46 Burkitt lymphoma cells, and inhibited the growth of several human cancer cell lines.
- Pinney, Kevin G.,Bounds, A. Dawn,Dingeman, Koren M.,Mocharla, Vani P.,Pettit, George R.,Bai, Ruoli,Hamel, Ernest
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- ESTROGEN RECEPTOR TARGETING ANTAGONISTS
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The present disclosure relates to compounds that act as antagonists via binding to the ER ligand binding domain non-covalently or covalently, or act as both antagonists and ER protein degraders, and the synthesis of the same. Further, the present disclosure teaches the utilization of such compounds in a treatment for proliferative diseases, including cancer, particularly breast cancer, and especially ER+ breast cancer.
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Paragraph 0030; 0103-0105
(2020/05/07)
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- Facile synthesis of 3-aryl benzofurans, 3-aryl benzothiophenes, 2-aryl indoles and their dimers
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The preparation of 3-aryl benzofuran and benzothiophenes and their dimers at 2-position and, 2-aryl indoles and their 3-position dimers preparation is described.
- Umareddy, Pailla,Arava, Veera Reddy
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p. 2156 - 2167
(2019/07/04)
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- Efficient synthetic approach to substituted benzo[b]furans and benzo[b]thiophenes by iodine-promoted cyclization of enaminones
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An efficient synthetic approach to the substituted benzo[b]furan and benzo[b]thiophene scaffolds by iodine-mediated cyclization of the corresponding enaminones is described. This protocol was applied to a large series of these latter precursors to afford the respective benzoheterocycles substituted at the C-2 position by a carbonyl group functionality. A study of the factors that control this process reveals that the reactivity depends on the presence of electron-donor groups in the aryl ring of the aryloxycarbonylic and arylthiocarbonylic moieties.
- Labarrios, Ehecatl,Jerezano, Alberto,Jimenez, Fabiola,Del Carmen Cruz, Maria,Delgado, Francisco,Zepeda, L. Gerardo,Tamariz, Joaquin
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p. 954 - 971
(2014/08/05)
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- PROCESS FOR THE PREPARATION OF RALOXIFENE HYDROCHLORIDE
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The present invention provides an improved process for the preparation of α-(3- methoxyphenylthio)-4-methoxyacetophenone. The present invention also provides a process for the preparing free flowing solid of 6-methoxy-2-(4-methoxyphenyl)- benzo[b]-thiophene. The present invention further provides a process for the preparation of substantially pure 6-methoxy-2-(4-methoxyphenyl)-benzo[b]-thiophene. The present invention further provides a process for purification of raloxifene hydrochloride.
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Page/Page column 8
(2011/11/06)
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- Rhodium-catalyzed organothio exchange reaction of α-organothioketones with disulfides
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RhH(PPh3)4 and 1,2-bis(diphenylphosphino)ethane (dppe) catalyzed the organothio exchange reaction of α-organothioketones and organic disulfides. The reaction was affected by the structure of the substrate: α-phenylthio and α-alkylthio aryl ketones reacted effectively with diaryl and dialkyl disulfides; α-phenylthio dialkyl ketones reacted with diaryl disulfides but not with dialkyl disulfides; diaryl disulfides with electron-donating p-substituents were more reactive than those with electron-withdrawing p-substituents.
- Arisawa, Mieko,Toriyama, Fumihiko,Yamaguchi, Masahiko
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experimental part
p. 1349 - 1352
(2010/12/24)
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- Method for the production of alpha-(3-arylthio)-acetophenones
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A process for preparing α-(3-arylthio)acetophenones of the general formula I in which the substituents R1 and R2 are each independently C1-C6-alkyl, SiR33 where the substituent R3 is a C1-C6-alkyl radical, or an optionally substituted phenyl or benzyl radical, which comprises reacting, in methanol acetophenones of the general formula II in which the substituent X is Cl or Br with a thiolate of the general formula III in which M is an alkali metal.
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- METHOD FOR THE PRODUCTION OF Γ(A)-(3-ARYLTHIO)-ACETOPHENONES
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The invention relates to a method for the production of α-(3-arylthio)-acetophenones of general formula (I), wherein the substituents R1 and R2 independently represent C1-C6-alkyl, SiR33, and the substituent R3 represents a C1-C6-alkyl radical, or an optionally substituted phenyl or benzyl radical.The invention is characterised in that acetophenons of general formula (II), wherein the substitutent X represents Cl or Br, is reacted in methanol with a thiolate of general formula (III) wherein M represents an alkali metal.
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Page/Page column 4
(2010/02/11)
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- Process for preparing benzoic acids
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An improved process for the preparation of 4[(2-piperidin-1-yl)ethoxy]benzoic acid derivatives, comprising reacting a haloalkyl amine of formula (III) with a compound of formula (IV) in the presence of a hydrated inorganic base in an appropriate solvent.
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Page/Page column 7
(2010/02/12)
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- METHOD FOR PRODUCING α-(3-ARYLTHIO)-ACETOPHENONES
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The invention relates to a method for producing α-(3-arylthio)-acetophenones of general formula (I), in which substituents R1 and R2, independent of one another, represent C1-C6 alkyl or an optionally substituted phenyl radical or benzyl radical. The inventive method is characterized in that: A) acetophenones of general formula (II), in which substituent R1 has the aforementioned meaning, are reacted with sulfuryl chloride and are subsequently hydrolyzed, and; B) the reaction mixture obtained in this manner is reacted with a thiophenol of general formula (III), in which substituent R2 has the aforementioned meaning.
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Page/Page column 4-5
(2010/02/08)
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- A facile synthesis of 3-aryl-substituted-benzothiophenes via a Lewis acid mediated cyclization of 2-arylthio-acetophenones
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The boron trifluoride-etherate mediated cyclization of 2-arylthio- ketones 1a-h at ambient temperature gave 3-aryl-substituted benzothiophenes 2a-h in excellent yield. None of the rearranged 2-aryl-substituted benzothiophenes were observed.
- Kim, Seongkon,Yang, Jane,DiNinno, Frank
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p. 2909 - 2912
(2007/10/03)
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- Benzothiophene compounds, and uses and formulations thereof
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Benzothiophenes, and uses and formulations thereof, are provided by the present invention. The compounds are of the formula wherein R1and R2are independently -OH, -OCO(C1-C6alkyl), -O(CO)O(C1-C6alkyl), -OCO-Ar, where Ar is phenyl or substituted phenyl, or -O(CO)Ophenyl; and R3is a substituent in the 3 or 4 position of the phenyl ring selected from the group of -H, -Cl, -Br, -CH3, or -CH2CH3; or a pharmaceutically acceptable salt or solvate thereof, with the proviso that when R1and R2are both hydroxy, R3is not -H, -CH3, or -CH2CH3.
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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...
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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.
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p. 1057 - 1066
(2007/10/02)
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