- Synthesis of 2-substituted tetrahydroisoquinolin-6-ols: Potential scaffolds for estrogen receptor modulation and/or microtubule degradation
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6-Methoxytetrahydroisoquinoline hydrochloride was converted into four small libraries of substituted ureas, thioureas, sulfonamides and N-aryls, using the tetrahydroisoquinoline nitrogen as the scaffold-linking atom. Some of the compounds were evaluated for their ability to inhibit cell proliferation using the MCF7 (invasive ductal carcinoma) cell line.
- Mabank, Tanya,Alexandre, Kabamba B.,Pelly, Stephen C.,Green, Ivan R.,van Otterlo, Willem A.L.
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p. 245 - 279
(2020/02/13)
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- SAR based design of nicotinamides as a novel class of androgen receptor antagonists for prostate cancer
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Molecular knowledge of pure antagonism and systematic SAR study offered a direction for structural optimization of DIMN to provide nicotinamides as a novel series of AR antagonists. Nicotinamides with extended linear scaffold bearing sterically bulky alkoxy groups on isoquinoline end were synthesized for H12 displacement. AR binding affinity and molecular basis of antiandrogenic effect establish the optimized derivatives, 7au and 7bb, as promising candidates of second generation AR antagonists for advanced prostate cancer.
- Yang, Su Hui,Song, Chin-Hee,Van, Hue Thi My,Park, Eunsook,Khadka, Daulat Bikram,Gong, Eun-Yeung,Lee, Keesook,Cho, Won-Jea
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p. 3414 - 3418
(2013/06/05)
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- PROCESS FOR THE PREPARATION OF SUBSTITUTED-1,2,3,4-TETRAHYDROISOQUINOLINE DERIVATIVES
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The present invention is directed to a process for the synthesis of substituted-1,2,3,4-tetrahydroisoquinoline derivatives, useful as intermediates in the synthesis of pharmaceutical agents.
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Page/Page column 9
(2008/06/13)
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- Improved and practical synthesis of 6-methoxy-1,2,3,4- tetrahydroisoquinoline hydrochloride
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6-Methoxy-1,2,3,4-tetrahydroisoquinoline (1) or its hydrochloride salt (4) is an expensive chemical with limited commercial availability. We report an improved and practical synthesis of 4 from inexpensive 2-(3-methoxyphenyl) ethylamine (2) using a Pictet-Spengler condensation via a novel aminal intermediate. The synthesis significantly lowers the cost and provides easy access to 6-methoxy-1,2,3,4-tetrahydroisoquinoline or its HCl salt on a large scale.
- Zhong, H. Marion,Villani, Frank J.,Marzouq, Ramzy
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p. 463 - 465
(2012/12/31)
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- 5-HT7 receptor antagonists
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The invention relates to compounds having pharmacological activity towards the 5-HT7 receptor, and more particularly to some tetrahydroisoquinoline substituted sulfonamide compounds of the formula I: to processes of preparation of such compounds, to pharm
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Page/Page column 13
(2008/06/13)
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- COMPOUNDS
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The invention provides compounds of formula (I): wherein A and B represent the groups -(CH2)m- and -(CH2)n- respectively;R1 represents hydrogen or C1-6alkyl;R2 represents hydrogen, halogen, hydroxy, cyano, nitro, hydroxyC1-6alkyl, trifluoromethyl, trifluoromethoxy, C1-6alkyl, C1-6alkoxy, C1-6fluoroalkoxy, -(CH2)pC3-6cycloalkyl, -(CH2)pOC3-6cycloalkyl, -COC1-6alkyl, -SO2C1-6alkyl, -SOC1-6alkyl, -S-C1-6alkyl, -CO2C1-6alkyl, -CO2NR5R6, -SO2NR5R6, -(CH2)pNR5R6, -(CH2)pNR5COR6, optionally substituted aryl ring, optionally substituted heteroaryl ring or optionally substituted heterocyclyl ring;R3 represents optionally substituted aryl ring or optionally substituted heteroaryl ring;R4 represents hydrogen, hydroxy, C1-6alkyl, C1-6alkoxy, trifluoromethyl, trifluoromethoxy, halogen, -OSO2CF3, -(CH2)pC3-6cycloalkyl, -(CH2)qOC1-6alkyl or -(CH2)pOC3-6cycloalkyl;R5 and R6 each independently represent hydrogen, C1-6alkyl or, together with the nitrogen or other atoms to which they are attached, form an azacycloalkyl ring or an oxo-substituted azacycloalkyl ring;Z represents -(CH2)rX- wherein the -(CH2)r- group is attached to R3, or -X(CH2)r- wherein X is attached to R3, and wherein any of the -CH2- groups may be optionally substituted by one or more C1-6alkyl groups;X represents oxygen, -NR7 or -CH2- wherein the -CH2- group may be optionally substituted by one or more C1-6alkyl groups;R7 represents hydrogen or C1-6alkyl;m and n independently represent an integer selected from 1 and 2;p independently represents an integer selected from 0, 1, 2 and 3; q independently represents an integer selected from 1, 2 and 3; r independently represents an integer selected from 0, 1, and 2; or a pharmaceutically acceptable salt or solvate thereof.The compounds are useful in therapy, in particular as antipsychotic agents.
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- TETRAHYDROISOQUINOLINES AS ALPHA-2 ANTAGONISTS AND BIOGENIC AMINE UPTAKE INHIBITORS
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The present invention provides a tetrahydroisoquinoline compound of the formula STR1 or a pharmaceutically acceptable salt thereof which is an antagonist for alpha-2 adrenoreceptors and/or which inhibits biogenic amine uptake.
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- Pharmaceutically active compounds
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The invention relates to a class of tetrahydroisoquinolinylalkanoic acids containing an aryl sulphonamide group which have activity as thromboxane A2 antagonists.
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