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A high-throughput screen identified 3-(3,4-dihydroisoquinolin-2(1H)- ylsulfonyl)benzoic acid as a novel, highly potent (low nM), and isoform-selective (1500-fold) inhibitor of aldo-keto reductase AKR1C3: a target of interest in both breast and prostate cancer. Crystal structure studies showed that the carboxylate group occupies the oxyanion hole in the enzyme, while the sulfonamide provides the correct twist to allow the dihydroisoquinoline to bind in an adjacent hydrophobic pocket. SAR studies around this lead showed that the positioning of the carboxylate was critical, although it could be substituted by acid isosteres and amides. Small substituents on the dihydroisoquinoline gave improvements in potency. A set of “reverse sulfonamides” showed a 12-fold preference for the R stereoisomer. The compounds showed good cellular potency, as measured by inhibition of AKR1C3 metabolism of a known dinitrobenzamide substrate, with a broad rank order between enzymic and cellular activity, but amide analogues were more effective than predicted by the cellular assay.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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A practical synthesis of fused benzimidazoles 5 has been developed by simply heating o-halonitrobenzenes 1 with tetrahydroisoquinolines 2. In this transformation, 2 played multiple roles as a building block, base and a double hydride donor in a cascade of uncatalyzed aromatic substitution, reduction of the nitro group, oxidation of the alpha-methylene group and condensation.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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New Advances in Chemical Research in 2021. In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 17680-55-6, name is 7-Bromo-1,2,3,4-tetrahydroisoquinoline, introducing its new discovery. Synthetic Route of 17680-55-6

PRMT4 is a type I protein arginine methyltransferase and plays important roles in various cellular processes. Overexpression of PRMT4 has been found to be involved in several types of cancers. Selective and in vivo effective PRMT4 inhibitors are needed for demonstrating PRMT4 as a promising therapeutic target. On the basis of compound 6, a weak dual PRMT4/6 inhibitor, we constructed a tetrahydroisoquinoline scaffold through a cut-and-sew scaffold hopping strategy. The subsequent SAR optimization efforts employed structure-based approach led to the identification of a novel PRMT4 inhibitor 49. Compound 49 exhibited prominently high potency and selectivity, moderate pharmacokinetic profiles, and good antitumor efficacy in acute myeloid leukemia xenograft model via oral administration, thus demonstrating this compound as a useful pharmacological tool for further target validation and drug development in cancer therapy.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

15-Sep News The important role of 17680-55-6

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Chemical Research Letters, May 2021. Research speed reading in 2021. category: tetrahydroisoquinoline, The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 17680-55-6, Name is 7-Bromo-1,2,3,4-tetrahydroisoquinoline, molecular formula is C9H10BrN. In a Article,once mentioned of 17680-55-6

Direct alpha-phosphonylation of an unprotected secondary amine in a single step is of practical importance to amino phophophates. However, this protocol is limited due to the high redox barrier of unprotected amine. In this paper, we report C-H phosphonylation of an unprotected secondary amine via an electrochemical approach in the presence of catalytic carboxylate salt. This metal-free and exogenous oxidant-free method furnishes diverse target molecules with satisfactory yield under mild reaction conditions. Successful application of the protocol in a gram-scale experiment demonstrates the potential utility for further functionalization.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Abstract: Graphene oxide (GO), an inexpensive, environment-friendly, and metal-free carbocatalyst, used for the N-formylation of amines is developed. In this reaction, GO shows good activity, selectivity, and recyclability. This strategy has an array of advantages, such as being metal free, without additive, wide-scope protocol, scalable with a low catalyst loading of 3 wt%, use of readily available and recyclable carbocatalyst, and DMF as a readily available formyl source. Furthermore, this strategy provides an avenue for the convenient hydroformylation of various amines. Graphical abstract: [Figure not available: see fulltext.].

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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The present invention provides novel compounds having the general formula (I): wherein R1, R 2, R 3, U, V, W, X and Y are as described herein, compositions including the compounds and methods of using the compounds.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Sep 2021 News Chemical Properties and Facts of 17680-55-6

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The present invention provides an alpha2c-adrenoceptor antagonist comprising, as an active ingredient, a condensed-ring-pyrimidine derivative represented by general formula (I) below or a pharmaceutically acceptable salt thereof useful for treating and/or preventing various diseases induced by hyperactivity of alpha2c-adrenoceptor (for example, Parkinson”s disease, L-DOPA-induced dyskinesia, tardive dyskinesia and depression) and the like. 1 {wherein p represents an integer of 1 to 3; R1 represents a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl, or the like;R2 represents ?N(?R4)(?R5) (wherein R4 and R5 are the same or different, and each represents a hydrogen atom, substituted or unsubstituted aralkyl, or the like, or R4 and R5 form a substituted or unsubstituted heterocyclic group together with the adjacent nitrogen atom) or the like; and-Q- represents ?N?C(?R7)? [wherein R7 represents ?N(?R9)(?R10) (wherein R9 and R10 are the same or different, and each represents substituted or unsubstituted aralkyl, or the like, or R9 and R10 form a substituted or unsubstituted heterocyclic group together with the adjacent nitrogen atom) or the like] or the like}

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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An efficient and convenient synthesis of MGAT2 inhibitor, 2-[2-(4-tert-butylphenyl)ethyl]-N-[4-(3-cyclopentylpropyl)-2-fluorophenyl]-1,2,3, 4-tetrahydroisoquinoline-6-sulfonamide (1), is reported. The optimized route consists of an effective chlorosulfonylation and debromination, resulting in an increase in the total yield from 6.8% to 45%, compared with our previous method. This synthetic approach enabled the synthesis of 1 to be scaled-up to a multi-gram scale.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Lactam and oxazolidinone derived potent 5-hydroxytryptamine 6 (5-HT 6) receptor antagonists have been disclosed. One potent member from the lactam series, racemic compound 14 (Ki of 2.6 nM in binding assay, IC50 of 15 nM in functional cAMP antagonism assay) was separated into corresponding enantiomers that displayed the effect of chirality on binding potency (Ki of 1.6 nM and 3000 nM, respectively). The potent enantiomer displayed an IC50 of 8 nM in cAMP antagonism assay, selectivity against a number of family members as well as brain permeability in rats after 6 h post oral administration.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

06/9/2021 News The important role of 17680-55-6

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New Advances in Chemical Research in 2021. Chemistry is a science major with cience and engineering. The main research directions are chemical synthesis, and research on the structure and performance of functional materials.In a patent, 17680-55-6, name is 7-Bromo-1,2,3,4-tetrahydroisoquinoline, introducing its new discovery. SDS of cas: 17680-55-6

In this work, catalytic hydrogen transfer as an effective, green, convenient and economical strategy is for the first time used to synthesize anilines and N-heterocyclic aromatic compounds from nitrobenzene and N-heterocycles in one step. Nevertheless, how to effectively reduce the possible effects of water on the catalyst by removal of the by-product water, and to further introduce water as the solvent based on green chemistry are still challenges. Since the structures and properties of carbon nanocomposites are easily modified by controllable construction, a one step pyrolysis process is used for controllable construction of micro/nano hierarchical carbon nanocomposites with core-shell structures and magnetic separation performance. Using various characterization methods and model reactions the relationship between the structure of NiaNCFs (nickel-nitrogen-doped carbon frameworks) and catalytic performance was investigated, and the results show that there is a positive correlation between the catalytic performance and hydrophobicity of catalysts. Besides, the possible catalytically active sites, which are formed by the interaction of pyridinic N and graphitic N in the structure of nitrogen-doped graphene with the surfaces of Ni nanoparticles, should be pivotal to achieving the relatively high catalytic performance of materials. Due to its unique structure, the obtained NiaNCF-700 catalyst with superhydrophobicity shows extraordinary performances toward the hydrogen transfer reaction of nitrobenzene and N-heterocycles in the aqueous state; meanwhile, it was also found that NiaNCF-700 still retained its excellent catalytic activity and structural integrity after three cycles. Compared with traditional catalytic systems, our catalytic systems offer a highly effective, green and economical alternative for nitrobenzene and N-heterocycle transformation, and may open up a new avenue for simple construction of structure and activity defined carbon nanocomposite heterogeneous catalysts with superhydrophobicity.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem