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A series of indazole arylsulfonamides were synthesized and examined as human CCR4 antagonists. Methoxy- or hydroxyl- containing groups were the more potent indazole C4 substituents. Only small groups were tolerated at C5, C6, or C7, with the C6 analogues being preferred. The most potent N3-substituent was 5-chlorothiophene-2-sulfonamide. N1 meta-substituted benzyl groups possessing an alpha-amino-3-[(methylamino)acyl]- group were the most potent N1-substituents. Strongly basic amino groups had low oral absorption in vivo. Less basic analogues, such as morpholines, had good oral absorption; however, they also had high clearance. The most potent compound with high absorption in two species was analogue 6 (GSK2239633A), which was selected for further development. Aryl sulfonamide antagonists bind to CCR4 at an intracellular allosteric site denoted site II. X-ray diffraction studies on two indazole sulfonamide fragments suggested the presence of an important intramolecular interaction in the active conformation.

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

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Dirhodium caprolactamate [Rh2(cap)4] is a highly effective catalyst for the oxidative Mannich reaction. The reaction proceeds via C-H oxidation of a tertiary amine followed by nucleophilic capture. This green transformation is conducted in protic solvent using inexpensive T-HYDRO (70% t-BuOOH in water). Synthetically valuable gamma-aminoalkyl butenolides are obtained. Copyright

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

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The photoexcited state lifetimes of iron complexes are typically much shorter than those of iridium and ruthenium complexes. For that reason, iron complexes find less application in photochemical organic synthesis. Through iron photocatalysis, a mild and effective protocol for decarboxylative C?C and C?N bond formation has been achieved. The carboxylic acids readily undergo radical decarboxylation in the presence of Fe2(SO4)3 and di-(2-picolyl)amine under visible light irradiation. The resulting alkyl radicals then react with Michael acceptors or azodicarboxylates to furnish the adducts.

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

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A continuous flow procedure for the efficient metal-free, visible light photoredox-catalyzed alpha-functionalization of tertiary amines has been developed. Rose Bengal has been identified as an effective organic photocatalyst for continuous flow C-C and C-P bond formations as well as multicomponent reactions.

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Tetrahydroisoquinoline – Wikipedia,
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Hindered ethers are of high value for various applications; however, they remain an underexplored area of chemical space because they are difficult to synthesize via conventional reactions1,2. Such motifs are highly coveted in medicinal chemistry, because extensive substitution about the ether bond prevents unwanted metabolic processes that can lead to rapid degradation in vivo. Here we report a simple route towards the synthesis of hindered ethers, in which electrochemical oxidation is used to liberate high-energy carbocations from simple carboxylic acids. These reactive carbocation intermediates, which are generated with low electrochemical potentials, capture an alcohol donor under non-acidic conditions; this enables the formation of a range of ethers (more than 80 have been prepared here) that would otherwise be difficult to access. The carbocations can also be intercepted by simple nucleophiles, leading to the formation of hindered alcohols and even alkyl fluorides. This method was evaluated for its ability to circumvent the synthetic bottlenecks encountered in the preparation of 12 chemical scaffolds, leading to higher yields of the required products, in addition to substantial reductions in the number of steps and the amount of labour required to prepare them. The use of molecular probes and the results of kinetic studies support the proposed mechanism and the role of additives under the conditions examined. The reaction manifold that we report here demonstrates the power of electrochemistry to access highly reactive intermediates under mild conditions and, in turn, the substantial improvements in efficiency that can be achieved with these otherwise-inaccessible intermediates.

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

Awesome and Easy Science Experiments about 99365-69-2

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COA of Formula: C9H11ClN2O2, New Advances in Chemical Research, May 2021. Chemistry is the experimental science by definition. We want to make observations to prove hypothesis. For this purpose, we perform experiments in the lab. 99365-69-2, Name is 7-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride,introducing its new discovery.

A series of benzene-substituted analogues of the novel hypoxia-selective cytotoxin N,N-bis(2-chloroethyl)-N-methyl-N-(2-nitrobenzyl)ammonium chloride (3a), together with three corresponding tetrahydroisoquinolinium ‘cyclic’ analogues 21a-23a and two naphthalene derivatives (19a and 20a), have been prepared and evaluated for cytotoxicity in cultured mammalian tumor cells under aerobic and hypoxic conditions. The parent compound 3a has a one- electron reduction potential of -358 mV and undergoes reductively-induced fragmentation to release the nitrogen mustard mechlorethamine. The compounds were prepared by halogenation (SOCl2) of the corresponding quaternary diols, which in turn were synthesized from N-methyldiethanolamine and substituted nitrobenzyl chlorides. The reduction potentials of the benzene-substituted compounds were generally well-predicted by Hammett substituent relationships. All of the compounds were much more toxic toward repair-deficient UV4 cells than the corresponding wild-type AA8 cells, as expected if the active cytotoxic species is a DNA alkylating agent. They were also more toxic toward the human cell lines EMT6 and FME compared to AA8, but the reasons for this are not known. Analogues of 3a substituted in the phenyl ring with electron- donating substituents provided compounds with widely differing selectivities for hypoxic AA8 cells, ranging from no selectivity for the 3-Me compound 9a to 3000-fold (at least as great as that of the parent 3a) for the 4-OMe compound 14a. The naphthalene derivatives 19a and 20a and the tetrahydroisoquinolinium compounds 21a-23a showed no hypoxic selectivity. Selective chemical reduction of 22a and 23a with nickel boride resulted in isolation of the corresponding stable amine derivatives, indicating that reduction of these compounds does not result in fragmentation. The reason(s) for the marked differences in hypoxic selectivity of the nitrobenzyl quaternary mustards is unknown, but may reflect differences in radical chemistry, cell uptake, or sensitivity to enzymatic reduction.

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

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The successfully developed polydimethylsiloxane (PDMS, a green and highly transparent polymer material) sponge photocatalyst can catalyze cross-dehydrogenative coupling (CDC) of tertiary amines and various nucleophiles with high efficiency and reusability under visible light irradiation. Through an easy-to-build continuous flow reactor, the sponge photocatalytic reaction can be facilely scaled up.

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

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A series of novel nitrofuranyl methyl N-heterocycles based on the structure of IIIM-MCD-211 were designed and synthesized. Compounds 6d, 8b and 12a show excellent activity against MTB H37Rv strain (MIC: 0.031?0.062 mug/mL) roughly comparable to INH and IIIM-MCD-211. In addition, a three-dimensional quantitative structure-activity relationship (3D-QSAR) study was performed on the above mentioned chemical series employing comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA) techniques. The developed CoMFA and CoMSIA models display high external predictability (r2pred of 0.954 and 0.935, respectively) and good statistical robustness. More importantly, the newly designed compounds 16a and 16b (MIC: <0.016 mug/mL) based on the two models, as expected, were found to be more active than 12a and IIIM-MCD-21. Design and synthesis of more potent nitrofuranyl methyl N-heterocycles as anti-TB agents are currently in progress. If you are interested in 17680-55-6, you can contact me at any time and look forward to more communication. Application In Synthesis of 7-Bromo-1,2,3,4-tetrahydroisoquinoline

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

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Recommanded Product: 78183-55-8, New Advances in Chemical Research, May 2021. Chemistry is the experimental science by definition. We want to make observations to prove hypothesis. For this purpose, we perform experiments in the lab. 78183-55-8, Name is (S)-Methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride,introducing its new discovery.

-The following derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid have been prepared in their (S)-form and as racemates: hydrochloride of methyl ester, N-carboxy anhydride, and N-acetyl derivative. All the substances were fully characterised by elemental analyses, 1H and 13C NMR spectra, and optical rotation, as the case may be; the N-carboxy anhydride was also characterised by means of X-Ray diffraction. Also identified was the intermediate of the reaction of the title acid with phosgene, the N-chlorocarbonyl derivative, and the respective methyl ester was prepared. The dioxopiperazine of the title acid was prepared and characterised both in pure (S,S)-form and in the form of a mixture of two racemates. The optically pure dioxopiperazine was prepared by a reaction of the N-carboxy anhydride in solid phase.

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

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Novel thiazole- and isoquinoline- containing compounds are presented that are useful for treating and/or preventing broad-spectrum viral infections. Methods of treating and/or preventing broad-specturm viral infections are also presented. These compounds have shown inhibitio of HCMV, influenza viruses, Zika virus, BK Virus and RSV replication in cell-based assays.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
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