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A series of substituted 4,5,6,7-tetrahydrothieno[3,2-c]pyridines (THTPs) was synthesized and evaluated for their human phenylethanolamine N-methyltransferase (hPNMT) inhibitory potency and affinity for the alpha2-adrenoceptor. The THTP nucleus was suggested as an isosteric replacement for the 1,2,3,4-tetrahydroisoquinoline (THIQ) ring system on the basis that 3-thienylmethylamine (18) was more potent as an inhibitor of hPNMT and more selective toward the alpha2-adrenoceptor than benzylamine (15). Although the isosterism was confirmed, with similar influence of functional groups and chirality in both systems on hPNMT inhibitory potency and selectivity, the THTP compounds proved, in general, to be less potent as inhibitors of hPNMT than their THIQ counterparts, with the drop in potency being primarily attributed to the electronic properties of the thiophene ring. A hypothesis for the reduced hPNMT inhibitory potency of these compounds has been formed on the basis of molecular modeling and docking studies using the X-ray crystal structures of hPNMT co-crystallized with THIQ-type inhibitors and S-adenosyl-l-homocysteine as a template.

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

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An organocatalytic oxidative synthesis of N-protected tetrahydroisoquinolines is described by C-H functionalization via intermediate peroxides. The peroxides were synthesized from tert-butylhydroperoxide under metal-free thermal conditions and were converted into the final products by Bronsted acid catalyzed substitution. The nucleophile scope was investigated in detail and proved to be broad; N-deprotection of the coupling products could also be achieved. An organocatalytic oxidative synthesis of N-protected tetrahydroisoquinolines was achieved by C-H functionalization via Intermediate PeroxideS (CHIPS). The peroxides were synthesized under metal-free thermal conditions and were converted into the final products by reaction with a variety of nucleophiles by using Bronsted acid catalysis. Copyright

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

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A novel C(sp 3)-H bond arylation of tetrahydroisoquinoline (THIQ) derivatives with Knochel-type arylzinc reagents has been developed. In the presence of MgCl 2, arylzinc reagents readily reacted with THIQ derivatives under oxidative conditions, affording a wide range of potentially biologically active compounds in good yields. Moreover, the developed method can tolerate a variety of sensitive functional groups such as an ester group.

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

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The invention relates to a medicine intermediate, in particular to a (S)- 1 – phenyl – 1, 2, 3, 4 – tetrahydroisoquinoline preparation method; the benzoyl chloride or benzoic acid, phenethylamine, alkali metal hydroxide is mixed with water to the reaction, a proportion of N – (2 – phenylethyl) benzamide, phosphorus pentoxide, phosphorus chloride mixed with organic solvent is heating, the obtained 1 – phenyl – 3, 4 – ISO-quinoline with the 1st alcohol solvent, borohydride mixed reaction, the obtained 1 – phenyl – 1, 2, 3, 4 – ISO-quinoline with the 2nd alcohol solvent, water, D – tartaric acid mixing, heating the reaction, the obtained (S)- 1 – phenyl – 1, 2, 3, 4 – tetrahydroisoquinoline tartrate with an alkali metal hydroxide, water mixing, to obtain the target product; the invention provides (S)- 1 – phenyl – 1, 2, 3, 4 – tetrahydroisoquinoline preparation method has the preparation method, operation and the advantages of the simple post-treatment. (by machine translation)

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

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Here, we describe an efficient and environmentally friendly synthesis of polycyclic N-heterocycles under electrochemical external oxidant-free conditions. The extent of the sequential electrochemical oxidative aromatization can be regulated with the assistance of redox mediators.

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

The Absolute Best Science Experiment for 166591-85-1

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Electric Literature of 166591-85-1, 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. 166591-85-1, Name is 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid,introducing its new discovery.

The present invention provides a to oxygen or air oxygen in the air as the oxidizing agent or method for preparing acid, is at room temperature, in an organic solvent, in order to ferric nitrate (Fe (NO3 )3 · 9 H2 O), 2, 2, 6, 6 – tetramethyl piperidine nitrogen oxides (TEMPO) and inorganic halide as a catalyst, in order to oxygen or air as the oxidizing agent, by alcohol or aldehyde oxidation generating acid, glycol oxidation generating lactone; or, to aqueous raw material, in order to nitric acid iron as catalyst, reaction under the neutral condition, said aldehyde oxidation acid generating and peroxyacids. The invention has environmental protection of green, low cost, high yield, the atom economy is high, the substrate functional group compatibility is good, mild reaction conditions, the reaction scale can be enlarged and the like, and is applicable to industrial production. (by machine translation)

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

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The invention provides compounds of formula (I): wherein R1, R 2, A, A1 and B are as defined in the specification; processes for their preparation; pharmaceutical compositions containing them; a process for preparing the pharmaceutical compositions; and their use in therapy. The compounds are useful as MMP inhibitors.

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

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Provided herein, inter alia, are compounds and methods of treating diseases including cancer, neurological disease, alcohol withdrawal, depression and anxiety, and neuropathic pain.

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

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A zirconium(IV)-based UiO-topological metal-organic framework (UiO-68Se) containing benzoselenadiazole was synthesized by an approach of the mixed dicarboxylate struts, which show highly efficient and recycalable photocatalytic activity for aerobic cross-dehydrogenative coupling reactions between tertiary amines and various carbon nucleophiles under visible-light irradiation.

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

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The reaction of different five- or six-membered nitrogen- containing heterocycles such as N-isopropyl-2-phenylpyrrolidine (1), N-phenyl-3-pyrroline (6), N-phenylisoindoline (10), N- phenyltetrahydroisoquinoline (13) and N- methyltetrahydroisoquinoline (19) with an excess of lithium powder ad a catalytic amount of DTBB (4.5 mol %), followed by treatment with electrophiles [H2O, D2O, MeI, CH2=CHCH2Br, Pr(i)CHO,Bu(t)CHO, PhCHO, Me2CO, Pr(n)COMe, PhCOMe, (CH2)4CO, (CH2)5CO, CO2] and final hydrolysis gives a wide series of functionalised amines 3, 8, 9, 12 and 19, the key step in the process, being the reductive opening of the starting material giving a dianionic remote functionalised organolithium compound.

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