Category: tetrahydroisoquinoline

Hamidi, Tewfik published the artcileIdentification of Rpl29 as a major substrate of the lysine methyltransferase Set7/9, Application In Synthesis of 1627607-87-7, the publication is Journal of Biological Chemistry (2018), 293(33), 12770-12780, database is CAplus and MEDLINE.

Set7/9 (also known as Set7, Set9, Setd7, and Kmt7) is a lysine methyltransferase that catalyzes the methylation of multiple substrates, including histone H3 and non-histone proteins. Although not essential for normal development and physiol., Set7/9-mediated methylation events play important roles in regulating cellular pathways involved in various human diseases, making Set7/9 a promising therapeutic target. Multiple Set7/9 inhibitors have been developed, which exhibit varying degrees of potency and selectivity in vitro. However, validation of these compounds in vivo has been hampered by the lack of a reliable cellular biomarker for Set7/9 activity. Here, we report the identification of Rpl29, a ribosomal protein abundantly expressed in all cell types, as a major substrate of Set7/9. We show that Rpl29 lysine 5 (Rpl29K5) is methylated exclusively by Set7/9 and can be demethylated by Lsd1 (also known as Kdm1a). Rpl29 is not a core component of the ribosome translational machinery and plays a regulatory role in translation efficiency. Our results indicate that Rpl29 methylation has no effect on global protein synthesis but affects Rpl29 subcellular localization. Using an Rpl29 methylation-specific antibody, we demonstrate that Rpl29K5 methylation is present ubiquitously and validate that (R)-PFI-2, a Set7/9 inhibitor, efficiently reduces Rpl29K5 methylation in cell lines. Thus, Rpl29 methylation can serve as a specific cellular biomarker for measuring Set7/9 activity.

Journal of Biological Chemistry published new progress about 1627607-87-7. 1627607-87-7 belongs to tetrahydroisoquinoline, auxiliary class Epigenetics,Histone Methyltransferase, name is (R)-8-Fluoro-N-(1-oxo-1-(pyrrolidin-1-yl)-3-(3-(trifluoromethyl)phenyl)propan-2-yl)-1,2,3,4-tetrahydroisoquinoline-6-sulfonamide hydrochloride, and the molecular formula is C23H26ClF4N3O3S, Application In Synthesis of 1627607-87-7.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydroisoquinoline,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Wiczk, Wieslaw published the artcilePhotophysics of 7-hydroxytetrahydroisoquinoline-3-carboxylic acid and its derivatives, HPLC of Formula: 142335-42-0, the publication is Journal of the American Chemical Society (1996), 118(35), 8300-8307, database is CAplus.

Derivatives of 7-hydroxytetrahydroisoquinoline-3-carboxylic acid {Tic(OH) [I]}, a conformationally restricted analog of tyrosine, were synthesized for photophys. studies aimed at elucidating the nature of tyrosine fluorescence and its decay. The derivatives included Ac-Tic(OH) [II], Ac-Tic(OH)-NHMe [III], Tic(OH)-NHMe [IV], Ala-Tic(OH) [V], Ac-Ala-Tic(OH) [VI], and Tic(OH)-Gly-NH₂ [VII]. For the I-IV derivatives the N-methylamide was more effective quencher than the acetyl group. For the V-VII derivatives the highest quenching of fluorescence of the phenolic chromophore was observed in Ala-Tic(OH). The simple Tic(OH) derivatives I-IV were also the subject of theor. studies (MOPAC 93). The obtained thermodn. parameters (MOPAC calculations) and the fluorescence components were discussed on the basis of the rotamer theory in order to explain the participation of an individual rotamer in the complex process of the fluorescence decay of tyrosine.

Journal of the American Chemical Society published new progress about 142335-42-0. 142335-42-0 belongs to tetrahydroisoquinoline, auxiliary class Tetrahydroisoquinoline,Chiral,Carboxylic acid,Amide,Alcohol, name is (S)-2-(tert-Butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, and the molecular formula is C10H12O5, HPLC of Formula: 142335-42-0.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydroisoquinoline,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Calo, Sanuele published the artcileConstrained dansyl derivatives reveal bacterial specificity of highly conserved thymidylate synthases, Application In Synthesis of 142335-42-0, the publication is ChemBioChem (2008), 9(5), 779-790, database is CAplus and MEDLINE.

The elucidation of the structural/functional specificities of highly conserved enzymes remains a challenging area of investigation, and enzymes involved in cellular replication are important targets for functional studies and drug discovery. Thymidylate synthase (TS, ThyA) governs the synthesis of thymidylate for use in DNA synthesis. The present study focused on Lactobacillus casei TS (LcTS) and Escherichia coli TS (EcTS), which exhibit 50% sequence identity and strong folding similarity. The authors have successfully designed and validated a chem. model in which linear, but not constrained, dansyl derivatives specifically complement the LcTS active site. Conversely, chem. constrained dansyl derivatives showed up to 1000-fold improved affinity for EcTS relative to the inhibitory activity of linear derivatives This study demonstrates that the accurate design of small ligands can uncover functional features of highly conserved enzymes.

ChemBioChem published new progress about 142335-42-0. 142335-42-0 belongs to tetrahydroisoquinoline, auxiliary class Tetrahydroisoquinoline,Chiral,Carboxylic acid,Amide,Alcohol, name is (S)-2-(tert-Butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, and the molecular formula is C15H19NO5, Application In Synthesis of 142335-42-0.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydroisoquinoline,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Verschueren, Kris published the artcileA facile synthesis of 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid, a conformationally constrained tyrosine analog, Related Products of tetrahydroisoquinoline, the publication is Synthesis (1992), 458-60, database is CAplus.

A rapid synthesis of 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid (I) is given. Pictet-Spengler reaction on diiodo- or dibromo-substituted tyrosine, followed by catalytic dehalogenation gives the desired compound in high optical purity.

Synthesis published new progress about 142335-42-0. 142335-42-0 belongs to tetrahydroisoquinoline, auxiliary class Tetrahydroisoquinoline,Chiral,Carboxylic acid,Amide,Alcohol, name is (S)-2-(tert-Butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, and the molecular formula is C27H23F6NO6S, Related Products of tetrahydroisoquinoline.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydroisoquinoline,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Tourwe, Dirk published the artcileConformational restriction of Tyr and Phe side chains in opioid peptides: information about preferred and bioactive side-chain topology, Product Details of C15H19NO5, the publication is Biopolymers (1996), 38(1), 1-12, database is CAplus and MEDLINE.

The side chain of Tyr and Phe was fixed into the gauche(-) or gauche(+) conformation by using 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) or 7-hydroxy-Tic (Htc) structures, and into the trans conformation by using aminobenzazepine-type structure I. When incorporated into dermorphin or deltorphin II, the Tic and Htc analogs all showed a large decrease in both μ and δ affinities and activities. Fixation of Phe³ in the trans rotamer resulted in a large increase in δ affinity in the dermorphin analog, whereas in the I-containing deltorphin II analog, good δ affinity is maintained despite the removal of the Glu side chain. Whereas several authors propose a gauche(-) preferred conformation for the Phe³ side chain, these results suggest a trans conformation at the δ receptor. The use of these conformationally constrained residues for evaluating the preferred solution conformation in the flexible N-terminal tripeptide Tyr-D-Ala-Phe is illustrated. The ¹H-NMR parameters-chem. shift, temperature dependence, and nuclear Overhauser effects to the D-Ala² Me protons in the different analogs-provide direct evidence to confirm the proposed sandwich conformation in the native peptides.

Biopolymers published new progress about 142335-42-0. 142335-42-0 belongs to tetrahydroisoquinoline, auxiliary class Tetrahydroisoquinoline,Chiral,Carboxylic acid,Amide,Alcohol, name is (S)-2-(tert-Butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, and the molecular formula is C17H18N2O6, Product Details of C15H19NO5.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydroisoquinoline,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Zhou, Nan published the artcileDiscovery of a tetrahydroisoquinoline-based HDAC inhibitor with improved plasma stability, Application In Synthesis of 142335-42-0, the publication is Bioorganic & Medicinal Chemistry (2017), 25(17), 4614-4619, database is CAplus and MEDLINE.

Histone deacetylase inhibitors with desirable pharmacokinetic profiles which can be delivered to solid tumor tissues in large amount might be promising to treat solid tumor effectively. Herein, structural modification of a previously reported tetrahydroisoquinoline-based HDAC inhibitor 2-[(2S,3S)-2-[(3,3-dimethyl-1-oxobutyl)amino]-3-methyl-1-oxopentyl]-1,2,3,4-tetrahydro-7-[2-(hydroxyamino)-2-oxoethoxy]-N-(4-methoxyphenyl)-, (3S)-3-Isoquinolinecarboxamide [1314556-93-8] (I) was carried out to improve its plasma stability for more feasible drug delivery. Among three newly synthesized analogs, the in vitro rat plasma stability of compound (II) (t_1/2 = 630 min) was over 5-fold improved than its parent I (t_1/2 = I03 min). In vitro activity evaluation showed that compound II and I exhibited similar HDACs inhibitory activity, which was validated by western blot anal. and antiproliferative assay. Moreover, compared with I, compound II exhibited comparable, if not higher, in vivo antitumor activity in a human breast carcinoma (MDA-MB-231) xenograft model.

Bioorganic & Medicinal Chemistry published new progress about 142335-42-0. 142335-42-0 belongs to tetrahydroisoquinoline, auxiliary class Tetrahydroisoquinoline,Chiral,Carboxylic acid,Amide,Alcohol, name is (S)-2-(tert-Butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, and the molecular formula is C9H6FNO, Application In Synthesis of 142335-42-0.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydroisoquinoline,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem