Tag: M.W=250-300

Kormos, Chad M. published the artcilePotent and Selective Tetrahydroisoquinoline Kappa Opioid Receptor Antagonists of Lead Compound (3R)-N-[1R)-1-(Cyclohexylmethyl)-2-methylpropyl]-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxamide (CDTic), Synthetic Route of 142335-42-0, the publication is Journal of Medicinal Chemistry (2018), 61(17), 7546-7559, database is CAplus and MEDLINE.

Animal pharmacol. studies suggest that potent and selective κ opioid receptor antagonists have potential as pharmacotherapies targeting depression, anxiety, and substance abuse (opiates, alc., nicotine, cocaine). The authors recently reported lead compound 1 as a new class of κ opioid receptor antagonists with only one basic amine group. Analogs were synthesized and evaluated for their in vitro opioid receptor antagonist properties using a [35S]GTPγS binding assay. All analogs were pure opioid receptor antagonists with no agonist activity. Compounds 1, 8 ((3R)-N-[(1R)-2-Cyclohexyl-1-cyclopropylethyl]-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxamide), 9 ((3R)-N3-[(1R)-1-(Cyclohexylmethyl)-2-methylpropyl]-1,2,3,4-tetrahydroisoquinoline-3,7-dicarboxamide), 13 ((3R)-N-[(1R)-1-(Cyclopentylmethyl)-2-methylpropyl]-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxamide), and 14 (Ke values 0.058-0.64 nM) are highly potent and highly selective for the κ relative to the μ and δ opioid receptors. Favorable calculated physiochem. properties were confirmed in rat PK studies, demonstrating brain penetration for selected compounds 1, 9, and 13. High κ opioid receptor potency and selectivity, and highly favorable calculated physiochem. and PK properties for brain penetration, suggest these compounds should be considered for further development.

Journal of 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 C15H19NO5, Synthetic Route of 142335-42-0.

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