Author: tianli

New tetrahydroisoquinoline-based P-glycoprotein modulators: decoration of the biphenyl core gives selective ligands was written by Contino, Marialessandra;Guglielmo, Stefano;Perrone, Maria Grazia;Giampietro, Roberta;Rolando, Barbara;Carrieri, Antonio;Zaccaria, Daniele;Chegaev, Konstantin;Borio, Vanessa;Riganti, Chiara;Zabielska-Koczywas, Katarzyna;Colabufo, Nicola A.;Fruttero, Roberta. And the article was included in MedChemComm in 2018.Application In Synthesis of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride This article mentions the following:

P-glycoprotein (P-gp, MDR1) is a membrane transporter expressed in several regions of our v. It plays a crucial defense role as it mediates the efflux of hundreds of potentially toxic substances. However, P-gp is one of the main causes of failure in cancer chemotherapy, as a number of chemotherapeutic agents are P-gp substrates. Another interesting implication concerns the correlation between P-gp expression impairment and the onset of several central nervous system pathologies such as Alzheimer’s and Parkinson’s diseases. In view of these considerations, in the present study, a new series of P-gp modulators have been designed, synthesized and evaluated for their activity towards P-gp and two other sister proteins (BCRP and MRP1). The compounds, structurally correlated to the potent but non-selective P-gp inhibitor MC70 [4′-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)biphenyl-4-ol], proved fairly selective towards P-gp, with a potency in the micromolar range. Compounds 5a, 5d and 12d proved capable of restoring doxorubicin toxicity in resistant cancer cells. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Application In Synthesis of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. Because of the high biological relevance of compounds possessing the 1,2,3,4-tetrahydroisoquinoline framework, a large number of synthetic approaches towards the creation of an isoquinoline or 1,2,3,4-tetrahydroisoquinoline core are presently known. However, synthetic routes to tetrahydroisoquinoline derivatives containing fluorine atom(s) in their structure are not particularly abundant.Application In Synthesis of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

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

Discovery of Potent and Selective Inhibitors for ADAMTS-4 through DNA-Encoded Library Technology (ELT) was written by Ding, Yun;O’Keefe, Heather;DeLorey, Jennifer L.;Israel, David I.;Messer, Jeffrey A.;Chiu, Cynthia H.;Skinner, Steven R.;Matico, Rosalie E.;Murray-Thompson, Monique F.;Li, Fan;Clark, Matthew A.;Cuozzo, John W.;Arico-Muendel, Christopher;Morgan, Barry A.. And the article was included in ACS Medicinal Chemistry Letters in 2015.Electric Literature of C11H16ClNO2 This article mentions the following:

The aggrecan degrading metalloprotease ADAMTS-4 has been identified as a novel therapeutic target for osteoarthritis. Here, the authors use DNA-encoded Library Technol. (ELT) to identify novel ADAMTS-4 inhibitors from a DNA-encoded triazine library by affinity selection. Structure-activity relationship studies based on the selection information led to the identification of potent and highly selective inhibitors. For example I has IC₅₀ of 10 nM against ADAMTS-4, with >1000-fold selectivity over ADAMT-5, MMP-13, TACE, and ADAMTS-13. These inhibitors have no obvious zinc ligand functionality. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Electric Literature of C11H16ClNO2).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline, as a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids. An oxidative C1 arylation of tetrahydroisoquinolines with aryl Grignard reagents is mediated by diethyl azodicarboxylate (DEAD). This C-H activation under metal-free conditions delivers target compounds, including some naturally occurring alkaloids, in good yields.Electric Literature of C11H16ClNO2

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

Discovery of Antiglioma Activity of Biaryl 1,2,3,4-Tetrahydroisoquinoline Derivatives and Conformationally Flexible Analogues was written by Mohler, Michael L.;Kang, Gyong-Suk;Hong, Seoung-Soo;Patil, Renukadevi;Kirichenko, Oleg V.;Li, Wei;Rakov, Igor M.;Geisert, Eldon E.;Miller, Duane D.. And the article was included in Journal of Medicinal Chemistry in 2006.Application In Synthesis of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride This article mentions the following:

Cultured rat astrocytes and C6 rat glioma were used as a differential screen for a variety of 1,2,3,4-tetrahydroisoquinoline (THI) derivatives Compound (I) selectively blocked the growth of C6 glioma leaving normal astrocytes relatively unaffected. The potential for clin. utility of I was further substantiated in human gliomas and other tumor cell lines. Preliminary SAR of this activity was characterized by synthesis and testing of several THI and conformationally flexible variants. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Application In Synthesis of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. The tetrahydroisoquinoline skeleton is present in a number of drugs, such as tubocurarine, one of the quaternary ammonium muscle relaxants. An intramolecular Friedel-Crafts cyclization of an in situ generated tosylate intermediate enables an efficient construction of 3-substituted 1,2,3,4-tetrahydroisoquinolines from N,N-dibenzyl-伪-aminols.Application In Synthesis of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

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

Synthesis and Structure Activity Relationship of Tetrahydroisoquinoline-Based Potentiators of GluN2C and GluN2D Containing N-Methyl-D-aspartate Receptors [Erratum to document cited in CA159:150256] was written by Santangelo Freel, Rose M.;Ogden, Kevin K.;Strong, Katie L.;Khatri, Alpa;Chepiga, Kathryn M.;Jensen, Henrik S.;Traynelis, Stephen F.;Liotta, Dennis C.. And the article was included in Journal of Medicinal Chemistry in 2014.Category: tetrahydroisoquinoline This article mentions the following:

The description of the model shown in Figure 3 predicts the wrong stereochem. of the amine resulting from the stereoselective reduction of the imine; the corrected stereochem. is given, along with a discussion of the effects. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Category: tetrahydroisoquinoline).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. An intramolecular Friedel-Crafts cyclization of an in situ generated tosylate intermediate enables an efficient construction of 3-substituted 1,2,3,4-tetrahydroisoquinolines from N,N-dibenzyl-伪-aminols.Category: tetrahydroisoquinoline

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

Quinolizidines. XXXI. A synthesis of the dibenzo[a,h]quinolizidine ring system: an application of the mercuric acetate-edetic acid oxidation method to 1,2,3,4-tetrahydroisoquinoline was written by Ohba, Masashi;Shinbo, Yoko;Ohashi, Takako;Toda, Mitsuhiro;Fujii, Tozo. And the article was included in Heterocycles in 1992.Application of 2328-12-3 This article mentions the following:

A formal synthesis of 2,3-dimethoxydibenzo[a,h]quinolizidine (I) has been achieved through a route including mercuric acetate-edetic acid oxidation of a benzene-fused piperidine. The route started with an initial condensation of 1,2,3,4-tetrahydroisoquinoline with 3,4-dimethoxyphenacyl bromide and proceeded through the amino ketone, amino alc. II, lactam alc., and the lactam III. A parallel sequence of reactions concluded a formal synthesis of the 2,3,11,12-tetramethoxy analog. In the mercuric acetate-edetic acid oxidations of the amino alcs. II under acidic or alk. conditions gave oxazoloisoquinoline derivatives besides the desired lactam alcs. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Application of 2328-12-3).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. There has been increasing research interest and speculation since 1968 in the potential formation of tetrahydroisoquinoline (TIQ) alkaloids in mammalian cells via such interactions, and in the role such TIQs may have in alcohol dependence. An efficient CuCl2-catalyzed coupling of nonfunctionalized tetrahydroisoquinolines with organozinc reagents under aerobic conditions proceeds in high yields under mild reaction conditions and is broadly applicable to a wide range of substrates. The reaction involves an iminium ion intermediate that is formed via a SET process.Application of 2328-12-3

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

An intracerebral injection study on the role of striatal dopamine and 5-hydroxytryptamine in the production of tremor by harmine was written by Kelly, D. M.;Naylor, R. J.. And the article was included in Neuropharmacology in 1976.Reference of 2328-12-3 This article mentions the following:

When injected directly into the neostriatum of rats, dopamine-HCl [62-31-7], noradrenaline hydrogen tartrate [51-40-1], (+)-amphetamine sulfate [51-63-8], apomorphine-HCl [314-19-2], and tetrahydroisoquinoline derivatives reduced the intensity of tremor produced by s.c. harmine-HCl [40828-94-2] (10 mg/kg), but tetrahydronaphthalene derivatives were ineffective. Direct application of serotonin bimaleate [18525-25-2] to the neo- but not the paleostriatum enhanced peripherally induced harmine tremor. The data suggest a relation between dopamine and serotonin and in the mediation of tremor and indicate that, whereas both pallidal and caudate dopamine functions are important for tremor antagonism, th site of a serotonin involvement with tremor is the neostriatum. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Reference of 2328-12-3).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. Because of the high biological relevance of compounds possessing the 1,2,3,4-tetrahydroisoquinoline framework, a large number of synthetic approaches towards the creation of an isoquinoline or 1,2,3,4-tetrahydroisoquinoline core are presently known. However, synthetic routes to tetrahydroisoquinoline derivatives containing fluorine atom(s) in their structure are not particularly abundant.Reference of 2328-12-3

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

Synthesis and SAR of tetrahydroisoquinolines as Rev-erb伪 agonists was written by Noel, Romain;Song, Xinyi;Shin, Youseung;Banerjee, Subhashis;Kojetin, Douglas;Lin, Li;Ruiz, Claudia H.;Cameron, Michael D.;Burris, Thomas P.;Kamenecka, Theodore M.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Formula: C12H15NO2 This article mentions the following:

The design and synthesis of a novel series of Rev-erb伪 agonists is described. The development and optimization of the tetrahydroisoquinoline series was carried out from an earlier acyclic series of Rev-erb伪 agonists. Through the optimization of the scaffold I, several potent compounds with good in vivo profiles were discovered. In the experiment, the researchers used many compounds, for example, Ethyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate (cas: 41234-43-9Formula: C12H15NO2).

Ethyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate (cas: 41234-43-9) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. The dopamine-derived tetrahydroisoquinolines (TIQ) synthesized endogeneously from aldehydes and catecholamines have shown to modulate neurotransmission, central metabolism and motor activity.Formula: C12H15NO2

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

Optimisation of Tetrahydroisoquinoline-Based Chimeric Microtubule Disruptors was written by Dohle, Wolfgang;Leese, Mathew P.;Jourdan, Fabrice L.;Chapman, Christopher J.;Hamel, Ernest;Ferrandis, Eric;Potter, Barry V. L.. And the article was included in ChemMedChem in 2014.Computed Properties of C11H16ClNO2 This article mentions the following:

Tetrahydroisoquinoline (THIQ)-based “chimeric” microtubule disruptors were optimized through modification of the N-benzyl motif, in concert with changes at C3 and C7, resulting in the identification of compounds with improved in vitro antiproliferative activities, e.g. I with GI₅₀ 20 nM in DU-145. The broad anticancer activity of these novel structures was confirmed in the NCI 60-cell line assay, with two compounds displaying MGM values in the 40 nM region. In addition, their profiles as inhibitors of tubulin polymerization and colchicine binding to tubulin were confirmed. Compound I, for example, inhibited tubulin polymerization with an IC₅₀ of 1.8 渭M, close to that of the clin. drug combretastatin A-4, and also proved effective at blocking colchicine binding. Only one phenol compound in the series to date was identified as showing both better in vitro antiproliferative properties than its corresponding sulfamate and excellent antitubulin data (IC₅₀=1.6 渭M). Compound II was selected for in vivo evaluation at the NCI in the hollow fiber assay and showed very good activity and wide tissue distribution, illustrating the value of this template for further development. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Computed Properties of C11H16ClNO2).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline, as a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids. An oxidative C1 arylation of tetrahydroisoquinolines with aryl Grignard reagents is mediated by diethyl azodicarboxylate (DEAD). This C-H activation under metal-free conditions delivers target compounds, including some naturally occurring alkaloids, in good yields.Computed Properties of C11H16ClNO2

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

Antineoplastic activity of some tetrahydroisoquinoline derivatives was written by Chachoyan, A. A.;Garibdzhanyan, B. T.;Markaryan, E. Z.. And the article was included in Biologicheskii Zhurnal Armenii in 1972.COA of Formula: C11H16ClNO2 This article mentions the following:

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline-HCl (I) [2328-12-3] and similar compounds inhibited by 60-79% the growth of sarcoma 45 in rats. The compound had little or no activity against Walker carcinosarcoma or Ehrlich ascites carcinoma. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3COA of Formula: C11H16ClNO2).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline, as a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids. An oxidative C1 arylation of tetrahydroisoquinolines with aryl Grignard reagents is mediated by diethyl azodicarboxylate (DEAD). This C-H activation under metal-free conditions delivers target compounds, including some naturally occurring alkaloids, in good yields.COA of Formula: C11H16ClNO2

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

Ring-opening reactions of N-aryl-1,2,3,4-tetrahydroisoquinolines: synthesis of novel isoquino[2,1-a][3,1]benzoxazine derivatives was written by Stanforth, Stephen P.. And the article was included in Tetrahedron in 2000.HPLC of Formula: 2328-12-3 This article mentions the following:

The aldehydes 2,4-AcOCH₂(O₂N)C₆H₃NHCH₂CH₂C₆H₂R₂CHO-4,5,2 [I, R = H, OMe] were prepared by treatment of the corresponding 1,2,3,4-tetrahydroisoquinolines with N-bromosuccinimide (NBS). Basic hydrolysis of I gave the 4bH,6H-isoquino[2,1-a][3,1]benzoxazine derivatives An ethoxy derivative was obtained directly from the reaction of the tetrahydroisoquinolines with NBS. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3HPLC of Formula: 2328-12-3).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline, as a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.HPLC of Formula: 2328-12-3

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