Heterocyclic Building Blocks-Tetrahydroisoquinoline

Malamas, Michael S.; Lamani, Manjunath; Farah, Shrouq I.; Mohammad, Khadijah A.; Miyabe, Christina Yume; Rajarshi, Girija; Wu, Simiao; Zvonok, Nikolai; Chandrashekhar, Honrao; Wood, JodiAnne; Makriyannis, Alexandros published the artcile< Design and Synthesis of Highly Potent and Specific ABHD6 Inhibitors>, Related Products of 893566-75-1, the main research area is design synthesis biol activity ABHD6 inhibitor SAR; monoacylglycerol lipase; neuroinflammation.; neuroprotection; α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid; α/β-hydrolase domain containing 6.

Fine-tuning than complete disruption of 2-arachidonoylglycerol (2-AG) metabolism in the brain represents a promising pharmacol. approach to limit potential untoward effects associated with complete blockade of monoacylglycerol lipase (MGL), the primary hydrolase of 2-AG. This could be achieved through a/b-hydrolase domain containing 6 (ABHD6) inhibition, which will provide a smaller and safer contribution to 2-AG regulation in the brain. Pharmacol. studies with ABHD6 inhibitors have recently been reported, where modulation of ABHD6 activity either through CB1R-dependent or CB1R-independent processes showed promise in preclin. models of epilepsy, neuropathic pain and inflammation. Furthermore in the periphery, ABHD6 modulates 2-AG and other fatty acid monoacylglycerols (MAGs) and is implicated in Type-2 diabetes, metabolic syndrome and potentially other diseases. Herein, we report the discovery of single-digit nanomolar potent and highly specific ABHD6 inhibitors with >1000-fold selectivity against MGL and FAAH. The new ABHD6 inhibitors provide early leads to develop therapeutics for neuroprotection and the treatment of inflammation and diabetes.

ChemMedChem published new progress about Brain. 893566-75-1 belongs to class tetrahydroisoquinoline, and the molecular formula is C14H18BrNO2, Related Products of 893566-75-1.

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

Ruel, Rejean; L’Heureux, Alexandre; Thibeault, Carl; Lapointe, Philippe; Martel, Alain; Qiao, Jennifer X.; Hua, Ji; Price, Laura A.; Wu, Qimin; Chang, Ming; Zheng, Joanna; Huang, Christine S.; Wexler, Ruth R.; Rehfuss, Robert; Lam, Patrick Y. S. published the artcile< Potent P2Y1 urea antagonists bearing various cyclic amine scaffolds>, Application of C9H12N2, the main research area is isoindolinyloxypyridyl trifluoromethoxyphenylurea preparation purinergic P2Y1 inhibitor; piperidinyloxypyridyl trifluoromethoxyphenylurea preparation purinergic P2Y1 inhibitor; Isoindolines; P2Y(1) antagonists; Piperidines; Purinergic receptors; Tetrahydroisoquinolines.

A number of new amine scaffolds with good inhibitory activity in the ADP-induced platelet aggregation assay have been found to be potent antagonists of the P2Y1 receptor. SAR optimization led to the identification of isoindoline and piperidine derivatives which showed good in vitro binding and functional activities, as well as improved aqueous solubility Among them, the piperidine I showed the best overall profile with favorable PK parameters.

Bioorganic & Medicinal Chemistry Letters published new progress about Cyclic amines Role: PAC (Pharmacological Activity), RCT (Reactant), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation), USES (Uses). 115955-90-3 belongs to class tetrahydroisoquinoline, and the molecular formula is C9H12N2, Application of C9H12N2.

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

Clark, Robin D.; Berger, Jacob; Garg, Pushkal; Weinhardt, Klaus K.; Spedding, Michael; Kilpatrick, Andrew T.; Brown, Christine M.; MacKinnon, Alison C. published the artcile< Affinity of 2-(tetrahydroisoquinolin-2-ylmethyl)- and 2-(isoindolin-2-ylmethyl)imidazolines for α-adrenoceptors. Differential affinity of imidazolines for the [3H]idazoxan-labeled α2-adrenoceptor vs. the [3H]yohimbime-labeled site [Erratum to document cited in CA112(7):55713w>, COA of Formula: C9H12N2, the main research area is Erratum imidazoline tetrahydroisoquinolinylmethyl isoindolinylmethyl adrenoreceptor affinity; adrenoreceptor affinity tetrahydroisoquinolinylmethylimidazoline isoindolinylmethylimidazoline Erratum.

An error in Table I has been corrected The error was not reflected in the abstract or the index entries.

Journal of Medicinal Chemistry published new progress about α1-Adrenoceptors Role: RCT (Reactant), RACT (Reactant or Reagent). 115955-90-3 belongs to class tetrahydroisoquinoline, and the molecular formula is C9H12N2, COA of Formula: C9H12N2.

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

Zhang, Wen-Xiong; Nishiura, Masayoshi; Hou, Zhaomin published the artcile< Catalytic addition of amine N-H bonds to carbodiimides by half-sandwich rare-earth metal complexes: efficient synthesis of substituted guanidines through amine protonolysis of rare-earth metal guanidinates>, Recommanded Product: 1,2,3,4-Tetrahydroisoquinolin-5-amine, the main research area is half sandwich rare earth catalyst guanidine synthesis carbodiimide amine.

Reaction of [Ln(CH2SiMe3)3(thf)2] (Ln = Y, Yb, and Lu) with one equivalent of Me2Si(C5Me4H)NHR’ (R’ = Ph, 2,4,6-Me3C6H2, tBu) affords straightforwardly the corresponding half-sandwich rare-earth metal alkyl complexes [{Me2Si(C5Me4)(NR’)}Ln(CH2SiMe3)(thf)n] (1: Ln = Y, R’ = Ph, n = 2; 2: Ln = Y, R’ = C6H2Me3-2,4,6, n = 1; 3: Ln = Y, R’ = tBu, n = 1; 4: Ln = Yb, R’ = Ph, n = 2; 5: Ln = Lu, R’ = Ph, n = 2) in high yields. These complexes, especially the yttrium complexes 1-3, serve as excellent catalyst precursors for the catalytic addition of various primary and secondary amines to carbodiimides, efficiently yielding a series of guanidine derivatives with a wide range of substituents on the nitrogen atoms. Functional groups such as CN, CCH, and aromatic C-X (X: F, Cl, Br, I) bonds can survive the catalytic reaction conditions. A primary amino group can be distinguished from a secondary one by the catalyst system, and therefore, the reaction of 1,2,3,4-tetrahydro-5-aminoisoquinoline with iPrN=C=NiPr can be achieved stepwise first at the primary amino group to selectively give the monoguanidine, and then at the cyclic secondary amino unit to give the biguanidine. Some key reaction intermediates or true catalyst species, such as the amido complexes [{Me2Si(C5Me4)(NPh)}Y(NEt2)(thf)2] and [{Me2Si(C5Me4)(NPh)}Y(NHC6H4Br-4)(thf)2], and the guanidinate complexes [{Me2Si(C5Me4)(NPh)}Y{iPrNC(NEt2)(NiPr)}(thf)] and [{Me2Si(C5Me4)(NPh)}Y{iPrN}C(NC6H4Br-4)(NHiPr)(thf)] have been isolated and structurally characterized. Reactivity studies on these complexes suggest that the present catalytic formation of a guanidine compound proceeds mechanistically through nucleophilic addition of an amido species, formed by acid-base reaction between a rare-earth metal alkyl bond and an amine N-H bond, to a carbodiimide, followed by amine protonolysis of the resultant guanidinate species.

Chemistry – A European Journalpublished new progress about Amines, triamines Role: PEP (Physical, Engineering or Chemical Process), RCT (Reactant), PROC (Process), RACT (Reactant or Reagent). 115955-90-3 belongs to class tetrahydroisoquinoline, and the molecular formula is C9H12N2, Recommanded Product: 1,2,3,4-Tetrahydroisoquinolin-5-amine.

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

Mach, Ulrich R.; Hackling, Anneke E.; Perachon, Sylvie; Ferry, Sandrine; Wermuth, Camille G.; Schwartz, Jean-Charles; Sokoloff, Pierre; Stark, Holger published the artcile< Development of novel 1,2,3,4-tetrahydroisoquinoline derivatives and closely related compounds as potent and selective dopamine D3 receptor ligands>, Recommanded Product: 1,2,3,4-Tetrahydroisoquinolin-5-amine, the main research area is tetrahydroisoquinoline derivative dopamine D3 receptor ligand.

Based on N-alkylated 1,2,3,4-tetrahydroisoquinoline derivatives which are structurally related to the partial agonist BP 897, a series of novel, selective dopamine D3 receptor antagonists has been synthesized. Derivatization included changes in the arylamide moiety and the tetrahydroisoquinoline substructure leading to compounds with markedly improved selectivities and affinities in the low nanomolar concentration range. From the 55 structures presented here, (E)-3-(4-iodophenyl)-N-(4-(1,2,3,4-tetrahydroisoquinolin-2-yl)butyl)acrylamide (51) has high affinity (Ki(hD3) = 12 nM) and a 123-fold preference for the D3 receptor relative to the D2 receptor subtype. Its pharmacol. profile offers the prospect of a novel radioligand as a tool for various dopamine D3-receptor-related in vitro and in vivo investigations.

ChemBioChempublished new progress about Dopamine D3 receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 115955-90-3 belongs to class tetrahydroisoquinoline, and the molecular formula is C9H12N2, Recommanded Product: 1,2,3,4-Tetrahydroisoquinolin-5-amine.

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

Lemos, Agostinho; Gomes, Ana Sara; Loureiro, Joana B.; Brandao, Pedro; Palmeira, Andreia; Pinto, Madalena M. M.; Saraiva, Lucilia; Sousa, Maria Emilia published the artcile< Synthesis, biological evaluation, and in silico studies of novel aminated xanthones as potential p53-activating agents>, Product Details of C9H12N2, the main research area is aminated xanthone preparation antitumor human docking p53 activator; dimethoxy oxo xanthene carbaldehyde preparation; MDM2-p53 interaction; antitumor activity; computational docking; xanthones; yeast-based assays.

In this work, a series of eleven aminated xanthones possessing a 3,4-dioxygenated pattern of substitution e.g., I was efficiently constructed in moderate to good yields. From this group of compounds, xanthone I was identified for the first time as a putative p53-activating agent, using a yeast-based screening assay. Xanthone I was revealed to inhibit the growth of human HCT116 p53+/+ colon cancer cells, being that this effect was associated with cell cycle arrest through activation of the p53 pathway. Nevertheless, further studies were required to confirm the mechanism of action of compound I, which may lead to the identification of a novel xanthone derivative with promising antitumor activity. These results demonstrated the potential usefulness of coupling amine-containing structural motifs of known MDM2-p53 disruptors into the 3,4-dioxygenated xanthone scaffold as a starting point for the design of novel and improved p53-activating agents with antitumor activity and drug like properties.

Moleculespublished new progress about Amines Role: PAC (Pharmacological Activity), PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation), USES (Uses). 115955-90-3 belongs to class tetrahydroisoquinoline, and the molecular formula is C9H12N2, Product Details of C9H12N2.

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

Duan, Xiaonan; Wang, Xuepeng; Chen, Xingkun; Zhang, Jisong published the artcile< Continuous and Selective Hydrogenation of Heterocyclic Nitroaromatics in a Micropacked Bed Reactor>, Electric Literature of 115955-90-3, the main research area is nitroisoquinoline nickel silica palladium aluminumoxide catalyst continous flow hydrogentaion; aminoisoquinoline regioselective preparation.

A continuous flow system based on a micropacked bed reactor was developed for the selective hydrogenation of heterocyclic nitroaroms. and the reductions of 5-nitroisoquinoline to 5-aminoisoquinoline and 5-amino-1,2,3,4-tetrahydroisoquinoline are selected as the model reactions. With the optimal reaction conditions, maximal yields of 99.9% (5-aminoisoquinoline) and 99.3% (5-amino-1,2,3,4-tetrahydroisoquinoline) were obtained successfully. Moreover, this system exhibits remarkable performance for the selective hydrogenation of relevant heterocyclic nitroaroms. with all yields beyond the level of 97.5%. The continuous flow system enables efficient hydrogenation of heterocyclic nitroaroms. and remarkable selectivity of target products with shorter reaction time and safer operation compared with batch reactors.

Organic Process Research & Developmentpublished new progress about Hydrogenation catalysts, regioselective. 115955-90-3 belongs to class tetrahydroisoquinoline, and the molecular formula is C9H12N2, Electric Literature of 115955-90-3.

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

Clark, Robin D.; Berger, Jacob; Garg, Pushkal; Weinhardt, Klaus K.; Spedding, Michael; Kilpatrick, Andrew T.; Brown, Christine M.; MacKinnon, Alison C. published the artcile< Affinity of 2-(tetrahydroisoquinolin-2-ylmethyl)- and 2-(isoindolin-2-ylmethyl)imidazolines for α-adrenoceptors. Differential affinity of imidazolines for the [3H]idazoxan-labeled α2-adrenoceptor vs. the [3H]yohimbime-labeled site [Erratum to document cited in CA112(7):55713w>, Related Products of 115955-90-3, the main research area is Erratum imidazoline tetrahydroisoquinolinylmethyl isoindolinylmethyl adrenoreceptor affinity; adrenoreceptor affinity tetrahydroisoquinolinylmethylimidazoline isoindolinylmethylimidazoline Erratum.

An error in Table I has been corrected The error was not reflected in the abstract or the index entries.

Journal of Medicinal Chemistrypublished new progress about α1-Adrenoceptors Role: RCT (Reactant), RACT (Reactant or Reagent). 115955-90-3 belongs to class tetrahydroisoquinoline, and the molecular formula is C9H12N2, Related Products of 115955-90-3.

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

Ruel, Rejean; L’Heureux, Alexandre; Thibeault, Carl; Lapointe, Philippe; Martel, Alain; Qiao, Jennifer X.; Hua, Ji; Price, Laura A.; Wu, Qimin; Chang, Ming; Zheng, Joanna; Huang, Christine S.; Wexler, Ruth R.; Rehfuss, Robert; Lam, Patrick Y. S. published the artcile< Potent P2Y1 urea antagonists bearing various cyclic amine scaffolds>, Safety of 1,2,3,4-Tetrahydroisoquinolin-5-amine, the main research area is isoindolinyloxypyridyl trifluoromethoxyphenylurea preparation purinergic P2Y1 inhibitor; piperidinyloxypyridyl trifluoromethoxyphenylurea preparation purinergic P2Y1 inhibitor; Isoindolines; P2Y(1) antagonists; Piperidines; Purinergic receptors; Tetrahydroisoquinolines.

A number of new amine scaffolds with good inhibitory activity in the ADP-induced platelet aggregation assay have been found to be potent antagonists of the P2Y1 receptor. SAR optimization led to the identification of isoindoline and piperidine derivatives which showed good in vitro binding and functional activities, as well as improved aqueous solubility Among them, the piperidine I showed the best overall profile with favorable PK parameters.

Bioorganic & Medicinal Chemistry Letterspublished new progress about Cyclic amines Role: PAC (Pharmacological Activity), RCT (Reactant), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation), USES (Uses). 115955-90-3 belongs to class tetrahydroisoquinoline, and the molecular formula is C9H12N2, Safety of 1,2,3,4-Tetrahydroisoquinolin-5-amine.

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

Wang, Hai; Wang, Liang; Wang, Sai; Dong, Xue; Zhang, Jian; Xiao, Feng-Shou published the article 《Aerobic Activation of C-H Bond in Amines Over a Nanorod Manganese Oxide Catalyst》. Keywords: aerobic activation amine nanorod manganese oxide catalyst; amide preparation green chem.They researched the compound: Picolinamide( cas:1452-77-3 ).Application of 1452-77-3. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:1452-77-3) here.

The development of heterogeneous catalysts for the synthesis of pharmaceutically relevant compounds is always important for chem. research. Here, we report a selective aerobic oxidation of aromatic and aliphatic amines to corresponding amides over a nanorod manganese oxide (NR-MnOx) catalyst. The kinetic studies reveal that the NR-MnOx catalyzed amine-to-amide reaction proceeds the oxidative dehydrogenation of the amines into nitriles, followed by hydrolysis of nitrile into amides. The NR-MnOx exhibits fast kinetics and high selectivities in these steps, as well as hinders the byproduct formation. More importantly, the NR-MnOx catalyst is stable and reusable in the continuous recycle tests with water as a sole byproduct, exhibiting superior sustainability and significant advancement to outperform the traditional amide production route in acidic or basic media with toxic byproducts.

Different reactions of this compound(Picolinamide)Application of 1452-77-3 require different conditions, so the reaction conditions are very important.

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