Month: October 2022

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]yohimbine-labeled site>, Safety of 1,2,3,4-Tetrahydroisoquinolin-5-amine, the main research area is imidazoline tetrahydroisoquinolinylmethyl isoindolinylmethyl preparation adrenoreceptor affinity; adrenoreceptor affinity tetrahydroisoquinolinylmethylimidazoline isoindolinylmethylimidazoline.

Tetrahydroisoquinolin-2-ylmethyl- (I, R = H, 1-Me, Et, allyl, 3-, 5-Me, 5-, 8-F, 5-, 6-, 8-Cl, 5-OMe, NO2, NH2, etc.) and 2-(isoindolin-2-ylmethyl)imidazolines II (R1 = H, Cl) were prepared and tested for α1- and α2-adrenoceptor affinity with radioligand binding. I [R = 5-F, 5-Cl, 5,8-(MeO)2, 5,8,1-(MeO)2Me] were selective α2-adrenoceptor ligands on the basis of displacement of [3H]yohimbine from rat cerebral cortical membranes. I (R = 8-Cl) showed a 36-fold difference in affinity for the [3H]idazoxan-labeled α2-adrenoceptor relative to the [3H]yohimbine-labeled site, which may be evidence for α2-adrenoceptor subtypes.

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, Safety of 1,2,3,4-Tetrahydroisoquinolin-5-amine.

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

Resende, Diana I. S. P.; Almeida, Joana R.; Pereira, Sandra; Campos, Alexandre; Lemos, Agostinho; Plowman, Jeffrey E.; Thomas, Ancy; Clerens, Stefan; Vasconcelos, Vitor; Pinto, Madalena; Correia-da-Silva, Marta; Sousa, Emilia published the artcile< From Natural Xanthones to Synthetic C-1 Aminated 3,4-Dioxygenated Xanthones as Optimized Antifouling Agents>, Application In Synthesis of 115955-90-3, the main research area is aminated dioxygenated xanthone preparation antifouling antibacterial; anti-settlement; antifouling; eco-friendly alternatives; molecular targets; xanthones.

In this work, the antifouling activity of a series of 24 xanthones I [R1 = Me, CH2Br, 4-ClC6H4CH2NHCH2, etc.; R2 = H, Cl; R3 = OMe; R4 = OH, OMe; R5 = H, OMe], with chem. similarities to natural products, was exploited. Nine of the tested xanthones presented highly significant anti-settlement responsed against the settlement of mussel Mytilus galloprovincialis larvae and low toxicity to this macrofouling species. Addnl., xanthone I [R1 = piperidinylmethyl; R2 = H; R3 = OMe; R4 = OMe; R5 = H] exhibited a therapeutic ratio (LC50/EC50) >15, as required by the US Navy program attesting its suitability as natural antifouling agents. From the nine tested xanthones, none of the compounds were found to significantly inhibit the growth of the marine biofilm-forming bacterial strains tested. Insights on the antifouling mode of action suggested that these two compounds affected similar mol. targets and cellular processes in mussel larvae, including that related to mussel adhesion capacity. This work exposed for the first time the relevance of C-1 aminated xanthones with a 3,4-dioxygenated pattern of substitution as new non-toxic products to prevent marine biofouling.

Marine Drugs published new progress about Antibacterial agents. 115955-90-3 belongs to class tetrahydroisoquinoline, and the molecular formula is C9H12N2, Application In Synthesis of 115955-90-3.

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

Lee, Wongyu; Kim, Dongwook; Seo, Sangwon; Chang, Sukbok published the artcile< Photoinduced α-C-H Amination of Cyclic Amine Scaffolds Enabled by Polar-Radical Relay>, Electric Literature of 893566-75-1, the main research area is cyclic amine photoinduced amination regioselective polar radical relay; Amination; Amines; Radicals; Reaction Mechanisms; Sustainability.

Herein, a polar-radical relay strategy for α-C-H amination of cyclic amines with N-chloro-N-sodio-carbamates is reported. The relay is initiated by in situ generation of a cyclic iminium intermediate using N-iodosuccinimide oxidant as an initiator, which then operates through a series of polar (addition and elimination) and radical (homolysis, hydrogen- and halogen atom transfer) reactions to enable the challenging C-N bond formation in a controlled manner. A broad range of α-amino cyclic amines were readily accessed with excellent regioselectivity, and the superb applicability was further demonstrated by functionalization of biol. relevant compounds

Angewandte Chemie, International Edition published new progress about Aminals Role: SPN (Synthetic Preparation), PREP (Preparation). 893566-75-1 belongs to class tetrahydroisoquinoline, and the molecular formula is C14H18BrNO2, Electric Literature of 893566-75-1.

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

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