The important role of 6,7-Dimethoxy-1-methyl-3,4-dihydroisoquinoline

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Imine reductase based all-enzyme hydrogel with intrinsic cofactor regeneration for flow biocatalysis

All-enzyme hydrogels are biocatalytic materials, with which various enzymes can be immobilized in microreactors in a simple, mild, and efficient manner to be used for continuous flow processes. Here we present the construction and application of a cofactor regenerating hydrogel based on the imine reductase GF3546 from Streptomyces sp. combined with the cofactor regenerating glucose-1-dehydrogenase from Bacillus subtilis. The resulting hydrogel materials were characterized in terms of binding kinetics and viscoelastic properties. The materials were formed by rapid covalent crosslinking in less than 5 min, and they showed a typical mesh size of 67 ¡À 2 nm. The gels were applied for continuous flow biocatalysis. In a microfluidic reactor setup, the hydrogels showed excellent conversions of imines to amines for up to 40 h in continuous flow mode. Variation of flow rates led to a process where the gels showed a maximum space-time-yield of 150 g.(L.day)-1 at 100 muL/min.

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Josiphos-Type Binaphane Ligands for Iridium-Catalyzed Enantioselective Hydrogenation of 1-Aryl-Substituted Dihydroisoquinolines

Convenient synthesis and useful application of a series of Josiphos-type binaphane ligands were described. The iridium complexes of these chiral diphosphines displayed excellent enantioselectivity and good reactivity in the asymmetric hydrogenation of challenging 1-aryl-substituted dihydroisoquinoline substrates (full conversions, up to >99% ee, 4000 TON). The use of 40% HBr (aqueous solution) as an additive dramatically improved the asymmetric induction of these catalysts. This transformation provided a highly efficient and enantioselective access to chiral 1-aryl-substituted tetrahydroisoquinolines, which were of great importance and common in natural products and biologically active molecules.

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BISPHOSPHOLANES FOR USE AS CATALYSTS IN ASYMMETRIC REACTIONS

The invention is a set of novel bisphospholane ligands that can be complexed with transition metals. These complexes are useful as catalysts in asymmetric reactions such as asymmetric hydrogenation.

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Discovery of 6,7-Dimethoxy-1-methyl-3,4-dihydroisoquinoline

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Synthesis of multi ring-fused 2-pyridones via an acyl-ketene imine cyclocondensation

Polycyclic ring-fused 2-pyridones (5a-e and 9a-e) have been prepared via a microwave-assisted acyl-ketene imine cyclocondensation. Starting from 3,4-dihydroisoquinolines (4a-b) or 3,4-dihydroharman (8), fused 2-pyridones could be prepared in a one-step procedure. By using either Meldrum’s acid derivatives (1a-d) or 1,3-dioxine-4-ones (7a-b) as acyl-ketene sources, mono- or disubstitution of the fused 2-pyridone ring could be accomplished. As an application of the method, a formal synthesis of the indole alkaloid sempervilam was performed.

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Synthesis of [1,2,4]triazolo[3,4-a]isoquinolines and pyrrolo[2,1-a]isoquinolines using alpha-keto hydrazonoyl halides

Treatment of alpha-keto hydrazonoyl halides 1 with 3,4-dihydro-6,7-dimethoxyisoquinoline 3 and its 1-methyl derivative 4 in the presence of triethylamine in tetrahydrofuran at reflux afforded the corresponding cycloadducts 6 and 9, respectively. The same halides 1 react with 1-cyanomethyl-3,4-dihydro-6,7-dimethoxyisoquinoline 5 and afforded pyrrolo[2,1-a]isoquinoline derivatives 12 in high yield.

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Isoquinoline – Wikipedia,
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FSH RECEPTOR ANTAGONISTS

The invention relates to FSH receptor antagonist according to general formula (I) or a pharmaceutically acceptable salt thereof and to a pharmaceutical composition containing the same. The compounds can be used for the treatment and prevention of endometriosis, for the treatment and prevention of pre-menopausal and peri-menopausal hormone-dependent breast cancer, for contraception, and for the treatment of uterine fibroids and other menstrual-related disorders

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

More research is needed about 6,7-Dimethoxy-1-methyl-3,4-dihydroisoquinoline

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Synthetic and mechanistic study on the microwave assisted fries rearrangement of 1-methylidene-3,4-dihydroisoquinoline-2(1H)-yl-methanones

Formerly, an unexpected acyl migration of 1-methylidene-3,4-dihydroisoquinoline- 2(1H)-yl-methanone derivatives was observed, and on this basis a microwave assisted synthetic method was developed for the preparation of members of the 2?-(3,4- dihydroisoquinoline-1-ylidene)-1-ethan-1-one family, potential CB2 receptor agonists and PDE7 inhibitors. The reaction mechanism was studied with experimental and theoretical methods in order to propose intra- and intermolecular radical pathways.

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Ruthenium-catalyzed dehydrogenation of ammonia boranes

The dehydrogenation of ammonia borane (AB) and methylammonia borane (MeAB) is shown to be catalyzed by several Ru-amido complexes. Up to 1 equiv of H2 (1.0 system wt %) is released from AB by as little as 0.03 mol % Ru within 5 min, and up to 2 equiv of H2 (3.0 system wt %) are released from MeAB with 0.5 mol % Ru in under 10 min at room temperature, the first equivalent emerging within 10 s. Also, a mixture of AB/MeAB yields up to 3.6 system wt % H2 within 1 h with 0.1 mol % Ru. Computational studies were performed to elucidate the mechanism of dehydrogenation of AB. Finally, it was shown that alkylamine-boranes can serve as a source of H2 in the Ru-catalyzed reduction of ketones and imines. Copyright

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The biochemical characterization of three imine-reducing enzymes from Streptosporangium roseum DSM43021, Streptomyces turgidiscabies and Paenibacillus elgii

Recently imine reductases (IREDs) have emerged as promising biocatalysts for the synthesis of a wide variety of chiral amines. To promote their application, many novel enzymes were reported, but only a few of them were biochemically characterized. To expand the available knowledge about IREDs, we report the characterization of two recently identified (R)-selective IREDs from Streptosporangium roseum DSM43021 and Streptomyces turgidiscabies and one (S)-selective IRED from Paenibacillus elgii. The biochemical properties including pH profiles, temperature stabilities, and activities of the enzymes in the presence of organic solvents were investigated. All three enzymes showed relatively broad pH spectra with maximum activities in the neutral range. While the (R)-selective IREDs displayed only limited thermostabilities, the (S)-selective enzyme was found to be the most thermostable IRED known to date. The activity of this IRED proved also to be most tolerant towards the investigated co-solvents DMSO and methanol. We further studied activities and selectivities towards a panel of cyclic imine model substrates to compare these enzymes with other IREDs. In biotransformations, IREDs showed high conversions and the amine products were obtained with up to 99?% ee. By recording the kinetic constants for these compounds, substrate preferences of the IREDs were investigated and it was shown that the (S)-IRED favors the transformation of bulky imines contrary to the (R)-selective IREDs. Finally, novel exocyclic imine substrates were tested and also high activities and selectivities detected.

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Isoquinoline – Wikipedia,
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Gold Particles Supported on Amino-Functionalized Silica Catalyze Transfer Hydrogenation of N-Heterocyclic Compounds

In this work we demonstrate that exceptionally small gold particles (d=0.6¡À0.2 nm) supported on amino-functionalized mesoporous silicate SBA-15 are highly active in transfer hydrogenation of structurally diverse unsaturated N-heterocyclic compounds. The heterocyclic ring is reduced selectively. The gold particles aggregate to a diameter of 4?5 nm in the presence of formic acid/triethylamine (hydrogen donor) during the first catalytic run. In subsequent cycles the nanoparticles maintain their size, yielding a very stable catalytic system that was recycled more than five times. In contrast, analogous SBA catalysts featuring larger (?5?35 nm) gold particles are not active. Excess formic acid also leads to the formation of formamide derivatives of the products of hydrogenation, which can be deformylated quantitatively. Fifteen structurally different substrates, including the scaffolds of quinoline, isoquinoline, quinoxaline, acridine, phenanthroline, quinazoline, and phenanthridine are hydrogenated and deformylated to give the amine products in >90% overall yield. Deuterium labeling experiments indicate that 1,2-addition with subsequent disproportionation of the formed intermediate is the preferred reaction path over the 1,4-addition one, suggesting the participation of a gold hydride species. (Figure presented.).

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem