38925-70-1

Upstream product

• 609-65-4 o-chlorobenzoyl chloride 
• 64-04-0 phenethylamine 
• 95-49-8 2-methylchlorobenzene 
• 68185-98-8 o-chlorobenzoyltrimethylsilane 
• 1590361-11-7 O-diethylcarbamoyl-N-phenethylhydroxylamine 
• 1590361-20-8 N-tert-butoxycarbonyl-O-diethylcarbamoyl-N-phenethylhydroxylamine 
• 103-63-9 1-phenyl-2-bromoethane 
• 777878-92-9 1,3-dioxoisoindolin-2-yl 2-chlorobenzoate 
• 118-91-2 ortho-chlorobenzoic acid 

Downstream Products

• 246851-84-3 (-)-1-(2-chlorophenyl)-1,2,3,4-tetrahydroisoquinoline 
• 19007-59-1 2-(3,4-dihydro-isoquinolin-1-yl)-N-methyl-aniline 
• 19209-04-2 1-(2-methylamino)-1,2,3,4-tetrahydroisoquinoline 
• 439614-58-1 1-(2-chlorophenyl)isoquinoline 
• 304463-94-3 1-o-chlorophenyl-1,2,3,4-tetrahydroisoquinoline 
• 174784-50-0 1-(2-chlorophenyl)-3,4-dihydroisoquinoline 

Relevant academic research and scientific papers

Chemoselective Amide-Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions

We report the facile amide-forming ligation of acylsilanes with hydroxylamines (ASHA ligation) under aqueous conditions. The ligation is fast, chemoselective, mild, high-yielding and displays excellent functional-group tolerance. Late-stage modifications of an array of marketed drugs, peptides, natural products, and biologically active compounds showcase the robustness and functional-group tolerance of the reaction. The key to the success of the reaction could be the possible formation of the strong Si?O bond via a Brook-type rearrangement. Given its simplicity and efficiency, this ligation has the potential to unfold new applications in the areas of medicinal chemistry and chemical biology.

Visible Light-Driven Efficient Synthesis of Amides from Alcohols using Cu?N?TiO2 Heterogeneous Photocatalyst

Amides were synthesized from alcohols and amines in high yields using an in situ generated active ester of N-hydroxyimide with our developed Cu?N?TiO2 catalyst at room temperature using oxygen as a sole oxidant under visible light. The catalyst can be easily prepared, robust, and recycled four times without a considerable change in catalytic activity. This developed protocol applies to a wide substrate scope and has good functional group tolerance. The application of this amidation reaction has been successfully demonstrated for the synthesis of moclobemide, an antidepressant drug, and an analog of the itopride drug on a gram scale.

Substituent effects on axial chirality in 1-aryl-3,4-dihydroisoquinolines: controlling the rate of bond rotation

A series of 1-aryl-3,4-dihydroisoquinolines (DHIQs) were synthesized and their barriers to bond rotation were determined by means of VT-NMR, dynamic HPLC or racemization studies. Although they all presented lower rotational stability than the related 1-ar

Enantioselective Synthesis of 1-Aryl-Substituted Tetrahydroisoquinolines Through Ru-Catalyzed Asymmetric Transfer Hydrogenation

A convenient and general asymmetric transfer hydrogenation of a wide array of 1-aryl-3,4-dihydroisoquinoline derivatives using a [RuIICl(η6-benzene)TsDPEN] complex in combination with a 5:2 HCOOH-Et3N azeotropic mixture as a hydrogen source was developed. Under mild reaction conditions, the described catalytic transformation secured a practical synthetic access to the corresponding valuable chiral 1-aryltetrahydroisoquinoline units with high atom economy, a broad substrate scope, high isolated yields (up to 97%) and good to excellent enantioselectivities (up to 99% ee). It was found that the stereochemical outcome of the reaction was strongly influenced by both the structure of the catalyst and the substituents present on the substrate. The synthetic utility of the present protocol has been demonstrated through the asymmetric synthesis of several biologically important alkaloids including the antiepileptic drug agent 1c, as well as (-)-nor-cryptostyline alkaloids I and II.

MnO2 promoted sequential C-O and C-N bond formation via C-H activation of methylarenes: A new approach to amides

A novel and efficient approach for the synthesis of amides has been developed through manganese dioxide promoted nondirected C-H activation of methylarenes under mild reaction conditions employing N-chloroamines as effective coupling partners.

Optimization and antifungal activity of chalcone analogues

Using chalcone as a leading compound, a series of its analogues (compounds 1-16) were designed and synthesized. Their activity of antipathogenic fungi of plants has been evaluated in the laboratory. The results showed that these compounds had certain antifungal activity against Sclerotinia sclerotiorum and Botrytis cinerea. Among them, the inhibition of growth for 2-chloro-N- phenylbenzamide (compound 2) reached 92.6 and 90.1 % at a concentration of 100 mg L-1, respectively.

Design, synthesis, and inhibition of platelet aggregation for some 1-o-chlorophenyl-1,2,3,4-tetrahydroisoquinoline derivatives

Four analogs proved to be potential antiplatelet aggregation agents, and compound 9 (TQP-3, applying for patent), which inhibits ADP-induced human platelet aggregation with IC50 values of approximately 0.206 nM was the most active. Based on ticlopidine active as an ADP receptor antagonist for inhibiting platelet aggregation in clinical test, and upon finding (±)-1,2-substituted-7-sulfonylamide/amide-1,2,3,4-tetrahydroisoquinoline (11-31) inhibited of platelet aggregation, a series of (±)-1-o- chlorophenyl-2-substituted-tetrahydroisoquinoline derivatives was designed and synthesized. Four analogs proved to be potential antiplatelet aggregation agents, and compound 9 (TQP-3, applying for patent) which inhibits ADP-induced human platelet aggregation with IC50 values of approximately 0.206 nM was the most active. Compound 2 is more active than compound 1, which (Type I) is similar to ticlopidine. This is because there is a spacial hindrance in compound 1, and the o-chloro group of compound 2 may play the same a role as o-chloro group of ticlopidine. On the other hand, with the different substitutions at different positions on the 2-substituted phenylacyl group, their inhibition of platelet aggregation differs. These compounds with m-substituted group (5, 7, 9) showed a higher IC50 value for inhibiting ADP-induced human platelet aggregation than those with o-substituted group (4, 6) or p-substituted group (3, 8). It was observed that their inhibition is bromine-substituted derivative (9), chlorine-substituted derivative (7), and nitro-substituted derivative (5) in turn. Moreover, these compounds (Type II) may be more similar to clopidogrel than to ticlopidine due to the acyl group at 2 position of the nucleus playing a role as the ester group of clopidogrel. It was conjectured that these analogs function as a potential antiplatelet aggregation role by acting as ADP receptor antagonists.

REMEDIES FOR STRESS DISEASES COMPRISING MITOCHONDRIAL BENZODIAZEPINE RECEPTOR ANTAGONISTS

A pharmaceutical composition for the prophylaxis and/or treatment of diseases induced, exacerbated or reignited by stressors comprising the compound of formula (I) wherein all symbols have the same meanings as described in the specification, etc. as an active ingredient.

Synthetic approaches to 1-(2-chlorophenyl)isoquinoline-3-carboxylic acid

In connection with our research of new antitumor compounds, previously undescribed approaches to the 1-(2-chlorophenyl)isoquinoline-3-carboxylic acid 9 are reported here. Two related accesses from phenylethylamine or amphetamine were investigated and were found to be successful. A more robust synthesis, using Suzuki's cross-coupling between 2-chlorophenylboronic acid 15 and the previously unreported methyl-1-bromoisoquinoline-3-carboxylate 14 was also developed. This synthetic route provides the ground for a combinatorial approach to the core structure of new potential peripheral benzodiazepine receptor ligands.

Synthesis of racemic 1,2,3,4-tetrahydroisoquinolines and their resolution

1-Aniline-substituted 3,4-dihydroisoquinolines were obtained in various ways using the Bischler-Napieralski reaction. The effect of the protecting group at the aniline nitrogen atom on the course of the reaction has been studied and it was found that the N-phthalyl group was stable under the cyclization conditions. The dihydroisoquinolines were reduced to the racemic 1,2,3,4-tetrahydroisoquinolines which were resolved by crystallization of the diastereomeric tartrates. Two examples of 1,2,3, 4-tetrahydroisoquinolines were obtained in optically pure form (>99% ee).