60518-41-4

Usage

Uses

Used in Pharmaceutical Industry:
7-chloro-3,4-dihydroisoquinoline is used as an intermediate in the synthesis of various pharmaceuticals for its ability to impart specific chemical and biological properties to the final product.
Used in Agrochemical Industry:
7-chloro-3,4-dihydroisoquinoline is used as an intermediate in the synthesis of agrochemicals, contributing to the development of effective agricultural products.
Used in Organic Chemistry:
7-chloro-3,4-dihydroisoquinoline is used as a building block in the synthesis of complex organic molecules, making it a valuable compound in the field of organic chemistry for creating diverse chemical structures.

Upstream product

• 73075-45-3 7-chloro-1,2,3,4-tetrahydroisoquinoline hydrochloride 
• 82771-60-6 7-chloro-1,2,3,4-tetrahydro-isoquinoline 

Downstream Products

• 1346176-91-7 C₁₇H₁₃ClN₂O₂ 
• 1346177-11-4 C₂₅H₂₁ClN₂O₄S 

Relevant academic research and scientific papers

Aza-Nazarov Cyclization Reactions via Anion Exchange Catalysis

A catalytic aza-Nazarov cyclization between 3,4-dihydroisoquinolines and α,β-unsaturated acyl chlorides has been developed to access α-methylene-?-lactam products in good yields (up to 79%) as single diastereomers. The reactions proceed efficiently when AgOTf is used as an anion exchange catalyst with a 20 mol % loading at 80 °C. Computational studies were performed to investigate the reaction mechanism, and the findings support the role of the ?TMS group in reducing the reaction barrier of the key cyclization step.

Enantioselective synthesis of 1-aryl tetrahydroisoquinolines by the rhodium-catalyzed reaction of 3,4-dihydroisoquinolinium tetraarylborates

The 1-aryl tetrahydroisoquinolines (1-aryl THIQs) are omnipresent in biologically active molecules. Here we report on the direct asymmetric synthesis of these valuable compounds via the reaction of 3,4-dihydroisoquinolinium tetraarylborates. The dual roles of anionic tetraarylborates, which function as both prenucleophiles and stabilizers of 3,4-dihydroisoquinolinium cations, enable this rhodium(I)-catalyzed protocol to convergently provide enantioenriched 1-aryl THIQs in good yields (≤95%) with ≤97% ee, as demonstrated by the formal synthesis of (?)-solifenacin and the facile synthesis of (?)-Cryptostyline I.

Peganumine A alkaloid structure simplifier and application thereof

The invention discloses a Peganumine A alkaloid structure simplifier, a stereoisomer or a pharmaceutical salt thereof. The structure is shown in the following general formula: each substituent group is defined in the specification. The simplified structure of the Peganumine A alkaloid provided by the invention has a relatively obvious proliferation inhibition effect on liver cancer HepG2, lung cancer A549 and intestinal cancer HCT116, and the anti-tumor activity of part of compounds is higher than the anti-liver cancer HepG2 activity of Peganumine A reported in literatures.

Discovery of TAK-981, a First-in-Class Inhibitor of SUMO-Activating Enzyme for the Treatment of Cancer

SUMOylation is a reversible post-translational modification that regulates protein function through covalent attachment of small ubiquitin-like modifier (SUMO) proteins. The process of SUMOylating proteins involves an enzymatic cascade, the first step of which entails the activation of a SUMO protein through an ATP-dependent process catalyzed by SUMO-activating enzyme (SAE). Here, we describe the identification of TAK-981, a mechanism-based inhibitor of SAE which forms a SUMO-TAK-981 adduct as the inhibitory species within the enzyme catalytic site. Optimization of selectivity against related enzymes as well as enhancement of mean residence time of the adduct were critical to the identification of compounds with potent cellular pathway inhibition and ultimately a prolonged pharmacodynamic effect and efficacy in preclinical tumor models, culminating in the identification of the clinical molecule TAK-981.

Aza-Nazarov Cyclization Reactions via Anion Exchange Catalysis

A catalytic aza-Nazarov cyclization between 3,4-dihydroisoquinolines and α,β-unsaturated acyl chlorides has been developed to access α-methylene-γ-lactam products in good yields (up to 79%) as single diastereomers. The reactions proceed efficiently when AgOTf is used as an anion exchange catalyst with a 20 mol % loading at 80 °C. Computational studies were performed to investigate the reaction mechanism, and the findings support the role of the -TMS group in reducing the reaction barrier of the key cyclization step.

HETEROARYL COMPOUNDS USEFUL AS INHIBITORS OF SUMO ACTIVATING ENZYME

Disclosed are chemical entities which are compounds of formula (I); or pharmaceutically acceptable salts thereof; wherein Y, Ra, Ra', Rb, Rc, X1, X2, X3, Rd, Z1, and Z2 have the values described herein and stereochemical configurations depicted at asterisked positions indicate absolute stereochemistry. Chemical entities according to the disclosure can be useful as inhibitors of Sumo Activating Enzyme (SAE). Further provided are pharmaceutical compositions comprising a compound of the disclosure and methods of using the compositions in the treatment of proliferative, inflammatory, cardiovascular, and neurodegenerative diseases or disorders.

Decahydro-8H-isoquino[2,1-g][1,6]naphthyridine and decahydrobenzo[a]pyrrolo [2,3-e]quinolizine derivatives

Compounds of the formula STR1 wherein: m is an integer of 1-6;n is an integer of 1 or 2;X and Y are independently hydrogen; hydroxy; lower alkyl; lower alkoxy; or halo; or X and Y when adjacent and taken together are methylenedioxy or ethylene-1,2-dioxy;R is STR2 wherein: R 1 and R 2 are independently hydrogen or lower alkyl, or when taken together with the carbon to which they are attached are cycloalkyl;R 3 is hydrogen, lower alkyl, lower alkoxy, hydroxy, trifluoromethyl or halo; and STR3 and pharmaceutically acceptable acid addition salts thereof. The compounds and salts exhibit useful pharmacological properties, including selective α 2 -adrenoceptor antagonist properties and 5-HT 1A receptor partial agonist properties, and are particularly useful for the treatment of sexual dysfunction, depression and anxiety.

Process for the preparation of (8As,12AS,13AS)-decahydroisoquino ((2,1-G) (1,6)-naphthyridin-8-one derivatives

The invention provides a process for preparing single enantiomers of compounds represented by the formula: STR1 and chiral acid addition salts thereof; wherein: X and Y are independently hydrogen; lower alkyl; lower alkoxy; or halo; or X and Y taken together is methylenedioxy or ethylene-1,2-dioxy; which includes reduction of a compound represented by the formula: STR2 to give a mixture of stereoisomers represented by the formula: STR3 wherein each wavy line independently represents a bond in either the α or β position; followed by dissolving the mixture of stereoisomers and a chiral resolving acid in a suitable solvent and allowing the solution to crystallize, giving a salt of the desired enantiomer.

Decahydro-8H-isoquino[2,1-g][1,6]naphthyridine and decahydrobenzo[a]pyrrolo[2,3-e]quinolizine derivatives

Compounds of the formula ψψ ψwherein:ψ X and Y are independently hydrogen; hydroxy; lower alkyl of 1-6 carbon atoms; lower alkoxy of 1-6 carbon atoms; or halo; or X and Y when adjacent and taken together are methylenedioxy or ethylene-1,2-dioxy;ψ R is lower alkyl of 1-6 carbon atoms; cycloalkyl of 3-8 carbon atoms; phenyl or phenyl lower alkyl in which any phenyl group may be optionally substituted by one or two substituents chosen from the group consisting of halo, lower alkyl of 1-4 carbon atoms and lower alkoxy of 1-4 carbon atoms; or -ANHSO2R1; wherein A is lower alkylene of 1-6 carbon atoms; and R1 is lower alkyl of 1-6 carbon atoms or -NRyR3; whereinψ Ry and R3 are independently hydrogen or lower alkyl of 1-6 carbon atoms, or Ry and R3 taken together are cycloalkyl of 3-8 carbon atoms; andψ n is 1 or 2;ψ and the pharmaceutically acceptable salts thereof, are useful as à2-adrenoceptor antagonists, in particular as peripherally selective à2 -adrenoceptor antagonists.ψ