82925-01-7

Basic information

• Product Name: 1,2,3,4-Tetrahydro-6,7-dimethoxy-2-[2-(4-nitrophenyl)ethyl]isoquinoline
• Synonyms: 1,2,3,4-Tetrahydro-6,7-dimethoxy-2-[2-(4-nitrophenyl)ethyl]isoquinoline;6,7-Dimethoxy-2-[2-(4-nitro-phenyl)-ethyl]-1,2,3,4-tetrahydro-isoquinoline;6,7-diMethoxy-2-(4-nitrophenethyl)-1,2,3,4-tetrahydroisoquinoline;6-Methoxy-2-(4-nitrophenethyl)-1,2,3,4-tetrahydro-7-isoquinolinyl Methyl ether;Isoquinoline, 1,2,3,4-tetrahydro-6,7-diMethoxy-2-[2-(4-nitrophenyl)ethyl]-
• CAS NO: 82925-01-7
• Molecular Formula: C₁₉H₂₂N₂O₄
• Molecular Weight: 342.38898
• EINECS: 604-604-1
• Product Categories: Aromatics;Heterocycles
• Mol File: 82925-01-7.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 496.2°C at 760 mmHg
• Flash Point: 253.9°C
• Appearance: /
• Density: 1.199g/cm³
• Vapor Pressure: 5.52E-10mmHg at 25°C
• Refractive Index: 1.585
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: 1,2,3,4-Tetrahydro-6,7-dimethoxy-2-[2-(4-nitrophenyl)ethyl]isoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-Tetrahydro-6,7-dimethoxy-2-[2-(4-nitrophenyl)ethyl]isoquinoline(82925-01-7)
• EPA Substance Registry System: 1,2,3,4-Tetrahydro-6,7-dimethoxy-2-[2-(4-nitrophenyl)ethyl]isoquinoline(82925-01-7)

Safety Data

• Hazardous Substances Data: 82925-01-7(Hazardous Substances Data)

Usage

Description

1,2,3,4-Tetrahydro-6,7-dimethoxy-2-[2-(4-nitrophenyl)ethyl]isoquinoline is a white solid compound with the chemical formula C20H23N2O3. It is an organic synthesis intermediate and has a unique structure that makes it a valuable component in the synthesis of various organic compounds.

Uses

Used in Organic Synthesis:
1,2,3,4-Tetrahydro-6,7-dimethoxy-2-[2-(4-nitrophenyl)ethyl]isoquinoline is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows it to be a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,2,3,4-Tetrahydro-6,7-dimethoxy-2-[2-(4-nitrophenyl)ethyl]isoquinoline is used as a key intermediate in the synthesis of various drug molecules. Its presence in the molecular structure can impart specific biological activities, making it a valuable component in the development of new drugs.
Used in Agrochemical Industry:
1,2,3,4-Tetrahydro-6,7-dimethoxy-2-[2-(4-nitrophenyl)ethyl]isoquinoline is also used in the agrochemical industry as a precursor for the synthesis of various agrochemicals, such as pesticides and herbicides. Its unique structure can contribute to the development of new and effective agrochemicals with improved properties.
Used in Specialty Chemicals:
In the specialty chemicals industry, 1,2,3,4-Tetrahydro-6,7-dimethoxy-2-[2-(4-nitrophenyl)ethyl]isoquinoline is used as a building block for the synthesis of various specialty chemicals, such as dyes, pigments, and fragrances. Its unique structure can provide specific properties to these chemicals, making them suitable for various applications.

InChI:InChI=1/C19H22N2O4/c1-24-18-11-15-8-10-20(13-16(15)12-19(18)25-2)9-7-14-3-5-17(6-4-14)21(22)23/h3-6,11-12H,7-10,13H2,1-2H3

Upstream product

• 5339-26-4 (4-nitrophenyl)ethyl bromide 
• 2328-12-3 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride 
• 100-27-6 2-(4-nitrophenyl)ethanol 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 1610805-19-0 2-(2-(4-azidophenyl)ethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1610804-89-1 N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3,4-dimethoxybenzamide 
• 1610804-86-8 N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-2-methoxybenzamide 
• 1610804-87-9 N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-methoxybenzamide 
• 1610804-88-0 N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-4-methoxybenzamide 
• 1610804-85-7 N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)benzamide 
• 1610804-90-4 N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3,5-dimethoxybenzamide 
• 1610804-91-5 N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-methylbenzamide 
• 1610804-92-6 N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-4-methylbenzamide 
• 1610804-93-7 N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-4-(dimethylamino)benzamide 
• 1610804-94-8 N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-2-nitrobenzamide 
• 1610804-95-9 N-(4-(tert-butyl)phenyl)-2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)benzamide 
• 1610804-96-0 3-chloro-N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)benzamide 
• 1610804-97-1 4-chloro-N-(2-((1-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)benzamide 

Relevant articles and documents

4-hydroxyquinoline derivative as well as preparation method and application thereof in antitumor drugs

The invention belongs to the technical field of medicines, and particularly relates to a 4-hydroxyquinoline derivative as well as a preparation method and application thereof, the 4-hydroxyquinoline derivative can be used as a P-gp inhibitor to reverse dr

Water-soluble inhibitors of ABCG2 (BCRP) – A fragment-based and computational approach

A good balance between hydrophilicity and lipophilicity is a prerequisite for all bioactive compounds. If the hydrophilicity of a compound is low, its solubility in water will be meager. Many drug development failures have been attributed to poor aqueous solubility. ABCG2 inhibitors are especially prone to be insoluble since they have to address the extremely large and hydrophobic multidrug binding site in ABCG2. For instance, our previous, tariquidar-related ABCG2 inhibitor UR-MB108 (1) showed high potency (79 nM), but very low aqueous solubility (78 nM). To discover novel potent ABCG2 inhibitors with improved solubility we pursued a fragment-based approach. Substructures of 1 were optimized and the fragments ‘enlarged’ to obtain inhibitors, supported by molecular docking studies. Synthesis was achieved, i.a., via Sonogashira coupling, click chemistry and amide coupling. A kinetic solubility assay revealed that 1 and most novel inhibitors did not precipitate during the short time period of the applied biological assays. The solubility of the compounds in aqueous media at equilibrium was investigated in a thermodynamic solubility assay, where UR-Ant116 (40), UR-Ant121 (41), UR-Ant131 (48) and UR-Ant132 (49) excelled with solubilities between 1 μM and 1.5 μM – an up to 19-fold improvement compared to 1. Moreover, these novel N-phenyl-chromone-2-carboxamides inhibited ABCG2 in a Hoechst 33342 transport assay with potencies in the low three-digit nanomolar range, reversed MDR in cancer cells, were non-toxic and proved stable in blood plasma. All properties make them attractive candidates for in vitro assays requiring long-term incubation and in vivo studies, both needing sufficient solubility at equilibrium. 41 and 49 were highly ABCG2-selective, a precondition for developing PET tracers. The triple ABCB1/C1/G2 inhibitor 40 qualifies for potential therapeutic applications, given the concerted role of the three transporter subtypes at many tissue barriers, e.g. the BBB.

Structure-Based Discovery of Pyrimidine Aminobenzene Derivatives as Potent Oral Reversal Agents against P-gp- And BCRP-Mediated Multidrug Resistance

Overexpression of ATP binding cassette (ABC) transporters, including P-glycoprotein (P-gp) and breast cancer resistance protein (BCRP), is an important factor leading to multidrug resistance (MDR) in cancer treatments. Three subclasses of dual inhibitors of P-gp and BCRP were designed based on the active moieties of BCRP inhibitors, tyrosine kinase inhibitors, and P-gp inhibitors, of which compound 21 possessed low cytotoxicity, high reversal potency, and good lipid distribution coefficient. 21 also increased the accumulation of Adriamycin (ADM) and Mitoxantrone (MX), blocked Rh123 efflux, and made no change in the protein expression of P-gp and BCRP. Importantly, coadministration of 21 can significantly improve the oral bioavailability of paclitaxel (PTX). It was also demonstrated that 21 significantly inhibited the growth of K562/A02 xenograft tumors by increasing the sensitivity of ADM in vivo. In summary, 21 has the potential to overcome MDR caused by P-gp and BCRP and to improve the oral bioavailability of PTX.