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4-[2-(3,4-DIHYDRO-6,7-DIMETHOXY-2(1H)-ISOQUINOLINYL)ETHYL]-BENZENAMINE is a white solid compound that serves as an intermediate in the preparation of Elacridar, a drug used to treat various conditions.

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  • 82925-02-8 Structure
  • Basic information

    1. Product Name: 4-[2-(3,4-DIHYDRO-6,7-DIMETHOXY-2(1H)-ISOQUINOLINYL)ETHYL]-BENZENAMINE
    2. Synonyms: 4-[2-(6,7-DIMETHOXY-1,2,3,4-TETRAHYDRO-2-ISOQUINOLINYL)ETHYL]ANILINE;4-[2-(3,4-DIHYDRO-6,7-DIMETHOXY-2(1H)-ISOQUINOLINYL)ETHYL]-BENZENAMINE;[4-[2-(6,7-DiMethoxy-3,4-dihydro-1H-isoquinolin-2-yl)ethyl]phenyl]aMine;BenzenaMine, 4-[2-(3,4-dihydro-6,7-diMethoxy-2(1H)-isoquinolinyl)ethyl]-;4-(2-(6,7-DiMethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)aniline;EOS-62095
    3. CAS NO:82925-02-8
    4. Molecular Formula: C19H24N2O2
    5. Molecular Weight: 312.41
    6. EINECS: N/A
    7. Product Categories: Amines;Aromatics;Heterocycles
    8. Mol File: 82925-02-8.mol
  • Chemical Properties

    1. Melting Point: 129 °C
    2. Boiling Point: 473.704 °C at 760 mmHg
    3. Flash Point: 240.288 °C
    4. Appearance: /
    5. Density: 1.132 g/cm3
    6. Vapor Pressure: 0mmHg at 25°C
    7. Refractive Index: 1.592
    8. Storage Temp.: -20°C Freezer, Under inert atmosphere
    9. Solubility: Soluble in dichloromethane, ethyl acetate and methanol.
    10. PKA: 8.00±0.20(Predicted)
    11. CAS DataBase Reference: 4-[2-(3,4-DIHYDRO-6,7-DIMETHOXY-2(1H)-ISOQUINOLINYL)ETHYL]-BENZENAMINE(CAS DataBase Reference)
    12. NIST Chemistry Reference: 4-[2-(3,4-DIHYDRO-6,7-DIMETHOXY-2(1H)-ISOQUINOLINYL)ETHYL]-BENZENAMINE(82925-02-8)
    13. EPA Substance Registry System: 4-[2-(3,4-DIHYDRO-6,7-DIMETHOXY-2(1H)-ISOQUINOLINYL)ETHYL]-BENZENAMINE(82925-02-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 82925-02-8(Hazardous Substances Data)

82925-02-8 Usage

Uses

Used in Pharmaceutical Industry:
4-[2-(3,4-DIHYDRO-6,7-DIMETHOXY-2(1H)-ISOQUINOLINYL)ETHYL]-BENZENAMINE is used as an intermediate for the preparation of Elacridar, a drug that has potential applications in treating various conditions. Its role as an intermediate is crucial in the synthesis process, enabling the development of effective pharmaceuticals.

Check Digit Verification of cas no

The CAS Registry Mumber 82925-02-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,2,9,2 and 5 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 82925-02:
(7*8)+(6*2)+(5*9)+(4*2)+(3*5)+(2*0)+(1*2)=138
138 % 10 = 8
So 82925-02-8 is a valid CAS Registry Number.
InChI:InChI=1/C19H24N2O2/c1-22-18-11-15-8-10-21(13-16(15)12-19(18)23-2)9-7-14-3-5-17(20)6-4-14/h3-6,11-12H,7-10,13,20H2,1-2H3

82925-02-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Alfa Aesar

  • (H54156)  4-[2-(6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolinyl)ethyl]aniline, 97%   

  • 82925-02-8

  • 250mg

  • 294.0CNY

  • Detail
  • Alfa Aesar

  • (H54156)  4-[2-(6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolinyl)ethyl]aniline, 97%   

  • 82925-02-8

  • 1g

  • 882.0CNY

  • Detail
  • Alfa Aesar

  • (H54156)  4-[2-(6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolinyl)ethyl]aniline, 97%   

  • 82925-02-8

  • 5g

  • 3528.0CNY

  • Detail

82925-02-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)ethyl]aniline

1.2 Other means of identification

Product number -
Other names 4-[2-(3,4-Dihydro-6,7-dimethoxy-2(1H)-isoquinolinyl)ethyl]-benzenamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:82925-02-8 SDS

82925-02-8Relevant articles and documents

ACETAMIDO-PHENYLBENZAMIDE DERIVATIVES AND METHODS OF USING THE SAME

-

, (2022/04/09)

The present disclosure relates to compounds of Formula (I): and to their prodrugs, pharmaceutically acceptable salts, pharmaceutical compositions, methods of use, and methods for their preparation. The compounds disclosed herein are useful for the treatment of disorders in which expression of P-glycoprotein and/or cytochrome P450 (e.g., CYP3A4) is modulated (e.g., cancers which have developed multi-drug resistance).

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

Qiu, Qianqian,Zou, Feng,Li, Huilan,Shi, Wei,Zhou, Daoguang,Zhang, Ping,Li, Teng,Yin, Ziyu,Cai, Zilong,Jiang, Yuxuan,Huang, Wenlong,Qian, Hai

, p. 6179 - 6197 (2021/06/01)

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.

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

Antoni, Frauke,Wifling, David,Bernhardt, Günther

, (2020/11/20)

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.

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

-

, (2021/05/01)

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

Dimethoxy tetrahydroisoquinoline substituted purine derivative as well as preparation method and application thereof in anti-tumor drugs

-

, (2021/06/02)

The invention belongs to the technical field of medicines, and particularly relates to a dimethoxy tetrahydroisoquinoline substituted purine derivative and a preparation method thereof. The dimethoxy tetrahydroisoquinoline substituted purine derivative ca

Discovery of Encequidar, First-in-Class Intestine Specific P-glycoprotein Inhibitor

Smolinski, Michael P.,Urgaonkar, Sameer,Pitzonka, Laura,Cutler, Murray,Lee, GwanSun,Suh, Kwee Hyun,Lau, Johnson Y. N.

, p. 3677 - 3693 (2021/04/12)

Many chemotherapeutics, such as paclitaxel, are administered intravenously as they suffer from poor oral bioavailability, partly because of efflux mechanism of P-glycoprotein in the intestinal epithelium. To date, no drug has been approved by the U.S. Foo

Tariquidar-related triazoles as potent, selective and stable inhibitors of ABCG2 (BCRP)

Antoni, Frauke,Bauer, Stefanie,Bause, Manuel,Bernhardt, Günther,Buschauer, Armin,Jackson, Scott M.,K?nig, Burkhard,Locher, Kaspar P.,Manolaridis, Ioannis,Scholler, Matthias,Stark, Simone A.

, (2020/02/26)

Tariquidar derivatives have been described as potent and selective ABCG2 inhibitors. However, their susceptibility to hydrolysis limits their applicability. The current study comprises the synthesis and characterization of novel tariquidar-related inhibit

6,7-Dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline amides and corresponding ester isosteres as multidrug resistance reversers

Bartolucci, Gianluca,Braconi, Laura,Colabufo, Nicola Antonio,Contino, Marialessandra,Dei, Silvia,Giampietro, Roberta,Manetti, Dina,Perrone, Maria Grazia,Riganti, Chiara,Romanelli, Maria Novella,Teodori, Elisabetta,Chiaramonte, Niccolò

, p. 974 - 992 (2020/04/24)

Aiming to deepen the structure–activity relationships of the two P-glycoprotein (P-gp) modulators elacridar and tariquidar, a new series of amide and ester derivatives carrying a 6,7-dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline scaffold linked to different methoxy-substituted aryl moieties were synthesised. The obtained compounds were evaluated for their P-gp interaction profile and selectivity towards the two other ABC transporters, multidrug-resistance-associated protein-1 and breast cancer resistance protein, showing to be very active and selective versus P-gp. Two amide derivatives, displaying the best P-gp activity, were tested in co-administration with the antineoplastic drug doxorubicin in different cancer cell lines, showing a significant sensitising activity towards doxorubicin. The investigation on the chemical stability of the derivatives towards spontaneous or enzymatic hydrolysis, showed that amides are stable in both models while some ester compounds were hydrolysed in human plasma. This study allowed us to identify two chemosensitizers that behave as non-transported substrates and are characterised by different selectivity profiles.

Fluorescent probe based on small molecule inhibitor as well as preparation method and application thereof

-

, (2020/09/20)

The invention relates to a fluorescent probe based on a small-molecule inhibitor as well as a preparation method and application thereof, and belongs to the field of small-molecule labeled probes forfluorescence imaging. According to the invention, a smal

DEUTERATED ANALOGS OF TARIQUIDAR

-

, (2019/11/22)

The present invention relates to efflux inhibitor compounds, compositions, and methods of using the same. More specifically, the instant invention comprises deuterated analogs of tariquidar with superior pharmacokinetic properties such that it is now poss

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