146074-43-3

Basic information

• Product Name: (S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE
• Synonyms: 3-ISOQUINOLINECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-, METHYL ESTER, HYDROCHLORIDE;METHYL (S)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINE CARBOXYLATE HYDROCHLORIDE;METHYL (R)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINE CARBOXYLATE HYDROCHLORIDE;METHYL 1,2,3,4-TETRAHYDRO-ISOQUINOLINE-3(R)-CARBOXYLATE HYDROCHLORIDE;METHYL 1,2,3,4-TETRAHYDRO-ISOQUINOLINE-3(S)-CARBOXYLATE HYDROCHLORIDE;L-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE;(S)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE;(S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE
• CAS NO: 146074-43-3
• Molecular Formula: C₁₁H₁₃NO₂*ClH
• Molecular Weight: 227.69
• Mol File: 146074-43-3.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: (S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE(146074-43-3)
• EPA Substance Registry System: (S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE(146074-43-3)

Safety Data

• Hazardous Substances Data: 146074-43-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its application is primarily due to its ability to be transformed into a range of bioactive molecules with potential therapeutic benefits.
Used in Matrix Metalloproteinase Inhibitors:
In the pharmaceutical industry, (S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE is used as a starting material for the preparation of 2-arylsulfonylisoquinoline-3-carboxylic and hydroxamic acids and their analogs. These compounds serve as matrix metalloproteinase inhibitors, which are important in the treatment of various diseases, such as cancer and inflammatory conditions, by regulating the activity of matrix metalloproteinases.
Used in Melanocortin Receptor Modulators:
(S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE is also utilized in the preparation of peptides for pharmaceutical use as modulators of melanocortin receptors. These modulators have potential applications in treating various conditions, including obesity, sexual dysfunction, and skin disorders, by targeting specific melanocortin receptors.
Used in Cholecystokinin Antagonist Peptide Analogs:
Furthermore, (S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE serves as an intermediate in the preparation of cholecystokinin antagonist peptide analogs. These analogs have potential therapeutic applications in the treatment of gastrointestinal disorders, such as irritable bowel syndrome and pancreatitis, by blocking the action of cholecystokinin, a hormone that regulates digestion.

Upstream product

• 67-56-1 methanol 
• 41220-48-8 (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride 
• 74163-81-8 L-Tic-OH 
• 103733-65-9 (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 

Relevant articles and documents

Design, synthesis and pharmacological evaluation of N-(5-chloro-2,4-dihydroxybenzoyl)-(R)-N-arylmethyl-1,2,3,4-tetrahydro-3-isoquinolinecarboxamides as potent Hsp90 inhibitors

Using diverse arylmethyl groups to replace the benzyl moiety of the lead Hsp90 inhibitor 1 (N-(5-chloro-2,4-dihydroxybenzoyl)-(R)-N-benzyl-1,2,3,4-tetrahydro-3-iso quinolinecarboxamide), thirty four derivatives (10–43) were developed, and exhibited improved Hsp90 inhibitory and antiproliferative activities. SAR analysis indicated that the southeastern aryl substitutions influenced their antiproliferative activities obviously, with the para-pyridyl group (41) outperforming all other substitution patterns. In this regard, compound 41 was selected for further evaluation. CETSA melt and ITDRFCETSA (isothermal dose-response fingerprint) curves for Hsp90α further proved that 41 interacted with intracellular Hsp90α powerfully. Compared with the lead compound 1, docking and MD refinement of the Hsp90α-41 complex revealed a favorable H-bonding interaction between the side-chain of Tyr139 and the pyridine moiety of 41, which is the first time to be used for resorcinol-based Hsp90 inhibitors. With broad-spectral antitumor activity, compound 41 induced time- and dose-dependent growth inhibition and G0/G1 cell cycle arrest on human breast cancer MDA-MB-453 cell line. In addition, flow cytometry and Western blot analyses confirmed that 41 induced apoptosis of human breast cancer MDA-MB-453 cell line. Via degradation of IKKs and suppression of IKKs activity, compound 41 inhibited TNF-α-induced NF-κB activation. The overall properties warrant compound 41 a promising Hsp90 inhibitor and further biological characterizations. This study provides insights into the chemical evolution of Hsp90 inhibitors, and may facilitate the design of next generation Hsp90 inhibitors for the antitumor drug development.

Structure-guided optimization of D-captopril for discovery of potent NDM-1 inhibitors

β-lactam antibiotics have long been the mainstay for the treatment of bacterial infections. New Delhi metallo-β-lactamase 1 (NDM-1) is able to hydrolyze nearly all β-lactam antibiotics and even clinically used serine-β-lactamase inhibitors. The wide and rapid spreading of NDM-1 gene among pathogenic bacteria has attracted extensive attention, therefore high potency NDM-1 inhibitors are urgently needed. Here we report a series of structure-guided design of D-captopril derivatives that can inhibit the activity of NDM-1 in vitro and at cellular levels. Structural comparison indicates the mechanisms of inhibition enhancement and provides insights for further inhibitor optimization.

Tetrahydroisoquinoline-3-carboxylic acid heat shock protein 90 inhibitor and application thereof

The invention discloses a tetrahydroisoquinoline-3-carboxylic acid heat shock protein 90 inhibitor. The heat shock protein 90 inhibitor is a compound with a formula (I), or is an optical isomer, a diastereoisomer or a despinner mixture, or a pharmaceutically acceptable salt, a solvate or a predrug. The invention further discloses the application of the inhibitor to preparation of a medicine used for preventing or treating a heat shock protein 90 related disease. The experiment proves that the tetrahydroisoquinoline-3-carboxylic acid heat shock protein 90 inhibitor has a remarkable effect of inhibiting various tissues like tumor cells from the mammary gland and respiratory and reproductive systems, the toxicity to the normal hepatocyte of human is low, and the druggability is relatively good. The tetrahydroisoquinoline-3-carboxylic acid heat shock protein 90 inhibitor has a broad clinical application prospect.

SUBSTITUTED SULFONAMIDES USEFUL AS ANTIAPOPTOTIC BCL INHIBITORS

Disclosed are compounds of Formula (I), or a pharmaceutically acceptable salt thereof, wherein: W and Q and G are defined herein. Also disclosed are methods of using such compounds as inhibitors of Bcl-2 family antiapoptotic proteins for the treatment of cancer; and pharmaceutical compositions comprising such compounds.

Dynamic combinatorial chemistry with hydrazones: Libraries incorporating heterocyclic and steroidal motifs

We expand the possibilities in hydrazone based dynamic combinatorial chemistry with a series of new building blocks incorporating heterocyclic motifs. The synthetic procedure allows efficient access to building blocks with the general structure (MeO)2CH-Heterocycle-C(O)NHNH2, originating from heterocycles with an amine and an ester functionality. The equilibrium distribution of macrocyclic N-acyl hydrazones formed upon deprotection of the building blocks with TFA in organic solvents is reported. The mixing behaviour of these heterocycle-based building blocks with our cholate-based building blocks is described, particularly the observation of kinetic intermediates that disappear following 'proof-reading'. The Royal Society of Chemistry.