67123-97-1

Basic information

• Product Name: H-DL-TIC-OH
• Synonyms: DL-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;H-DL-TIC-OH;1,2,3,4-Tetrahydroisoquinoline-3Carboxylic;rac 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid;rac 3-Carboxy-1,2,3,4-tetrahydroisoquinoline;(RS)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid;rac-(3R*)-1,2,3,4-Tetrahydro-3β*-isoquinolinecarboxylic acid;rac-(3R*)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
• CAS NO: 67123-97-1
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.19984
• EINECS: 266-580-4
• Product Categories: Quinoline&Isoquinoline;Aromatics Compounds;Aromatics
• Mol File: 67123-97-1.mol
• Article Data: 29

Chemical Properties

• Melting Point: 358°C
• Boiling Point: 372.02 °C at 760 mmHg
• Flash Point: 178.791 °C
• Appearance: White solid
• Density: 1.226 g/cm³
• Storage Temp.: -20°C Freezer
• Solubility: Sodium Hydroxide, Water
• PKA: 2.21±0.20(Predicted)
• CAS DataBase Reference: H-DL-TIC-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-DL-TIC-OH(67123-97-1)
• EPA Substance Registry System: H-DL-TIC-OH(67123-97-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 67123-97-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

rac 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid (cas# 67123-97-1) is a compound useful in organic synthesis.

InChI:InChI=1/C10H11NO2/c12-10(13)9-5-7-3-1-2-4-8(7)6-11-9/h1-4,9,11H,5-6H2,(H,12,13)

Upstream product

• 150-30-1 Phenylalanine 
• 76884-33-8 3-chloromethylisoquinoline hydrochloride 
• 90-41-5 2-phenylaniline 
• 673-06-3 D-(R)-phenylalanine 
• 159596-06-2 (-)menthyl D-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 91-13-4 α,α'-dibromo-o-xylene 
• 612-12-4 o-Xylylene dichloride 
• 143767-55-9 dimethyl 2-acetyl-1,2,3,4-tetrahydroisoquinoline-3,3-dicarboxylate 
• 143767-54-8 (R,S)-2-acetyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 6624-49-3 isoquinoline-3-carboxylic acid 
• 50-00-0 formaldehyd 
• 63-91-2 L-phenylalanine 
• 109-87-5 Dimethoxymethane 

Downstream Products

• 15912-55-7 ethyl 1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate 
• 151838-62-9 N-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 101195-63-5 (+/-)-10,10a-Dihydro-2-phenylimidazo<1,5-b>isoquinoline-1,3(2H,5H)-dione 
• 103733-65-9 (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 82717-30-4 decahydro-3-isoquinolinecarboxylic acid 
• 54329-54-3 2-Methyl-1,2,3,4-tetrahydroisochinolin-3-carbonsaeure 
• 1337992-37-6 (E)-2-(4-(dimethylamino)phenyl)-N-(3-oxo-3,4-dihydroisoquinolin-2(1H)-yl)-3-phenylacrylamide 
• 1337992-19-4 C₉H₁₀N₂O*ClH 

Relevant articles and documents

Discovery of pyridine tetrahydroisoquinoline thiohydantoin derivatives with low blood-brain barrier penetration as the androgen receptor antagonists

Prostate cancer (PC) is the most diagnosed type of malignancy in men and the major frequently cause of cancer-related death worldwide. The androgen receptor (AR) has become a promising drug target for the treatment of PC. Here, we reported the design, optimization and evaluation of pyridine tetrahydroisoquinoline thiohydantoin derivatives with improved activity and safety as potent AR antagonists. The most promising compound 42f exhibited potent inhibitory activity on AR and strongly blocked AR nuclear translocation. Moreover, 42f displayed promising in vitro antitumor activity toward AR-dependent prostate cancer cell lines (LNCaP) and also demonstrated therapeutic effects in LNCaP xenograft tumor model in mice (TGI: 79%) with no apparent toxicity observed in vivo. More importantly, 42f showed negligible penetration of the brain-blood barrier (BBB) compared with enzalutamide. These results provide a foundation for the development of a new class of androgen receptor antagonists for potential therapeutics against PC with lower seizurogenic risk for patients.

Gene delivery system

The invention discloses a preparation method of a gene nano-liposome carrier Isoquinoline-3-acyl-RGDV(IRV) and an IRV/STAT3-siRNA gene delivery system. The IRV/STAT3-siRNA gene delivery system is composed of liposome carriers IRV and STAT3-siRNA, protamine and calf thymus DNA in a proportion, and has slow release and targeting effects. The cell transfection efficiency, the in-vitro anti-tumor activity, and the gene silencing efficiency and a cell action mechanism on the mRNA level and the protein level of a compound are evaluated with the lung cancer A549 cell strain as a model, and the result shows the IRV/STAT3-siRNA gene delivery system has more excellent anti-tumor activity and gene silencing efficiency compared with control groups. According to the system, the anti-tumor activity of the IRV/STAT3-siRNA gene delivery system is evaluated with an S180 ascites tumor mouse as a model, and the result shows that a 100% IRV/STAT3-siRNA group has an anti-tumor effect.

SYNTHESIS OF 8H-3A-AZA-CYCLOPENTA[A]INDENES AND 5,10-DIHYDROPYRROLO[1,2-B]ISOQUINOLINES DERIVATIVES AND THEIR USE AS ANTITUMOR THERAPEUTIC AGENTS

The present disclosure relates to a series of bis(hydroxymethyl) and its bis(carbamate) of 8H-3a-azacyclopenta[a]indene-1-yl and 5,10-dihydropyrrolo-[1,2-b]isoquinolines derivatives (Formula I-Formula IV) as DNA di-alkylating agents. The preliminary antitumor studies indicated that compounds disclosed herein could exhibit potent cytotoxicity in vitro and antitumor therapeutic efficacy in human tumor xenografts and could have little or no cross-resistance to either Taxol or Vinblastine. The results demonstrated that compounds disclosed herein possess potent antitumor therapeutic efficacy and are expected to have potential for clinical applications.