Chemical modification of tetrahydroisoquinoline and their cytotoxic activity was written by Terenteva, Ekaterina O.;Khashimova, Zaynat S.;Tsay, Elena A.;Zhurakulov, Sherzod N.;Saidov, Abdusalom Sh.;Vinogradova, Valentina I.;Azimova, Shakhnoz S.. And the article was included in Asian Journal of Pharmacy and Pharmacology in 2017.Electric Literature of C11H16ClNO2 This article mentions the following:
A variety of differently functionalized 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines I [R = H, Me, CH2CH2OH; R1 = H, Ph, 1,3-benzodioxol-5-yl, etc.], bis tetrahydroisoquinolines II [X = (CH2)4, 1,3-phenylene, (CH2)11, etc.; R2 = MeO, R2R2 = OCH2O] and chromanones III [R3 = 2-(1,3-benzodioxol-5-yl)ethylamino, 2-(3,4-dimethoxyphenyl)ethylamino, 6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl, etc.] were synthesized. Classic intramol. Bischler-Napieralski cyclodehydration was employed to generate the isoquinoline core. All the structures were characterized by NMR and mass spectrometry. The cytotoxic activities against three human cancer cell lines and primary culture of healthy hepatocyte cells were evaluated for all the synthesized compounds and structure-activity relationships were established by MTT assay. It was shown that compound I [R = H, R1 = hexyl] was demonstrated selective cytotoxicity against breast adenocarcinoma (IC50: 43.3 μM), I [R = H, R1 = 6-chloro-1,3-benzodioxol-5-yl; R = Me, R1 = 1,3-benzodioxol-5-yl] against laryngeal adenocarcinoma (IC50: 18.0 and 2.3 μM resp.) with the absence of toxicity to healthy cells. Bis compounds II exhibited greater cytotoxic effect than mono-series compounds I. Among bis samples compound II [X = (CH2)11, R2 = MeO] showed the greatest cytotoxic properties with an IC50 value of 3.1-4.0 μM. The all conjugate compounds completely lacked cytotoxicity toward cancer cell lines and III [R3 = 2-(1,3-benzodioxol-5-yl)ethylamino, 6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl] demonstrated proliferative activity. The most promising compounds for further study in-vitro and in-vivo methods were dibasic compounds II [X = (CH2)7, (CH2)8; R2 = MeO]. Later these substances can be offered as a basis for drugs with anti-tumor properties. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Electric Literature of C11H16ClNO2).
6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. The tetrahydroisoquinoline skeleton is encountered in a number of bioactive compounds and drugs. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.Electric Literature of C11H16ClNO2
Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem