scholarly journals Nitrophenyl-group-containing Heterocycles. Part I. Synthesis, Characterization, Anticancer Activity and Antioxidant Properties of Some New 5,6,7,8-tetrahydro-isoquinolines Bearing 3(4)-nitrophenyl Group

Author(s):  
Eman M. Sayed ◽  
Reda Hassanien ◽  
Nasser Farhan ◽  
Hanan F. Aly ◽  
Khaled Mahmoud ◽  
...  

Abstract Regioselective cyclocondensation of 2,4-diacetyl-5-hydroxy-5-methyl-3-(3-nitrophenyl/4-nitrophenyl)cyclohexanones 1a,b with cyanothioacetamide afforded the corresponiing 7-acetyl-4-cyano-1,6-dimethyl-6-hydroxy-8-(3-nitrophenyl/4-nitrophenyl)-5,6,7,8-tetrahydro-soquinoline-3(2H)-thiones 2a,b in 93-96% yield. Reaction of compounds 2a,b with some ethyl iodide, 2-chloroacetamide (4a) or its N-aryl derivatives 4b-e by refluxing in ethanol, in the presence of slightly excess molar amounts of sodium acetate trihydrate, for one hour gave 3-ethylthio-5,6,7,8-tetrahydro-isoquinoline 3 and (5,6,7,8-tetrahydroisoquinolin-3-ylthio)acetamides 5a-i, respectively. On heating compounds 5b-d,f,g in ethanol containing a catalytic amount of sodium carbonate, they converted into their isomeric 1-amino- 6,7,8,9-tetrahydrothieno[2,3-c]isoquinoline-2-carboxamides 6b-d,f,g. Structural formulae of all synthesized compounds were characterized on the basis of their elemental analyses and spectroscopic data. Also, the biological evaluation of the synthesized isoquinolines as anticancer and antioxidant agents have been carried out and the obtained results are reported herein.

2021 ◽  
Author(s):  
Eman M. Sayed ◽  
Reda Hassanien ◽  
Nasser Farhan ◽  
Hanan F. Aly ◽  
Khaled Mahamoud ◽  
...  

Abstract Regioselective cyclocondensation of 2,4-diacetyl-5-hydroxy-5-methyl-3-(3-nitrophenyl/4-nitrophenyl)cyclohexanones 1a,b with cyanothioacetamide fforded the corresponiing 7-acetyl-4-cyano-1,6-dimethyl-6-hydroxy-8-(3-nitrophenyl/4-nitrophenyl)-5,6,7,8-tetrahydro-soquinoline-3(2H)-thiones 2a,b in 93-96%. Reaction of compounds 2a,b ethyl iodide, 2-chloroacetamide or N-(naphthalen-1-yl)-2-chloroacetamide (5) in the presence of sodium acetate gave the corresponding p(5,6,7,8-tetrahydroisoquinolin-3-yl)thio derivatives 3a,b, 4a,b and 6a,b. In a similar manner, reaction of a,b with other N-aryl-2-chloroacetamides 7a-d gave 2-[(7-acetyl-4-cyano-1,6-dimethyl-6-hydroxy-8-(3-nitrophenyl/4-nitrophenyl)-5,6,7,8-tetrahydroisoquinolin-3-yl)thio]-N-arylacetamides (8a-g). On heating of compounds 8a-e in ethanol containing anhydrous sodium carbonate, they converted into 7-acetyl-1-amino-N-aryl-5,8-dimethyl-8-hydroxy-6-(3-nitrophenyl/4-nitrophenyl)-6,7,8,9-tetrahydrothieno[2,3-c]isoquinoline-2-carboxamides 9a-e. Structural formulae of all synthesized compounds were characterized on the basis of their spectroscopic data. Also, the applications of most synthesized isoquinolines as anticancer and as antioxidant agents have been carried out and the obtained results are reported herein.


2021 ◽  
Vol 40 ◽  
pp. 102780
Author(s):  
Gang Wang ◽  
Chao Xu ◽  
Weiqiang Kong ◽  
Gerald Englmair ◽  
Jianhua Fan ◽  
...  

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