Synthesis and Biological Properties of Isoquinolines Spirofused with Carbocycles and Heterocycles at Position 4

Abstract

KISEL, V. M.; KOSTYRKO, E. O.; KOVTUNENKO, V. A.; Chem. Heterocycl.

Nitrophenyl-Group-Containing Heterocycles. I. Synthesis, Characterization, Crystal Structure, Anticancer Activity, and Antioxidant Properties of Some New 5,6,7,8-Tetrahydroisoquinolines Bearing 3(4)-Nitrophenyl Group

“…Thus, the IR spectra of 2a,b showed characteristic absorption bands in the regions 3482−3429 cm −1 for (O−H), 3235−3230 cm −1 for (NH), 2221−2220 cm −1 for (CN), and 1710−1708 cm −1 for (CO, acetyl). 1 H NMR spectra of 2a,b are in agreement with those of their analogues, which were reported previously. 27 The IR spectrum of 3 revealed the disappearance of ν NH , whereas its 1 H NMR spectrum showed the presence of an ethyl group.…”

“…1 H NMR spectra of 2a,b are in agreement with those of their analogues, which were reported previously. 27 The IR spectrum of 3 revealed the disappearance of ν NH , whereas its 1 H NMR spectrum showed the presence of an ethyl group. The IR spectra of 5a,e showed absorption bands in the regions 3481−3355 cm −1 for (OH and NH 2 ), 2222−2215 cm −1 for (CN), 1709−1701 cm −1 for (CO, acetyl), and 1662−1660 cm −1 for (CO, amide).…”

“…IR spectra of 6b−d,f,g revealed the disappearance of the carbonitrile band and the presence of four absorption bands in the region 3517−3314 cm −1 characteristic for OH, NH 2 , and NH groups in addition to two other bands in the regions 1705−1698 and 1651−1624 cm −1 corresponding to an acetyl group and an amidic carbonyl group, respectively. 1 H NMR spectra of 6b−d,f,g showed a singlet signal at δ values ranging from 9.33 to 9.56 for the NH group and a broad singlet signal for the amino group at δ value ranging from 7.05 to 7.13 instead of the signal of the SCH 2 group, which exists in the 1 H NMR spectra of 5b−d,f,g. The presence of a tertiary alcoholic group in all compounds was ascertained from their 1 H NMR spectra which possess a singlet signal at δ values ranging from 4.84 to 5.05 for one proton of the OH group.…”

“…The 5,6,7,8-tetrahydroisoquinoline ring system is a structural fragment of many alkaloids that are next to indole alkaloids in abundance. − Compounds containing a 5,6,7,8-tetrahydroisoquinoline fragment are used as intermediate products in the synthesis of alkaloids, − precursors to enzyme inhibitors, , fungicides, , potassium receptor antagonists, and drugs for the treatment of cardiovascular diseases, bronchial asthma, tumors, and viral infections. , 5,6,7,8-Tetrahydroisoquinoline derivatives have also been shown to exhibit anticonvulsant, − antibacterial, neurotropic, and antimicrobial activities . On the other hand, many nitro-group-containing compounds are reported to possess versatile applications in the fields of biochemistry and medicine. − …”

Synthesis, crystallographic characterization, DFT and TD-DFT studies of Oxyma-sulfonate esters

“…The natural bond orbital (NBO) calculations were performed using NBO 3.1 program as implemented in the Gaussian 03W package at the DFT/B3LYP level in order to understand various intramolecular charge transfer interactions between the filled orbitals of one subsystem and vacant orbitals of another subsystem, which is a measure of the intermolecular delocalization or hyper-conjugation. 32,33…”