Synthesis, structure, antimycobacterial and anticancer evaluation of new pyrrolo-phenanthroline derivatives

Abstract

A study concerning design, synthesis, structure and in vitro antimycobacterial and anticancer evaluation of new fused derivatives with pyrrolo[2,1-c] [4,7]phenanthroline skeleton is described. The strategy adopted for synthesis involves a [3 + 2] dipolar cycloaddition of several in situ generated 4,7-phenanthrolin-4-ium ylides to different substituted alkynes and alkenes. Stereo-and regiochemistry of cycloaddition reactions were discussed. The structure of the new compounds was proven unambiguously, single-crystal X-ray diffraction studies including. The antimycobacterial and anticancer activity of a selection of new synthesized compounds was evaluated against Mycobacterium tuberculosis H37Rv under aerobic conditions and 60 human tumour cell line panel, respectively. Five of the tested compounds possess a moderate antimycobacterial activity, while two of the compounds have a significant antitumor activity against renal cancer and breast cancer.

Microwave Assisted Reactions of Azaheterocycles Formedicinal Chemistry Applications

“…Five membered ring azaheterocycles, especially pyrroles, pyrazoles, imidazoles, triazoles, tetrazoles and their fused derivatives, are multitarget pharmacophores with a large variety of biological activities such as antibacterial, antifungal, antitubercular, antihelmintic, antiplasmodial, anticancer, anti-inflammatory, cardiotonic, antihypertensive, antithrombotic, antihistaminic, antiulcer, analgesic, neuroleptic, etc. [16][17][18][19][20][21][22][23][24]. Having these considerations in view, a lot of attention was paid by researchers for obtaining new compounds with such skeleton, using both conventional TH and MW technology.…”

“…Compounds containing pyridine, pyridazine, pyrimidine, pyrazine, -and their fused derivatives-, are described to possess a wide range of biological activities, with these including antiviral, anti-HIV, antituberculosis, antimalarial, antileishmanial, antibacterial, antifungal, anti-inflammatory, anticancer, antihypertensive, diuretics, antiaggregative, antiplatelet, cardiotonics, antineurodegenerative, antidepressant, anxiolytics, anticonvulsivant, analgesic, sedatives, antiallergic, etc. [16,21,[40][41][42][43][44][45][46][47][48][49][50][51][52][53]. A large variety of syntheses are described for these compounds, with some of them using MW technology.…”

Microwave‐assisted Synthesis of Dihydro Dibenzophenanthroline and Its Derivatives Using a Self‐catalyzed Friedlander Reaction

“…Synthesis of quinoline heterocycles has received attention worldwide owing to their structural motif found in numerous natural and synthetic compounds with broad applications in medicinal and materials chemistry. More specifically, derivatives of dibenzophenanthrolines are immensely important targets in organic synthesis because of their biological activities, such as anticancer , antibacterial , and antiparasitic properties. In addition to that, some of their derivatives were used as chelating ligands in the manufacture of organic semiconductor materials .…”

Hybrid imidazole (benzimidazole)/pyridine (quinoline) derivatives and evaluation of their anticancer and antimycobacterial activity

“…In previously research work, we successfully identify azaheterocycles derivatives (imidazole/benzimidazole and pyridine/quinoline included) with anticancer 9,10,[16][17][18][19] and anti-TB [15][16][17][20][21][22][23] activity. In the light of the above consideration, it appears rational to combine the pharmacophoric potential of the two core scaffolds, imidazole (and its benzo-derivative benzimidazole) and pyridine (and its benzo-derivative quinoline), intending to obtain new entities with better anticancer and antimycobacterial activity and, also, with better pharmaceutical properties (i.e.…”

“…; anticancer [5][6][7][8][9][10] and anti-TB 11-15 also included). Encouraged by the above considerations and in continuation of our research in the area of novel anticancer 9,10,[16][17][18][19] and anti-TB [15][16][17][20][21][22][23] derivatives with azaheterocyclic skeleton, we report here the design, synthesis, structure, and in vitro anticancer and antimycobacterial activity of new hybrid imidazole (benzimidazole)/pyridine (quinoline) derivatives.…”