Synthesis and Biological Activity of 1H-Pyrrolo[2,3-b]pyridine Derivatives:  Correlation between Inhibitory Activity against the Fungus Causing Rice Blast and Ionization Potential

Abstract

Synthesis and biological activity of a variety of 3- and 6-substituted 1H-pyrrolo[2,3-b]pyridine (7-azaindole) derivatives are described. Many of the synthesized 7-azaindoles exhibited considerable fungicidal activity toward Pyricularia oryzae, a fungus which causes rice blast, in vivo. When quantum parameters of the tested 7-azaindoles were evaluated by semiempirical molecular orbital calculations, a relationship was observed between the activity and the calculated ionization potentials of the 7-azaindole derivatives. Keywords: 1H-Pyrrolo[2,3-b]pyridine; fungicidal activity; ionization potential; rice blast

Synthesis of chitosan‐graft‐poly[2‐cyano‐1‐(pyridin‐3‐yl)allyl acrylate] copolymer from a novel monomer, prepared using a Morita–Baylis–Hillman reaction, and characterization of its antimicrobial activity

“…Pyridines are an important class of nitrogen heterocycles that possess a broad range of biological activities, such as fungicidal, insecticidal and herbicidal activities . As a consequence of these biological properties, the effects of chitosan graft copolymers on selected microorganisms (bacteria: Bacillus subtilis , Escherichia coli ; fungi: Aspergillus niger , Penicillium digitatum , Staphylococcus aureus ) were studied (Table ).…”

Synthesis and evaluation of biological activities of new sulfonamide and carbamate derivatives of 1H-pyrrolo[2,3-b]pyridine (7-azaindole)

“…They have attracted considerable interest from the chemical community because of their potential applications in natural product synthesis and pharmaceuticals due to their hydrogen bonding properties and excellent water solubility. The 1H-pyrrolo [2,3-b]pyridine moiety exhibits a broad spectrum of biological activities, including anticancer [2], antitumor [3][4][5], anti-angiogenic [6], antimicrobial [7], as inhibitor of HIV-1 [8,9] and cell division cycle of 7-kinase [10], antifungal [11], analgesic [12], antimalarial [13], antiproliferative [14,15], antibacterial [16], reducing chronic pain [17], as cisplatin and transplatin derivatives [18], antimycobacterial [19], as Topoisomerase I inhibitors [20] and protein kinase inhibition [21], etc. Azaindole and its core containing compounds which include neocryptolepine (1), variolin-B (VAR-B) (2) and grossularines (3) are natural products, while 7-aza-rebeccamycin (4) and 5-azaellipticine (5) are of synthetic origin, whose activity is related to DNA, i.e.…”

Synthesis and antibacterial activity against ralstonia solanacearum for novel hydrazone derivatives containing a pyridine moiety

“…Pyridine is an important class of heterocyclic ring, which have been attracted more and more attention in the pesticides areas due to their broad-activities, such as fungicidal activity [ 6 - 8 ], insecticidal activity [ 9 , 10 ] and herbicidal activity [ 11 , 12 ]. In fungicidal activity regard, some pyridine derivatives can prevent Erysiphe graminis , Botrytis cinerea [ 13 ], Pyricularia oryzae [ 14 ] and Phytophthora infestans [ 15 ].…”