First synthesis of (±)-vertilecanin A

Abstract

5 [(Hydroxy)(phenyl)methyl]pyridine 2 carboxylic acid ((±) vertilecanin A) was prepared from nicotinic acid in four steps with an overall yield of 29%.Five phenopicolonic acid analogs 1-5 named vertilecanins have recently 1 been isolated from solid sub strate fermentation cultures of Verticilium lecanii. The most abundant component (-) vertilecanin A (1) was reported to possess insecticidal activity against Helicoverpa zea. 1: Х = ОН (vertilecanin A) 2: Х = ОMe (vertilecanin A methyl ester ) 3: Х = HNCH 2 CO 2 H (vertilecanin B) 4: X = HNCH 2 CO 2 Me (vertilecanin B methyl ester) 5: X = HNCH 2 CO 2 Me (vertilecanin C)

Mutagenic assessment of three synthetic pyridine-diaryl ketone derivatives

“…MP 92-94 C (from CHCl3hexane); mp 95-96 C from cyclohexane (Langhals et al, 1982). The 1 H-NMR data and 13 C-NMR data are in agreement with literature (Tümer et al, 2005).…”

“…MP 78.0-78.5 C (Herbert & Sears, 1951). The 1 H-NMR data and 13 C-NMR data are in agreement with literature (Tümer et. al., 2005).…”

“…The ketone was synthesized from nicotinic acid following a well described literature procedure (Langhals et al, 1982) (90% yield); MP 44-46 C (solidified). 1 H-NMR and 13 C-NMR data are in agreement with the data given in the literature (Tümer et al, 2005) p-Tolyl-3-pyridinylmethanone (2). The literature procedure (Villiani & King, 1963) described for the synthesis of phenyl-3-pyridinylmethanone (1) was applied to nicotinyl chloride by using toluene instead of benzene to give p-tolyl-3-pyridinylmethanone (2) (45%).…”

Amino Acids in Entomopathogenic Fungi Cultured In Vitro

“…Group of chemicals use in processes such as biodegradable plastics for consumer products and nontoxic and easily degradable solvents, cleaning agents, plasticizers, etc., global commercial [59,80] Verlamelin A,B B-MF C 44 H 69 N 7 O 11 , MW 872.06 g mol −1 Cyclic hexadepsipeptide lipopeptide, exhibits antifungal activity against plant pathogenic fungi [81], drugs [81,82] Vertilecanin A, B, C A-MF C 13 H 11 NO 3 , MW 229.21 g mol −1 Phenopicolinic acid derivatives were synthesized from nicotinic acid, antibacterial activity against Bacillus subtilis [83,84], insecticidal activity against Helicoverpa zea [85] Phospholipids toxic Insecticidal [86] Cyclic depsipeptides consisting of 5 amino acids and D-α-hydroxy acid, insecticidal [35], antitumor, herbicidal, cytoxicity [20], bioinsecticide [39,89], phytotoxin, cancer cell, anti-immunity of Metarhizium anisopliae antimicrobial peptides [89], virustatic against, LD 50 = 13.2-16.9 mg/kg-mice [3] Enniatin A, B (fusafungine) Bioinsecticide [39], mycotoxin, antibacterial, antiviral, antifungal, cytostatic activity, anorexia, hematuria, leukocytosis, leukopenia, inhibitors of protein and DNA synthesis, natural intoxications of animals and man [36], sesquiterpenoid chemicals characterized by a tetracyclic 12,13-epoxytrichothecene, LD 50 = 0.5-300 mg kg −1 -animal, LD 50 = 13-140 µg kg −1 -rat brain [90] 6. Isaria coleopterorum Pathogens of Lepidoptera and Coleoptera [91] Table 7 shows the list of mycotoxins produced by examined entomopathogenic fungi in our study and their physicochemical properties, and physiological activity.…”

Antimicrobial Potential of Nicotinic Acid Derivatives Against Various Pathogenic Microbes

“…Calcium, magnesium, and potassium salts of picolinic acid are used as food and beverage supplements to improve the nutritive capacity of food stuffs and beverages [24]. 5 The preparation of vertilecanin A starting from nicotinic acid in 4 steps (Tumer, et al, 2005). The first synthetic preparation of vertilecanin C and 2 phenyl-substituted derivatives of vertilecanin A.…”