Synthesis, biological activity and X-ray analysis of 11,12-p-tolyl-pyridazonyl-drim-5(6),8(9)-en-7-one
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LUNGU, Lidia, ARICU, Aculina, CIOCARLAN, Alexandru, SHOVA, Sergiu, ZBANCIOC, Gheorghita N., MANGALAGIU, Ionel, VORNICU, Nicoleta. Synthesis, biological activity and X-ray analysis of 11,12-p-tolyl-pyridazonyl-drim-5(6),8(9)-en-7-one. In: Physical Methods in Coordination and Supramolecular Chemistry, 8-9 octombrie 2015, Chişinău. Chisinau, Republic of Moldova: 2015, XVIII, p. 93.
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Physical Methods in Coordination and Supramolecular Chemistry
XVIII, 2015
Conferința ""Physical Methods in Coordination and Supramolecular Chemistry""
Chişinău, Moldova, 8-9 octombrie 2015

Synthesis, biological activity and X-ray analysis of 11,12-p-tolyl-pyridazonyl-drim-5(6),8(9)-en-7-one


Pag. 93-93

Lungu Lidia1, Aricu Aculina1, Ciocarlan Alexandru1, Shova Sergiu1, Zbancioc Gheorghita N.2, Mangalagiu Ionel2, Vornicu Nicoleta3
 
1 Institute of Chemistry,
2 Alexandru Ioan Cuza University of Iaşi,
3 Metropolitan Center of Research TABOR, The Metropolitanate of Moldavia and Bukovina
 
Disponibil în IBN: 21 aprilie 2020


Rezumat

The results of investigations devoted to the synthesis of new drimanic compound containing heterocyclic structural units are reported. The 11,12-p-tolyl-pyridazonyl-drim5(6),8(9)-en-7-one 3 was prepared by interaction of bromide 1 with p-tolyl-pyridazone 2 under depicted conditions.1 As result of “in vitro” biological assessment tested compound 3 showed exceptional activity against five strains of fungi (Aspergillus flavus, Fusarium solani, Penicillium chrysogenum, P. frequentans, Alternaria alternata) and against both Gram-positive (Bacillus polymyxa) and Gram-negative (Pseudomonas aeruginosa) bacteria at MIC values 510-3 μg/mL and 3.210-2 μg/mL, respectively.2figureScheme 1. Reagents and conditions: K2CO3, DMAA, r.t., 24h, 77%. The structure and stereochemistry of the compound 3 was confirmed unambiguously by X-ray diffraction on monocrystal (Figure 1). According to single crystal X-ray study compound 3 crystallizes in C2 space group of monoclinic system comprising two crystallographic asymmetric but chemically equivalent molecular entities (denoted A and B). One of the azaheterocyclic fragments in molecule A, as well as the whole molecule B, were found to be disordered into two resolvable positions in 1:1 ratio.3Figure 1. The X-ray molecular structure of compound 3. H atoms are omitted for clarity