575-61-1Relevant articles and documents
Design, Synthesis, and Bioactivities of Phthalide and Coumarin Derivatives Based on the Biosynthesis and Structure Simplification of Gossypol
Guo, Zhonglin,Zhou, Pan,Song, Hongjian,Liu, Yuxiu,Zhang, Jingjing,Li, Yongqiang,Wang, Qingmin
, p. 15123 - 15135 (2021/12/27)
Because gossypol and hemigossypol show antiviral activity but are structurally complex, we designed and synthesized a series of structurally simpler phthalide and coumarin derivatives. The phthalide derivatives were synthesized by opening the naphthalene ring of hemigossypol, and the coumarin derivatives were synthesized by ring-opening reactions of the phthalide derivatives with the goal of investigating the effect of the lactone ring size on bioactivity. The bioassay results showed that the two series of target compounds possessed moderate to good activities against tobacco mosaic virus, One of the compounds showed in vivo inactivation, curative, and protection activities of 50 ± 1, 53 ± 3, and 48 ± 2% at 500 mg/L, values which are higher than those of gossypol (32 ± 1, 35 ± 1, 29 ± 1%, respectively) and comparable to those of hemigossypol (55 ± 1, 49 ± 1, and 48 ± 1%, respectively) and the commercial antiviral agent ningnanmycin (56 ± 2, 54 ± 1, 58 ± 1%) at the same dose. Thus, this compound is a promising candidate for the development of new anti-plant-virus agents. In addition, most of the synthesized compounds showed broad-spectrum activity when tested against 14 kinds of phytopathogenic fungi and showed selectivity against Sclerotinia sclerotiorum, Physalospora piricola, and Rhizoctonia cerealis. Moreover, some of the compounds exhibited activity against Plutella xylostella larvae; the two most active compounds exhibited larvicidal activities (LC50) of 4.10 and 5.47 mg/L, respectively. Further studies showed that these compounds also exhibited insecticidal activities against Mythimna separata, Helicoverpa armigera, and Pyrausta nubilalis larvae.
Synthesis and vasorelaxant and antiplatelet activities of a new series of (4-Benzylphthalazin-1-ylamino)alcohol derivatives
Munín, Javier,Quezada, Elías,Campos-Toimil, Manuel,Cano, Ernesto,Uriarte, Eugenio,Vi?a, Dolores
, p. 1682 - 1688 (2017/06/27)
A new series of phthalazine derivatives was synthesized by reaction of phthalic anhydride and different substituted phenylacetic acids to yield the benzyliden-3H-isobenzofuran-1-one intermediates 2a–d. Treatment of them with hydrazine afforded 4-benzyl-2H-phthalazin-1-one derivatives 3a–d, which were substituted with the corresponding aminoalkylalcohol to obtain the (4-benzylphthalazin-1-ylamino)alcohol derivatives 4a–h. In general, these phthalazine derivatives relaxed the contractions produced by phenylephrine both in intact or endothelium-denuded aortic rings. In addition, platelet aggregation induced by thrombin was also inhibited by compounds 4c and 4g.
Tuning of photoluminescence properties of functional phthalides for OLED applications
Shanmugasundaram, Madhesh,Joseph, Joshy,Ramaiah, Danaboyina
, p. 156 - 162 (2016/08/15)
With an objective to develop simple organic systems and tailor their properties for optoelectronic applications, we have synthesized three functionalized phthalide derivatives and have investigated their electroluminescence and photophysical properties under different conditions. These derivatives showed good solubility in common organic solvents and exhibited strong absorption in the range 320–400?nm, having molar extinction coefficient values of ca. 104?M?1?cm?1. The monomeric solution of these derivatives exhibited very low fluorescence quantum yields (ΦF) of ca. 0.003–0.04 owing to their inherent structural features such as intramolecular free rotation and decay to the dark triplet states. However, upon complexation with Lewis acids, such as BCl3, these derivatives showed increased fluorescence quantum yields up to ca. 0.21?±?0.01 and also exhibited aggregation induced emission (AIE) in water/acetonitrile mixtures with the emission yields in the range ca. 0.11–0.16. The morphological analysis of the aggregates through SEM and TEM showed the formation of rod-like structures in 90% water/acetonitrile mixture with an average size of ca. 100?nm. Supporting the observed aggregation induced enhancement in emission properties, these derivatives also exhibited significantly enhanced solid state fluorescence quantum yields of ca. 0.58–0.60. As a representative example, organic light emitting diode (OLED) fabricated using the derivative 3 as the emissive layer showed an efficient electroluminescence centered at 524?nm with a turn on voltage of 9?V, demonstrating thereby their potential use in optoelectronic applications.
