621-34-1Relevant articles and documents
Synthesis and antiplatelet activity of 2-(diethylamino)-7-ethoxychromone and related compounds
Mazzei, M.,Sottofattori, E.,Braccio, M. Di,Balbi, A.,Leoncini, G.,et al.
, p. 617 - 622 (1990)
2-(Diethylamino)-7-ethoxychromone 3a and its 2-(1-piperidinyl)analogue 3b were synthesized by reaction of 3-ethoxyphenol 1 with 3-(dialkylamino)-3-oxo-propanoic acid ethyl ester 2 in the presence of phosphorus oxychloride.With a view to improve their biological activity the above 7-ethoxychromones 3 were submitted to some structural modifications firstly involving the 4-CO group.The 4H-chromenes 4 and the 4-thiochromones 5 were obtained by action of suitable reagents.The compounds 5 were then easily transformed to 4-(methylthio)chromenylium iodides 6.Then from the 2-(diethylamino)-7-ethoxychromone 3a were obtained with suitable reactions the 3,6-diamino derivative 8, the 3- and 6-formyl derivatives 9a,b and the Mannich base 10.By action of acetic anhydride this latter compound yielded the methylenebis derivative 11.Most of the above compounds were tested in vitro for their inhibitory activities against human platelet aggregation induced by collagen, ADP and arachidonic acid.Among the tested compounds the 2-(diethylamino)-7-ethoxychromone 3a showed the highest activity.
Phthalocyanine-based discotic liquid crystals switching from a molten alkyl chain type to a flying-seed-like type
Nakamura, Hiromu,Sugiyama, Kouki,Ohta, Kazuchika,Yasutake, Mikio
, p. 7297 - 7306 (2017/08/03)
We have synthesised a series of phthalocyanine-based discotic liquid crystals, (m-CnOPhO)8PcCu (n = 1-20: 2a-o), and investigated their mesomorphism by using a polarizing optical microscope (POM), a differential scanning calorimeter (DSC) and a temperature-dependent small angle X-ray diffractometer. We found that each of the derivatives 2a-o shows mesomorphism. However, the mesomorphism of the (m-CnOPhO)8PcCu derivatives strongly depends on the alkoxy chain length (n). The mesomorphism of the short chain-substituted derivatives 2a-e for n = 1-5 is a flying-seed-like type induced by flip-flop of the peripheral bulky substituents, whereas the mesomorphism of the long chain-substituted derivatives 2j-o for n = 10-20 is a conventional molten alkyl chain type induced by melting of the long alkyl chains. The moderately long chain derivatives (2f-i) for n = 6-9 in between show both types of mesophases. The detailed temperature-dependent X-ray diffraction measurements were carried out for three representative derivatives, 2b (n = 2 for n = 1-5), 2h (n = 8 for n = 6-9), and 2o (n = 20 for n = 10-20). As a result, we revealed that the Colro(P2m) mesophase in 2b (n = 2) gave a halo denoted as Haloarom. at d ? 5.2 ? due to flip-flop of the bulky aromatic substituents, and that the Colho mesophase in 2o (n = 20) gave a halo denoted as Haloalkyl at d ? 4.6-4.8 ? due to melting of the long alkyl chains. Therefore, we can distinguish the type of mesophase from Haloarom. and Haloalkyl. Very interestingly, the (m-C8OPhO)8PcCu (2h) derivative having moderately long alkyl chains gave Haloalkyl at about 4.8 ? in the lower temperature mesophase of Colho, but Haloarom. at about 5.2 ? in the higher temperature mesophase of Colro(P21/a). This means that melting of the alkyl chains induces the Colho phase in the lower temperature region, but that flip-flop of the bulky aromatic substituents induces the Colro(P21/a) phase in the higher temperature region. This unusual reverse phase transition sequence from a higher symmetry of the Colh mesophase to a lower symmetry of the Colr mesophase on a heating stage is attributable to such a unique stepwise melting of these two different types of substituents. To the best of our knowledge, this mesogen (2h) is the first example switching mesomorphism from the molten alkyl chain type to the flying-seed-like type in a discotic liquid crystal.
Dialkoxybenzene and dialkoxyallylbenzene feeding and oviposition deterrents against the cabbage looper, trichoplusia ni: Potential insect behavior control agents
Akhtar, Yasmin,Yu, Yang,Isman, Murray B.,Plettner, Erika
scheme or table, p. 4983 - 4991 (2011/08/06)
The antifeedant, oviposition deterrent, and toxic effects of individual dialkoxybenzene compounds/sets and of hydroxy- or alkoxy-substituted allylbenzenes, obtained through Claisen rearrangement of substituted allyloxybenzenes, were assessed against the cabbage looper, Trichoplusia ni, in laboratory bioassays. Most of the compounds/sets strongly deterred larval feeding, with some exhibiting mild toxic and oviposition deterrent effects as well. Some of the compounds/sets were more active than the commercial insect repellent, DEET (N,N-diethyl-m-toluamide), as both feeding and oviposition deterrents against the cabbage looper. On the basis of the obtained oviposition data a general hypothesis was proposed regarding the oviposition sites: one binding mode with the alkyl and allyl groups on the same side of the benzene ring resulted in deterrence, the other with alkyl and allyl groups on opposite sides of the benzene ring resulted in stimulation. The results suggest some structure-activity relationships useful in improving the efficacy of the compounds and designing new, nontoxic insect control agents for agriculture.
