220882-37-1Relevant articles and documents
Triazole compounds as well as preparation method and application thereof
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Paragraph 0233; 0490-0491; 0498-0500, (2020/07/29)
The invention belongs to the technical field of medicinal chemistry, and particularly relates to triazole compounds and a preparation method and application thereof. The triazole compounds have excellent LPAR1 antagonistic activity and selectivity, are lo
Enantioselective Anion Recognition by Chiral Halogen-Bonding [2]Rotaxanes
Lim, Jason Y. C.,Marques, Igor,Félix, Vítor,Beer, Paul D.
supporting information, p. 12228 - 12239 (2017/09/12)
The application of chiral interlocked host molecules for discrimination of guest enantiomers has been largely overlooked, which is surprising given their unique three-dimensional binding cavities capable of guest encapsulation. Herein, we combined the stringent linear geometric interaction constraints of halogen bonding (XB), the noncovalent interaction between an electrophilic halogen atom and a Lewis base, with highly preorganized and conformationally restricted chiral cavities of [2]rotaxanes to achieve enantioselective anion recognition. Representing the first detailed investigation of the use of chiral XB rotaxanes for this purpose, extensive 1H NMR binding studies and molecular dynamics (MD) simulation experiments revealed that the chiral rotaxane cavity significantly enhances enantiodiscrimination compared to the non-interlocked free axle and macrocycle components. Furthermore, by examining the enantioselectivities of a family of structurally similar XB [2]rotaxanes containing different combinations of chiral and achiral macrocycle and axle components, the dominant influence of the chiral macrocycle in our rotaxane design for determining the effectiveness of chiral discrimination is demonstrated. MD simulations reveal the crucial geometric roles played by the XB interactions in orientating the bound enantiomeric anion guests for chiral selectivity, as well as the critical importance of the anions' hydration shells in governing binding affinity and enantiodiscrimination.
Tandem Claisen Rearrangement/6-endo Cyclization Approach to Allylated and Prenylated Chromones
Schmidt, Bernd,Riemer, Martin,Schilde, Uwe
supporting information, p. 7602 - 7611 (2016/01/25)
Allyl, dimethylallyl and prenyl ethers derived from o-acylphenols reacted upon microwave irradiation to form C-allylated or -prenylated chromone derivatives, depending on the substitution pattern of the arene and the allyl substituent. The reaction proceeds through a tandem Claisen rearrangement and 6-endo-trig or 6-endo-dig cyclization sequence. For prenyl ethers, the tandem sequence can be extended by a Cope rearrangement to furnish 6-prenylchromones. The method is potentially useful for the synthesis of natural products and drugs.
Diphenyltriacetylenes: Novel nematic liquid crystal materials and analysis of their nematic phase-transition and birefringence behaviours
Arakawa, Yuki,Kang, Sungmin,Nakajima, Shunpei,Sakajiri, Koichi,Cho, Yokan,Kawauchi, Susumu,Watanabe, Junji,Konishi, Gen-Ichi
, p. 8094 - 8102 (2014/01/06)
Improvements in birefringence properties of LC materials are actively being pursued because of the increase in their applications in optical devices. 1,6-Diphenyl-1,3,5-hexatriyne, i.e., diphenyltriacetylenes (DPTAs; number of acetylene units, n = 3) are
K3PO4-KOH mixture as efficient reagent for the deprotection of 4-aryl-2-methyl-3-butyn-2-ols to terminal acetylenes
Smeyanov, Alexey,Schmidt, Andreas
, p. 2809 - 2816 (2013/08/23)
A mixture of potassium hydroxide and potassium phosphate was found to be an active reagent mixture for the cleavage of 2-hydroxypropyl-protected acetylenes. The reaction was performed in toluene at reflux temperature and gave terminal acetylenes in good to excellent yields within very short periods of time. Numerous other functional groups are tolerated. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for full experimental and spectral details.
Palladium-catalyzed routes to geranylated or farnesylated phenolic stilbenes: Synthesis of pawhuskin C and schweinfurthin J
Singh, Mandeep,Argade, Narshinha P.
, p. 2895 - 2902 (2012/10/29)
Starting from double MOM-protected phloroglucinol, the facile total syntheses of bioactive natural products pawhuskin C and schweinfurthin J were accomplished in good overall yields. The Heck, Stille, or Suzuki coupling reactions of two different electron
Phenolic bis-styrylbenzenes as β-amyloid binding ligands and free radical scavengers
Flaherty, Daniel P.,Kiyota, Tomomi,Dong, Yuxiang,Ikezu, Tsuneya,Vennerstrom, Jonathan L.
supporting information; experimental part, p. 7992 - 7999 (2011/03/19)
Starting from bisphenolic bis-styrylbenzene DF-9 (4), β-amyloid (Aβ) binding affinity and specificity for phenolic bis-styrylbenzenes, monostyrylbenzenes, and alkyne controls were determined by fluorescence titration with β-amyloid peptide Aβ1-40 and a fluorescence assay using APP/PS1 transgenic mouse brain sections. Bis-styrylbenzene SAR is derived largely from work on symmetrical compounds. This study is the first to describe Aβ binding data for bis-styrylbenzenes unsymmetrical in the outer rings. With one exception, binding affinity and specificity were decreased by adding and/or changing the substitution pattern of phenol functional groups, changing the orientation about the central phenyl ring, replacing the alkene with alkyne bonds, or eliminating the central phenyl ring. The only compound with an Aβ binding affinity and specificity comparable to 4 was its 3-hydroxy regioisomer 8. Like 4, 8 crossed the blood-brain barrier and bound to Aβ plaques in vivo. By use of a DPPH assay, phenol functional groups with para orientations seem to be a necessary, but insufficient, criterion for good free radical scavenging properties in these compounds.
A one-pot synthesis of unsymmetrical bis-styrylbenzenes
Flaherty, Daniel P.,Dong, Yuxiang,Vennerstrom, Jonathan L.
supporting information; experimental part, p. 6228 - 6230 (2010/01/18)
An efficient and widely applicable one-pot synthesis of unsymmetrical (E,E)-bis-styrylbenzenes using successive Heck and Horner-Wadsworth-Emmons reactions is described.
Bi-aromatic compounds linked via a heteroethylene radical, and pharmaceutical and cosmetic compositions using them
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, (2008/06/13)
Bi-aromatic compounds linked via a heteroethynylene radical are provided along with pharmaceutical and cosmetic compositions containing these compounds and methods for their use.
