28447-15-6Relevant articles and documents
Formation of Polycyclic Skeletons by Photochemical Transformations of Pyridyl- and Thienylbutadiene Derivatives
?agud, Ivana,Leva?i?, Marko,Marini?, ?eljko,?kori?, Irena
, p. 3787 - 3794 (2017)
In order to study the influence of heterocyclic nuclei on the photochemical behavior of conjugated butadiene systems, novel butadiene derivatives E,Z- and E,E-2/3-[4-(2-vinylphenyl)buta-1,3-dienyl]thiophene as well as E,Z- and E,E-3/4-[4-(2-vinylphenyl)buta-1,3-dienyl]pyridine have been synthesized. The Wittig reaction was utilized in a two-step reaction course. During the first Wittig reaction, the corresponding aldehydes, namely 2/3-thiophenecarboxaldehyde and 3/4-pyridinecarboxaldehyde, reacted with formylmethylenetriphenylphosphorane to give the corresponding acrylaldehydes, which reacted with the diphosphonium salt of α,α′-o-xylenedibromide in the second Wittig reaction to give new butadiene derivatives. These butadiene derivatives afforded, by photochemical intramolecular cycloaddition, new fused tricyclic as well as tetracyclic derivatives. For the first time, a study of efficiency was conducted where the efficiency of intramolecular cycloaddition of these heterocyclic butadiene derivatives was investigated by simultaneous use of ferrioxalate and valerophenone actinometers.
Synthesis and Assessment of Novel Probes for Imaging Tau Pathology in Transgenic Mouse and Rat Models
McMurray, Lindsay,MacDonald, Jennifer A.,Ramakrishnan, Nisha Kuzhuppilly,Zhao, Yanyan,Williamson, David W.,Tietz, Ole,Zhou, Xiaoyun,Kealey, Steven,Fagan, Steven G.,Smolek, Tomá?,Cubinkova, Veronika,?ilka, Norbert,Spillantini, Maria Grazia,Tolkovsky, Aviva M.,Goedert, Michel,Aigbirhio, Franklin I.
, p. 1885 - 1893 (2021)
Aggregated tau protein is a core pathology present in several neurodegenerative diseases. Therefore, the development and application of positron emission tomography (PET) imaging radiotracers that selectively bind to aggregated tau in fibril form is of importance in furthering the understanding of these disorders. While radiotracers used in human PET studies offer invaluable insight, radiotracers that are also capable of visualizing tau fibrils in animal models are important tools for translational research into these diseases. Herein, we report the synthesis and characterization of a novel library of compounds based on the phenyl/pyridinylbutadienylbenzothiazoles/benzothiazolium (PBB3) backbone developed for this application. From this library, we selected the compound LM229, which binds to recombinant tau fibrils with high affinity (Kd = 3.6 nM) and detects with high specificity (a) pathological 4R tau aggregates in living cultured neurons and mouse brain sections from transgenic human P301S tau mice, (b) truncated human 151-351 3R (SHR24) and 4R (SHR72) tau aggregates in transgenic rat brain sections, and (c) tau neurofibrillary tangles in brain sections from Alzheimer's disease (3R/4R tau) and progressive supranuclear palsy (4R tau). With LM229 also shown to cross the blood-brain barrier in vivo and its effective radiolabeling with the radioisotope carbon-11, we have established a novel platform for PET translational studies using rodent transgenic tau models.
Design, synthesis, and biological evaluation of 1,9-diheteroarylnona-1,3,6,8-tetraen-5-ones as a new class of anti-prostate cancer agents
Zhang, Xiaojie,Wang, Rubing,Perez, German Ruiz,Chen, Guanglin,Zhang, Qiang,Zheng, Shilong,Wang, Guangdi,Chen, Qiao-Hong
, p. 4692 - 4700 (2016)
In search of more effective chemotherapeutics for the treatment of castration-resistant prostate cancer and inspired by curcumin analogues, twenty five (1E,3E,6E,8E)-1,9-diarylnona-1,3,6,8-tetraen-5-ones bearing two identical terminal heteroaromatic rings have been successfully synthesized through Wittig reaction followed by Horner–Wadsworth–Emmons reaction. Twenty-three of them are new compounds. The WST-1 cell proliferation assay was employed to assess their anti-proliferative effects toward both androgen-sensitive and androgen-insensitive human prostate cancer cell lines. Eighteen out of twenty-five synthesized compounds possess significantly improved potency as compared with curcumin. The optimal compound, 78, is 14- to 23-fold more potent than curcumin in inhibiting prostate cancer cell proliferation. It can be concluded from our data that 1,9-diarylnona-1,3,6,8-tetraen-5-one can serve as a new potential scaffold for the development of anti-prostate cancer agents and that pyridine-4-yls and quinolin-4-yl act as optimal heteroaromatic rings for the enhanced potency of this scaffold. Two of the most potent compounds, 68 and 75, effectively suppress PC-3 cell proliferation by activating cell apoptosis and by arresting cell cycle in the G0/G1phase.
RIPK1 INHIBITORS AND METHODS OF USE
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Page/Page column 76, (2021/12/31)
The invention relates to compounds of formula (I) or a pharmaceutically acceptable salt thereof. Formula (I) compounds act as RIPK1 inhibitors and may be useful in preventing, treating, or acting as a therapeutic agent against, diseases associated with RIPK1.
Method for preparing olefine aldehyde by catalyzing terminal alkyne or terminal conjugated eneyne and diphosphine ligand used in method
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Paragraph 0163; 0164, (2021/05/29)
The invention discloses a method for preparing olefine aldehyde by catalyzing terminal alkyne or terminal conjugated eneyne and a diphosphine ligand used in the method. According to the invention, indole-substituted phosphoramidite diphosphine ligand which is stable in air and insensitive to light is synthesized by utilizing a continuous one-pot method, and the indole-substituted phosphoramidite diphosphine ligand and a rhodium catalyst are used for jointly catalyzing to successfully achieve a hydroformylation reaction of aromatic terminal alkyne and terminal conjugated eneyne under the condition of synthesis gas for the first time, so that an olefine aldehyde structure compound can be rapidly and massively prepared, and particularly, a polyolefine aldehyde structure compound which is more difficult to synthesize in the prior art can be easily prepared and synthesized, and a novel method is provided for synthesis and modification of drug molecules, intermediates and chemical products.
Iron-Catalyzed ?±,?-Dehydrogenation of Carbonyl Compounds
Zhang, Xiao-Wei,Jiang, Guo-Qing,Lei, Shu-Hui,Shan, Xiang-Huan,Qu, Jian-Ping,Kang, Yan-Biao
supporting information, p. 1611 - 1615 (2021/03/03)
An iron-catalyzed α,β-dehydrogenation of carbonyl compounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their α,β-unsaturated counterparts in a simple one-step reaction with high yields.
HETEROCYCLIC AMIDES AS KINASE INHIBITORS
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Page/Page column 76; 77, (2016/12/07)
Disclosed are compounds having the formula: (I) wherein R1, R2, and R3 are as defined herein, and methods of making and using the same.
Structure-Activity Relationship Study of Heterocyclic Phenylethenyl and Pyridinylethenyl Derivatives as Tau-Imaging Agents That Selectively Detect Neurofibrillary Tangles in Alzheimers Disease Brains
Matsumura, Kenji,Ono, Masahiro,Kitada, Ayane,Watanabe, Hiroyuki,Yoshimura, Masashi,Iikuni, Shimpei,Kimura, Hiroyuki,Okamoto, Yoko,Ihara, Masafumi,Saji, Hideo
, p. 7241 - 7257 (2015/10/05)
In order to explore novel tau-imaging agents that can selectively detect neurofibrillary tangles in Alzheimers disease (AD) brains, we designed and synthesized a series of heterocyclic phenylethenyl and (3-pyridinyl)ethenyl derivatives with or without a dimethyl amino group. In in vitro autoradiography using AD brain sections, all radioiodinated ligands with a dimethyl amino group bound to Aβ deposits in the sections. In contrast, the ligands without a dimethyl amino group showed different patterns of radioactivity accumulation in the sections depending on the kind of heterocycle contained in their molecules. Particularly, a phenylethenyl benzimidazole derivative ([125I]64) showed marked radioactivity accumulation in the temporal lobe which corresponded with the distribution of tau deposits. [125I]64 also showed the most favorable pharmacokinetics in normal mouse brains (3.69 and 0.06% ID/g at 2 and 60 min postinjection, respectively) among all ligands in this study. Taken together, these results suggest that [123I]64 may be a new candidate tau-imaging agent.
2-Iodoxybenzoic acid organosulfonates: Preparation, X-ray structure and reactivity of new, powerful hypervalent iodine(v) oxidants
Yusubov, Mekhman S.,Svitich, Dmitrii Yu.,Yoshimura, Akira,Nemykin, Victor N.,Zhdankin, Viktor V.
supporting information, p. 11269 - 11271 (2013/12/04)
New powerful hypervalent iodine(v) oxidants, tosylate and mesylate derivatives of 2-iodoxybenzoic acid (IBX), were prepared by the reaction of IBX with the corresponding sulfonic acids. Single crystal X-ray crystallography of the diacetate derivative of IBX-tosylate revealed an unusual heptacoordinated iodine geometry without any significant intermolecular secondary interactions.
Direct oxidative conversion of 3-aryl propionaldehydes to 3-aryl acroleins promoted by SOMO catalysis
Zhu, Jin,Yu, Shunting,Lu, Wenchao,Deng, Jing,Li, Jian,Wang, Wei
scheme or table, p. 1207 - 1209 (2012/03/26)
A new direct oxidative transformation of 3-aryl propionaldehydes to 3-aryl acroleins promoted by SOMO catalysis has been realized with high efficiency under mild reaction conditions.
