78238-98-9Relevant academic research and scientific papers
Linear Relationship between 13C NMR Chemical Shifts and the Bending of sp-Carbon Chains
Kreuzahler, Mathis,Adam, Abdulselam,Haberhauer, Gebhard
, p. 12689 - 12693 (2019)
Polyynes show a strictly linear relationship between the energy impact and the bending of the polyyne chain. The energy, which is necessary to bend the acetylenic chain, decreases with the increasing number of acetylene units. A deviation from linearity i
Triphenylbutanamines: Kinesin spindle protein inhibitors with in vivo antitumor activity
Wang, Fang,Good, James A. D.,Rath, Oliver,Kaan, Hung Yi Kristal,Sutcliffe, Oliver B.,MacKay, Simon P.,Kozielski, Frank
, p. 1511 - 1525 (2012/04/10)
The human mitotic kinesin Eg5 represents a novel mitotic spindle target for cancer chemotherapy. We previously identified S-trityl-l-cysteine (STLC) and related analogues as selective potent inhibitors of Eg5. We herein report on the development of a series of 4,4,4-triphenylbutan-1-amine inhibitors derived from the STLC scaffold. This new generation systematically improves on potency: the most potent C-trityl analogues exhibit Kiapp ≥ 10 nM and GI50 ≈ 50 nM, comparable to results from the phase II clinical benchmark ispinesib. Crystallographic studies reveal that they adopt the same overall binding configuration as S-trityl analogues at an allosteric site formed by loop L5 of Eg5. Evaluation of their druglike properties reveals favorable profiles for future development and, in the clinical candidate ispinesib, moderate hERG and CYP inhibition. One triphenylbutanamine analogue and ispinesib possess very good bioavailability (51% and 45%, respectively), with the former showing in vivo antitumor growth activity in nude mice xenograft studies.
Synthesis of bridged molecular gyroscopes with closed topologies: Triple one-pot macrocyclization
Commins, Patrick,Nunez, Jose E.,Garcia-Garibay, Miguel A.
experimental part, p. 8355 - 8363 (2011/12/04)
We describe the synthesis and characterization of six bridged molecular gyroscopes with m-alkoxy-substituted trityl stators and dialkynylphenylene rotators. All of the bridged molecular gyroscopes were synthesized convergently to form the phenolic stator-
Directed Metalation of Benzenesulfinamides. A Novel Route to Meta-Substituted Aromatic Compounds
Katritzky, Alan R.,Lue, Ping
, p. 74 - 78 (2007/10/02)
Directed lithiation ortho to the sulfinamide group of readily available ortho- and para-substituted N-phenylbenzenesulfinamides (5a-d) and reaction with a variety of electrophiles followed by mercuridesulfination (HgCl2) or dehydrodesulfination (Ra/Ni) co
RADICAL-ANIONS OF AROMATIC COMPOUNDS. V. EFFECT OF THE STRUCTURE OF THE ELECTROPHILE ON THE RATIO OF THE ELECTRON-DONATING AND NUCLEOPHILIC CHARACTERISTICS OF THE BENZOPHENONE RADICAL-ANION IN REACTIONS WITH N,N,N-TRIMETHYLARYLAMMONIUM PERCHLORATES
Selivanov, B. A.,Bil'kis, I. I.,Varand, V. L.,Shteingarts, V. D.
, p. 865 - 877 (2007/10/02)
In reaction with N,N,N-trimethylammonium perchlorates in THF the potassium salt of the benzophenone radical-anion exhibits dual reactivity, acting both as nucleophile (as SN process) and as a one-electron reducing agent (an ET process).The effect of the structure of the aryl fragment of the ammonium salt on the ratio of the rates WET/WSN is determined by the higher sensitivity of the electron transfer rate to the effect of this factor compared with nucleophilic substitution and varies in the following order: p-Methoxyphenyl p-tolyl m-tolyl phenyl m-methoxyphenyl p-biphenylyl m-chlorophenyl 1-naphthyl.I t was found that the structure of the aryl fragment of the ammonium salt has a significant effect on the regioselectivity of the methylation of the benzophenone radical-anion.
Anomalous Acetoxylation of Aromatic Nuclei: Some Structural Requirements in the Substrate
Bandaranayake, Wickramasinghe M.,Riggs, Noel V.
, p. 115 - 129 (2007/10/02)
For certain aromatic nuclei, bromination in acetic acid in the presence of pyridine is accompanied by nuclear acetoxylation.As first observed with galbulin, when two alkoxyl groups, one meta and one para to a benzylic centre of the substrate are present, acetoxylation occurs at the intervening ortho position.Under the given conditions, acetoxylation occurs at position 8 of 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene, and at position 2 of 3,4-dimethoxy diphenyl and triphenyl-methanes.Acetoxylation does not occur in the absence of either of the alkoxy groups or in the absence of pyridine, not does it occur in the pendant ring of 1-(3',4'-dimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene.These results are consistent with the earlier suggestion that the reaction occurs by way of initial oxidative formation of a doubly benzylic cation
