5452-73-3Relevant academic research and scientific papers
Electrochemical-Induced Ring Transformation of Cyclic α-(ortho-Iodophenyl)-β-oxoesters
Strehl, Julia,Kahrs, Christoph,Müller, Thomas,Hilt, Gerhard,Christoffers, Jens
supporting information, p. 3222 - 3225 (2020/02/11)
Cyclic α-(ortho-iodophenyl)-β-oxoesters were converted in a ring-expanding transformation to furnish benzannulated cycloalkanone carboxylic esters. The reaction sequence started by electrochemical reduction of the iodoarene moiety. In a mechanistic rationale, the resulting carbanionic species was adding to the carbonyl group under formation of a strained, tricyclic benzocyclobutene intermediate, which underwent carbon–carbon bond cleavage and rearrangement of the carbon skeleton by retro-aldol reaction. The scope of the reaction sequence was investigated by converting cyclic oxoesters with different ring sizes yielding benzocycloheptanone, -nonanone and -decanone derivatives in moderate to good yields. Furthermore, acyclic starting materials and cyclic compounds carrying additional substituents on the iodophenyl ring were submitted to this reaction sequence. The starting materials for this transformation are straightforwardly obtained by conversion of β-oxoesters with phenyliodobis(trifluoroacetate).
Discovery of a new class of valosine containing protein (VCP/P97) inhibitors for the treatment of non-small cell lung cancer
Wang, Xueyuan,Bai, Enhe,Zhou, Hui,Sha, Sijia,Miao, Hang,Qin, Yanru,Liu, Zhaogang,Wang, Jia,Zhang, Haoyang,Lei, Meng,Liu, Jia,Hai, Ou,Zhu, Yongqiang
, p. 533 - 544 (2019/01/04)
Valosine containing protein (VCP/p97) is a member of the AAA ATPase family involved in several essential cellular functions and plays an important role in the ubiquitin-mediated degradation of misfolded proteins. P97 has a significant role in maintaining the cellular protein homeostasis for tumor cell growth and survival and has been found overexpressed in many tumor types. No new molecule entities based on p97 target were approved in clinic. Herein, a series of novel pyrimidine structures as p97 inhibitors were designed and synthesized. After enzymatic evaluations, structure-activity relationships (SAR) were discussed in detailed. Among the screened compounds, derivative 35 showed excellent enzymatic inhibitory activity (IC50, 36 nM). The cellular inhibition results showed that compound 35 had good antiproliferative activity against the non-small cell lung cancer A549 cells (IC50, 1.61 μM). Liver microsome stability showed that the half-life of compound 35 in human liver microsome was 42.3 min, which was more stable than the control CB-5083 (25.8 min). The in vivo pharmacokinetic results showed that the elimination phase half-lives of compound 35 were 4.57 h for ig and 3.64 h for iv, respectively and the oral bioavailability was only 4.5%. These results indicated that compound 35 could be effective for intravenous treatment of non-small cell lung cancer.
FUSED TETRA OR PENTA-CYCLIC PYRIDOPHTHALAZINONES AS PARP INHIBITORS
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Paragraph 0200; 0201, (2017/12/01)
Provided are certain fused tetra or penta-cyclic compounds and salts thereof, compositions thereof, and methods of use thereof.
Rh2(II)-catalyzed ester migration to afford 3 H-indoles from trisubstituted styryl azides
Kong, Chen,Driver, Tom G.
supporting information, p. 802 - 805 (2015/04/27)
Rh2(II)-Complexes trigger the formation of 3H-indoles from ortho-alkenyl substituted aryl azides. This reaction occurs through a 4π-electron-5-atom electrocyclization of the rhodium N-aryl nitrene followed by a [1,2]-migration to afford only 3H-indoles. The selectivity of the migration is dependent on the identity of the β-styryl substituent.
FUSED TETRA OR PENTA-CYCLIC PYRIDOPHTHALAZINONES AS PARP INHIBITORS
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Paragraph 0243, (2015/02/18)
Provided are certain fused tetra or penta-cyclic compounds and salts thereof, compositions thereof, and methods of use thereof.
The profound effect of the ring size in the electrocyclic opening of cyclobutene-fused bicyclic systems
Ralph, Michael J.,Harrowven, David C.,Gaulier, Steven,Ng, Sean,Booker-Milburn, Kevin I.
supporting information, p. 1527 - 1531 (2015/01/30)
Fused cyclobutenes, prepared by the photocycloaddition of propargyl alcohols to cyclic anhydride chromophores, undergo facile thermochemical ring opening to fused γ-lactones. The size of the fused ring profoundly influences the temperature that is required to facilitate the ring opening (from 50°C to 180°C) and the nature of the product that is formed. Our studies provide new insights into the mechanistic course of these reactions and have been extended to facilitate the preparation of lactams fused to medium-sized rings.
Promoting reductive tandem reactions of nitrostyrenes with Mo(CO)6 and a palladium catalyst to produce 3 h -indoles
Jana, Navendu,Zhou, Fei,Driver, Tom G.
supporting information, p. 6738 - 6741 (2015/06/16)
The combination of Mo(CO)6 and 10 mol % of palladium acetate catalyzes the transformation of 2-nitroarenes to 3H-indoles through a tandem cyclization-[1,2] shift reaction of in situ generated nitrosoarenes. Mo(CO)6 appears to have dual roles in this transformation: generate CO and promote C-N bond formation to increase the yield of the N-heterocycle product.
FUSED TETRA OR PENTA-CYCLIC PYRIDOPHTHALAZINONES AS PARP INHIBITORS
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Page/Page column 40, (2013/07/19)
Provided are certain fused tetra or penta-cyclic compounds and salts thereof, compositions thereof, and methods of use thereof.
Gold-catalyzed synthesis of carbon-bridged medium-sized rings
Barabe, Francis,Betournay, Genevieve,Bellavance, Gabriel,Barriault, Louis
supporting information; experimental part, p. 4236 - 4238 (2009/12/31)
Bicyclo[m.n.1]alkenone frameworks possessing quaternary carbon centers adjacent to a bridged ketone are frequently found in bioactive natural products. Although several methods have been developed to construct such frameworks, most of them are specific to a particular scaffold. Herein, we report a mild and highly efficient method to generate carbon-bridged frameworks of various sizes using phosphlno gold(I) catalysts.
Synthesis of ring-substituted bis-η5-cyclopentadienyl derivatives of the Group IV elements containing the bicyclic ligands η5-C5H3(1,2-CH2-)n, n=4, 5, or 6
Polo, Eleonora,Bellabarba, Ronan M.,Prini, Giansiro,Traverso, Orazio,Green, Malcolm L.H.
, p. 211 - 218 (2007/10/03)
The synthesis of unsubstituted and substituted bicyclic η5-cyclopentadienyl ligands and their Group IV metal complexes [M{η5-C5H3(1,2-CH2-) n}2Cl2], where n=4, 5, 6 and M=Ti, Zr, Hf, is reported. An example of an ansa-bridged zirconium analogue is also described.
