10349-38-9Relevant articles and documents
Isonitriles as source and fate of imidoyl radicals: A novel homolytic α-fragmentation
Nanni, Daniele,Pareschi, Patrizia,Tundo, Antonio
, p. 9337 - 9340 (1996)
Imidoyl radicals 4a-c react with phenylacetylene to give annulation products and nitrile 12, arising from β-scission of the intermediate iminyl radical that is involved in the rearrangement of azaspirocyclohexadienyl 8. In contrast, imidoyls 4d and 15 do not react with the alkyne and give good yields of the corresponding isonitriles through a novel example of homolytic α-fragmentation.
Bis-Selenoureas for Anion Binding: A 1H NMR and Theoretical Study
Caltagirone, Claudia,Ciancaleoni, Gianluca,Lippolis, Vito,Mocci, Rita,Picci, Giacomo,Zielińska-B?ajet, Mariola
, p. 1389 - 1395 (2020)
The anion binding ability of a family of bis-selenoureas L1-L3 obtained by the reaction of 1,3-bis(aminomethyl)-benzene and phenylisoselenocyanate, p-methoxyphenylisoselenocyanate and naphtylisoselenocyanate, for L1, L2, and L3, respectively, has been tested and compared to that of previously described bis-urea analogues. Results suggest that the introduction of selenium leads to an increase in the acidity of the urea NH hydrogen atoms, and therefore to a stronger affinity (more than three-fold higher) towards anion species, in particular dihydrogen phosphate, in DMSO-d6. Theoretical calculations allowed for the optimization of the adducts receptors corroborating the experimental results.
Novel hexakis(areneisonitrile)technetium(I) complexes as radioligands targeted to the multidrug resistance P-glycoprotein
Herman,Sharma,Kronauge,Barbarics,Herman,Piwnica- Worms
, p. 2955 - 2963 (1995)
Transport substrates and modulators of the human multidrug resistance (MDR1) P-glycoprotein (Pgp) are generally lipophilic cationic compounds, many with substituted aryl moieties. We sought to synthesize aromatic technetium isonitrile complexes to enable
Synthesis of isonitriles from N-substituted formamides using triphenylphosphine and iodine
Wang, Xia,Wang, Qing-Gang,Luo, Qun-Li
, p. 49 - 54 (2015)
Treatment of N-substituted formamides with the reagent combination of triphenylphosphine and molecular iodine, in the presence of a tertiary amine, quickly produces the corresponding isocyanides in high yields under ambient conditions. The process employs readily available and low-cost reagents, a convenient synthetic procedure, and mild reaction conditions for the synthesis of various alkyl and aryl isocyanides.
Synthesis and cation-binding studies of gold(i) complexes bearing oligoether isocyanide ligands with ester and amide as linkers
Hau, Franky Ka-Wah,Yam, Vivian Wing-Wah
, p. 300 - 306 (2015)
A series of dinuclear gold(i) isocyanide complexes of bis(alkynyl)calix[4]arene was designed and synthesized, and their photophysical and cation recognition properties were studied. Complex 1, [{calix[4]arene-(OCH2CONH-C6H4CC)2}{Au(CN-C6H4O(CH2CH2O)2CH3)}2], was found to show a high selectivity towards Al3+ in CH2Cl2-MeCN (1-1 v/v). Upon addition of Al3+, drastic changes in the electronic absorption, emission and 1H NMR spectra were observed. These changes have been attributed to the formation of Au(i)?Au(i) interactions induced by the high binding affinity of the amide site for the Al3+ ion, instead of the high binding affinity expected of the oligoether site for alkali and alkaline earth metal ions. Further studies with the control complex, [{calix[4]arene-(OOC-C6H4CC)2}{Au(CN-C6H4O(CH2CH2O)2CH3)}2] (4), indicated that the amide carbonyl oxygen in the flexible pendants is crucial for the binding of Al3+. The Royal Society of Chemistry 2016.
Thermal oligomerisation of aryl isocyanides: Formation of pyrazino[1,2-a:4,5-a′]diindoles and indigo diarylimines
Boeyens, Jan C.A.,Cook, Leanne M.,Ding, Yunxiang,Fernandes, Manuel A.,Reid, David H.
, p. 2168 - 2172 (2003)
The aryl isocyanides 1-4 are converted at 150°C into the hexameric pyrazino[1,2-a:4,5-a′]diindoles 15-19. 4-Fluorophenyl isocyanide, when heated at 135°C, gave the hexamer 19 and the tetrameric indigo di-arylimine 9, and when kept at ambient temperature g
Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: Synthesis of cyclopenta[: B] quinoxalines
Yuan, Yao,Dong, Wu-Heng,Gao, Xiao-Shuang,Xie, Xiao-Min,Zhang, Zhao-Guo
, p. 11900 - 11903 (2019)
A visible-light-induced radical cascade cyclization of aryl isonitriles and cyclobutanone oxime esters for the synthesis of cyclopenta[b]quinoxalines has been accomplished for the first time. The key to the success of this process was the integration of the in situ-formed nitrile radical followed by the cascade radical isonitrile/nitrile insertion-cyclization. The easy introduction of substituents for both substrates and the high functional group tolerance of the reaction make it an efficient strategy to give various quinoxaline derivatives in moderate to good yields.
Development of an Industrial Process Based on the Groebke-Blackburn-Bienaymé Multicomponent Reaction: Efficient Preparation- of 3-Aminoimidazo[1,2-a]pyrazines
Baenziger, Markus,Durantie, Estelle,Mathes, Christian
, p. 2266 - 2274 (2017)
3-Aminoimidazo[1,2-a]pyrazine is an important scaffold that is found in many drugs. This scaffold is rapidly accessible through a Groebke-Blackburn-Bienaymé cyclisation starting from an aminopyrazine, an aldehyde and an isocyanide. A scale-up process of this multicomponent reaction has been achieved in high yield and with excellent purity. The scope and limitations of this process leading to various 3-aminoimidazo[1,2-a]pyrazines are disclosed.
Design, synthesis and anticancer evaluation of 3-methyl-1H-indazole derivatives as novel selective bromodomain-containing protein 4 inhibitors
Dong, Ru,Zhang, Cheng,Wang, Chao,Zhou, Xin,Li, Wen,Zhang, Jin-Yang,Wang, Min,Xu, Yong,Sun, Li-Ping
, (2022/01/11)
Bromodomain-containing Protein 4 (BRD4), an ‘epigenetic reader’, regulates chromatin structure and gene expression via recognizing and binding acetylated lysine in histones. BRD4 has become a therapeutic target for cancers because it promotes the expression of the tumor genes, such as c-Myc, NF-κB, and Bcl-2. In this study, a new series of 3-methyl-1H-indazole derivatives were designed via virtual screening and structure-based optimization. All compounds were synthesized and evaluated for their inhibitory activities to BRD4-BD1 and their antiproliferative effects in cancer cell lines. Among them, several compounds (such as 9d, 9u and 9w) exhibited strong BRD4-BD1 affinities and inhibition activities, and potently suppressed MV4;11 cancer cell line proliferation. Among them, compound 9d showed excellent selectivity for BRD4 and effectively suppressed c-Myc, the downstream protein of BRD4. This study provided new lead compounds for further biological evaluation on BRD4.
Silver-Catalyzed Selective Multicomponent Coupling Reactions of Arynes with Nitriles and Isonitriles
Ghorai, Sourav,Lin, Yongjia,Xia, Yuanzhi,Wink, Donald J.,Lee, Daesung
supporting information, p. 642 - 647 (2020/01/31)
Pathway selective aryne-based novel multicomponent coupling reactions with isonitriles and nitriles are described. Crucial to these reactions is the formation of a silver-aryne complex, which shows differential reactivity toward isonitriles and nitriles to form two different forms of ortho-nitrilium organosilver arene species. Interception of the nitrilium of an aryne-isonitrile adduct with another isonitrile leads to the formation of benzocyclobutene-1,2-diimines, whereas the nitrilium of an aryne-nitrile adduct renders selective formation of 3H-indol-3-imines or 3-iminoindolin-2-ol depending on the structure of the nitrile employed.
