67488-65-7Relevant articles and documents
Phenotypic Screening of Chemical Libraries Enriched by Molecular Docking to Multiple Targets Selected from Glioblastoma Genomic Data
Aryal, Uma K.,Bailey, Barbara J.,Bum-Erdene, Khuchtumur,Corson, Timothy W.,Fishel, Melissa L.,Lee, Jonathan A.,Liu, Sheng,Meroueh, Samy O.,Pollok, Karen E.,Sishtla, Kamakshi,Wan, Jun,Wells, Clark D.,Xu, David,Zhou, Donghui
, p. 1424 - 1444 (2020/07/15)
Like most solid tumors, glioblastoma multiforme (GBM) harbors multiple overexpressed and mutated genes that affect several signaling pathways. Suppressing tumor growth of solid tumors like GBM without toxicity may be achieved by small molecules that selec
Chemoselective Intramolecular Formal Insertion Reaction of Rh–Nitrenes into an Amide Bond Over C?H Insertion
Kono, Masato,Harada, Shingo,Nemoto, Tetsuhiro
supporting information, p. 3119 - 3124 (2019/02/13)
The past few decades have witnessed extensive efforts to disclose the unique reactivity of metal–nitrenes, because they could be a powerful synthetic tool for introducing the amine functionality into unactivated chemical bonds. The reactivity of metal–nitrenes, however, is currently mainly confined to aziridination (an insertion into a C=C bond) and C?H amination (an insertion into a C?H bond). Nitrene insertion into an amide C?N bond, however, has not been reported so far. In this work we have developed a rhodium-catalyzed one-nitrogen insertion into amide C?N and sulfonamide S?N bonds. Experimental and theoretical analyses based on density functional theory indicate that the formal amide insertion proceeds via a rhodium-coordinated ammonium ylide formed between the nitrene and the amide nitrogen, followed by acyl group transfer concomitant with C?N bond cleavage. Mechanistic studies have allowed rationalization of the origin of the chemoselectivity observed between the C?H and amide insertion reactions. The methodology presented herein is the first example of an insertion of nitrene into amide bonds and provides facile access to unique diazacyclic systems with an N?N bond linkage.
Synthesis of 2-carboxylated aza-ring derivatives through α-monohalogenation/ring-contraction of N-sulfonyl lactams
Sirindil, Fatih,Miaskiewicz, Solène,Kern, Nicolas,Lalaut, Arno,Felten, Anne-Sophie,Weibel, Jean-Marc,Pale, Patrick,Blanc, Aurélien
, p. 5096 - 5106 (2017/07/28)
2-Carboxylated aza-rings have been synthesized in two steps through a highly selective monohalogenation of N-sulfonylated lactams of various ring sizes (from 5- to 8-membered rings) followed by a ring contraction reaction. The selective monohalogenation of N-sulfonyl lactams has been achieved in modest to excellent yields (9 examples, 39–96%) using N-halogenosuccinimides via the in situ generation of trimethylsilyl ketene aminal derivatives. The so-obtained α-halogeno N-sulfonyl lactams were engaged in a ring opening/ring closing reaction in the presence of various alcohols or anilines under basic conditions affording 2-carboxylated aza-rings, such as azetidine, pyrrolidine or piperidine derivatives in high yields (24 examples, 61–99%).
