26465-37-2Relevant academic research and scientific papers
A Unified Catalytic Asymmetric (4+1) and (5+1) Annulation Strategy to Access Chiral Spirooxindole-Fused Oxacycles
Gao, Min,Gong, Xiangnan,Hu, Lin,Luo, Yanshu,Xia, Yuanzhi,Xu, Qianlan,Zhao, Yukun
supporting information, p. 19813 - 19820 (2021/08/03)
A unified catalytic asymmetric (N+1) (N=4, 5) annulation reaction of oxindoles with bifunctional peroxides has been achieved in the presence of a chiral phase-transfer catalyst (PTC). This general strategy utilizes peroxides as unique bielectrophilic four- or five-atom synthons to participate in the C?C and the subsequent umpolung C?O bond-forming reactions with one-carbon unit nucleophiles, thus providing a distinct method to access the valuable chiral spirooxindole-tetrahydrofurans and -tetrahydropyrans with good yields and high enantioselectivities under mild conditions. DFT calculations were performed to rationalize the origin of high enantioselectivity. The gram-scale syntheses and synthetic utility of the resultant products were also demonstrated.
Probing cytochrome P450 (CYP) bioactivation with chloromethylindoline bioprecursors derived from the duocarmycin family of compounds
Ortuzar, Natalia,Karu, Kersti,Presa, Daniela,Morais, Goreti R.,Sheldrake, Helen M.,Shnyder, Steve D.,Barnieh, Francis M.,Loadman, Paul M.,Patterson, Laurence H.,Pors, Klaus,Searcey, Mark
, (2021/05/04)
The duocarmycins belong to a class of agent which has great potential for use in cancer therapy. Their exquisite potency means they are too toxic for systemic use, and targeted approaches are required to unlock their clinical potential. In this study, we
Dihalide impurity in ziprasidone hydrochloride intermediate and preparation method of dihalide impurity
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Paragraph 0122; 0137-0139, (2021/05/01)
The invention provides a dihalide impurity in a ziprasidone hydrochloride intermediate. The dihalide impurity has a structure shown as a formula 1. On the basis that the ziprasidone hydrochloride intermediate can bring in the dechlorination impurity or the preparation process contains the dechlorination step, the dechlorination impurity with a specific structure is obtained, and the preparation steps of the corresponding impurity are provided, so a corresponding technical support is provided for preparation of ziprasidone hydrochloride. The synthesis method provided by the invention has the advantages of simple process, strong controllability and mild conditions, can be used for quality standard establishment and quality control links of ziprasidone hydrochloride process research and development, production and the like, and provides technical support for ziprasidone hydrochloride medication safety. The method can be used for quality research such as qualitative and quantitative analysis of impurities in ziprasidone hydrochloride synthesis, so that the quality of ziprasidone hydrochloride can be improved, and important guiding significance is provided for reducing the medication risk of ziprasidone hydrochloride.
Post-Assembly Photomasking of Potassium Acyltrifluoroborates (KATs) for Two-Photon 3D Patterning of PEG-Hydrogels
Song, Haewon,Wu, Dino,Mazunin, Dimitry,Liu, Sizhou M.,Sato, Yoshikatsu,Broguiere, Nicolas,Zenobi-Wong, Marcy,Bode, Jeffrey W.
, (2020/10/22)
Chemical ligation reactions of functional groups that can be masked with two-photon labile protecting groups provide a powerful technology for the three-dimensional patterning of molecules – including proteins – onto hydrogel scaffolds. In order to utiliz
Regio- and enantioselective synthesis of functionalized tetrahydroquinolines by palladium-catalyzed cyclization of 2- amidophenylmalonates with allylic bisacetates
Yoshida, Masahiro,Maeyama, Yohei,Shishido, Kozo
, p. 9962 - 9972,11 (2012/12/11)
A palladium-catalyzed cyclization of 2-amidophenylmalonates with allylic bisacetates is described. Tetrahydroquinolines having a vinyl group at the 3- or 2-position were produced, in which the regioselectivity of the resulting products was altered depending on the substituent on the amino group. The product was transformed to the azabicyclo[3.3.1]nonene via the ring-closing metathesis. Enantioselective reactions also successfully proceeded in the presence of (S)-BINAP to give the optically active tetrahydroquinoline with high enantioselectivity.
Asymmetic organocatalytic 1,3-dipolar cycloaddition of azomethine ylide to methyl 2-(2-nitrophenyl)acrylate for the synthesis of diastereoisomers of spirotryprostatin A
Cheng, Mou-Nuo,Wang, Hao,Gong, Liu-Zhu
supporting information; experimental part, p. 2418 - 2421 (2011/06/23)
Chemical equations presented. The total synthesis of two diastereomers of spirotryprostatin A has been established starting with an asymmetric 1,3-dipolar cycloaddition of methyl 2-(2-nitrophenyl)acrylate with azomethine ylides catalyzed by a Bronsted aci
Diphosphine-catalyzed mixed double-michael reaction: A unified synthesis of lndolines, Dihydropyrrolopyridines, Benzimidazolines, Tetrahydroquinolines, Tetrahydroisoquinolines, Dihydrobenzo-1,4-oxazines, and Dihydrobenzo-3,1- oxazines
Sriramurthy, Vardhineedi,Kwon, Ohyun
supporting information; experimental part, p. 1084 - 1087 (2010/06/15)
(Figure Presented) Seven different types of benzannulated N-heterocycles-indolines, dihydropyrrolopyridlnes, benzimidazolines, dihydrobenzo-3,1-oxazines, benzomorpholines, tetrahydroquinolines, and tetrahydroisoquinolines-can be obtained from simple dinuc
5-Substituted pyrido[2,3-d]pyrimidine, an inhibitor against three receptor tyrosine kinases
Kammasud, Naparat,Boonyarat, Chantana,Sanphanya, Kingkan,Utsintong, Maleeruk,Tsunoda, Satoshi,Sakurai, Hiroaki,Saiki, Ikuo,André, Isabelle,Grierson, David S.,Vajragupta, Opa
scheme or table, p. 745 - 750 (2009/09/25)
NP506, the 3-{2,4-dimethyl-5-[2-oxo-5-(N′-phenylhydrazinocarbonyl)-1,2-dihydro-indol-3-ylidenemethyl]-1H-pyrrol-3-yl}-propionic acid, was designed as FGF receptor 1 inhibitor by computational study and found to be more active against endothelial proliferation of HUVEC after the rhFGF-2 stimulation than SU6668 with minimum effective dose of 10 μM. NP506 inhibited the tyrosine phosphorylation in FGF, VEGF, and PDGF receptors and the activation of extracellular signal-regulated kinase (ERK), c-Jun-N-terminal-kinase (JNK) and AKT after the rhFGF-2 stimulation. The introduction of the phenyl hydrazide motif to the position 5 of the pyrido[2,3-d]pyrimidine scaffold led to the inhibitory effect in two signaling pathways: inhibition of AKT activation in the phosphatidyl inositol 3′-kinase (PI13K)/AKT signaling pathway and the inhibition of ERK and JNK activation in MAPK pathway.
Toward the improvement of the tandem halide displacement/amide coupling spiro-cyclization as a new route to γ-lactam and pyrroloisoquinoline templates
Allous, Iyad,Comesse, Sébastien,Berke?, Du?an,Alkyat, Amar,Da?ch, Adam
scheme or table, p. 4411 - 4415 (2009/10/26)
Two efficient and rapid accesses to spiro-oxindole entities bearing an imide function were presented, and their performance was compared. The key components are N-substituted α-bromoacetamides to reach these derivatives in tandem process. The resulting sp
