84902-24-9Relevant articles and documents
WDR5 INHIBITORS AND MODULATORS
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Paragraph 00293, (2021/05/15)
Isoquinolmone compounds and derivatives inhibit WDR5 and associated protein-protein interactions, and the compounds and their pharmaceutical compositions are useful for treating disorders and conditions in a subject, such as cancer cell proliferation.
Enantioselective synthesis of tunable chiral pyridine-aminophosphine ligands and their applications in asymmetric hydrogenation
Liu, Youran,Chen, Fei,He, Yan-Mei,Li, Chenghao,Fan, Qing-Hua
, p. 5099 - 5105 (2019/05/29)
A small library of tunable chiral pyridine-aminophosphine ligands were enantioselectively synthesized based on chiral 2-(pyridin-2-yl)-substituted 1,2,3,4-tetrahydroquinoline scaffolds, which were obtained in high yields and with excellent enantioselectivities via ruthenium-catalyzed asymmetric hydrogenation of 2-(pyridin-2-yl)quinolines. The protocol features a wide substrate scope and mild reaction conditions, enabling scalable synthesis. These chiral P,N ligands were successfully applied in the Ir-catalyzed asymmetric hydrogenation of benchmark olefins and challenging seven-membered cyclic imines including benzazepines and benzodiazepines. Excellent enantio- and diastereoselectivity (up to 99% ee and >20:1 dr), and/or unprecedented chemoselectivity were obtained in the asymmetric hydrogenation of 2,4-diaryl-3H-benzo[b]azepines and 2,4-diaryl-3H-benzo[b][1,4]diazepines.
Chiral Phosphoric-Acid-Catalyzed Cascade Prins Cyclization
Sun, Huai-Ri,Zhao, Qingyang,Yang, Hui,Yang, Sen,Gou, Bo-Bo,Chen, Jie,Zhou, Ling
supporting information, p. 7143 - 7148 (2019/09/07)
Asymmetric Prins cyclization of in situ generated quinone methides and o-aminobenzaldehyde has been developed with chiral phosphoric acid as an efficient catalyst. This unconventional method provides a facile access to diverse functionalized trans-fused pyrano-/furo-tetrahydroquinoline derivatives in excellent yield and with excellent diastereo- and enantioselectivities (up to 99% yield and 99% ee). Mechanistic studies suggested that the three adjacent tertiary stereocenters were constructed through the sequential formation of C-O, C-C, and C-N bonds.
Ugi three-component reaction of alcohols, amines and isocyanides: A new approach to the synthesis of cyclic amidines
Dev, Kapil,Ramakrishna,Maurya, Saransh Wales,Siddiqui, Ibadur Rahman,Kant, Ruchir,Maurya, Rakesh
supporting information, p. 1202 - 1206 (2017/03/02)
We have developed a novel, simple, efficient and one pot synthetic protocol for the synthesis of cyclic amidines via Ugi three-component reaction of alcohols, amines, and isocyanides.
Synthesis of quinolines and naphthyridines: Via catalytic retro-aldol reaction of β-hydroxyketones with ortho -aminobenzaldehydes or nicotinaldehydes
Zhang, Song-Lin,Deng, Zhu-Qin
, p. 8966 - 8970 (2016/10/05)
A Cu(i)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα-Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields.
Metal free carboamination of internal alkynes - An easy access to polysubstituted quinolines
Stopka,Niggemann
supporting information, p. 5761 - 5764 (2016/05/19)
A metal free carboamination of unactivated alkynes towards highly substituted quinolines was realized in the presence of a synergistic Br?nsted acid catalyst system. Supported by mechanistic probes, the reaction proceeds via a highly reactive vinyl cation in a C-C bond formation - Schmidt reaction sequence. The irreversible extrusion of N2, as a powerful driving force, allows for a general conversion of poorly nucleophilic aliphatic alkynes.
Synthesis and insecticidal evaluation of novel N- pyridylpyrazolecarboxamides containing cyano substituent in the ortho-position
Mao, Mingzhen,Li, Yuxin,Liu, Qiaoxia,Zhou, Yunyun,Zhang, Xiulan,Xiong, Lixia,Li, Yongqiang,Li, Zhengming
, p. 42 - 46 (2013/02/23)
In an attempt to search for potent insecticides targeting the ryanodine receptor (RyR), a series of novel N-pyridylpyrazolecarboxamides containing cyano substituent in the ortho-position were designed and synthesized. Their insecticidal activities of targ
Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands
Ida, Yoshihiro,Matsubara, Ayaka,Nemoto, Toru,Saito, Manabu,Hirayama, Shigeto,Fujii, Hideaki,Nagase, Hiroshi
, p. 5810 - 5831 (2012/11/06)
We have reported previously the novel δ opioid agonist KNT-127 which showed high affinity and selectivity for the δ receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical δ agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5′-, 6′-, 7′- or 8′-position of the quinoline ring and revealed that many derivatives with 5′- or 8′-substituents showed high affinities and selectivities for the δ receptor. Especially, SYK-153 with an 8′-OH group showed the highest affinity and the most balanced and highest selectivity for the δ receptor among the synthesized compounds.
Metal Template Reactions. XIV. Synthesis of Macrocyclic Metal Complexes from 2,2'-(Oxalyldiimino)bisbenzaldehyde and Related Oxamido Aldehydes and Ketones
Black, David St. C.,Vanderzalm, Corrie H. Bos,Wong, Laurence C. H.
, p. 2435 - 2443 (2007/10/02)
Numerous macrocyclic nickel(II) complexes and occasional copper(II) and cobalt(II) complexes have been obtained from template reactions of the dialdehydes (3a-c) with diamines (4).Related complexes from the diketones (3d,e) were prepared in some cases wit