86685-98-5Relevant academic research and scientific papers
An enantioselective aza-Friedel-Crafts reaction of 5-aminoisoxazoles with isatin-derived: N -Boc ketimines
Liu, Hui,Yan, Yingkun,Li, Min,Zhang, Xiaomei
supporting information, p. 3820 - 3824 (2021/05/14)
By employing a chiral phosphoric acid as a catalyst, an enantioselective aza-Friedel-Crafts reaction of 5-aminoisoxazoles with isatin-derived N-Boc ketimines was realized. The reaction provided a wide variety of novel 3-isoxazole 3-amino-oxindoles with good yields (up to 99%) and moderate to good enantioselectivities (up to 99%). The absolute configuration of one product was assigned by X-ray crystal structural analysis and a plausible reaction mechanism was proposed. In addition, a scale-up reaction was performed successfully. Finally, one product was subjected to Suzuki-Miyaura coupling with phenylboronic acid to afford the product in a moderate yield without erosion of the enantioselectivity. This journal is
HIGHLY POTENT TACC3 INHIBITOR AS A NOVEL ANTICANCER DRUG CANDIDATE
-
, (2020/02/14)
The present invention relates to a new inhibitor chemotype 3-(4-methoxyphenyl)-N-(2-morpholinopyrimidin-4-yl) isoxazol-5-amine (BO-264) targeting TACC3 protein with high potency as a mitotic blocker for the treatment of breast and potentially other cancers.
Identification of diphenylalkylisoxazol-5-amine scaffold as novel activator of cardiac myosin
Boggu, Pulla Reddy,Venkateswararao, Eeda,Manickam, Manoj,Sharma, Niti,Kang, Jong Seong,Jung, Sang-Hun
, (2020/09/16)
To identify novel potent cardiac myosin activator, a series of diphenylalkylisoxazol-5-amine compounds 4–7 have been synthesized and evaluated for cardiac myosin ATPase activation. Among the 37 compounds, 4a (CMA at 10 μM = 81.6%), 4w (CMA at 10 μM = 71.2%) and 6b (CMA at 10 μM = 67.4%) showed potent cardiac myosin activation at a single concentration of 10 μM. These results suggested that the introduction of the amino-isoxazole ring as a bioisostere for urea group is acceptable for the cardiac myosin activation. Additional structure–activity relationship (SAR) studies were conducted. Para substitution (-Cl, –OCH3, -SO2N(CH3)2) to the phenyl rings or replacement of a phenyl ring with a heterocycle (pyridine, piperidine and tetrahydropyran) appeared to attenuate cardiac myosin activation at 10 μM. Additional hydrogen bonding acceptor next to the amino group of the isoxazoles did not enhance the activity. The potent isoxazole compounds showed selectivity for cardiac myosin activation over skeletal and smooth muscle myosin, and therefore these potent and selective isoxazole compounds could be considered as a new series of cardiac myosin ATPase activators for the treatment of systolic heart failure.
Reactions of 5-Aminoisoxazoles with α-Diazocarbonyl Compounds: Wolff Rearrangement vs N-H Insertion
Ge, Yun,Sun, Wangbin,Chen, Yang,Huang, Yulin,Liu, Zhuang,Jiang, Yaojia,Loh, Teck-Peng
, p. 2676 - 2688 (2019/02/26)
A highly chemoselective reaction between 5-aminoisoxazoles and α-diazocarbonyl compounds has been described. Both Wolff rearrangement and N-H insertion products can be obtained selectively by the judicious choice of reaction conditions. In the case of the
Hoveyda-Grubbs II Catalyst: A Useful Catalyst for One-Pot Visible-Light-Promoted Ring Contraction and Olefin Metathesis Reactions
Ge, Yun,Sun, Wangbin,Pei, Bingbing,Ding, Jia,Jiang, Yaojia,Loh, Teck-Peng
supporting information, p. 2774 - 2777 (2018/05/22)
A one-pot reaction to synthesize functionalized 2H-azirines through visible-light-mediated ring contraction and olefin metathesis of isoxazoles is described. Hoveyda-Grubbs II catalyst was found to function as a photocatalyst for these transformations, al
Human carbonic anhydrase inhibitory profile of mono- and bis-sulfonamides synthesized via a direct sulfochlorination of 3- and 4-(hetero)arylisoxazol-5-amine scaffolds
Krasavin, Mikhail,Korsakov, Mikhail,Zvonaryova, Zhanna,Semyonychev, Evgenii,Tuccinardi, Tiziano,Kalinin, Stanislav,Tan?, Muhammet,Supuran, Claudiu T.
, p. 1914 - 1925 (2017/03/08)
Three distinct series of isoxazole-based primary mono- and bis-sulfonamides have been synthesized via direct sulfochlorination, each of them delivering nanomolar inhibitors of human carbonic anhydrase. Certain pronounced SAR trends have been established a
Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers
Shen, Hang,Li, Jiaqiang,Liu, Qing,Pan, Jing,Huang, Ruofeng,Xiong, Yan
, p. 7212 - 7218 (2015/07/28)
An efficient method to synthesize β-ketonitriles from silyl enol ethers by an umploung hypervalent iodine(III)-CN species generated in situ from PhIO/BF3·Et2O/TMSCN has been developed for the first time. This method can be applied to structurally diverse aromatic and aliphatic substrates and further extended to preparation of bioactive compounds like 5-aminopyrazole and 5-aminoisoxazole.
The study of reactions of α-chlorocinnamonitriles with hydroxylamine
Nenajdenko,Golubinskii,Lenkova,Shastin,Balenkova
, p. 1728 - 1732 (2007/10/03)
The E-isomers of α-chlorocinnamonitriles react with hydroxylamine to give a mixture of isomeric aminoisoxazoles, while the Z-isomers yield 3-aryl-2-chloroacrylamide oximes.
A modified procedure for the synthesis of 5-amino-3-arylisoxazoles and their reactions with tetrasulfur tetranitride antimony(V) chloride complex (S4N4·SbCl5): Novel synthesis of 3-aryl-1,2,5-thiadiazole-4-carboxamides
Kong, Yung Cheol,Kim, Kyongtae,Park, Yung Ja
, p. 75 - 89 (2007/10/03)
Dropwise addition of α-bromo ketoximes to a solution of KCN in MeOH at room temperature gave 5-amino-3-arylisoxazoles in moderate to good yields. Treatment of the isoxazoles prepared with tetrasulfur tetranitride antimony (V) chloride complex (S4N4·SbCl5) in toluene at 100°C afforded novel 3-aryl-1,2,5-thiadiazole-4-carboxamides.
