119162-53-7Relevant articles and documents
Gramine-based structure optimization to enhance anti-gastric cancer activity
Zhang, Xin-Hui,Guo, Qian,Wang, Heng-Ying,Li, Yi-Han,Khamis, Mussa Yussuf,Ma, Li-Ying,Wang, Bo,Liu, Hong-Min
, (2021)
Gramine is a natural indole alkaloid with a wide range of biological activities, but its anti-gastric cancer activity is poor. Herein, a pharmacophore fusion strategy was adopted to design and synthesize a new series of indole-azole hybrids on the structural basis of gramine. Based on our previous studies, different nitrogen-containing five-membered heterocyclic rings and terminal alkyne group were introduced into the indole-based scaffold to investigate their effect on improving the anti-gastric cancer activity of gramine derivatives. Structure-activity relationship (SAR) studies highlighted the role played by terminal alkyne in enhancing the inhibitory effect, and compound 16h displayed the best antiproliferative activity against gastric cancer MGC803 cells with IC50 value of 3.74 μM. Further investigations displayed compound 16h could induce mitochondria-mediated apoptosis, and caused cell cycle arrest at G2/M phase. Besides, compound 16h could inhibit the metastasis ability of MGC803 cells. Our studies may provide a new strategy for structural optimization of gramine to enhance anti-gastric cancer activity, and provide a potential candidate for the treatment of gastric cancer.
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
INHIBITING TRABID
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Paragraph 00170-00171; 00245-00246, (2020/11/23)
The present disclosure is directed to compounds of formulas (I) - (VII), which are useful as modulators of TRABID. The compounds are further useful in the inhibition of TRABID and the treatment of diseases or disorders associated with the inhibition of TRABID. For instance, the disclosure is concerned with compounds and compositions for inhibition of TRABID, methods of treating diseases associated with the inhibition of TRABID (e.g., autoimmune inflammatory diseases including, but not limited to, psoriasis), and methods of synthesis of these compounds.
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
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.