6584-60-7Relevant academic research and scientific papers
New hydroxamic acid derivatives of fluoroquinolones: Synthesis and evaluation of antibacterial and anticancer properties
Rajulu, Gavara Govinda,Naik, Halehatty Seephya Bhojya,Viswanadhan, Abhilash,Thiruvengadam, Jayaraman,Rajesh, Kondodiyil,Ganesh, Sambasivam,Jagadheshan, Hiriyan,Kesavan, Poonimangadu Koppolu
, p. 168 - 175 (2014)
A series of new hydroxamic acid derivatives (6a-f) at C-3 position of fluoroquinolones were designed and synthesized through multistep synthesis. The design concept involved replacement of the 3-carboxylic acid in fluoquinolones with hydroxamic acid as an acid mimicking group. The synthetic work employed in this work provides a good example for the synthesis of pure hydroxamic acid based fluoroquinolones. The synthesized compounds were characterized by 1H-NMR, electrospray ionization (ESI)-MS and IR. The new compounds were tested for their in vitro antimicrobial and anti-proliferative activity. Out of the six derivatives, compound 6e exhibited moderate antibacterial activity by inhibiting the growth of Escherichia coli and Klebsiella pneumoniae (MIC: 4.00-8.00 μg/mL). Compounds 6b and 6f displayed good growth inhibition against A549 Lung adenocarcinoma and HCT-116 Colon carcinoma cell lines.
Photo-induced radical borylation of hemiacetals via C–C bond cleavage
Liu, Qianyi,Zhang, Jianning,Zhang, Lei,Mo, Fanyang
supporting information, (2021/01/05)
In this study, we reported a photo-induced radical borylation of hemiacetal derivatives via C–C bond cleavage. This transformation can be realized under mild conditions with simple reaction settings and irradiation of visible light. A series of substrates, including both cyclic and linear hemiacetal derivatives, were effectively transformed to the borylation product in moderate to good yields. Finally, the mechanism was studied in detail by DFT calculations, suggesting insight of the radical borylation process.
Photoinduced Fragmentation Borylation of Cyclic Alcohols and Hemiacetals
Aggarwal, Varinder K.,Madhavachary, Rudrakshula,Noble, Adam,Shu, Chao
supporting information, p. 7213 - 7218 (2020/10/12)
A visible-light photoinduced fragmentation borylation of O-phthalimido cycloalkanols with bis(catecholato)diboron is described. Structurally diverse keto and formyloxy alkyl boronic esters are shown to be conveniently prepared by radical-mediated ring opening of cyclic alcohols and hemiacetals, respectively. The reactions proceed under mild conditions in the absence of additives or photocatalysts, display excellent functional group tolerance, and are shown to allow cleavage of 4-, 5-, 6-, and 7-membered ring substrates. The mechanism proceeds via sequential homolytic N-O and C-C bond cleavages, the latter of which involves β-scission of an alkoxy radical, generating a carbonyl and an alkyl radical that is trapped by the diboron reagent. Spectroscopic studies suggest direct photoexcitation of either the phthalimide or diboron substrates with blue light can initiate a radical chain mechanism.
Ultrasound accelerated synthesis of: O-alkylated hydroximides under solvent- A nd metal-free conditions
Jiang, Hongmei,Tang, Xiaoyue,Liu, Sihan,Wang, Lian,Shen, Haicheng,Yang, Jiankui,Wang, Huixian,Gui, Qing-Wen
, p. 10223 - 10227 (2019/12/26)
A novel, sustainable, environmentally friendly, high substrate scope, efficient, solvent-free and metal catalyst-free method for the cross-dehydrogenative coupling (CDC) reaction between N-hydroxyphthalimide (NHPI) and benzyl/ether compounds is described. This coupling reaction proceeds through ultrasound acceleration. Compared to conventional heating conditions, the use of ultrasound techniques not only improves the reaction efficiency and enhances the reaction rate but also minimizes the side reactions.
Synthesis of α-oxygenated ketones and substituted catechols via the rearrangement of N-enoxy- and N-aryloxyphthalimides
Kroc, Michelle A.,Patil, Aditi,Carlos, Anthony,Ballantine, Josiah,Aguilar, Stephanie,Mo, Dong-Liang,Wang, Heng-Yen,Mueller, Daniel S.,Wink, Donald J.,Anderson, Laura L.
supporting information, p. 4125 - 4137 (2017/06/29)
A common approach to the synthesis of α-oxygenated carbonyl compounds and catechols is the treatment of a carbonyl compound or a phenol with an electrophilic oxygen source. As an alternative approach to these important structures, formal [3,3]-rearrangements of N-enoxyphthalimides, N-enoxyisoindolinones, and N-aryloxyphthalimides have been explored. When used in combination with an initial Chan-Lam coupling, these transformations facilitate the dioxygenation of alkenylboronic acids for the synthesis of α-oxygenated ketones and the dioxygenation of arylboronic acids for the synthesis of catechols. The rearrangements of N-enoxyisoindolinones have also been shown to be diastereoselective.
Copper nitrate-catalyzed oxidative coupling of unactivated C(sp3)-H bonds of ethers and alkanes with: N -hydroxyphthalimide: Synthesis of N -hydroxyimide esters
Xu, Xiaohe,Sun, Jian,Lin, Yuyan,Cheng, Jingya,Li, Pingping,Yan, Yiyan,Shuai, Qi,Xie, Yuanyuan
supporting information, p. 9875 - 9879 (2017/12/12)
A copper nitrate-catalyzed cross-dehydrogenative coupling reaction between N-hydroxyphthalimide (NHPI) and ethers/alkanes has been described. The reaction is accomplished smoothly by using simple and green molecular oxygen as the oxidant, providing an alternative for the efficient synthesis of N-alkoxyphthalimides. In addition, it was found that when tert-butyl ethers were used as substrates, unexpected N-hydroxyimide ester derivatives were obtained in moderate to excellent yields. To further understand this unusual transformation, control experiments were performed and a plausible mechanism was proposed.
Copper(II)-catalyzed cross dehydrogenative coupling reaction of N-hydroxyphthalimide with alkanes and ethers via unactivated C(sp3)-H activation at room temperature
Guo, Zhicheng,Jin, Can,Zhou, Jiadi,Su, Weike
, p. 79016 - 79019 (2016/09/09)
A copper(ii)-catalyzed cross dehydrogenative coupling reaction between N-hydroxyphthalimide and unactivated C(sp3)-H bonds of alkanes and ethers using Selectfluor as an oxidant is described. This efficient reaction system shows mild conditions and a broad substrate scope for the generation of O-substituted N-hydroxyphthalimide derivatives.
Oseltamivir hydroxamate and acyl sulfonamide derivatives as influenza neuraminidase inhibitors
Hong, Bei-Tao,Chen, Chun-Lin,Fang, Jim-Min,Tsai, Keng-Chang,Wang, Shi-Yun,Huang, Wen-I,Cheng, Yih-Shyun E.,Wong, Chi-Huey
supporting information, p. 6647 - 6654 (2015/02/19)
Tamiflu, the ethyl ester form of oseltamivir carboxylic acid (OC), is the first orally available anti-influenza drug for the front-line therapeutic option. In this study, the OC-hydroxamates, OC-sulfonamides and their guanidino congeners (GOC)
HDAC INHIBITING DERIVATIVES OF CAMPTOTHECIN
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Page/Page column 37-38, (2012/07/28)
The disclosure includes hydroxamic compounds of Formula I: (Formula I) wherein Z, L, R1, R2, and R3 are defined herein. Also disclosed is a method for treating a neoplastic disease or an immune disease with these compounds.
Hydroxamic acid-based bisubstrate analog inhibitors of Ras farnesyl protein transferase
Patel, Dinesh V.,Young, Marian G.,Robinson, Simon P.,Hunihan, Lisa,Dean, Brenda J.,Gordon, Eric M.
, p. 4197 - 4210 (2007/10/03)
The rational design, synthesis, and activity of novel, hydroxamic acid- based, collective bisubstrate analog inhibitors of farnesyl protein transferase (FPT) is described. This class of compounds differ structurally from the conventional FPT inhibitors by
