4319-36-2Relevant academic research and scientific papers
PRODUCTION METHOD FOR HYDROXY-CARBOXYLIC ACID AMIDE COMPOUND, AND NOVEL ARYLBORONIC ACID COMPOUND
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Paragraph 0025; 0028; 0037, (2015/01/18)
A method for production of hydroxycarboxylic acid amide compounds, comprising performing amide condensation between an α- or β-hydroxycarboxylic acid compound and an amine compound in the presence as a catalyst of an alkylboronic acid represented by R3B(OH)2 (wherein R3 is a primary alkyl group) or an arylboronic acid compound to produce a hydroxycarboxylic acid amide compound, the arylboronic acid compound being represented by Formula (1): (in Formula (1), -(CH2)nNR1R2 is bonded at an ortho position or a para position, n is 1 or 2, R1 is a tertiary alkyl group, R2 is a secondary or tertiary alkyl group, and -NR1R2 may be a ring).
Structural optimization of berberine as a synergist to restore antifungal activity of fluconazole against drug-resistant Candida albicans
Liu, Hong,Wang, Liang,Li, Yan,Liu, Jiang,An, Maomao,Zhu, Shaolong,Cao, Yongbing,Jiang, Zhihui,Zhao, Mingzhu,Cai, Zhan,Dai, Li,Ni, Tingjunhong,Liu, Wei,Chen, Simin,Wei, Changqing,Zang, Chengxu,Tian, Shujuan,Yang, Jingyu,Wu, Chunfu,Zhang, Dazhi,Liu, Hua,Jiang, Yuanying
supporting information, p. 207 - 216 (2014/01/17)
We have conducted systematic structural modification, deconstruction, and reconstruction of the berberine core with the aim of lowering its cytotoxicity, investigating its pharmacophore, and ultimately, seeking novel synergistic agents to restore the effectiveness of fluconazole against fluconazole-resistant Candida albicans. A structure-activity relationship study of 95 analogues led us to identify the novel scaffold of N-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-2- (substituted phenyl)acetamides 7 a-l, which exhibited remarkable levels of in vitro synergistic antifungal activity. Compound 7 d (N-(2-(benzo[d][1,3]dioxol- 5-yl)ethyl)-2-(2-fluorophenyl)acetamide) significantly decreased the MIC 80 values of fluconazole from 128.0 μg mL-1 to 0.5 μg mL-1 against fluconazole-resistant C. albicans and exhibited much lower levels of cytotoxicity than berberine toward human umbilical vein endothelial cells. Build it better: Structural optimization of berberine led to the identification of the novel scaffold of N-(2-(benzo[d][1,3]dioxol-5-yl) ethyl)-2-(substituted phenyl)acetamides 7 a-l, which exhibited remarkable in vitro synergistic antifungal activity against fluconazole-resistant Candida albicans in combination with fluconazole. Compound 7 d exhibited much lower cytotoxicity than berberine toward human umbilical vein endothelial cells. Copyright
Direct synthesis of esters and amides from unprotected hydroxyaromatic and -aliphatic carboxylic acids
Katritzky, Alan R.,Singh, Sanjay K.,Cai, Chunming,Bobrov, Sergey
, p. 3364 - 3374 (2007/10/03)
A facile method for the activation of hydroxy-substituted carboxylic acids using benzotriazole chemistry without prior protection of the hydroxy substituents is presented. The N-acylbenzotriazole intermediates 2a-g, 6a-d, and 9a-c have been used for high-yielding synthesis of both aliphatic (3a-1) and aromatic (7a-h, 10a-f) hydroxy carboxamides. High yields of aromatic hydroxy esters 12a-h and 13a-i were obtained using either neat alcohols in neutral microwave conditions or nucleophilic alkoxides and the intermediate N-(arylacyl)benzotriazoles. Moderate yields were obtained in the case of aliphatic hydroxy esters 11a,b and thiolesters 11e-g from the intermediates 2a-c.
A one pot procedure for the synthesis of α-hydroxyamides from the corresponding α-hydroxyacids
Kelly,LaCour
, p. 859 - 869 (2007/10/02)
α-Hydroxyamides are synthesized from the corresponding α-hydroxyacids by generation of the bis-trimethylsilyl derivative and treating it with oxalyl chloride. Following addition of the appropriate amine, the TMS ether is hydrolized in the workup to provid
Base-Promoted Reaction of O-Sulfonylated Hydroxamic Acids with Nucleophiles. A New Mehtod for the Synthesis of α-Substituted Amides
Hoffman, Ribert V.,Nayyar, Naresh K.,Chen, Wenting
, p. 5700 - 5707 (2007/10/02)
Treatment of a series of hydroxamic acids 2 with mesyl chloride in the presence of 2 equiv of triethylamine at 0 deg C gives 2-chloroamides 3 in good yields.Use of a single equivalent of triethylamine gives the N-(mesyloxy)amides 1, which are versatile sy
