2039-66-9Relevant articles and documents
An efficient synthesis and bioactivity evaluation of oxazole-containing natural hinduchelins A-D and their derivatives
Ke, Shaoyong,Zhang, Zhigang,Shi, Liqiao,Liu, Manli,Fang, Wei,Zhang, Yani,Wu, Zhaoyuan,Wan, Zhongyi,Long, Tong,Wang, Kaimei
, p. 3635 - 3639 (2019)
Oxazoles are an important class of biologically active metabolites from nature, and exhibit broad biological activities as the lead for drug discovery. Hinduchelins are a class of unusual natural products with an oxazole unit, isolated from Streptoalloteichus hindustanus, and with a potential iron-chelating ability. These compounds are the first identified naturally occurring unusual oxazole derivatives to possess a catechol unit. However, some of these compounds are not abundant in nature, and thus, the efficient syntheses of these compounds are advantageous in exploring their potential applications. This paper reports the efficient synthesis and bio-evaluation of hinduchelins A-D and their derivatives with convenient procedures and high yields.
Continued Exploration of Trifunctional Alkyl 4-Chloro-2-diazo-3-oxobutanoates: Streamlined Entry into [1,2,3]Triazolo[5,1- c ][1,4]benzoxazines and [1,2,3]Triazolo[5,1- c ][1,4]benzoxazepines
Budeev, Anton V.,Kantin, Grigory,Dar'In, Dmitry,Krasavin, Mikhail
, p. 2155 - 2166 (2021/02/22)
Further exploration of the trifunctional character of previously introduced alkyl 4-chloro-2-diazo-3-oxobutanoates in reactions with N -protected substituted o -aminophenols followed by deprotection provided a convenient entry into [1,2,3]triazolo[5,1- c ][1,4]benzoxazines, which are of high medicinal importance, as documented in the literature. The same approach applied to N -protected substituted o -(aminomethyl)phenols afforded [1,2,3]triazolo[5,1- c ][1,4]benzoxazepines, which are practically unexplored compounds from a medicinal chemistry perspective. The syntheses start with S N 2-type alkylation of the phenol. Removal of the protecting group triggers imine formation followed by Wolff 1,2,3-triazole synthesis.
Monoligated Pd(0)-catalyzed intramolecular ortho- and para-arylation of phenols for the synthesis of aporphine alkaloids. Synthesis of (-)-lirinine
Hellal, Malik,Singh, Shambhavi,Cuny, Gregory D.
, p. 1674 - 1681 (2012/03/10)
An intramolecular palladium(0)-mediated ortho-arylation of phenols applied to the synthesis of various substituted aporphines is reported. Most significantly, the efficiency of the transformation was enhanced by the use of monoligated Pd(0) complexes. This methodology was extended to para-arylation of phenols and employed in the synthesis of the aporphine alkaloid (-)-lirinine.
