59007-52-2Relevant articles and documents
Efficient synthesis of 2-substituted phthalimides from phthalic acids in one step
Chorell, Erik,Chorell, Elin
supporting information, p. 7512 - 7516 (2013/12/04)
Efficient procedures for synthesizing 2-substituted phthalimide (isoindole-1,3-dione) analogues starting from phthalic acids have been developed by using experimental design. The phthalimide central fragment frequently appears in biologically active compounds, materials, catalysts, and fluorescent probes, and therefore the development of general, fast, and convenient synthetic methods to this scaffold under neutral, acidic, and basic conditions would be attractive. After an initial screening, the use of acetonitrile, acetic acid, or pyridine in combination with microwave heating proved most promising. Experimental design was applied to these conditions to optimize the time, temperature, and concentration. This strategy has successfully generated synthetic methods that have been used to synthesize a series of phthalimides from phthalic acids and various amines or anilines in excellent yields. The developed methods have proven to be general, fast, convenient, and economic, and thus are expected to have broad utility to efficiently construct novel compounds for future biological and chemical applications. Efficient procedures for synthesizing 2-substituted phthalimide (isoindole-1,3-dione) analogues starting from phthalic acids have been developed by using experimental design. The developed methods are fast, general, high-yielding, do not use additives, and are based on 1:1 molar ratios.
Aza analogues of thalidomidesynthesis and evaluation as inhibitors of tumor necrosisfactor-α production in vitro
Gütschow, Michael,Hecker, Thomas,Thiele, Andrea,Hauschildt, Sunna,Eger, Kurt
, p. 1059 - 1065 (2007/10/03)
A synthetic entry to derivatives of the new classes of 5-phthalimidouracils and 5-phthalimidobarbituric acids is reported. These 5-phthalimidopyramines as well as phthalimido-2,4-difluorobenzenes were designed as analogues of thalidomide, a well known inhibitor of TNF-α production. A preliminary in vitro investigation of the compounds as inhibitors of the TNF-α production was performed. Among the compounds of the present series, (5-ethyl-1-phenyl-5- tetrafluorophthalimido)barbituric acid and (2- 2,4-difluorophenyl)-4,5,6,7-tetrafluoro-1H-isoindole-1,3 2H)-dione were proved to be potent inhibitors. Both compounds showed inhibitory activity in the lower micromolar range of the LPS-induced TNF-α production in human monocytes. Copyright
