Uses
5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid is a yellow crystalline substance, mainly used as pharmaceutical intermediates.
Application
5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid can be used to prepare a drug carrier (cRGD-PEG-N＝CH-R6-Por (cPRP) triblock copolymer) for achieving highly efficient synergistic combined chemotherapy-photodynamic cancer therapy.
Synthesis
Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate (19.4 g, 100 mmol) was used as a raw material and dissolved in a solvent mixture of methanol (100 mL) and water (400 mL). A 5N KOH solution (200 mL) was slowly added under stirring conditions. The reaction mixture was heated to reflux and stirred continuously for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted with 5N HCl solution to 3. Subsequently, the precipitate was collected by filtration and washed with distilled water. Finally, the resulting solid was dried under vacuum to afford the target product 2,4-dimethyl-5-formyl-1H-pyrrole-3-carboxylic acid (15.5 g, 94% yield) as a yellow-brown solid.
References
[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 1, p. 248 - 262
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 1, p. 139 - 146
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 3062 - 3065
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 14, p. 2782 - 2787
[5] Journal of Medicinal Chemistry, 2003, vol. 46, # 7, p. 1116 - 1119
