Synthesis of diversely substituted bis-pyrrolizidino/ thiopyrrolizidino oxindolo/acenaphthyleno curcuminoids via sequential azomethine ylide cycloaddition

Meenakshi Singh; Abhijit Hazra; Yogesh P Bharitkar; Ritu Kalia; Ashutosh Sahoo; Sneha Saha; V Ravichandiran; Shekhar Ghosh; Nirup B Mondal

doi:10.1039/c8ra02725k

Synthesis of diversely substituted bis-pyrrolizidino/ thiopyrrolizidino oxindolo/acenaphthyleno curcuminoids via sequential azomethine ylide cycloaddition

RSC Adv. 2018 May 23;8(34):18938-18951. doi: 10.1039/c8ra02725k. eCollection 2018 May 22.

Authors

Meenakshi Singh¹, Abhijit Hazra¹, Yogesh P Bharitkar¹, Ritu Kalia¹, Ashutosh Sahoo², Sneha Saha¹, V Ravichandiran¹, Shekhar Ghosh², Nirup B Mondal²

Affiliations

¹ National Institute of Pharmaceutical Education and Research (NIPER) (IICB Campus), 4, Raja S. C. Mullick Road, Jadavpur Kolkata - 700 032 India.
² Department of Organic and Medicinal Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research 4, Raja S. C. Mullick Road, Jadavpur Kolkata - 700 032 India apuhazra@gmail.com yogeshbharitkar@gmail.com.

Abstract

Curcumin has been transformed to several diversely substituted bis-pyrrolizidino/thiopyrrolizidino oxindolo/acenaphthyleno curcuminoids via a sequential azomethine ylide cycloaddition reaction using isatins/acenaphthoquinone and proline/thioproline as the reagents. The products were separated via extensive chromatography and characterized by 1D/2D NMR and HRMS analysis.