Synthesis of Bis-pyrrolizidine-Fused Dispiro-oxindole Analogues of Curcumin via One-Pot Azomethine Ylide Cycloaddition: Experimental and Computational Approach toward Regio- and Diastereoselection.
Curcumin has been transformed to racemic curcuminoids via an azomethine ylide cycloaddition reaction using isatin/acenaphthoquinone and proline as the reagents. The products were characterized by extensive 1D/2D NMR analysis and single-crystal X-ray crystallographic studies. The enantiomers of one racemic product were separated by HPLC on a Chiralcel OD-H column and were indeed confirmed by the CD spectra of the separated enantiomers.
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.
Yogesh P
YP
Bharitkar
National Institute of Pharmaceutical Education and Research, Indian Institute of Chemical Biology , 4, Raja S. C. Mullick Road, Jadavpur, Kolkata 700 032, India.
Mohua
M
Das
National Institute of Pharmaceutical Education and Research, Indian Institute of Chemical Biology , 4, Raja S. C. Mullick Road, Jadavpur, Kolkata 700 032, India.
Neha
N
Kumari
National Institute of Pharmaceutical Education and Research, Indian Institute of Chemical Biology , 4, Raja S. C. Mullick Road, Jadavpur, Kolkata 700 032, India.
M Padma
MP
Kumari
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.
Abhijit
A
Hazra
Department of Chemical Technology, University of Calcutta , Kolkata, West Bengal 700 009, India.
Sagar S
SS
Bhayye
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.
Ramalingam
R
Natarajan
National Institute of Pharmaceutical Education and Research, Indian Institute of Chemical Biology , 4, Raja S. C. Mullick Road, Jadavpur, Kolkata 700 032, India.
Siddharth
S
Shah
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.
Sourav
S
Chatterjee
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.
Nirup B
NB
Mondal
D001391:Azo Compounds / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D003474:Curcumin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D007211:Indoles / Q000737:chemistry; D007510:Isatin / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D000078183:Oxindoles; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry*
D001391:Azo Compounds; D007211:Indoles; D000078183:Oxindoles; D011763:Pyrrolizidine Alkaloids; D013882:Thiosemicarbazones; C512188:azomethine; C022960:2-oxindole; D007510:Isatin; D003474:Curcumin