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Molecules 2012, 17(9), 10131-10141; doi:10.3390/molecules170910131

Mechanistic Study of the Spiroindolones: A New Class of Antimalarials

1,* , 1, 1, 1, 1 and 2
1 Novartis Institute for Tropical Diseases, 10 Biopolis Road, #05-01 Chromos, Singapore 2 Experimental Therapeutics Centre, 31 Biopolis Drive, #03-01 Nanos, Singapore
* Author to whom correspondence should be addressed.
Received: 4 July 2012 / Revised: 11 August 2012 / Accepted: 16 August 2012 / Published: 24 August 2012
(This article belongs to the Special Issue Spiro Compounds)
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During the synthesis of the new antimalarial drug candidate NITD609, a high degree of diastereoselectivity was observed in the Pictet-Spengler reaction. By isolating both the 4E and 4Z imine intermediates, a systematic mechanistic study of the reaction under both kinetic and thermodynamic conditions was conducted. This study provides insight into the source of the diastereoselectivity for this important class of compounds.
Keywords: malaria; spiroindolones; NITD609; Pictet-Spengler reaction; mechanism malaria; spiroindolones; NITD609; Pictet-Spengler reaction; mechanism
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Zou, B.; Yap, P.; Sonntag, L.-S.; Leong, S.Y.; Yeung, B.K.S.; Keller, T.H. Mechanistic Study of the Spiroindolones: A New Class of Antimalarials. Molecules 2012, 17, 10131-10141.

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