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

Mechanistic Study of the Spiroindolones: A New Class of Antimalarials

Bin Zou 1,* email, Peiling Yap 1 , Louis-Sebastian Sonntag 1 , Seh Yong Leong 1 , Bryan K. S. Yeung 1  and Thomas H. Keller 2 email
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; in revised form: 11 August 2012 / Accepted: 16 August 2012 / Published: 24 August 2012
(This article belongs to the Special Issue Spiro Compounds)
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Abstract: 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

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MDPI and ACS Style

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.

AMA Style

Zou B, Yap P, Sonntag L-S, Leong SY, Yeung BKS, Keller TH. Mechanistic Study of the Spiroindolones: A New Class of Antimalarials. Molecules. 2012; 17(9):10131-10141.

Chicago/Turabian Style

Zou, Bin; Yap, Peiling; Sonntag, Louis-Sebastian; Leong, Seh Yong; Yeung, Bryan K. S.; Keller, Thomas H. 2012. "Mechanistic Study of the Spiroindolones: A New Class of Antimalarials." Molecules 17, no. 9: 10131-10141.

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