ChemInform Abstract: SIMPLE SYNTHESES OF 3‐SUBSTITUTED INDOLES AND THEIR APPLICATION FOR HIGH YIELD CARBON‐14 LABELING

Schallenberg, J.; Meyer, Edgar F.

doi:10.1002/chin.198319190

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2005

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“…The indole-3-methanamine 25 of brassinin 1 was prepared through the reductive amination of indole-3-carboxaldehyde. Although there are several different reductive amination procedures reported in the literature, , we found Mehta's procedure 9a to be the most effective. Homotryptamine 26 , the amine reagent for 4 , was synthesized in three steps from indole-3-propanoic acid following literature precedent .…”

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confidence: 59%

Structure−Activity Study of Brassinin Derivatives as Indoleamine 2,3-Dioxygenase Inhibitors

et al. 2005

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A screen of indole-based structures revealed the natural product brassinin to be a moderate inhibitor of indoleamine 2,3-dioxygenase (IDO), a new cancer immunosuppression target. A structure-activity study was undertaken to determine which elements of the brassinin structure could be modified to enhance potency. Three important discoveries have been made, which will impact future IDO inhibitor development: (i) The dithiocarbamate portion of the brassinin lead is a crucial moiety, which may be binding to the heme iron of IDO; (ii) an indole ring is not necessary for IDO inhibition; and (iii) substitution of the S-methyl group of brassinin with large aromatic groups provides inhibitors that are three times more potent in vitro than the most commonly used IDO inhibitor, 1-methyl-tryptophan.

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Section: Resultsmentioning

confidence: 59%

Structure−Activity Study of Brassinin Derivatives as Indoleamine 2,3-Dioxygenase Inhibitors

et al. 2005

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ChemInform Abstract: SIMPLE SYNTHESES OF 3‐SUBSTITUTED INDOLES AND THEIR APPLICATION FOR HIGH YIELD CARBON‐14 LABELING

Abstract: Die Indolderivate (IIa) bzw. (IIb) können in sehr guten Ausb. ausgehend vom bekannten Oxim (Ia) bzw. Aldehyd (Ib) gewonnen werden [nachfolgende Reduktion von (IIb) analog (Ia)‐(IIa) gibt (IIc) ].

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Structure−Activity Study of Brassinin Derivatives as Indoleamine 2,3-Dioxygenase Inhibitors

Structure−Activity Study of Brassinin Derivatives as Indoleamine 2,3-Dioxygenase Inhibitors

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