Chloroquine → (2S)-2-methyl-N-((S)-1-phenylethyl)octanamide

HRID 633786

Reaktionsgleichung

CCN(CCCC([NH:11][C:12]1[CH:13]=CN=[C:16]2[CH:21]=[C:20](Cl)[CH:19]=[CH:18][C:17]=12)C)CC.CC1N(/N=C/C2OC([N+]([O-])=O)=CC=2)CCS(=O)(=O)C1.C[C@@H]1[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)[CH2:68][C@H:67](O)[CH2:66][C@@:64]2(O)[O:65][C@H:60]([C@H:61]([C:93](O)=O)[C@@H:62](O)[CH2:63]2)C[C@@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H](N)[C@@H]2O)C=CC=CC=CC=CC=CC=CC=C1>>[CH3:93][C@@H:61]([CH2:62][CH2:63][CH2:64][CH2:66][CH2:67][CH3:68])[C:60]([NH:11][C@H:12]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:16]=1)[CH3:13])=[O:65]

Komponenten

Edukt 3

HCID 2719Chloroquine

HCID 5280965Amphotericin B

HCID 6842999Nifurtimox

Produkt 1

HCID 46237307(2S)-2-methyl-N-((S)-1-phenylethyl)octanamide

Versuchsvorschrift

Bioassays. All bioassays were performed in duplicate, testing at 10, 2, 0.4, 0.08 and 0.016 μg/mL. Malaria bioassays were performed as previously reported by our program, using chloroquine as a positive control (IC50=80-100 nM). Chagas bioassays were performed following the protocol of Buckner et al, and using nifurtimox as a positive control (IC50 3-5 μg/mL). Leishmaniasis bioassays were performed using a method previously employed in our laboratory, based on parasite DNA fluorescence. In this latter assay, amphotericin-B was used as the positive control and had an IC50 value of 80 ng/mL. Cytotoxicity bioassays were performed following an MTT cell proliferation assay protocol with green monkey Vero kidney cells.

Quellen und Nachweise

ORD-Eintrag: ord-d5698f8c8111443ab472a715ce2a2ac4
Quelldatensatz: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09321811B2

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