Sulfoxides and stereochemical control in organometallic chemistry

Griffiths, Sib L.; Marcos, Carlos F.; Perrio, StBphane; Saberi, Stephen P.; Thomas, Susan E.; Tustin, Gary J.; Wierzchleyski, Adam T.

doi:10.1351/pac199466071565

Cited by 11 publications

(3 citation statements)

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“…Thus, substituent and conformation effects might affect the charge distribution at the oxygens, and even Fe À O bond. Recent experimental evidences for O...p through-space interactions [60,61] indicate that some artemisinin oxygens, that from the peroxyde group which is not bound to iron, could participate in such interactions. A recent finding by Ziegler et al [62] ™that substrate recognition is based on porphyrin moiety rather than specific metal recognition∫, supports the possibility of various heme-artemisinine non-bonding interactions.…”

Section: Resultsmentioning

confidence: 99%

Artemisinin Derivatives with Antimalarial Activity against Plasmodium falciparum Designed with the Aid of Quantum Chemical and Partial Least Squares Methods

et al. 2003

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Artemisinin derivatives with antimalarial activity against Plasmodium falciparum resistant to mefloquine are designed with the aid of Quantum Chemical and Partial Least Squares Methods. The PLS model with three principal components explaining 89.55% of total variance, Q 2 0.83 and R 2 0.92 was obtained for 14/5 molecules in the training/external validation set. The most important descriptors for the design of the model were one level above the lowest unoccupied molecular orbital energy (LUMO 1), atomic charges in atoms C9 and C11 (Q 9 ) and (Q 11 ) respectively, the maximum number of hydrogen atoms that might make contact with heme (NH) and RDF030 m (a radial distribution function centered at 3.0 ä interatomic distance and weighted by atomic masses). From a set of ten proposed artemisinin derivatives, a new compound (26), was predicted with antimalarial activity higher than the compounds reported in literature. Molecular graphics and modeling supported the PLS results and revealed heme-ligand and protein-ligand stereoelectronic relationships as important for antimalarial activity. The most active 26 and 29 in the prediction set possess substituents at C9 able to extend to hemoglobin exterior, what determines the high activity of these compounds.

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Section: Resultsmentioning

confidence: 99%

Artemisinin Derivatives with Antimalarial Activity against Plasmodium falciparum Designed with the Aid of Quantum Chemical and Partial Least Squares Methods

et al. 2003

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“…These include the oxidative chlorination of a-(phenylthio) amides to give (2)-3-chloro-2-phenylthio acrylamides (Scheme 62), 95 the Vilsmaier reaction of dithioketals for the synthesis of /3-(alkylthio)ethylenic aldehydes (Scheme monoacetal of a /3-ketoaldehyde, or an a, /3-unsaturated ketone and oxidation, for the synthesis of /3-(alkyl-or ary1thio)-a, /3-unsaturated ketones (Scheme 64). 97 and addition of thiols to the…”

Section: Pdclddppf)mentioning

confidence: 99%

Synthesis of thiols, sulfides, sulfoxides and sulfones

Rayner¹

1995

Contemp. Org. Synth.

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“…Silyl enol ethers, reactions in water, 159 Singlet oxidation reactions, 23 Sol-gel chemistry, 66 Spiro compounds, 181 Steroidal alkaloids, from natural products, 101 Steroids, 187 sapogenins, 188 saponins, 188 synthetic enzymes, 75 Sulfoxides, chiral, in natural products, 123 organometallic reactions, 94 Sulfur compounds, 69 Sulfur,vinyl ethers,141,143 Supramolecular chemistry, 42, 100 1,10-Phenanthroline derivatives, 39 Supramolecular complexes, 36 Synthesis of actones, 81 of aldehydes, 67 of alkaloids, 122 of /3-amino acids, with sulfonyl radicals, 69 Taxol, 43 Terpenoids, 177 diterpenoids, 186 sesquiterpenoids, 186 synthesis, 78,79 tri terpenoids, 189 Tetrapropylammonium perruthenate, 158 Tetrazoles, 72 Thiiranes, synthesis, 143 Thin-layer chromatography, 195 Thiocarbamates, synthesis, 143 Triazoles, synthesis of nitro derivatives,…”

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confidence: 99%