Listunov, Dymytrii; Joly, Etienne; Duhayon, Carine; Saffon-Merceron, Nathalie; Fabing, Isabelle; Genisson, Yves; Maraval, Valerie; Chauvin, Remi published an article in 2018, the title of the article was Methinylogation Approach in Chiral Pharmacophore Design: from Alkynyl- to Allenyl-carbinol Warheads against Tumor Cells.Application In Synthesis of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate And the article contains the following content:
Extension of a structure-activity relationship study of the antitumor cytotoxicity of lipidic dialkynylcarbinols (DACs) is envisaged by formal methinylogation of one of the ethyndiyl moieties of the DAC warhead into the corresponding allenylalkynylcarbinol (AllAC) counterpart. External AllACs were directly obtained by methinylation of the parent DACs with formaldehyde in either the racemic or scalemic series. Isomers containing external propargyl and propynyl motifs were also prepared Internal AllACs were obtained as racemic statistical mixtures of stereoisomers in two steps from the key C5-DAC rac-TIPS-C C-CH(OH)-C CH and aldehydes. Kinetic resolution of the (S)-C5-DAC in 97 % ee and (R)-C5-DAC in 99 % ee was achieved by sequential lipase-mediated acetylation/hydrolysis using the Candida antartica lipase (Novozyme 435). The four internal AllAC stereoisomers were prepared by asym. methinylation with (R)- or (S)-diphenylprolinol as chiral auxiliary. Cytotoxicity assays on HCT116 cancer cells showed that the most active (eutomeric) external or internal AllAC exhibits an S configuration, a fatty chain length of n=12, and a 50 % inhibitory concentration IC50≈1.0 μM. The experimental process involved the reaction of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate(cas: 14602-86-9).Application In Synthesis of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate
The Article related to methinylogation chiral pharmacophore alkynyl allenyl carbinol preparation antitumor, alkynes, allenes, antitumor agents, asymmetric synthesis, lipidic alkynylcarbinols, Pharmacology: Structure-Activity and other aspects.Application In Synthesis of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate
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Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics