53463-68-6Relevant articles and documents
Hydroxyl-Assisted trans-Reduction of 1,3-Enynes: Application to the Formal Synthesis of (+)-Aspicilin
Schaubach, Sebastian,Michigami, Kenichi,Fürstner, Alois
, p. 202 - 208 (2017)
1,3-Enynes are hardly amenable to trans-hydrometalation reactions, because they tend to bind the standard ruthenium catalysts too tightly. However, catalysts comprising a [Cp?Ru-Cl] unit allow such compounds to be used, provided they contain an OH group next to the triple bond. This aspect is illustrated by a formal synthesis of the lichen-derived macrolide aspicilin. The required macrocyclic enyne precursor was formed by an efficient ring-closing alkyne metathesis reaction.
Improvement of antimalarial activity of a 3-alkylpiridine alkaloid analog by replacing the pyridine ring to a thiazole-containing heterocycle: Mode of action, mutagenicity profile, and Caco-2 cell-based permeability
Guimar?es, Daniel Silqueira Martins,de Sousa Luz, Letícia Silveira,do Nascimento, Sara Batista,Silva, Lorena Rabelo,de Miranda Martins, Natália Rezende,de Almeida, Heloísa Gon?alves,de Souza Reis, Vitória,Maluf, Sarah El Chamy,Budu, Alexandre,Marinho, Juliane Aparecida,Abramo, Clarice,Carmona, Adriana Karaoglanovic,da Silva, Marina Goulart,da Silva, Gisele Rodrigues,Kemmer, Victor Matheus,Butera, Anna Paola,Ribeiro-Viana, Renato Márcio,Gazarini, Marcos Leoni,Júnior, Clébio Soares Nascimento,Guimar?es, Luciana,dos Santos, Fabio Vieira,de Castro, Whocely Victor,Viana, Gustavo Henrique Ribeiro,de Brito, Cristiana Ferreira Alves,de Pilla Varotti, Fernando
, (2019)
The development of new antimalarial drugs is urgent to overcome the spread of resistance to the current treatment. Herein we synthesized the compound 3, a hit-to?lead optimization of a thiazole based on the most promising 3-alkylpyridine marine alkaloid analog. Compound 3 was tested against Plasmodium falciparum and has shown to be more potent than its precursor (IC50 values of 1.55 and 14.7 μM, respectively), with higher selectivity index (74.7) for noncancerous human cell line. This compound was not mutagenic and showed genotoxicity only at concentrations four-fold higher than its IC50. Compound 3 was tested in vivo against Plasmodium berghei NK65 strain and inhibited the development of parasite at 50 mg/kg. In silico and UV–vis approaches determined that compound 3 acts impairing hemozoin crystallization and confocal microscopy experiments corroborate these findings as the compound was capable of diminishing food vacuole acidity. The assay of uptake using human intestinal Caco-2 cell line showed that compound 3 is absorbed similarly to chloroquine, a standard antimalarial agent. Therefore, we present here compound 3 as a potent new lead antimalarial compound.
A New Asymmetric Synthesis of (S)-14-Methyloctadec-1-ene, the Sex Pheromone of the Peach Leafminer Moth
Bai, Hongjin,Du, Zhen-Ting,He, Guo-Guo,Liu, Lu,Tang, Meng,Wei, Liang,Zhang, Tao
, p. 1089 - 1095 (2020/07/25)
Abstract: An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of thepeach leafminer moth has been achieved. Based on the asymmetric methylation ofchiral (S)-4-benzyloxazolidin-2-one, thecarbon chain of the target molecule was assembled through aC1+C10+C4+C3procedure. The γ-lactone was transformed into 4-(benzyloxy)butanoic acid andthen, with the induction of Evan’s template, a chiral methyl group wasintroduced to the position of the carboxylic group in 97percent de. After reduction and a couple of chemicaloperations, the designed key intermediate A1was obtained. The synthesis of another moiety was started from decane-1,10-diolwhich was selectively protected and oxidized. The long carbon chain wasinstalled according to a Wittig protocol. After deprotection, oxidization, andmethylenation, the target molecule was synthesized in 7 linear steps with anoverall yield of 30.3percent.
Industrial synthesis method of dichocrocis punctiferalis sex pheromone
-
Paragraph 0023-0025, (2020/06/30)
The invention belongs to the field of chemical synthesis, and particularly relates to an industrial synthesis method of a dichocrocis punctiferalis sex pheromone. The method comprises the following steps: taking 1, 10-decanediol as a raw material; carrying out a single-side bromination reaction to prepare 10-bromodecanol; then reacting the 10-bromodecanol with triphenylphosphine to obtain 10-hydroxydecyltriphenylphosphine salt; performing a Wittig reaction with n-hexaldehyde under the action of alkali to obtain cis-based 10-hexadecene-1-ol; performing isomerization on the cis-based enol underthe action of p-methylthiophenol to obtain trans-based 10-hexadecene-1-ol; and finally performing oxidation under the action of an oxidant to obtain the final product 10-hexadecenal. The method is mild in reaction condition and suitable for large-scale production.
