1611-56-9Relevant articles and documents
Synthesis of Terminally Substituted 9-Alkylidene-10-methyl Acridans
Varveri, Fannie S.,Nikokavouras, John,Mantaka-Marketou, Anastasia E.,Micha-Screttas, Maria
, p. 967 - 972 (1989)
ω-Substituted undecanals 1 and 2 reacted with acridine derivatives 3 and 5 to give the terminally substituted 9-alkylidene-10-methylacridans 6.The compounds prepared were highly fluorescent and exhibited chemiluminescent activity. - Keywords: Acridans; Chemiluminescence.
Synthesis of (Z/E)-11-tetradecen-1-ol, a component of Ostrinia nubilalis sex pheromone
Li,Yong,Aisa
, p. 224 - 226 (2008)
11-Tetradecen-1-ol acetate is a mixture of geometric isomers with the Z/E-conformations in a 94:6 ratio that is used as an attractant to trap corn pests. It has a powerful attractive action similar to that of an isomeric mixture of 11-tetradecenyl acetate with the Z/E-conformation in a 95:5 ratio that was extracted from the peritoneal cavity of male Ostrinia nubilalis Hubner in Xinjing (PRC).
Synthesis and antibacterial evaluation of a new series of N-Alkyl-2-alkynyl/(E)-alkenyl-4-(1H)-quinolones
Wube, Abraham,Guzman, Juan-David,Huefner, Antje,Hochfellner, Christina,Blunder, Martina,Bauer, Rudolf,Gibbons, Simon,Bhakta, Sanjib,Bucar, Franz
, p. 8217 - 8240 (2012)
To gain further insight into the structural requirements of the aliphatic group at position 2 for their antimycobacterial activity, some N-alkyl-4-(1H)-quinolones bearing position 2 alkynyls with various chain length and triple bond positions were prepared and tested for in vitro antibacterial activity against rapidly-growing strains of mycobacteria, the vaccine strain Mycobacterium bovis BCG, and methicillin-resistant Staphylococcus aureus strains, EMRSA-15 and -16. The compounds were also evaluated for inhibition of ATP-dependent MurE ligase of Mycobacterium tuberculosis. The lowest MIC value of 0.5 mg/L (1.2-1.5 μM) was found against M. fortuitum and M. smegmatis. These compounds displayed no or only weak toxicity to the human lung fibroblast cell line MRC-5 at 100 μM concentration. The quinolone derivatives exhibited pronounced activity against the epidemic MRSA strains (EMRSA-15 and -16) with MIC values of 2-128 mg/L 5.3-364.7 μM), and M. bovis BCG with an MIC value of 25 mg/L (66.0-77.4 μM). In addition, the compounds inhibited the MurE ligase of M. tuberculosis with moderate to weak activity showing IC50 values of 200-774 μM. The increased selectivity towards mycobacterial bacilli with reference to MRC-5 cells observed for 2-alkynyl quinolones compared to their corresponding 2-alkenyl analogues serves to highlight the mycobacterial specific effect of the triple bond. Exploration of a terminal bromine atom at the side chain of N-alkyl-2-(E)-alkenyl-4-(1H)-quinolones showed improved antimycobacterial activity whereas a cyclopropyl residue at N-1 was suggested to be detrimental to antibacterial activity.
Design, synthesis and antiparasitic evaluation of click phospholipids
Afroudakis, Pantelis,Barrias, Emile,Bifeld, Eugenia,Borsari, Chiara,Calogeropoulou, Theodora,Clos, Joachim,Costi, Maria Paola,Ellinger, Bernhard,Fotopoulou, Theano,Fragiadaki, Irini,Georgikopoulou, Kalliopi,Gul, Sheraz,Hachenberg, Julia,Kuzikov, Maria,Magoulas, George E.,Prousis, Kyriakos C.,Roussaki, Marina,Santarem, Nuno,Scoulica, Effie,Tejera Nevado, Paloma,da Silva, Anabela Cordeiro,de Souza, Wanderley
, (2021/07/26)
A library of seventeen novel ether phospholipid analogues, containing 5-membered heterocyclic rings (1,2,3-triazolyl, isoxazolyl, 1,3,4-oxadiazolyl and 1,2,4-oxadiazolyl) in the lipid portion were designed and synthesized aiming to identify optimised miltefosine analogues. The compounds were evaluated for their in vitro antiparasitic activity against Leishmania infantum and Leishmania donovani intracellular amastigotes, against Trypanosoma brucei brucei and against different developmental stages of Trypanosoma cruzi. The nature of the substituents of the heterocyclic ring (tail) and the oligomethylene spacer between the head group and the heterocyclic ring was found to affect the activity and toxicity of these compounds leading to a significantly improved understanding of their structure–activity relationships. The early ADMET profile of the new derivatives did not reveal major liabilities for the potent compounds. The 1,2,3-triazole derivative 27 substituted by a decyl tail, an undecyl spacer and a choline head group exhibited broad spectrum antiparasitic activity. It possessed low micromolar activity against the intracellular amastigotes of two L. infantum strains and T. cruzi Y strain epimastigotes, intracellular amastigotes and trypomastigotes, while its cytotoxicity concentration (CC50) against THP-1 macrophages ranged between 50 and 100 μM. Altogether, our work paves the way for the development of improved ether phospholipid derivatives to control neglected tropical diseases.
Me3SI-promoted chemoselective deacetylation: a general and mild protocol
Gurawa, Aakanksha,Kashyap, Sudhir,Kumar, Manoj
, p. 19310 - 19315 (2021/06/03)
A Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developedviaemploying KMnO4as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses an environmentally benign reagent system to perform quantitative and clean transformations under ambient conditions.
Highly Chemoselective Deprotection of the 2,2,2-Trichloroethoxycarbonyl (Troc) Protecting Group
Trost, Barry M.,Kalnmals, Christopher A.,Tracy, Jacob S.,Bai, Wen-Ju
supporting information, p. 8043 - 8046 (2019/01/04)
Nonreducing, pH-neutral conditions for the selective cleavage of the 2,2,2-trichloroethoxycarbonyl (Troc) protecting group are reported. Using trimethyltin hydroxide in 1,2-dichloroethane, Troc-protected alcohols, thiols, and amines can be selectively unmasked in the presence of various functionalities that are incompatible with the reducing conditions traditionally used to remove the Troc group. This mild deprotection protocol tolerates a variety of other hydrolytically sensitive and acid/base-sensitive moieties as well.
Mn(0)-mediated chemoselective reduction of aldehydes. Application to the synthesis of α-deuterioalcohols
Jimenez, Tania,Barea, Elisa,Oltra, J. Enrique,Cuerva, Juan M.,Justicia, Jose
experimental part, p. 7022 - 7025 (2010/11/18)
A mild, simple, safe, chemoselective reduction of different kinds of aldehydes to the corresponding alcohols mediated by the Mn dust/water system is described. In addition to this, the use of D2O leads to the synthesis of α-deuterated alcohols and constitutes an efficient, inexpensive alternative for the preparation of these compounds.
First syntheses of model long-chain trichloro[ω-(trimethylsilyl)alkynyl]silanes suitable for self-assembled monolayers on silicon surfaces
Banaszak, Estelle,Xu, Li-Wen,Bardeau, Jean-Fran?ois,Castanet, Anne-Sophie,Mortier, Jacques
experimental part, p. 3961 - 3966 (2009/09/30)
The preparation of the title compounds involves the introduction of the required Me3SiC{triple bond, long}C and trichlorosilyl groups at the termini of the alkyl chain via derivatization of easily accessible and inexpensive materials/reagents. Trichloro[ω-(trimethylsilyl)alkynyl]silanes are useful for the linkage to a hydroxylated silicon surface for multilayer formation and for further chemical modification of the tail group of the monolayer.
A dehydrohalogenation methodology for synthesizing terminal olefins under mild conditions
Berube, Marie,Kamal, Fatima,Roy, Jenny,Poirier, Donald
, p. 3085 - 3091 (2008/02/08)
A new methodology for preparing terminal olefins in good yield by dehydrohalogenation of primary alkyl iodide with tetrabutylammonium fluoride in dimethyl sulfoxide at room temperature is presented. Optimization of the mild reaction conditions and assays on various alkyl iodides are described. Georg Thieme Verlag Stuttgart.
Sodium bis(2-methoxyethoxy)aluminium hydride in petroleum ether; a reagent for the selective reduction of brominated fatty esters to bromo alcohols
Wells, Andy
, p. 1143 - 1147 (2007/10/03)
The combination of NaH2Al(OCH2CH2OMe)2/petroleum ether was found to be highly effective for the selective reduction of long chain esters to alcohols in the presence of alkyl bromides.
