51323-71-8Relevant academic research and scientific papers
Enantiomeric synthesis of natural alkylglycerols and their antibacterial and antibiofilm activities
Fernández Montoya, Deicy J.,Contreras Jordan, Luis A.,Moreno-Murillo, Bárbara,Silva-Gómez, Edelberto,Mayorga-Wandurraga, Humberto
supporting information, p. 2544 - 2550 (2019/11/13)
Alkylglycerols (AKGs) are bioactive natural compounds that vary by alkyl chain length and degree of unsaturation, and their absolute configuration is 2S. Three AKGs (5l–5n) were synthesised in enantiomerically pure form, and were characterised for the first time together with 12 other known and naturally occurring AKGs (5a–5k, 5o). Their structures were established using 1H and 13C APT NMR with 2D-NMR, ESI-MS or HRESI-MS and optical rotation data, and they were tested for their antibacterial and antibiofilm activities. AKGs 5a–5m and 5o showed activity against five clinical isolates and P. aeruginosa ATCC 15442, with MIC values in the range of 15–125 μg/mL. In addition, at half of the MIC, most of the AKGs reduced S. aureus biofilm formation in the range of 23%–99% and P. aeruginosa ATCC 15442 biofilm formation in the range of 14%–64%. The antibiofilm activity of the AKGs assessed in this work had not previously been studied.
Diamine derivative anti-Trichomonas vaginalis and anti-Tritrichomonas foetus activities by effect on polyamine metabolism
Rigo, Graziela Vargas,Trein, Márcia Rodrigues,da Silva Trentin, Danielle,Macedo, Alexandre José,de Oliveira, Bruno Assis,de Almeida, Angelina Maria,Giordani, Raquel Brandt,de Almeida, Mauro Vieira,Tasca, Tiana
, p. 847 - 855 (2017/09/13)
Human and bovine trichomoniasis are sexually transmitted diseases (STD) caused by Trichomonas vaginalis and Tritrichomonas foetus, respectively. Human trichomoniasis is the most common non-viral STD in the world and bovine trichomoniasis causes significant economic losses to breeders. Considering the significant impact of the infections caused by these protozoa and the treatment failures, the search for new therapeutic alternatives becomes crucial. In this study the effect of diamines and amino alcohols in the in vitro viability of trichomonads was evaluated. Screening demonstrated the high activity of diamine 4 against these protozoa. Although cytotoxicity against HMVII cell line and slight hemolysis were observed in vitro, the compound showed no toxic effect on the Galleria mellonella in vivo model. Importantly, diamine 4 was active against both trichomonads species at 6 h and 24 h of incubation, and these effects was reverted by putrescine, a polyamine, suggesting competition for the same metabolic pathway. These findings indicate that the mechanism of action of diamine 4 is through the polyamine metabolism, a pathway distinct from that presented by metronidazole, the drug usually used to treat trichomoniasis and to which resistance is widely reported. These data demonstrate the importance of diamines as potential novel candidates as anti-T. vaginalis and anti-T. foetus agents.
Method for synthesizing azanol
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Paragraph 0151; 0192-0194, (2016/10/08)
The invention relates to a hydroxylamine synthesis method. The hydroxylamine synthesis method comprises the following steps: (A) enabling alcohol to react with alkyl sulfonyl halide in the presence of an acid-binding agent to obtain sulphonate; (B) enabling the obtained sulphonate in the step (A) to react with N-hydroxycyclodiimide in the presence of alkali to generate alkylate of the N-hydroxycyclodiimide; and (C) enabling the alkylate obtained in the step (B) to react with an aminolysis reagent or a hydrazinolysis reagent to obtain the hydroxylamine. The method is high in yield and suitable for large-scale industrial hydroxylamine synthesis.
Catalytic nucleophilic fluorination by an imidazolium ionic liquid possessing trialkylphosphine oxide functionality
Paramanik, Minakshmi,Singh, Rekha,Mukhopadhyay, Sulekha,Ghosh, Sunil K.
, p. 47 - 55 (2015/07/15)
Abstract The synthesis of a new alkylmethylimidazolium ionic liquid wherein the alkyl group is functionalized with dihexylphosphine oxide moiety at the terminal position has been achieved in four steps from 1-methylimidazole. This hybrid ionic liquid effectively catalyzed the nucleophilic fluorination of primary alkyl mesylates under mild conditions using CsF as the fluoride source with a faster rate compared to butylmethylimidazolium mesylate. The hybrid catalyst was recycled 5 times without compromising the yield and purity of the product. The nucleophilic fluorination has been used for the synthesis of diethyl 2-(5-fluoropentyl)-2-methyl malonate, a precursor of 18F isotopomer of an apoptosis imaging agent and the protected form of O-(2'-fluoroethyl)-l-tyrosine, a 18F isotopomer of a tumor imaging agent.
Specific detection and imaging of enzyme activity by signal-amplifiable self-assembling 19Fa MRI probes
Matsuo, Kazuya,Kamada, Rui,Mizusawa, Keigo,Imai, Hirohiko,Takayama, Yuki,Narazaki, Michiko,Matsuda, Tetsuya,Takaoka, Yousuke,Hamachi, Itaru
supporting information, p. 12875 - 12883 (2013/10/01)
Specific turn-on detection of enzyme activities is of fundamental importance in drug discovery research, as well as medical diagnostics. Although magnetic resonance imaging (MRI) is one of the most powerful techniques for noninvasive visualization of enzy
Lipid Compounds Targeting VLA-4
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Paragraph 0147-0148, (2013/04/10)
The invention relates to the compounds of formula I: and pharmaceutically acceptable salts and esters thereof, wherein n, G, W, X, Y, and R1 are defined in the detailed description and claims. The compounds of formula I bind to or associate with VLA-4 and can be used in delivery formulations to deliver drugs, nucleic acids, or other therapeutic compounds to tissues or cells expressing VLA-4.
A mild, palladium-catalyzed method for the dehydrohalogenation of alkyl bromides: Synthetic and mechanistic studies
Bissember, Alex C.,Levina, Anna,Fu, Gregory C.
supporting information, p. 14232 - 14237 (2012/11/06)
We have exploited a typically undesired elementary step in cross-coupling reactions, β-hydride elimination, to accomplish palladium-catalyzed dehydrohalogenations of alkyl bromides to form terminal olefins. We have applied this method, which proceeds in excellent yield at room temperature in the presence of a variety of functional groups, to a formal total synthesis of (R)-mevalonolactone. Our mechanistic studies have established that the rate-determining step can vary with the structure of the alkyl bromide and, most significantly, that L2PdHBr (L = phosphine), an intermediate that is often invoked in palladium-catalyzed processes such as the Heck reaction, is not an intermediate in the active catalytic cycle.
Peroxopolyoxometalate-based room temperature ionic liquid as a self-separation catalyst for epoxidation of olefins
Li, Huan,Hou, Zhenshan,Qiao, Yunxiang,Feng, Bo,Hu, Yu,Wang, Xiangrui,Zhao, Xiuge
scheme or table, p. 470 - 475 (2010/11/21)
A new peroxopolyoxometalate-based room temperature ionic liquid (POM-RTIL) has been synthesized and used as catalyst for efficient epoxidation of various olefins. The RTIL catalyst was found to be well dissolved in the solvent (ethyl acetate) during the reaction, while it can self-separate from the reaction media at room temperature after the reaction completed, which made the recovery and reuse of the IL catalyst convenient. The POM-RTIL catalyst can be recycled for five times without significant loss of activity.
Synthesis and antileishmanial activity of lipidic amino alcohols
Coimbra, Elaine S.,De Almeida, Mauro V.,Junior, Celso O. R.,Taveira, Aline F.,Da Costa, Cristiane F.,De Almeida, Ana C.,Reis, Elaine F. C.,Da Silva, Adilson D.
scheme or table, p. 233 - 235 (2010/12/20)
In this work, a number of lipidic amino alcohols wereas synthesized and evaluated in vitro on cultures of Leishmania amazonensis and Leishmania chagasi. Nine amino alcohols showed inhibition of L. chagasi growth, and seven of them showed inhibition of L. amazonensis with IC50 below 10 μm. Compound 11f was more active than the reference drug amphotericin B against L. chagasi promastigote forms.
Polyoxometalate-based protic alkylimidazolium salts as reaction-induced phase-separation catalysts for olefin epoxidation
Qiao, Yunxiang,Hou, Zhenshan,Li, Huan,Hu, Yu,Feng, Bo,Wang, Xiangrui,Hua, Li,Huang, Qingfa
experimental part, p. 1955 - 1960 (2010/06/15)
Two protic alkylimidazolium polyoxometalates, together with two corresponding aprotic N-methyl-alkylimidazolium polyoxometalates were synthesized and characterized by the methods of NMR, IR and TGA etc. Then, these salts were employed as catalysts for the epoxidation of cyclooctene in different media. The novel protic N-dodecylimidazolium peroxotungstate [HDIm]2[{WO(O2)2}2(μ-O)] was found to be a room temperature liquid molten salt (ionic liquid) and the most effective catalyst for the epoxidation of cyclooctene among these salts. The ionic liquid catalyst [HDIm]2[{WO(O2)2} 2(μ-O)] can also be extended to the epoxidation of some other substrates. On the basis of this experimental observation, an efficient reaction-induced phase-separation catalyst system has been developed in this work. The reaction system can switch from tri-phase to emulsion and then to biphase and finally to all the catalyst self-precipitating at the end of the reaction, which made the recovery and reuse of the present catalyst very convenient.
