Mono-acylation of symmetric diamines in the presence of water

Tang, Wenxian; Fang, Shiyue

doi:10.1016/j.tetlet.2008.07.174

Cited by 23 publications

(23 citation statements)

References 20 publications

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“…M52950) and 1,4-diaminobutane (3.5 g, 40 mmol, Sigma-Aldrich, catalog no. D13208) in deionized water (2 ml) for 20 hours (28). Following removal of water and volatiles, the reaction was purified by silica flash column chromatography (gradient, 2:2:1:95 to 32:32:16:20, methanol/acetonitrile/triethylamine/diethylether) to yield ABINA (2.5 g, 32%) as a yellowish oil.…”

Section: Figurementioning

confidence: 99%

Multicolor microRNA FISH effectively differentiates tumor types

Renwick¹,

Čekan²,

Masry³

et al. 2013

J. Clin. Invest.

116

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MicroRNAs (miRNAs) are excellent tumor biomarkers because of their cell-type specificity and abundance. However, many miRNA detection methods, such as real-time PCR, obliterate valuable visuospatial information in tissue samples. To enable miRNA visualization in formalin-fixed paraffin-embedded (FFPE) tissues, we developed multicolor miRNA FISH. As a proof of concept, we used this method to differentiate two skin tumors, basal cell carcinoma (BCC) and Merkel cell carcinoma (MCC), with overlapping histologic features but distinct cellular origins. Using sequencing-based miRNA profiling and discriminant analysis, we identified the tumor-specific miRNAs miR-205 and miR-375 in BCC and MCC, respectively. We addressed three major shortcomings in miRNA FISH, identifying optimal conditions for miRNA fixation and ribosomal RNA (rRNA) retention using model compounds and high-pressure liquid chromatography (HPLC) analyses, enhancing signal amplification and detection by increasing probe-hapten linker lengths, and improving probe specificity using shortened probes with minimal rRNA sequence complementarity. We validated our method on 4 BCC and 12 MCC tumors. Amplified miR-205 and miR-375 signals were normalized against directly detectable reference rRNA signals. Tumors were classified using predefined cutoff values, and all were correctly identified in blinded analysis. Our study establishes a reliable miRNA FISH technique for parallel visualization of differentially expressed miRNAs in FFPE tumor tissues.

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Section: Figurementioning

confidence: 99%

Multicolor microRNA FISH effectively differentiates tumor types

Renwick¹,

Čekan²,

Masry³

et al. 2013

J. Clin. Invest.

116

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“…This approach was chosen considering published data on the synthesis of 1-substituted imidazolinones. [29][30][31][32][33][34] N-Oxides 8a,b were synthesized by condensation of accessible reactants: N-acetylalkylenediamines 9a,b (prepared by acylation of ethylenediamine [35][36][37] or prophylendiamine 38 ), paraformaldehyde, and α-ketooxime 10 (Scheme 4).…”

Section: Scheme 3 Plausible Mechanism For the Formation Of Imidazooxmentioning

confidence: 99%

Unusual formation of imidazooxazolone in the reaction of 1-[(2-acetylamino)ethyl]imidazolone with KSCN in the presence of AcOH

Баранов¹,

Antonova²,

Карноухова³

et al. 2017

Arkivoc

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Abstract1-[(2-Acetylamino)ethyl]imidazolone was introduced for the first time in the condensation with KSCN in the presence of AcOH and imidazooxazolone was unexpectedly obtained. This result was possible only because of the unique character of 1-((2-acetylamino)ethyl)imidazolone, which has an intramolecular N-H … О-Н hydrogen bond and, therefore, reacts with the NCS anion to give only imidazooxazolone.

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“…9 We recently found that diamines could be mono-acylated with lactones, alkyl esters, and phenyl and allyl carbonates in good to quantitative yields in the presence of suitable amount of water. 10,11 We hypothesized that the disruption of the hydrogen bonds between diamines by water along with other factors might be responsible for the good selectivity of mono-acylation. 10 The method has the following advantages.…”

Section: Introductionmentioning

confidence: 99%

“…10,11 We hypothesized that the disruption of the hydrogen bonds between diamines by water along with other factors might be responsible for the good selectivity of mono-acylation. 10 The method has the following advantages. (a) No organic solvent is used.…”

Section: Introductionmentioning

confidence: 99%

“…In some cases, to drive the reaction to completion, the reaction mixture must be heated to high temperature (more than 100°C). 10 In order to lower the temperature, we recently tested using phenyl esters as the acylating agent for the reaction. We found that the reaction could proceed with useful rates at 50°C and give mono-acylated products in good to excellent yields.…”

Section: Introductionmentioning

confidence: 99%

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