Improved method for the preparation of guanidines

Kim, Kyoung Soon; Qian, Ligang

doi:10.1016/s0040-4039(00)61537-x

Cited by 245 publications

(144 citation statements)

References 4 publications

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“…Guanidines 9 are prepared by displacement of sulfur in the presence of ethyl-3-aminopropyl carbodiimide hydrochloride (EDCI) 14 in 48 h without the formation of any major side products. The guanidines obtained via EDCI coupling (Table 3) Amines can be converted into guanidines 11 by the reaction di-Boc thiourea 5 15 in the presence of mercuric chloride or copper(II) chloride in the presence of triethylamine (Scheme 4). The influence of the desulphurizing agent is shown in Table 4.…”

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confidence: 99%

Recent developments in guanylating agents

Katritzky¹,

Rogovoy²

2005

Arkivoc

143

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Dedicated to Professor Nikolai Zefirov on the occasion of his 70th birthday (received 26 Oct 04; accepted 08 Jan 05; published on the web 05 Jan 05) AbstractGuanidines are important molecules with a wide range of interesting properties. In this overview we summarize recent advances in the development of guanylating reagents which we define as compounds forming a guanidine structure by a chemical transformation. We cover important classes of guanylating agents developed in the last two decades and representative examples are reported.

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confidence: 99%

Recent developments in guanylating agents

Katritzky¹,

Rogovoy²

2005

Arkivoc

143

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“…As a key step, guanidinylation of 4 was next carried out upon treatment with S-methylisothiourea in the presence of HgCl 2 and Et 3 N to furnish 5 in 88% yield. 13,14) Treatment of 5 with TBAF in the presence of acetic acid generated the alcohol 6 in 82% yield. Mesylation of 6 followed by substitution with sodium azide in DMF gave the Regular Article * To whom correspondence should be addressed.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 1-(4-Aminobutyl)-2-iminoimidazolidin-4-one Aimed at Preparation of a Creatinine-Specific Antibody

Moriya

Terayama

Hiramatsu

et al. 2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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For the purpose of obtaining a creatinine-specific antibody, a creatinine derivative with 4-aminobutyl, which was served as a linker for preparing the creatinine-bovine serum albumin (BSA) conjugate, was synthesized from 4-benzylaminobutan-1-ol in 8 steps. Production of anti-creatinine antibodies was observed in two rabbits using the creatinine-BSA conjugate, although their titer was rather low.Key words creatinine derivative; synthesis; guanidinylation; anti-creatinine immunoglobulin Recently, we developed an immunochromatographic system for determination of the N 1 ,N 12 -diacetyl spermine (DiAcSpm) concentration in human urine 1) (Fig. 1). DiAcSpm is a newly developed tumor marker and is unique among existing tumor markers in that it is sensitive in detecting early cancers. 2,3)The immunochromatographic testing device can be used for personal health control and would eventually contribute to improvement in the efficiency of early detection of cancer, which is important for reducing the number of fatal cases of cancer. The quantity of daily excretion of urine components is usually estimated from arbitrarily excreted spot urine samples by creatinine normalization and is expressed in nmol substance per g creatinine. The validity of creatinine normalization in estimating daily DiAcSpm excretion in urine was in fact confirmed, 4) and creatinine-normalized DiAcSpm in urine has been shown to be a promising tumor marker as described above. To determine the quantity of creatinine-normalized DiAcSpm by immunochromatography, it is necessary to simultaneously determine the quantities of creatinine in urine samples. Yaffe's reaction, which utilizes the reaction of creatinine with picric acid to form orange-red-colored creatinine picrate in an alkaline solution, can be used for this purpose.5) However, substances in urine such as pyruvate, glucose, ascorbate, and billirubin are also known to form colored complexes and interfere with accurate determination of creatinine. An enzymatic method utilizing creatinine imidohydrolase and glutamate dehydrogenase is more accurate 6) but is not readily applicable to creatinine assays on a solid support that are run in parallel with the immunochromatographic determination of DiAcSpm. A creatinine-specific antibody, if available, would be readily applicable to immunochromatographic determination of creatinine. Moreover, DiAcSpm and creatinine could be determined on the same strip by using gold nanoparticles labeled with two antibodies. To obtain a creatinine-specific antibody, creatinine as a hapten must be conjugated to an appropriate carrier macromolecule. With this in mind, we designed a creatinine derivative (10) with 4-aminobutyl.

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“…2,33,[42][43][44][45][46][47][48][49][50][51] Most importantly, Hg 2+ can easily promote desulfurization to transform a cyclic compound, as an imidazole (1-R-2-R′-4,5-dihydro-1H-imidazole), resulting in a change of the spectroscopy properties. 2,42,44,50,51 Also, this phenomenon can be ascribed to changes of the electronic delocalization in the chromophore.…”

Section: Sensitive and Selective Recognition Of Hgmentioning

confidence: 99%

Fabrication of Water-soluble Fluorescent Polymeric Micelles for Selective Detection of Hg2+ in Blood Serum

et al. 2017

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In this study, amphiphilic diblock copolymers were designed and synthesized via the incorporation of reversible additionfragmentation chain transfer radical polymerization (RAFT) and a subsequent grafting technique. Subsequently, Hg 2+ -sensitive water-soluble fluorescent polymeric micelles (FNs) were prepared by a reprecipitation strategy. The spectroscopic characteristics demonstrate that the fluorescein isothiocyanate (FITC) was successfully linked into the polymer. Due to the promoted reaction of desulfurization cyclization by Hg 2+ , the fluorescence of fluorescein in FNs was obviously quenched. The as-prepared FNs showed admirable Hg 2+ -sensitivity (detection limit: 54 nM), excellent water-solubility and high selectivity. In addition, FNs were successfully used to determine Hg 2+ in blood serum. We expected that the as-prepared FNs could perform potential applications in imaging, sensing, and bioanalytic chemistry.

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Improved method for the preparation of guanidines

Cited by 245 publications

References 4 publications

Recent developments in guanylating agents

Recent developments in guanylating agents

Synthesis of 1-(4-Aminobutyl)-2-iminoimidazolidin-4-one Aimed at Preparation of a Creatinine-Specific Antibody

Fabrication of Water-soluble Fluorescent Polymeric Micelles for Selective Detection of Hg2+ in Blood Serum

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