Novel and green protocol for the synthesis of 2-iminohydantoins

Kumar, Vinod; Rana, Hemlata; Kaushik, M. P.

doi:10.1016/j.tetlet.2012.09.057

Cited by 5 publications

(3 citation statements)

References 44 publications

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“…Finally, due to the reduced solubility of Cr in organic solvents, we prepared the lipophilic derivative HexCr . The compound was obtained, following a known protocol, by treating methyl N -cyano- N -hexyl-aminoacetate with aqueous ammonia at room temperature. HexCr proved to be soluble up to 1.5 mM in dichloromethane and chloroform, thereby enabling binding studies by NMR spectroscopy (see below).…”

Section: Results and Discussionmentioning

confidence: 99%

Optical Supramolecular Sensing of Creatinine

et al. 2020

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Calix[4]pyrrole phosphonate-cavitands were used as receptors for the design of supramolecular sensors for creatinine and its lipophilic derivative hexylcreatinine. The sensing principle is based on indicator displacement assays of an inherently fluorescent guest dye or a black-hole quencher from the receptor’s cavity by means of competition with the creatinine analytes. The systems were thermodynamically and kinetically characterized regarding their 1:1 binding properties by means of nuclear magnetic resonance spectroscopy (1H and 31P NMR), isothermal titration calorimetry, and optical spectroscopies (UV/vis absorption and fluorescence). For the use of the black-hole indicator dye, the calix[4]pyrrole was modified with a dansyl chromophore as a signaling unit that engages in Förster resonance energy transfer with the indicator dye. The 1:1 binding constants of the indicator dyes are in the range of 107 M–1, while hexylcreatinine showed values around (2–4) × 105 M–1. The competitive displacement of the indicators by hexylcreatinine produced supramolecular fluorescence turn-on sensors that work at micromolar analyte concentrations that are compatible with those observed for healthy as well as sick patients. The limit of detection for one of the systems reached submicromolar ranges (110 nM).

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Section: Results and Discussionmentioning

confidence: 99%

Optical Supramolecular Sensing of Creatinine

et al. 2020

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“…Chemistry In order to avoid handling highly polar and basic compounds as much as possible, we planned to perform the catalytic hydrogenation of guanidine 9 in the last stage, which was expected to construct iminoimidazolidinone framework, [7][8][9][10][11] as shown in Chart 1. Our synthesis started with installation of an acetic acid unit to commercially available 1.…”

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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“…The reaction of between 50 and aqueous ammonia took place to yield 2-iminohydantoin at room temperature in 10-30 minutes (Scheme 8). 107 Interestingly, the developed method has also followed several rules of green chemistry. The distinctive attributes of this reaction that promotes the green chemistry are solvent-free reaction, no extra heating, use of water as reaction medium, no formation of by-product, and no workup for the isolation or purification of the products as simple filtration can lead to the pure products.…”

Section: Synthesis Of Diversely Substituted Thiohydantoinsmentioning

confidence: 99%

Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

Kumar¹

2021

Synlett

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Hydantoin and its analogs such as thiohydantoin and iminohydantoin have received substantial attention both from a chemical and biological point of view. Several compounds of this class have shown useful pharmacological activities such as anticonvulsant, antitumor, antiarrhythmic, herbicidal, and others that lead in some cases to clinical applications. Because of broad-spectrum activities, intensive research efforts have been dedicated in industry and academia to the synthesis and structural modifications of hydantoin and its derivatives. Realizing the importance of hydantoin in organic and medicinal chemistry, we also initiated a research program to successfully design and develop the new routes/methods resulting in the formation of hydantoin, thiohydantoin, and iminohydantoin substituted at different positions particularly at the N-1 position without following protection-deprotection strategy. Given the fact that the combination of two or more pharmacophoric groups may lead to hybrid molecules which result in a mixed mechanism of action on the biological target. We, therefore, further extended the developed strategy for the synthesis of new types of hydantoin-based hybrid molecules by combining hydantoin with a triazole, isoxazoline, and phosphate scaffolds as another pharmacophoric group to exploit diverse biological functions.

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Novel and green protocol for the synthesis of 2-iminohydantoins

Cited by 5 publications

References 44 publications

Optical Supramolecular Sensing of Creatinine

Optical Supramolecular Sensing of Creatinine

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

Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

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