- Solid-phase synthesis of 2-cyanoquinazolin-4(3H)-one and 2,3-dihydrooxazolo[2,3-b]quinazolin-5-one derivatives utilizing resin-bound anthranilic acid derivatives
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We were able to obtain 2-cyanoquinazolin-4(3H)-ones 11 in 35-60% four-step overall isolated yields and 2,3-dihydrooxazolo[2,3-b]quinazolin-5-ones 12 in 20-71% four-step overall isolated yields utilizing polymer-bound anthranilic acid derivatives 1, and 6-amino-2-cyanoquinazolin-4(3H)-ones 19 in 30-44% six-step overall isolated yields making use of anthranilic acid derivative resin 2 via dithiazole resins 10 and 17. The reactions on solid phase were monitored by single bead ATR-FTIR spectroscopic method.
- Jeon, Moon-Kook,Kim, Dong-Su,Hyun, Ju La,Ha, Deok-Chan,Gong, Young-Dae
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Read Online
- Synthesis and evaluation of D-thioluciferin, a bioluminescent 6'-thio analog of Dluciferin
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All known light-emitting firefly-bioluminescent luciferin analogs are either derived from the 6'-hydroxy- and/or 6'-aminoluciferin. We report the synthesis of D-thioluciferin, a 6'-thio analog or isostere of D-luciferin, starting from p-aminothiophenol, using a unique thioacrylate-S-protecting-group strategy. Upon treatment of Dthioluciferin with purified Photinus pyralis (Ppy) luciferase (Luc), a bioluminescence emission with a red-shift λmax relative to D-luciferin was observed. It was also shown that disulphide and sulphide analogs of Dthioluciferin did not produce similar bioluminescences relative to D-thioluciferin when treated with Ppy Luc under standard conditions, thus, providing a foundation for the development of D-thioluciferin based probes based on disulphide reduction and S-dealkylation.
- Rylands, Marwaan,Jardine, Anwar
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p. 176 - 189
(2021/03/17)
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- DERIVATIVES OF LUCIFERIN AND METHODS FOR THEIR SYNTHESIS
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6-Thio derivatives of D-luciferin, also referred to as D-thioluciferins, having the general structure of Formula (I) are provided. Methods for synthesising D-luciferin, its derivatives, and their related 2-cyanobenzothiazole precursors are also provided. These compounds are commercially valuable due to their application in optical imaging, particularly in bioluminescence imaging.
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Page/Page column 26
(2019/02/13)
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- Preparation method of 2-cyano-6-hydroxyl benzimidazole
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The invention discloses a synthetic method of 2-cyano-6-hydroxyl benzimidazole. The synthetic method comprises the following steps of: dissolving 4-methoxyl o-phenylenediamine in a solvent; adding 4,5-dichloro-1,2,3-dithiazole chloride to react to generate 2-cyano-6-methoxyl benzimidazole; and then performing a reaction with a demethylation reagent to obtain the 2-cyano-6-hydroxyl benzimidazole. The preparation method disclosed by the invention simplifies the reaction steps, is simple in post-treatment, and is high in product purity. The raw materials are easily available and are low in price; no heavy metals and corrosive gas are used in the reaction, the reaction is mild, the production cost is low, scaled production is facilitated, and popularization and application are facilitated.
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Paragraph 0009
(2017/07/21)
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- Rapid and scalable assembly of firefly luciferase substrates
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Bioluminescence imaging with luciferase-luciferin pairs is a popular method for visualizing biological processes in vivo. Unfortunately, most luciferins are difficult to access and remain prohibitively expensive for some imaging applications. Here we report cost-effective and efficient syntheses of d-luciferin and 6′-aminoluciferin, two widely used bioluminescent substrates. Our approach employs inexpensive anilines and Appel's salt to generate the luciferin cores in a single pot. Additionally, the syntheses are scalable and can provide multi-gram quantities of both substrates. The streamlined production and improved accessibility of luciferin reagents will bolster in vivo imaging efforts. This journal is
- McCutcheon, David C.,Porterfield, William B.,Prescher, Jennifer A.
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supporting information
p. 2117 - 2121
(2015/03/18)
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- A qualitative comparison of the reactivities of 3,4,4,5-Tetrachloro-4H-1,2,6-thiadiazine and 4,5-Dichloro-1,2,3-dithiazolium Chloride
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The high yielding transformations of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine into 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (up to 85%) and 2-(3,5-dichloro-4H-1,2,6- thiadiazin-4-ylidene)malononitrile (up to 83%) have been investigated and compared to the a
- Kalogirou, Andreas S.,Koutentis, Panayiotis A.
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p. 14576 - 14594
(2015/09/21)
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- Rational multistep synthesis of a novel polyfunctionalized benzo[d]thiazole and its thiazolo[5,4-b]pyridine analogue
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Reliable synthetic routes were studied for an access to a novel polyfunctionalized 6-amino-2-cyanobenzo[d]thiazole-5-carboxylate ester (1) and its analogue 5-amino-2-cyanothiazolo[5,4-b]pyridine-6-carboxylate ester (2). Both compounds 1 and 2 are functionalized as molecular bricks for the synthesis of innovative molecular systems. Part of the chemistry performed in this study was achieved under microwave irradiation.
- Hédou, Damien,Deau, Emmanuel,Harari, Marine,Sanselme, Morgane,Fruit, Corinne,Besson, Thierry
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supporting information
p. 5541 - 5549
(2015/03/30)
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- BICYCLIC HETEROARYL DERIVATIVES AS KINASE INHIBITORS
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The present invention provides compounds, including resolved enantiomers, resolved diastereomers, solvates and pharmaceutically acceptable salts thereof, comprising the Formula 1: wherein Het, X, R1 and R2 are as defined herein.
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Paragraph 00291
(2013/06/06)
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- Novel synthesis of angular thiazolo[5,4-f] and [4,5-h]quinazolines, preparation of their linear thiazolo[4,5-g] and [5,4-g]quinazoline analogs
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Synthesis of 9-oxo-8,9-dihydrothiazolo[5,4-f]quinazoline-2-carbonitrile (1) or 6-oxo-6,7-dihydrothiazolo[4,5-h]quinazoline-2-carbonitrile (2) was reinvestigated with the ambition of varying the position of the thiazole ring linked to the quinazolin-4-one
- Hédou, Damien,Guillon, Rémi,Lecointe, Charlotte,Logé, Cédric,Chosson, Elizabeth,Besson, Thierry
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p. 3182 - 3191
(2013/04/24)
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- NOVEL FLUORESCENT DYES AND USES THEREOF
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The present invention provides fluorescent dyes that are based on firefly luciferin structure. These dyes are optimally excited at shorter wavelengths and have Stokes shift of at least 50 nm. The fluorescent dyes of the invention are useful for preparation of dye-conjugates, which can be used in detection of an analyte in a sample.
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Page/Page column 31
(2011/02/24)
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- HETEROCYCLYLAMIDES AS GUT MICROSOMAL TRIGLYCERIDE TRANSPORT PROTEIN INHIBITORS
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Compounds represented by formula (I) are inhibitors of gut microsomal triglyceride transfer protein. Such compounds are useful in treating diseases or conditions such as diabetes and obesity, along with patients are risk for developing such diseases or conditions.
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Page/Page column 82
(2009/03/07)
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- GUT MICROSOMAL TRIGLYCERIDE TRANSPORT PROTEIN INHIBITORS
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Compounds represented by formula (I): are inhibitors of gut microsomal triglyceride transfer protein. Such compounds are useful in treating diseases or conditions such as diabetes and obesity, along with patients are risk for developing such diseases or conditions.
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Page/Page column 89-90
(2008/12/08)
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- The preparation and characterization of 5-substituted-4-chloro-1,2,3- dithiazolium salts and their conversion into 4-substituted-3-chloro-1,2,5- thiadiazoles
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A series of monosubstituted acetonitriles were treated with disulfur dichloride at room temperature in CH2Cl2 to afford 5-substituted-4-chloro-1,2,3-dithiazolium chlorides 1. Where the 5-substituent was not a good leaving group the chloride salts were converted into the corresponding perchlorate salts 2 which were sufficiently stable and soluble to provide both 1H- and 13C-NMR and cyclic voltammetry data. Several of the dithiazolium chlorides were converted into their corresponding 4-substituted-3-chloro-1,2,5-thiadiazoles 13 on treatment with aqueous ammonia. Mechanisms for all reactions are proposed.
- Koutentis, Panayiotis A.
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p. 346 - 359
(2007/10/03)
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- Synthesis and Reactions of 4,5-Dichloro-1,2,3-dithiazolium Chloride
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Disulfur dichloride reacts with acetonitrile via chloro- and dichloroacetonitrile to give finally 4,5-dichloro-1,2,3-dithiazolium chloride (1).The reactivity of 1 with proton-active compounds is determined by the nucleophilic substitution of the chlorine at carbon atom C-5.Substrates like H2O, H2S, primary amines, and sulfonamides, having two active hydrogen atoms, form the covalent 4-chloro-5H-1,2,3-dithiazole derivatives 2, 3, 5. 1 reacts with phenols in o- or p-position by an electrophilic attack to form 4-chloro-5-(hydroxyphenyl)-1,2,3-dithiazolium chlorides 9a - d.HCl elimination from these leads to deep violet, metallic-reflecting crystals of the betaine-like neutral molecules 10a, b.X-ray analysis shows a planar structure of 10a and a molecular arrangement of a right and a left helix.Ring cleavage of 1 with chlorine gives compounds 14, 15; correspondingly, 2 reacts with chlorine to yield 2-chloro-2-(chlorothioimino)acetyl chloride (18).
- Appel, Rolf,Janssen, Heinrich,Siray, Mustafa,Knoch, Falk
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p. 1632 - 1643
(2007/10/02)
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- S,N-COMPOUNDS VIA AMINES AND SULPHUR HALIDES
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The many products got by reactions of amines with sulfur halides are discussed.Special attention is given to the intermediate thionitroso compounds, the N-thiosulfinylamines and the persistent radicals 1,2,3-dithiazolyles.New results about the course of the HERZ reaction are described.
- Mayer, Roland
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p. 277 - 296
(2007/10/02)
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