- A sulfonamidoquinoline-derived Zn2+ fluorescent sensor with 1:1 Zn2+ binding stoichiometry
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The integration of bis(pyridin-2-ylmethyl)amine (BPA) with 8-sulfonamidoquinoline (SQ) resulted in a new fluorescent Zn2+ sensor of 1:1 binding stoichiometry. The synergic Zn2+ coordination of BPA and SQ motifs provides the sensor the advantage over TSQ and its analogues in discriminating mobile Zn2+ from the bound Zn2+ of unoccupied coordination sites in living systems. Its pH-independent Zn 2+-enhanced emission in physiological condition and cell permeability make it an effective intracellular Zn2+ imaging agent. This sensor profits also from its confirmed Golgi-preferential affinity, and its pH-independent Zn2+ response in physiological pH range provides it the advantages over other xanthenone-based sensors.
- Zhang, Changli,Zhang, Yuming,Chen, Yuncong,Xie, Zhijun,Liu, Zhipeng,Dong, Xindian,He, Weijiang,Shen, Chen,Guo, Zijian
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Read Online
- β-(Cycloalkylamino)ethanesulfonyl azides as novel water-soluble reagents for the synthesis of diazo compounds and heterocycles
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[Figure not available: see fulltext.] Novel water-soluble sulfonyl azides were synthesized, which are basic by nature. The obtained compounds were used as donors of the diazo group in the diazo transfer reaction. Due to their good solubility in water and high polarity, the byproducts formed in this case were easily separated from the desired products by washing with water or column chromatography. It was also shown that new sulfonyl azides as a result of reactions can be incorporated in heterocyclic products, imparting them water solubility.
- Shafran, Yuri M.,Silaichev, Pavel S.,Bakulev, Vasiliy A.
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p. 1251 - 1261
(2020/01/11)
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- Iridinesulfonamide compound and use method thereof
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An iridinesulfonamide compound having isocitrate dehydrogenase 1 (IDH1) inhibitory activity, pharmaceutically-acceptable salts, solvates or hydrates thereof, a pharmaceutical composition, as well as use of the compound or the pharmaceutically-acceptable salts, solvates or hydrates thereof, and the pharmaceutical composition thereof in treating IDH1 mutation-induced cancers.
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Paragraph 0101-0103
(2018/03/29)
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- Styrylsulfonates and -Sulfonamides through Pd-Catalysed Matsuda–Heck Reactions of Vinylsulfonic Acid Derivatives and Arenediazonium Salts
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Arene diazonium salts undergo Matsuda–Heck reactions with vinylsulfonates and -sulfonamides to give styrylsulfonic acid derivatives in high to excellent yields and with high to excellent selectivities. By quantifying the evolution of nitrogen over time in a gas-meter apparatus, the reactivities of ethylvinylsulfonate and the benchmark olefin methyl acrylate were compared for an electron-rich and an -deficient arene diazonium salt. Tertiary sulfonamides react in Matsuda–Heck couplings with high conversions, but require long reaction times, which prevents the determination of kinetic data through the measurement of nitrogen evolution. Secondary sulfonamides were found to be unreactive. From these results, the following order of reactivity could be deduced: H2C=CHCO2Me > H2C=CHSO2OEt > H2C=CHSO2N(Me)Bn >> H2C=CHSO2NHBn. Through the Matsuda–Heck coupling of 5-indolyldiazonium salt and a tertiary vinylsulfonamide, the synthesis of the C-5-substituted indole part of the antimigraine drug naratriptan was accomplished in high yield.
- Schmidt, Bernd,Wolf, Felix,Brunner, Heiko
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supporting information
p. 2972 - 2982
(2016/07/11)
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- PROCESS FOR PREPARATION OF NARATRIPTAN HYDROCHLORIDE
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The present invention relates to an improved process for the preparation of N-methyl-3- (1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide hydrochloride of formula (I) having less than 0.15 % area by HPLC of 3-(1-methyl-4-piperidinyl)-1H-indole-5- ethanesulfonamide (1A) and intermediates thereof.
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Page/Page column 28-29
(2009/10/22)
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- The mechanism of hydrolysis of 2-hydroxyethanesulfonyl chloride: the intermediacy of 1,2-oxathietane 2,2-dioxide (β-sultone)
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The hydrolysis of 2-hydroxyethanesulfonyl chloride (1) has been investigated with the aid of kinetic and product analysis studies.The results are quantitatively consistent with the mechanism of hydrolysis shown in Scheme 1, the chief features of which are (a) formation of β-sultone (2) and its rapid further reaction (the major pathway), together with (b) a minor direct hydrolysis route.The kinetics of both the β-sultone formation and the direct hydrolysis shows two terms, one first order in 1 alone, and the other first order in hydroxide as well; the rates of the first- and second-order reactions are lowered by added sodium chloride.It is suggested (a) that the unimolecular β-sultone formation involves 1 in a complex with water (as in 9) and that the water acts as a general base in the cyclization to 2, and (b) the hydroxide-promoted reaction proceeds by cyclization of the conjugate base of 1 (i.e., 10).The unimolecular direct hydrolysis is regarded as a conventional hydrolysis of a sulfonyl chloride with attack of the water with general base assistence from a second water molecule.The hydroxide-promoted direct reaction in D2O leads to no uptake of deuterium, showing taht the reaction does not go by way of the sulfene, and a reaction by way of a six-membered cyclic transition state is tentatively proposed.Evidence is presented that the chloride ion rate suppression is not primarily due to reaction of β-sultone with Cl- to give back 1; the possible origins of the effect are discussed.Key words: sulfonyl chloride, 2-hydroxyethanesulfonyl chloride, β-sultone, kinetics of sulfonyl chloride hydrolysis, mechanism of sulfonyl chloride hydrolysis
- King, James Frederick,Khemani, Kishan Chand
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p. 2162 - 2172
(2007/10/02)
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- SYNTHESIS OF 3-(VINYLSULFONYL)ACRYLAMIDE
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3-(Vinylsulfonyl)acrylamide was synthesized by the addition of 2-chloroethane-1-sulfinic acid to 2-chloroacrylamide and dehydrochlorination of the obtained 3-(2-chloroethylsulfonyl)-2-chloropropionamide.
- Bogolyubskaya, L. T.,Bogolyubskii, A. V.
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p. 1674 - 1675
(2007/10/02)
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- Organic sulfur mechanisms. 24. Preparation and reaction of 2-hydroxyethanesulfonyl chloride, the first hydroxyalkanesulfonyl chloride
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2-Hydroxyethanesulfonyl chloride (1a) is readily made by reaction of an aqeous solution of 2-mercaptoethanol (4a) with chlorine.This is the first clearly proved preparation of a compound which is both an alcohol and a sulfonyl chloride.Reactions of 1a with water and alcohols evidently proceed largely by intramolecular cyclization to the transient β-sultone (2a), which then undergoes nucleophilic ring opening to form the products.In the presence of tertiary amines a minor but significant part of the reaction is shown by deuterium labelling to proceed via hydroxymethylsulfene (14), the principal reaction of which is simply to add the alcohol or water; only a small part, if any, of the sulfene (14) loses the hydroxyl group to give the ethenesulfonate derivatives (13 or 22).Aqueous chlorination of 3-mercapto-1-propanol gave 3-chloro-1-propanesulfonyl chloride (5a) and 1,3-propane sultone (2b) with no sign of any 3-hydroxy-1-propanesulfonyl chloride (1b).A mechanism for the aqueous chlorination process invoking a cyclic chlorooxasulfoxonium ion (27) is discussed.
- King, James Frederick,Hillhouse, John Henry
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p. 1583 - 1593
(2007/10/02)
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- Hydrocarbylethyl sulfonyl fluoride
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Hydrocarbylethyl sulfonyl fluorides in which the hydrocarbyl substituent contains at least 3 carbon atoms, can be prepared by reacting 2-mercaptoethanol with chlorine to form chloroethyl sulfonyl chloride which is treated with aqueous potassium fluoride to yield chloroethyl sulfonyl fluoride, followed by treatment with magnesium oxide to yield vinyl sulfonyl fluoride. The vinyl sulfonyl fluoride is adducted to a hydrocarbyl substituent precursor, such as an olefin or halogenated olefin. A representative compound is polyisobutenyl sulfonyl fluoride. The hydrocarbylethyl sulfonamide products for which the hydrocarbylethyl sulfonyl fluorides are intermediates are useful as additives for lubricating oils.
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- 2-Hydroxyethanesulphonyl Chloride: a Sulphonyl Chloride with a Primary Hydroxy-group
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The preparation of 2-hydroxyethanesulphonyl chloride (1), the first example of a compound containing both sulphonyl chloride and primary alcohol functions, is described; reaction of (1) with base gives products evidently derived from the sulphene (4) and the β-sultone (6).
- King, James F.,Hillhouse, John H.
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p. 295 - 296
(2007/10/02)
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- Studies on Sulphochlorination of Paraffins. VI. Studies on the Sulphochlorination of individual Alkyl Chlorides
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The products of sulphochlorination of individual C2-C7 alkyl chlorides were studied by means of 1H- and 13C-n.m.r. spectroscopy.Gaschromatographic determination of the isomers formed was possible after the reaction of the chloroalkane sulphochloride mixture with dimethyl amine in ether.In no case geminal chloroalkane sulphochlorides were formed.Vicinal chlorosulphochlorides are formed,but substitution in greater distance from thechlorine is preferred if possible.Thus higher alkyl chlorides yield only verylittle amounts of vicinal chloroalkane sulphochlorides.The relative rates of sulphochlorination of alkyl chlorides were determined by competitive rections.
- Helwig, D.,Pritzkow, W.,Radeglia, R.,Schmidt-Renner, W.,Ziegler, J.
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p. 281 - 290
(2007/10/02)
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- N-sulfonyl-N-dihalophenylimidazolidinediones
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3-(3' -Dihalophenyl)-1-sulfonylimidazolidine-2,4-5'-diones of the formula: STR1 wherein X is a halogen atom, R1 is a C1 -C12 alkyl group, a C2 -C4 alkenyl group or a halogenated C1 -C4 alkyl group having 1 to 3 halogen atoms, and R2 and R3 are individually a hydrogen atom or a methyl group, which show high microbicidal activities against various fungi and bacteria without any material toxicity to mammals and which plants and can be produced by reacting the corresponding 1-unsubstituted compound with a sulfonyl halide.
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