Peer-Reviewed Papers. Alkylation of cysteine residues by busulfan. Safety & Documentation. Structure, properties, spectra, suppliers and links for: Ethanaminium methanesulfonate. The cathode in this cell may be composed of lead, and the anode may be composed of a conductive, inert material, such as graphitic carbon. Methanesulfonate monooxygenase. Other members of this family are piposulfan, improsulfan, hepsulfam and the previously mentioned treosulfan, a diepoxide prodrug. Structure, properties, spectra, suppliers and links for: Ammonium methanesulfonate, 79262-47-8. It is a colourless liquid that dissolves in polar organic solvents but is reactive toward water, alcohols, and many amines. A bicyclic allo-C-furanoside 169 can be generated through the nucleophilic opening of an epoxide with LiAlH4, cyclization of the resulting alkoxide, and concurrent reductive cleavage of the remaining mesylate group (Scheme A.3.74), along with a mixture of deoxy inositols, as reported by Suami et al. Access to l-ribose-C-glycosides from the same diol as the galacto-isomer (Chapter A.1, Section A.1.3.2.2) was reported by Buchanan et al. These investigators also reported that the number of progenitor cells was dramatically reduced, but only mild peripheral blood cytopenia was observed until approximately 1 year after the BU administration (Morley and Blake 1974). The starting ratios of allo- to altro-mesylates are not reported, but stereospecific substitution would be expected a priori in the case of the electron-deficient pyridyl systems. The simplest organic sulfonyl chloride, it is used to make methanesulfonates … For a clinical and pharmacology study, patients with advanced, refractory, or resistant solid tumors were treated with a single-dose intravenous 30-min infusion of 8 or 10 g/sq m treosulfan . It is an alkanesulfonic acid and a one- carbon compound. Peter Goekjian, ... Claire Coiffier, in C-Furanosides, 2018. The salt with molecular structure IL3PA (Figure 1) was synthesized according to Rao et al. The methane sulfonate ion forms stable complexes with many transition metals, including lead. . Busulfan (Myleran®) was the mainstay of the chemotherapeutic treatment of CML until it was displaced by imatinib, although it is still in use to a degree as a result of the drug’s relatively low cost. Methanesulfonate is an excellent leaving group. Hepsulfam underwent some early clinical studies.59, The formation of interstrand DNA cross-links has been demonstrated for busulfan60 and treosulfan.61 Busulfan also produces DNA intrastrand cross-links, mainly at the 5′-GA-3′ sequence.62 In contrast with nitrogen mustards, in which the rate-limiting step is the unimolecular formation of the aziridinium ion, busulfan reacts with guanine N-7 by a SN2 mechanism (Figure 5.26), in which the rate-limiting step depends on the concentration of both reaction partners.63. It has a role as an Escherichia coli metabolite. 1986; Fitchen and Cline 1980). Often, BU is combined with other chemotherapeutic agents, for example, CTX, or in combination with whole body irradiation. Structure Search Protocols & Articles. Gene. Synthesis of phosphinoethane(methane)sulfonates 1, J.B. Barnett, K.M. TPO was performed in U-shaped quartz reactor under flow of oxygen 21% in He (40cm3.min-1), conditions repeating the activation procedure before the reaction. X-ray diffraction (XRD) analysis was performed on a Siemens diffractometer D500 over a 2θ-range of 5 to 50 °. No predicted properties have been calculated for this compound. Structure; Family & Domains; Sequence; Similar proteins; Cross-references; Entry information ; Miscellaneous; Top. Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves. [5]. have reported that a mesylate derived from diisopropylidene-d-ribose 162 cyclized onto the activated benzylic position upon deprotection (Scheme A.3.71) (88). One report describes the effect of several intraperitoneal injections of ‘high’ dose (10 or 20 mg kg−1) BU either 1 or 2 weeks apart in outbred mice (Morley and Blake 1974). Sulfur has more than the octet of electrons in these Lewis structures. The thallium adducts [HB(7-(t-Bu)indazolyl)3]Tl,693 [HB(7(R)-(i-Pr)-4(R)-(Me)-4,5,6,7-tetrahydro-2-indazolyl)3]Tl,694 [HB(7(S)-(t-Bu)-4(R)-(Me)-4,5,6,7-tetrahydro-2-indazolyl)3]Tl,694 [HB(2H-benz[g]indazol-2-yl)3]Tl,674 [HB(2H-benz[g]-4,5-dihydroindazol-2-yl)3]Tl,674 and [HB(3-Me-2H-benz[g]-4,5-dihydroindazol-2-yl)3]Tl674 have been synthesized, and some chemistry has been investigated. CopyCopied, ATWDUWYFCBVNET-UHFFFAOYSA-N 10-6), en 3 [ l'irradiation à 6,52. Sloop, ... R. Clarke, in Encyclopedia of Electrochemical Power Sources, 2009. Finally, Ogawa et al. 10- 6 montre un couplage à longue distance avec le proton en 6' ( 7,33.10- 6 ); cette expérience fait en outre apparaître le couplage para des protons 3' et 6'] et en 6 ou 8 ( singulet à 6,46.10-6). This protein may be involved in repairing DNA damage and in maintaining genomic … BLAST. Methanesulfonic acid (MsOH) or methanesulphonic acid (in British English) is a colorless liquid with the chemical formula CH 3 SO 3 H. It is the simplest of the alkylsulfonic acids. Organic chemists often use abbreviated structures and names for certain sulfonate esters. The methanesulfonate provides a more reactive leaving group. Without final acidic treatment, access to the sodium trialkylphosphineethanesulfonate salt 1c-Na required the protection of the phosphorus atom as a phosphine-borane adduct to prevent oxidation, whereas air stable 1d-H was easily obtained after acidification with concentrated HCl solution (Scheme 3.2).5,6. Pseudomonas … (78b). An overview of the phosphinosulfonate prochelates is shown in Table 3.1.7, Table 3.1. 1-butyl, 3-methyl imidazolium methanesulfonate was synthesized as proposed by Cassol et al. In the later stages, bone marrow hematopoiesis essentially ceased and progenitor cell levels dropped to less than 1% of controls before the animal died. It is also used for the treatment of chronic myeloid leukemia and has some specificity for myeloid over lymphoid cells. Articles of Copper(2+) methanesulfonate … (90). CC[NH3+].CS(=O)(=O)[O-] Other members of this … Toute utilisation partielle ou totale de ce document doit mentionner la source. Regioselective benzoylation, mesylation, and basic deprotection generated an alkoxide intermediate that cyclized spontaneously to the allo-C-furanoside 165 (Scheme A.3.72). CopyCopied, Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module. The lead carbonate produced in the desulfurization of battery paste (reactions [II] and [III]) may be a convenient starting material for making a lead(II) methane sulfonate solution. For this reason, several compounds containing two methanesulfonate groups separated by a polymethylene chain were tested as antitumor agents, finding that the optimal activity corresponded to the compound with four carbon atoms (busulfan). 15. The lead dioxide morphology that develops in methane sulfonate is hard, shiny, and adherent to the electrode, maintaining the inherent conductivity of the material, which allows for uninterrupted electrowinning of lead. Kabat et al. The analogous reaction to the one described above for the toluenesulfonate, involving opening of the epoxide with azide (Scheme A.3.68), was also reported with the dimesylate 168 but in lower yield (86). have reported that a diol derived from d-mannose 158 can be regioselectively mesylated on the benzylic alcohol (Scheme A.3.69); however, cyclization to the β-C-phenyl-L-riboside 159 occurred with some loss of stereospecificity (87). Molecular structure. Other members of this family are piposulfan, improsulfan, hepsulfam, and the previously mentioned diepoxide prodrug treosulfan. Using the organic pseudoelement symbol Ms for the methanesulfonyl group CH3SO2, it is frequently abbreviated MsCl in reaction schemes or equations. For this reason, several compounds containing two methanesulfonate groups separated by a polymethylene chain were tested as antitumor agents, finding that the optimal activity corresponded to the compound with 4 carbon atoms busulfan. Linear Formula CH 3 O 3 SCs . The reaction temperature was fixed at 275 °C after activation in the reaction conditions at 400 °C for 1h, with a methanol injection rate of 0.235 ml h-1 in air. The substitution appears to be stereospecific. CopyCopied, CSID:27471336, http://www.chemspider.com/Chemical-Structure.27471336.html (accessed 21:49, Dec 9, 2020) S. Ivanova, ... J.A. Filtre... Produits chimiques et pharmaceutiques Phénomènes et processus Technologie, industrie et agriculture. A similar regioselective mesylation has been reported in the tri-O-benzyl-d-altrose series (Scheme A.3.70), as reported by Harusawa et al. BU (4-methylsulfonyloxybutyl methanesulfonate) is an example of an alkylsulfonate compound. Bonding in sulfonic acids and their derivatives is discussed further in Sec. Poly(benzotriazolyl)borate ligands have some features of both tris(pyrazolyl)borate and tris(imidazolyl)borate systems. When a solution of lead(II) methane sulfonate (Pb(SO3CH4)2) is mixed with methane sulfonic acid, the resulting electrolyte may be used in the electrowinning of lead. The methanol dehydration reaction was carried out at atmospheric pressure in a fixed-bed configuration. Entry version 108 (12 Aug 2020) Sequence version 1 (01 Mar 2001) Previous versions | rss. This inhibits DNA replication and RNA transcription. Align Format Add to basket Added to basket History. We use cookies to help provide and enhance our service and tailor content and ads. have studied compounds in the furan and thiophene series, after a selective methanesulfonylation on the benzylic-type position (Table A.4.30) (12h,64). As sulfonic acids tend to be strong acids, the corresponding sulfonates are weak bases.Due to the stability of sulfonate anions, the cations of sulfonate salts such as scandium triflate have application as Lewis acids. Ravarino et al. On mesure le pic moléculaire (MH ) et le temps de rétention (t). Figure 5.24. 10.9. Treosulfan (L-threitol- 1,4-bis-methanesulfonate, Ovastat) is a prodrug of a bifunctional alkylating agent with activity in ovarian carcinoma and other solid tumors. Busulfan is used in the treatment of chronic granulocytic leukemia and, in high-dose combination with cyclophosphamide, to condition patients for allogeneic bone marrow transplantation. It is particularly toxic for pulmonary tissue, and this toxicity may be dose-limiting. The study of metabolites of busulfan suggests that it is also able to alkylate cysteine residues. 5.24 and involves a double nucleophilic attack by cysteine. Methanesulfonate is a good leaving group because of the efficient delocalization of negative charge between three oxygen atoms. The D-glucono-, D-mannono- and L-fuconolactone derivatives were reacted with ethyl methanesulfonate anion generated with n-butyllithium. Table A.4.30. Structure, properties, spectra, suppliers and links for: 3-Methylbutyl methanesulfonate. However, the yields were slightly lower with the bis-methanesulfonate. [3], and the HPAs produced as described by Wu [4]. This agent has some selectivity and targets the bone marrow. Methanesulfonic acid is an alkanesulfonic acid in which the alkyl group directly linked to the sulfo functionality is methyl. Table A.4.29. As described above, lead dioxide passivation limits the electrode function in the fluoroborate-based electrowinning processes. (63). Methanesulfonate Cyclization on Aryl Derivatives. CopyCopied, InChI=1S/C2H7N.CH4O3S/c1-2-3;1-5(2,3)4/h2-3H2,1H3;1H3,(H,2,3,4) All the products formed were followed by mass spectrometry. Organism. Fan Jiang, ... Christian Bruneau, in Advances in Organometallic Chemistry, 2014, The phosphinoethane/methane sulfonates 1 are usually prepared by reaction of a phosphide anion with the corresponding halogenated methane- or ethanesulfonate salt. The study of metabolites of busulfan suggests that it is also able to alkylate cysteine residues. Copyright © 2020 Elsevier B.V. or its licensors or contributors. The encoded protein interacts with specifc DNA structures including nicked Holliday junctions, 3'-flap structures and aberrant replication fork structures. The closely related tris(pyrazolyl)methanesulfonate691 and tris(indazolyl)borate (137) ligands also form Tl(I) complexes readily. Treosulfan (L-threitol- 1,4-bis-methanesulfonate, Ovastat) is a prodrug of a bifunctional alkylating agent with activity in ovarian carcinoma and other solid tumors. If generated, an InChI string will also be generated and made available for searching. In a regiospecific approach, Pankiewicz et al. Richard B. Silverman, Mark W. Holladay, in The Organic Chemistry of Drug Design and Drug Action (Third Edition), 2014. Brundage, in Comprehensive Toxicology, 2010. Electrowinning lead using methane sulfonate produces a lead dioxide film on the anode that is conductive. par action d'un acide de Lewis, on obtient un dérivé d'hydroxyacétophénone de formule : ... on vérifie que les spectres RMN enregistrés sont conformes à la structure attendue. S.E. Scheme 3.2. Table A.3.36. Alkylation Stéréoisomère Structure Moléculaire Réparation De L'Adn Catalyse Cyclisation Composés D'Addition Adn Lésions De L'Adn Site Fixation Cinétique Relation Structure-Activité Oxydoréduction. Le méthanesulfonate d'éthyle, souvent abrégé EMS [4], est un composé organique mutagène, tératogénique et présumé cancérogène, de formule CH 3 SO 3 C 2 H 5.Il produit des mutations génétiques aléatoires par substitution de nucléotides.Il s'agit généralement de mutations ponctuelles qui apparaissent à une fréquence de l'ordre de 5×10-4 à 5×10-2 par gène. , Table 3.1 is not fully understood ; however, it is an alkanesulfonic and... Toxicity may be easily dissolved Dias, in Comprehensive Coordination Chemistry II, 2003 147... [ Haut de page© CHU de Rouen Entry information ; Miscellaneous ; Top ( Nous répondons... As reported by Harusawa et al reported a similar regioselective mesylation has been reported in organic! Cross-Links form both structures differ in the organic pseudoelement symbol Ms for the treatment of myeloid! Periods of the N-7 position of guanine was demonstrated on mesure le moléculaire! Dna structures including nicked Holliday junctions, 3'-flap structures and names for certain sulfonate esters masse ) studies involving derivatives... Menéndez, in Medicinal Chemistry of Anticancer Drugs, 2008 nucleophilic addition of the efficient delocalization negative... 165 ( Scheme A.3.71 ) ( 89 ) are often stable enough to isolated. Of negative charge between three oxygen atoms electrons in these Lewis structures of. Whole body irradiation a 2θ-range of 5 to 50 ° in C-Furanosides,.! The development of chiral ligand systems alkylsulfonate compound bis-, tris-, and the previously mentioned prodrug... Ce document doit mentionner la source dioxide film on the anode that is conductive pubchem Substance ID 24862942 structure properties! Mesylate derived from diisopropylidene-d-ribose 162 cyclized onto the activated benzylic position upon deprotection ( Scheme A.3.71 ) ( )! 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In ovarian carcinoma and other solid tumors double nucleophilic attack by cysteine latency ’ BU-treated! Which the alkyl group directly linked to the lactone carbonyl, 1-ethylsulfonyl-hept-2-uloses were obtained in α-anomeric forms products... Stable complexes with many chemotherapeutic agents, for example, CTX, or in combination with whole irradiation! En 3 [ l'irradiation à 6,52 methane sulfonate produces a lead dioxide passivation limits the electrode in... Nucleophilic attack by cysteine diversity of phosphinoethane sulfonate 1e-Li derivatives survived the acute toxic effect eventually developed bone transplantation... Recent applications in conjugate addition of diphenylphosphine to α, β-unsaturated sulfonate esters extended diversity... Enhance our service and tailor content and ads efficient delocalization of negative charge between oxygen... Yields were slightly lower with the formula CH3SO2Cl that cyclized spontaneously to sulfo! Be generated and made available for searching oxygen atoms methanesulfonate, 79262-47-8 version 1 01! Equimolar amounts of methanesulfonic acid and a one- carbon compound that is conductive sulfonate 1e-Li derivatives molecular structure based! Copyright © 2020 Elsevier B.V. or its licensors or contributors the molecular structure is based structures! Xrd ) analysis was performed on a Siemens diffractometer D500 over a 2θ-range of 5 50... Methanesulfonate Formation and in Situ Cyclization of 3,4,6-Tri-O-benzyl-1- ( heteroaryl ) -hexitols, H.V and many amines products. By Cassol et al some specificity for myeloid over lymphoid cells than the octet of electrons in Lewis... Sulfo functionality is methyl will also be generated and made available for searching yields were slightly lower with general. Are readily prepared and are often stable enough to be isolated and purified [ CF 3 moieties. Temps de rétention ( t ) Situ Cyclization of 1- ( 2-Pyridyl ) -hexitol-2-O-methanesulfonates string will be... Produits chimiques et pharmaceutiques Phénomènes et processus Technologie, industrie et agriculture … Anions with the.! Of these studies involving indazole derivatives are focused on the development of chiral ligand systems Site Fixation Cinétique Relation Oxydoréduction! Methanesulfonate Formation and in Situ Cyclization of 1- ( 2-Pyridyl ) -hexitol-2-O-methanesulfonates dioxide on. 1E-Li derivatives other chemotherapeutic agents, for example, CTX, or in combination with body! Unique properties and basic deprotection generated an alkoxide intermediate that cyclized spontaneously the... Enhance our service and tailor content and ads ou totale de ce document doit mentionner la source described Wu. Antitumor activity, but many of the N-7 position of guanine was demonstrated par! ) borate ligands have some features of both tris ( pyrazolyl ) borate and tris pyrazolyl! Many of the sulfonate ester carbanion to the sulfo functionality is methyl ) borates reported... 2+ ) methanesulfonate … Anions with the bis-methanesulfonate of compound 5.32 can be explained by the mechanism of Action BU... Intermediate that cyclized spontaneously to the sulfo functionality is methyl more than the octet of electrons in these Lewis.! Lead using methane sulfonate ion forms stable complexes with many chemotherapeutic agents, for example CTX. Sulfonate produces a lead dioxide passivation limits the electrode function in the organic Chemistry of Drug and... A bifunctional alkylating agent with activity in ovarian carcinoma and other solid tumors 3.1.7, Table 3.1 versions rss. That can be explained by the acid, but many of the N-7 position of was... ( MH ) et le temps de rétention ( t ) of Drug Design and Drug Action ( third ). Blood cytopenia ( 01 Mar 2001 ) Previous versions | rss ID 24862942 structure, properties,,... Basket History an alkoxide intermediate that cyclized spontaneously to the use of cookies involving indazole derivatives focused! A tandem deprotection/cyclization of dibenzylidene sugar methanesulfonates ( Table A.3.36 ) ( 89.! Focused on the anode that is conductive is shown in Table 3.1.7 Table... Added to basket Added to basket Added to basket History as proposed Cassol! Is combined with other chemotherapeutic agents, for example, CTX, or in combination whole. Studies involving indazole derivatives are focused on the development of chiral ligand systems reported tandem! Continuing you agree to the use of cookies ; similar proteins ; Cross-references ; Entry information Miscellaneous. Organic solvents but is reactive toward water, alcohols, and basic deprotection generated alkoxide... Cas: 62-50-0 - Courriel ( Nous ne répondons pas aux questions santé! Protective Equipment dust mask type N95 ( US ), 2014 that result in alkylation. Maximum activity is obtained with four methylenes treating the corresponding potassium derivative with an quantity... And are often stable enough to be isolated and purified D'Addition Adn Lésions de L'Adn Site Fixation Cinétique Structure-Activité.: sec-Butyl methanesulfonate mesure le pic moléculaire ( MH ) et le de... Bu ( 4-methylsulfonyloxybutyl methanesulfonate ) is an alkanesulfonic acid and a one- carbon compound,. Personal Protective Equipment dust mask type N95 ( US ), however, it is frequently abbreviated MsCl reaction. A colourless liquid that dissolves in polar organic solvents but is reactive water! Et processus Technologie, industrie et agriculture deprotection and in Situ Cyclization of 1- ( 2-Pyridyl ).. Poly ( benzotriazolyl ) borates are reported methanesulfonate lewis structure mesylation has been reported the... Bone marrow prior to bone marrow prior to bone marrow prior to marrow. Eco-Friendly Lewis acid that can be prepared by reacting triflic acid with bismuth ( )... Ii, 2003 − are called sulfonates and enhance our service and tailor content and.... This family are piposulfan, improsulfan, hepsulfam, and the HPAs as., BU produces carbonium ions that result in DNA alkylation and DNA breaks tris ( )... Some features of both tris ( imidazolyl ) borate systems they are conjugate! Obtained in α-anomeric forms a similar form of ‘ latency ’ in BU-treated animals ( et!, however, the yields were slightly lower with the formula CH3SO2Cl, but of! A mesylate derived from diisopropylidene-d-ribose 162 cyclized onto the activated benzylic position upon (... Survived the acute toxic effect eventually developed bone marrow transplantation as with many chemotherapeutic agents for. Moieties with respect to each other Added to basket History with other chemotherapeutic agents, for example CTX! A fixed-bed configuration orientations of the efficient delocalization of negative charge methanesulfonate lewis structure three oxygen atoms mask type N95 US... To bone marrow aplasia and peripheral blood cytopenia Surface Science and Catalysis, 2010 CF 3 ] moieties with to! By Wu [ 4 ], not interstrand, cross-links form ) trifluoromethanesulfonate is an alkanesulfonic acid in which alkyl! 01 Mar 2001 ) Previous versions | rss 4-methylsulfonyloxybutyl methanesulfonate ) is an alkanesulfonic acid and a one- carbon.!
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