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Chiral Aryl Sulfonyl Hydantoins as Hypoglycemic Agents

  • Roshan Ahmad EMAIL logo , Rukhsana Jabeen , Mohammad Zia-ul-Haq , Humaira Nadeem , Helmut Duddeck and Eugen J. Verspohl
Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 55 Issue 2

Some novel chiral sulfonyl hydantoin derivatives 2a-e and 3 a-e have been prepared. p-Toluenesulfonyl chloride on treatment with L-amino acids in presence of K2CO3/H2O yielded N-(p-toluensulfonyl-)amino acids 1a - e which were cyclized in presence of NH4-SCN Ac2O to afford 1-(p-toluenesulfonyl)-5-substituted-2-thiohydantoins 2a-e. These compounds were oxidized with HNO3 to yield 1-(p-toluenesulfonyl)-5-substituted hydantoins 3a-e. The enantiomeric ratios of 3a-e were determined by 1H NMR spectroscopy using Eu(hfc)3. The antidiabetic activity of 3a-d has been determined.

: Hydantoins; Antidiabetic Activity; NMR Data
Received: 1999-9-2
Published Online: 2014-6-2
Published in Print: 2000-2-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Sila-Substitution of the α-Amino Acid Proline: Synthesis of rac- and (R)-4,4-Dimethyl-4-sila-proline Ethyl Ester
  2. Synthesis and Crystal Structures of ATi[Nb6Cl18] Compounds (A = K, Rb, Cs, In, Tl)
  3. Optisch aktive Übergangsmetall-Komplexe, 122. Synthese von Palladium(II)-Schiff-Base-Komplexen -intramolekulare Wechselwirkungen / Optically Active Transition Metal Complexes, 122. Synthesis of Palladium (II) Complexes with Schiff Base Ligands -Intramolecular Interactions
  4. Intermetallic Cerium Compounds with Ordered U3Si2 Type Structure
  5. Electrochemical Synthesis of a 6-Coordinate Cadmium(II) Complex with N-Methylisatin N(4)-cyclohexylthiosemicarbazone
  6. Synthese und Kristallstruktur des Bromdifluormethyl-triphenyl- phosphoniumbromids, [(C6H5)3PCF2Br]+ Br- / Synthesis and Crystal Structure of Bromodifluoromethyl-triphenylphosphonium Bromide, [(C6H5)3PCF2Br]+ Br-
  7. Synthesis, Structure and Properties of Poly > [(N-(2-Hydroxyethyl)- N'-carboxymethyl-1,2-ethylenediamine-N, N'-Diacetato)copper(II) Hydrate], {[Cu(Hhedta)] · H2O }n
  8. Kristallstrukturen, Schwingungsspektren und Normalkoordinatenanalyse von cis-(n-Bu4N)2[ReBr4(NCS)2 ], cis-(n-Bu4N)2[ReBr4(NCSe)2] und cis-(n-Bu4N)2[ReBr4(NCS)(NCSe)] / Crystal Structures, Vibrational Spectra and Normal Coordinate Analyses of cis-(n-Bu4N)2[ReBr4(NCS)2], cis-(n-Bu4N)2[ReBr4(NCSe)2,] and cis -(n -Bu4N)2[ReBr4(NCS)(NCSe)]
  9. Bis(diphenylphosphanyl)amine and its Disulfide and Diselenide. Application of the INEPT-HEED Pulse Sequence for Measurement of 1J(31P, 15N) and Isotope Induced Chemical Shifts 1⊿ 14/15N(31P) at Natural Abundance of 15N
  10. Synthesis, Multinuclear (1H, 13C and 17O ) Magnetic Resonance Spectroscopy and Conformational Analysis of Some Substituted Aryl Naphthoates
  11. Substituent Influences on the Keto-Enol Tautomerism in 1-(2-Hydroxyphenyl)-3-α-and -β-naphthylpropane-1,3-diones Monitored by 1H and 13C NMR Spectroscopy
  12. Chiral Aryl Sulfonyl Hydantoins as Hypoglycemic Agents
  13. Endogenous Alkaloids in Man, Part 33. Dimethyl (2S,4S)-and (2R,4S)-5,5-Dimethyl-1,3-thiazolidine-2,4-dicarboxylates, Two Diastereomeric Glyoxylate-Derived Heterocycles
  14. The Inclusion of Carbon Disulfide in p-tert-Butylcalix[4]-and [6 ]arene - A Combined Crystallographic and Vibrational Spectroscopic Study
  15. Facile Regioselective Synthesis of 1,2,6,8-Tetraazaspiro[4.4]nona-2,6-dien-9-ones
  16. A New Triterpenoidal Saponin from the Bark of Guaiacum officinale L.
  17. Alternative Method for the Preparation of 4,5-Ethylenedithio-1,3-dithiole-2- thione and Related Compounds
  18. A Diterpenoid with a New Modified Abietane Skeleton from Salvia palaestina
https://doi.org/10.1515/znb-2000-0212

Articles in the same Issue

  1. Sila-Substitution of the α-Amino Acid Proline: Synthesis of rac- and (R)-4,4-Dimethyl-4-sila-proline Ethyl Ester
  2. Synthesis and Crystal Structures of ATi[Nb6Cl18] Compounds (A = K, Rb, Cs, In, Tl)
  3. Optisch aktive Übergangsmetall-Komplexe, 122. Synthese von Palladium(II)-Schiff-Base-Komplexen -intramolekulare Wechselwirkungen / Optically Active Transition Metal Complexes, 122. Synthesis of Palladium (II) Complexes with Schiff Base Ligands -Intramolecular Interactions
  4. Intermetallic Cerium Compounds with Ordered U3Si2 Type Structure
  5. Electrochemical Synthesis of a 6-Coordinate Cadmium(II) Complex with N-Methylisatin N(4)-cyclohexylthiosemicarbazone
  6. Synthese und Kristallstruktur des Bromdifluormethyl-triphenyl- phosphoniumbromids, [(C6H5)3PCF2Br]+ Br- / Synthesis and Crystal Structure of Bromodifluoromethyl-triphenylphosphonium Bromide, [(C6H5)3PCF2Br]+ Br-
  7. Synthesis, Structure and Properties of Poly > [(N-(2-Hydroxyethyl)- N'-carboxymethyl-1,2-ethylenediamine-N, N'-Diacetato)copper(II) Hydrate], {[Cu(Hhedta)] · H2O }n
  8. Kristallstrukturen, Schwingungsspektren und Normalkoordinatenanalyse von cis-(n-Bu4N)2[ReBr4(NCS)2 ], cis-(n-Bu4N)2[ReBr4(NCSe)2] und cis-(n-Bu4N)2[ReBr4(NCS)(NCSe)] / Crystal Structures, Vibrational Spectra and Normal Coordinate Analyses of cis-(n-Bu4N)2[ReBr4(NCS)2], cis-(n-Bu4N)2[ReBr4(NCSe)2,] and cis -(n -Bu4N)2[ReBr4(NCS)(NCSe)]
  9. Bis(diphenylphosphanyl)amine and its Disulfide and Diselenide. Application of the INEPT-HEED Pulse Sequence for Measurement of 1J(31P, 15N) and Isotope Induced Chemical Shifts 1⊿ 14/15N(31P) at Natural Abundance of 15N
  10. Synthesis, Multinuclear (1H, 13C and 17O ) Magnetic Resonance Spectroscopy and Conformational Analysis of Some Substituted Aryl Naphthoates
  11. Substituent Influences on the Keto-Enol Tautomerism in 1-(2-Hydroxyphenyl)-3-α-and -β-naphthylpropane-1,3-diones Monitored by 1H and 13C NMR Spectroscopy
  12. Chiral Aryl Sulfonyl Hydantoins as Hypoglycemic Agents
  13. Endogenous Alkaloids in Man, Part 33. Dimethyl (2S,4S)-and (2R,4S)-5,5-Dimethyl-1,3-thiazolidine-2,4-dicarboxylates, Two Diastereomeric Glyoxylate-Derived Heterocycles
  14. The Inclusion of Carbon Disulfide in p-tert-Butylcalix[4]-and [6 ]arene - A Combined Crystallographic and Vibrational Spectroscopic Study
  15. Facile Regioselective Synthesis of 1,2,6,8-Tetraazaspiro[4.4]nona-2,6-dien-9-ones
  16. A New Triterpenoidal Saponin from the Bark of Guaiacum officinale L.
  17. Alternative Method for the Preparation of 4,5-Ethylenedithio-1,3-dithiole-2- thione and Related Compounds
  18. A Diterpenoid with a New Modified Abietane Skeleton from Salvia palaestina
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