메뉴 건너뛰기




Volumn 3, Issue 3, 2001, Pages 290-300

Synthesis of a sulfahydantoin library

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINO ACID; HYDANTOIN DERIVATIVE; SULFUR DERIVATIVE; THIAZOLE DERIVATIVE;

EID: 0035344436     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc000111u     Document Type: Article
Times cited : (30)

References (48)
  • 2
    • 20744456789 scopus 로고
    • Solid-phase peptide synthesis. 1. The synthesis of a tetrapeptide
    • Merrifield, R. B. Solid-Phase Peptide Synthesis. 1. The Synthesis of a Tetrapeptide. J. Am. Chem. Soc. 1963, 85, 2149-2154.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 2149-2154
    • Merrifield, R.B.1
  • 3
    • 0026419319 scopus 로고
    • Generation and use of synthetic peptide combinatorial libraries for basic research and drug discovery
    • Houghten, R. A.; Pinilla, C.; Blondelle, S. E.; Appel, J. R.; Dooley, C. T.; Cuervo, J. H. Generation and Use of Synthetic Peptide Combinatorial Libraries for Basic Research and Drug Discovery. Nature 1991, 354, 84-86.
    • (1991) Nature , vol.354 , pp. 84-86
    • Houghten, R.A.1    Pinilla, C.2    Blondelle, S.E.3    Appel, J.R.4    Dooley, C.T.5    Cuervo, J.H.6
  • 4
    • 0026419328 scopus 로고
    • A new type of synthetic peptide library for identifying ligand-binding activity
    • Lam, K. S.; Salmon, S. E.; Hersch, E. M.; Hruby, V. J.; Kazmierski, W. M.; Knapp, R. J. A New Type of Synthetic Peptide Library for Identifying Ligand-Binding Activity. Nature 1991, 354, 82-84.
    • (1991) Nature , vol.354 , pp. 82-84
    • Lam, K.S.1    Salmon, S.E.2    Hersch, E.M.3    Hruby, V.J.4    Kazmierski, W.M.5    Knapp, R.J.6
  • 5
    • 0032542115 scopus 로고    scopus 로고
    • Solid phase organic reactions. III. A review of the literature November 1996 to December 1997
    • Booth, S.; Hermkens, P. H. H.; Ottenheijm, H. C.; Rees, D. C. Solid Phase Organic Reactions. III. A Review of the Literature November 1996 to December 1997. Tetrahedron 1998, 54, 15385-15443.
    • (1998) Tetrahedron , vol.54 , pp. 15385-15443
    • Booth, S.1    Hermkens, P.H.H.2    Ottenheijm, H.C.3    Rees, D.C.4
  • 6
    • 11744322280 scopus 로고    scopus 로고
    • Combinatorial synthesis: A heterocyclic chemist's perspective
    • Loughlin, W. A. Combinatorial Synthesis: A Heterocyclic Chemist's Perspective. Aust. J. Chem. 1998, 51, 875-893.
    • (1998) Aust. J. Chem. , vol.51 , pp. 875-893
    • Loughlin, W.A.1
  • 7
    • 0034265578 scopus 로고    scopus 로고
    • Comprehensive survey of combinatorial library synthesis: 1999
    • Dolle, R. E. Comprehensive Survey of Combinatorial Library Synthesis: 1999. J. Comb.. Chem. 2000, 2, 383-433.
    • (2000) J. Comb.. Chem. , vol.2 , pp. 383-433
    • Dolle, R.E.1
  • 8
    • 0001502264 scopus 로고
    • Synthesen von Heterocyclen. 64. Mitt.: Uber reaktionen mit schwefelsaurediamid (About reactions of sulfuric acid diamide)
    • Vorreither, H. K.; Ziegler, E. Synthesen von Heterocyclen. 64. Mitt.: Uber Reaktionen mit Schwefelsaurediamid (About Reactions of Sulfuric Acid Diamide). Monatsh. Chem. 1965, 96, 216-219.
    • (1965) Monatsh. Chem. , vol.96 , pp. 216-219
    • Vorreither, H.K.1    Ziegler, E.2
  • 9
    • 0024784277 scopus 로고
    • Synthesis of 1,2,5-thiadiazolidin-3-one 1,1-dioxides: X-ray structure determination of 4,4-diphenyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide
    • Timberlake, J. W.: Ray, W. J.; Stevens, E. D.; Klein, C. L. Synthesis of 1,2,5-Thiadiazolidin-3-one 1,1-dioxides: X-ray Structure Determination of 4,4-Diphenyl-1,2,5-thiadiazolidin-3-one 1,1-Dioxide. J. Org. Chem. 1989, 54, 5824-5826.
    • (1989) J. Org. Chem. , vol.54 , pp. 5824-5826
    • Timberlake, J.W.1    Ray, W.J.2    Stevens, E.D.3    Klein, C.L.4
  • 10
    • 0000392211 scopus 로고
    • 3-Oxo-and 3-imino-4-substituted-1,2,5-thiadiazolidine 1,1-dioxides: Synthesis, spectral properties, and selected chemistry
    • Lee, C.-H.; Korp, J. D.; Kohn, H. 3-Oxo-and 3-Imino-4-Substituted-1,2,5-thiadiazolidine 1,1-Dioxides: Synthesis, Spectral Properties, and Selected Chemistry. J. Org. Chem. 1989, 54, 3077-3083.
    • (1989) J. Org. Chem. , vol.54 , pp. 3077-3083
    • Lee, C.-H.1    Korp, J.D.2    Kohn, H.3
  • 11
    • 0001740377 scopus 로고
    • Intra-and intermolecular α-sulfamidoalkylation reactions
    • Lee, C.-H.: Kohn, H. Intra-and Intermolecular α-Sulfamidoalkylation Reactions. J. Org. Chem. 1990, 55, 6098-6104.
    • (1990) J. Org. Chem. , vol.55 , pp. 6098-6104
    • Lee, C.-H.1    Kohn, H.2
  • 12
    • 0026075002 scopus 로고
    • Synthese et cyclisation de carboxysulfamides derives d'aminoacides
    • Aouf, N.; Dewynter, G.; Montero, J. L. Synthese et Cyclisation de Carboxysulfamides Derives d'Aminoacides (Synthesis and Cyclization of Carboxysulfamides Derived from Amino Acids). Tetrahedron Lett. 1991, 32, 6545-6546.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 6545-6546
    • Aouf, N.1    Dewynter, G.2    Montero, J.L.3
  • 13
    • 0030040762 scopus 로고    scopus 로고
    • Synthesis of pseudonucleosides containing chiral sulfahydantoins as aglycone (II)
    • Dewynter, G.; Aouf, N.; Regainia, Z.; Montero, J. L. Synthesis of Pseudonucleosides Containing Chiral Sulfahydantoins as Aglycone (II). Tetrahedron 1996, 52, 993-1004.
    • (1996) Tetrahedron , vol.52 , pp. 993-1004
    • Dewynter, G.1    Aouf, N.2    Regainia, Z.3    Montero, J.L.4
  • 14
    • 0007598546 scopus 로고
    • A general synthesis of 4-substituted 1,1-dioxo-1,2,5-thiadiazolidin-3-ones derived from α-amino acids
    • Muller, G. W.; DuBois, G. E. A General Synthesis of 4-Substituted 1,1-Dioxo-1,2,5-thiadiazolidin-3-ones Derived from α-Amino Acids. J. Org. Chem. 1989, 54, 4471-4473.
    • (1989) J. Org. Chem. , vol.54 , pp. 4471-4473
    • Muller, G.W.1    DuBois, G.E.2
  • 16
    • 0033536494 scopus 로고    scopus 로고
    • A general inhibitor scaffold for serine proteases with a (Chymo)trypsin-like fold: Solution-phase construction and evaluation of the first series of libraries of mechanism-base inhibitors
    • Kuang, R.; Epp, J. B.; Ruan, S.; Yu, H.; Huang, P.; He, S.; Tu, J.; Schechter, N. M.; Turbov, J.; Froelich, C. J.; Groutas, W. C. A General Inhibitor Scaffold for Serine Proteases with a (Chymo)trypsin-like Fold: Solution-Phase Construction and Evaluation of the First Series of Libraries of Mechanism-Base Inhibitors. J. Am. Chem. Soc. 1999, 121, 8128-8129.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 8128-8129
    • Kuang, R.1    Epp, J.B.2    Ruan, S.3    Yu, H.4    Huang, P.5    He, S.6    Tu, J.7    Schechter, N.M.8    Turbov, J.9    Froelich, C.J.10    Groutas, W.C.11
  • 17
    • 0033517091 scopus 로고    scopus 로고
    • Human chymase inhibitors based on the 1,2,5-thiadiazolidin-3-one 1,1-dioxide scaffold
    • Groutas, W. C.; Schechter, N. M.; He, S.; Yu, H.; Huang, P.; Tu, J. Human Chymase Inhibitors Based on the 1,2,5-Thiadiazolidin-3-one 1,1-Dioxide Scaffold. Bioorg. Med. Chem. Lett. 1999, 9, 2199-2204.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 2199-2204
    • Groutas, W.C.1    Schechter, N.M.2    He, S.3    Yu, H.4    Huang, P.5    Tu, J.6
  • 18
    • 0031835168 scopus 로고    scopus 로고
    • Potent and specific inhibition of human leukocyte elastase, cathepsin G and proteinase 3 by sulfone derivatives employing the 1,2,5-thiadiazolidin-3-one 1,1 -dioxides
    • Groutas, W. C.; Kuang, R.; Ruan, S.; Epp, J. B.; Venkataraman, R.; Truong, T. M. Potent and Specific Inhibition of Human Leukocyte Elastase, Cathepsin G and Proteinase 3 by Sulfone Derivatives Employing the 1,2,5-Thiadiazolidin-3-one 1,1 -Dioxides. Bioorg. Med. Chem. 1998, 6, 661-671.
    • (1998) Bioorg. Med. Chem. , vol.6 , pp. 661-671
    • Groutas, W.C.1    Kuang, R.2    Ruan, S.3    Epp, J.B.4    Venkataraman, R.5    Truong, T.M.6
  • 19
    • 0030993410 scopus 로고    scopus 로고
    • Structure-based design of a general class of mechanism-based inhibitors of the serine proteinases employing a novel amino acid-derived heterocyclic scaffold
    • Groutas, W. C.; Kuang, R.; Venkataraman, R.; Epp, J. B.; Ruan, S.; Prakash, O. Structure-Based Design of a General Class of Mechanism-Based Inhibitors of the Serine Proteinases Employing a Novel Amino Acid-Derived Heterocyclic Scaffold. Biochemistry 1997, 36, 4739-4750.
    • (1997) Biochemistry , vol.36 , pp. 4739-4750
    • Groutas, W.C.1    Kuang, R.2    Venkataraman, R.3    Epp, J.B.4    Ruan, S.5    Prakash, O.6
  • 22
    • 0031818222 scopus 로고    scopus 로고
    • Synthesis and antihypertensive activity of 2,4-dioxoimidazolidin-1-yl and perhydro-2,4-dioxopyrimidin-1-yl ergoline derivatives
    • Mantegani, S.; Brambilla, E.; Caccia, C.; Chiodini, L.; Ruggieri, D.; Lamberti, E.; Di Salle, E.; Salvati, P. Synthesis and Antihypertensive Activity of 2,4-Dioxoimidazolidin-1-yl and Perhydro-2,4-dioxopyrimidin-1-yl Ergoline Derivatives. Farmaco 1998, 53, 293-304.
    • (1998) Farmaco , vol.53 , pp. 293-304
    • Mantegani, S.1    Brambilla, E.2    Caccia, C.3    Chiodini, L.4    Ruggieri, D.5    Lamberti, E.6    Di Salle, E.7    Salvati, P.8
  • 25
    • 84987068183 scopus 로고
    • Acidic isostere design: Synthetic strategies and recent progress in understanding electronic properties and metabolic stability
    • Lipinski, C. A.; Chenard, B. L. Acidic Isostere Design: Synthetic Strategies and Recent Progress in Understanding Electronic Properties and Metabolic Stability. Pestic. Sci. 1990, 29, 227-240.
    • (1990) Pestic. Sci. , vol.29 , pp. 227-240
    • Lipinski, C.A.1    Chenard, B.L.2
  • 26
    • 0025892139 scopus 로고
    • pKa, log P and med chem clogP fragment values of acidic heterocyclic potential bioisosteres
    • Lipinski, C. A.; Fiese, E. F.; Korst, R. J. pKa, Log P and Med Chem ClogP Fragment Values of Acidic Heterocyclic Potential Bioisosteres Quant. Struct.-Act. Relat. 1991, 10, 109-117.
    • (1991) Quant. Struct.-Act. Relat. , vol.10 , pp. 109-117
    • Lipinski, C.A.1    Fiese, E.F.2    Korst, R.J.3
  • 27
    • 0028084261 scopus 로고
    • Phloem mobility of xenobiotics. V. Structural requirements for phloem systemic pesticides
    • Kleier, D. A. Phloem Mobility of Xenobiotics. V. Structural Requirements for Phloem Systemic Pesticides. Pestic. Sci. 1994, 42, 1-11.
    • (1994) Pestic. Sci. , vol.42 , pp. 1-11
    • Kleier, D.A.1
  • 28
    • 0028874159 scopus 로고
    • Phloem mobility of xenobiotics: Tabular review of physicochemical properties governing the output of the Kleier model
    • Brudenell, A. J. P.; Baker, D. A.; Grayson, B. T. Phloem Mobility of Xenobiotics: Tabular Review of Physicochemical Properties Governing the Output of the Kleier Model. Plant Growth Regul. 1995, 16, 215-231.
    • (1995) Plant Growth Regul. , vol.16 , pp. 215-231
    • Brudenell, A.J.P.1    Baker, D.A.2    Grayson, B.T.3
  • 29
    • 0346437708 scopus 로고    scopus 로고
    • Phloem mobility of crop protection products
    • Lichtner, F. Phloem mobility of crop protection products. Aust. J. Plant Physiol. 2000, 27, 609-614.
    • (2000) Aust. J. Plant Physiol. , vol.27 , pp. 609-614
    • Lichtner, F.1
  • 31
    • 0001325578 scopus 로고
    • Über das sulfamidsaurechlorid (about sulfamoyl chloride)
    • Graf, R. Über das Sulfamidsaurechlorid (About Sulfamoyl Chloride). Chem. Ber. 1959, 92, 509-513.
    • (1959) Chem. Ber. , vol.92 , pp. 509-513
    • Graf, R.1
  • 32
    • 35148900474 scopus 로고
    • A useful, alternative synthesis of unsymmetrical and symmetrical N,N′-disubstituted sulfamides by transamidation reactions of sulfamides with amines
    • McDermott, S. D.; Spillane, W. J. A Useful, Alternative Synthesis of Unsymmetrical and Symmetrical N,N′-Disubstituted Sulfamides by Transamidation Reactions of Sulfamides with Amines. Synthesis 1983, 192-195.
    • (1983) Synthesis , pp. 192-195
    • McDermott, S.D.1    Spillane, W.J.2
  • 33
    • 0042828565 scopus 로고    scopus 로고
    • note
    • a determination was performed in aqueous DMSO by Robertson-Microlit Laboratories, 29 Samson Avenue, Madison, NJ 07940, using a Sirius GLpKa potentiometric system manufactured by pION, Cambridge, MA.
  • 34
    • 0342993927 scopus 로고    scopus 로고
    • A reductive alkylation procedure applicable to both solution-and solid-phase syntheses of secondary amines
    • Szardenings, A. K.; Burkoth, T. S.; Look, G. C.; Campbell, D. A. A Reductive Alkylation Procedure Applicable to Both Solution-and Solid-Phase Syntheses of Secondary Amines. J. Org. Chem. 1996, 61, 6720-6722.
    • (1996) J. Org. Chem. , vol.61 , pp. 6720-6722
    • Szardenings, A.K.1    Burkoth, T.S.2    Look, G.C.3    Campbell, D.A.4
  • 35
    • 0028833961 scopus 로고
    • Reductive alkylation on a solid phase-synthesis of a piperazinedione combinatorial library
    • Gordon, D. W.; Steele, J. W. Reductive Alkylation on a Solid Phase-Synthesis of a Piperazinedione Combinatorial Library. Bioorg. Med. Chem. Lett. 1995, 5, 47-50.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 47-50
    • Gordon, D.W.1    Steele, J.W.2
  • 36
    • 0030914640 scopus 로고    scopus 로고
    • High throughput on-bead monitoring of solid phase reactions by diffuse reflectance in infrared fourier transform spectroscopy (DRIFTS)
    • Chan, T. Y.; Chen, R.; Sofia, M. J.; Smith, B. C.; Glennon, D. High Throughput On-Bead Monitoring of Solid Phase Reactions by Diffuse Reflectance in Infrared Fourier Transform Spectroscopy (DRIFTS). Tetrahedron Lett. 1997, 38, 2821-2824.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 2821-2824
    • Chan, T.Y.1    Chen, R.2    Sofia, M.J.3    Smith, B.C.4    Glennon, D.5
  • 37
    • 0000683556 scopus 로고    scopus 로고
    • Photoacoustic FTIR spectroscopy. A nondestructive method for sensitive analysis of solid-phase organic chemistry
    • Gosselini, F.; Direnzo, M.; Ellis, T. H.; Lubell, W. D. Photoacoustic FTIR Spectroscopy. A Nondestructive Method for Sensitive Analysis of Solid-Phase Organic Chemistry. J. Org. Chem. 1996, 61, 7980-7981.
    • (1996) J. Org. Chem. , vol.61 , pp. 7980-7981
    • Gosselini, F.1    Direnzo, M.2    Ellis, T.H.3    Lubell, W.D.4
  • 38
    • 0031206769 scopus 로고    scopus 로고
    • Phase-resolved depth profiling of thin films by step scan PAS spectroscopy
    • Jiang, E. Y.; Palmer, R. A.; Barr, N. E.; Morosoff, N. Phase-Resolved Depth Profiling of Thin Films by Step Scan PAS Spectroscopy. Appl. Spectrosc. 1997, 51, 1238-1244.
    • (1997) Appl. Spectrosc. , vol.51 , pp. 1238-1244
    • Jiang, E.Y.1    Palmer, R.A.2    Barr, N.E.3    Morosoff, N.4
  • 39
    • 0040725537 scopus 로고
    • Racemization of activated, urethane-protected amino-acids by p-dimethylaminopyridine. Significance in solid-phase peptide synthesis
    • Atherton, E.; Benoiton, N. L.; Brown, E.; Sheppard, R. C.; Williams, B. J. Racemization of Activated, Urethane-Protected Amino-acids by p-Dimethylaminopyridine. Significance in Solid-Phase Peptide Synthesis. J. Chem. Soc., Chem. Commun. 1981, 336-337.
    • (1981) J. Chem. Soc., Chem. Commun. , pp. 336-337
    • Atherton, E.1    Benoiton, N.L.2    Brown, E.3    Sheppard, R.C.4    Williams, B.J.5
  • 40
    • 0025265014 scopus 로고
    • An efficient method for anchoring fmoc-amino acids to hydroxyl-functionalized solid supports
    • Blankemeyer-Menge, B.; Nimtz, M.; Frank, R. An Efficient Method for Anchoring Fmoc-Amino Acids to Hydroxyl-Functionalized Solid Supports. Tetrahedron Lett. 1990, 31, 1701-1704.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 1701-1704
    • Blankemeyer-Menge, B.1    Nimtz, M.2    Frank, R.3
  • 41
    • 0000536276 scopus 로고
    • Protection of histidine in peptide synthesis: A reassessment of the trityl group
    • Sieber, P.; Riniker, B. Protection of Histidine in Peptide Synthesis: A Reassessment of the Trityl Group. Tetrahedron Lett. 1987, 28, 6031-6034.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 6031-6034
    • Sieber, P.1    Riniker, B.2
  • 42
    • 84987306013 scopus 로고
    • Synthesis of isomeric N-substituted 5-methyl-2H-1,2,6-thiadiazin-3(6H)one 1,1-dioxides from sulfamides and diketene
    • Diez, J.; García-Muñoz, G.; Modroñero, R.; Stud, M. Synthesis of Isomeric N-Substituted 5-Methyl-2H-1,2,6-Thiadiazin-3(6H)one 1,1-Dioxides from Sulfamides and Diketene. J. Heterocycl. Chem. 1973, 10, 469-472.
    • (1973) J. Heterocycl. Chem. , vol.10 , pp. 469-472
    • Diez, J.1    García-Muñoz, G.2    Modroñero, R.3    Stud, M.4
  • 44
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery anddevelopment settings
    • Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery andDevelopment Settings. Adv. Drug Delivery Rev. 1997, 23, 3-25.
    • (1997) Adv. Drug Delivery Rev. , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 45
    • 0034073605 scopus 로고    scopus 로고
    • Property distribution of drug-related chemical databases
    • Oprea, T. I. Property Distribution of Drug-Related Chemical Databases. J. Comput. Aided Mol. Des. 2000, 14, 251-264.
    • (2000) J. Comput. Aided Mol. Des. , vol.14 , pp. 251-264
    • Oprea, T.I.1
  • 46
    • 0035132705 scopus 로고    scopus 로고
    • Selecting the right compounds for screening: Does Lipinski's rule of 5 for pharmaceuticals apply to agrochemicals?
    • Tice, C. M. Selecting the Right Compounds for Screening: Does Lipinski's Rule of 5 for Pharmaceuticals Apply to Agrochemicals? Pestic. Manage. Sci. 2001, 57, 3-16.
    • (2001) Pestic. Manage. Sci. , vol.57 , pp. 3-16
    • Tice, C.M.1
  • 47
    • 0041826493 scopus 로고    scopus 로고
    • Advanced Chemistry Development Inc., 133 Richmond St. West, Suite 605, Toronto, ON M5H 2L3, Canada
    • ACDlogP, version 4.00. Advanced Chemistry Development Inc., 133 Richmond St. West, Suite 605, Toronto, ON M5H 2L3, Canada.
    • ACDlogP, Version 4.00
  • 48
    • 0031452355 scopus 로고    scopus 로고
    • Ion-exchange resins for combinatorial synthesis: 2,4-pyrrolidinediones by Dieckmann condensation
    • The corresponding methyl ester is a known compound. Kulkarni, B. A.; Ganesan, A. Ion-Exchange Resins for Combinatorial Synthesis: 2,4-Pyrrolidinediones by Dieckmann Condensation. Angew. Chem., Int. Ed. Engl. 1997, 36, 2454-2455.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 2454-2455
    • Kulkarni, B.A.1    Ganesan, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.