用户名: 密码: 验证码:
Synthesis and Biological Applications of Phosphinates and Derivatives
详细信息    查看全文
  • 作者:David Virieux (16)
    Jean-No毛l Volle (16)
    Norbert Bakalara (17)
    Jean-Luc Pirat (16)

    16. UMR 5253 - ICG Montpellier
    ; Equipe AM2N ; ENSCM ; 8 ; rue de l鈥橢cole ; Normale ; 34296 ; Montpellier Cedex 5 ; France
    17. INSERM U-1051. Institut des neurosciences de Montpellier
    ; 80 rue Augustin Fliche ; 34091 ; Montpellier ; France
  • 关键词:Bioisostere ; Phosphinate ; Phosphinic acid ; Tetrahedral transition state
  • 刊名:Topics in Current Chemistry
  • 出版年:2015
  • 出版时间:2015
  • 年:2015
  • 卷:360
  • 期:1
  • 页码:39-114
  • 全文大小:5,959 KB
  • 参考文献:1. Butusov, M, Jernel枚v, A (2013) Phosphorus: an element that could have been called Lucifer. Springer, New York
    2. Frank, AW (2013) Chemistry of plant phosphorus compounds. Elsevier, Amsterdam
    3. Peck, SC, Gao, J, Donk, WA (2012) Methods Enzymol 516: pp. 101
    4. Metcalf, WW, Donk, WA (2009) Annu Rev Biochem 78: pp. 65
    5. Nair, SK, Donk, WA (2011) Arch Biochem Biophys 505: pp. 13
    6. Bougioukou, DJ, Mukherjee, S, Donk, WA (2013) Proc Natl Acad Sci U S A 110: pp. 10952
    7. Meanwell, NA (2011) J Med Chem 54: pp. 2529
    8. Elliott, TS, Slowey, A, Ye, Y, Conway, SJ (2012) Med Chem Commun 3: pp. 735
    9. Mucha, A, Kafarski, P, Berlicki, L (2012) J Med Chem 54: pp. 5955
    10. Crofts, P, Kosolapoff, GM (1953) J Am Chem Soc 75: pp. 5738
    11. Jencks WP, Regenstein J (1976) In: Fasman GD (ed) Handbook of biochemistry and molecular biology. Physical and Chemical Data, p 305
    12. Haake, P, Hurst, G (1966) J Am Chem Soc 88: pp. 2544
    13. Kalgutkar AS, Daniels JS (2010) In: Smith DA (ed) RSC drug discovery series N 1. Royal Society of Chemistry, p 99
    14. Ballatore, C, Huryn, DM, Smith, AB (2013) ChemMedChem 8: pp. 835
    15. Schramm, VL (2011) Annu Rev Biochem 80: pp. 703
    16. Hall, RG, Riebli, P (1999) Synlett 10: pp. 1633
    17. Hall, RG, Riebli, P (2002) Phosphorus Sulfur Silicon 177: pp. 1557
    18. Mehellou Y, de Clercq E (2010) J Med Chem 53:521
    19. Alexandre, FR, Amador, A, Bot, S, Caillet, C, Convard, T, Jakubik, J, Musiu, C, Poddesu, B, Vargiu, L, Liuzzi, M, Roland, A, Seifer, M, Standing, D, Storer, R, Dousson, CB (2011) J Med Chem 54: pp. 392
    20. Cheek, MA, Sharaf, ML, Dobrikov, MI, Shaw, BR (2013) Antiviral Res 98: pp. 144
    21. Shaw BR, Madison J, Sood A, Spielvogel BF (1993). Chapter 11 Oligonuleoside boranophosphate (borane phosphonate). In: Methods in Molecular Biology (vol 20): protocols for oligonucleotides and analogues. Sudhir Agrawal Humana Press, p 225
    22. Barral, K, Priet, S, Michelis, C, Sire, J, Neyts, J, Balzarini, J, Canard, B, Alvarez, K (2010) Eur J Med Chem 45: pp. 849
    23. Sheldon, J, Barreiro, P, Soriano, V (2007) Expert Opin Investig Drugs 16: pp. 1171
    24. Fried, MW, Hadziyannis, SJ (2004) Semin Liver Dis 24: pp. 47
    25. Lin, C, Amberg, SM, Chambers, TJ, Rice, CM (1993) J Virol 67: pp. 2327
    26. Kolykhalov, AA, Mihalik, K, Feinstone, SM, Rice, CM (2000) J Virol 74: pp. 2046
    27. Bode, JG, Brenndorfer, ED, Haussinger, D (2007) Arch Biochem Biophys 462: pp. 254
    28. Lamarre, D, Anderson, PC, Bailey, M, Beaulieu, P, Bolger, G, Bonneau, P, Bos, M, Cameron, DR, Cartier, M, Cordingley, MG, Faucher, AM, Goudreau, N, Kawai, SH, Kukolj, G, Lagace, L, LaPlante, SR, Narjes, H, Poupart, MA, Rancourt, J, Sentjens, RE, St George, R, Simoneau, B, Weldon, SM, Yong, CL, Llinas-Brunet, M (2003) Nature 426: pp. 186
    29. Reesink, HW, Zeuzem, S, Weegink, CJ, Forestier, N, Vliet, A, Rooij, J, McNair, L, Purdy, S, Kauffman, R, Alam, J, Jansen, PLM (2006) Gastroenterology 131: pp. 997
    30. Sarrazin, C, Rouzier, R, Wagner, F, Forestier, N, Larrey, D, Gupta, SK, Hussain, M, Shah, A, Cutler, D, Zhang, J, Zeuzem, S (2007) Gastroenterology 132: pp. 1270
    31. Jacobson, IM, McHutchison, JG, Dushieko, G, Bisceglie, AM, Reddy, KR, Bzowej, NH, Marcellin, P, Muir, AJ, Ferenci, P, Flisiak, R, George, J, Rizzetto, M, Shouval, D, Sola, R, Terg, RA, Yoshida, EM, Adda, N, Bengtsson, L, Sankoh, AJ, Kieffer, TL, George, S, Kauffman, RS, Zeuzem, S (2011) N Engl J Med 364: pp. 2405
    32. Clarke MO, Chen X, Cho A, Delaney WE IV, Doerffler E, Fardis M, Ji M, Mertzman M, Pakdaman R, Pyun H-J, Rowe T, Yang CY, Sheng XC, Kim CU (2011) Biorg Med Chem Lett 21:3568
    33. Sheng, XC, Casarez, A, Cai, R, Clarke, MO, Chen, X, Cho, A, Delaney, WE, Doerffler, E, Ji, M, Mertzman, M, Pakdaman, R, Pyun, H-J, Rowe, T, Wu, Q, Xu, J, Kim, CU (2012) Bioorg Med Chem Lett 22: pp. 1394
    34. Pompei, M, Francesco, ME, Koch, U, Liverton, NJ, Summa, V (2009) Bioorg Med Chem Lett 19: pp. 2574
    35. McCauley JA (2008) Abstract of papers, 235th ACS National Meeting, New Orleans
    36. Casarez A, Chaudhary K, Cho A, Clarke M, Doerffler E, Fardis M, Kim CU, Pyun H-J, Sheng XC, Wang J (2008) WO patent 005565 A2
    37. Pyun, H-J, Chaudhary, K, Somoza, JR, Sheng, XC, Kim, CU (2009) Tetrahedron Lett 50: pp. 3833
    38. Sheng, XC, Pyun, H-J, Chaudhary, K, Wang, J, Doerffler, E, Fleury, M, McMurtrie, D, Chen, X, Delaney, WE, Kim, CU (2009) Bioorg Med Chem Lett 19: pp. 3453
    39. Liverton NJ (2008) HCV NS3 protease inhibitors, Patent WO 2008/051477
    40. Das, K (2012) J Med Chem 55: pp. 6263
    41. Thorlund, K, Awad, T, Boivin, G, Thabane, L (2011) BMC Infest Dis 11: pp. 134
    42. Meier, C, Habel, L, Laux, W, Clercq, E, Balzarini, J (1995) Nucleos Nucleot 14: pp. 759
    43. Neyts, J, Clercq, E (1997) Antimicrob Agents Chemother 41: pp. 2754
    44. Kralikova, S, Budesinsky, M, Masojidkova, M, Rozenberg, I (2000) Nucleos Nucleot 19: pp. 1159
    45. Snoeck, R, Holy, A, Dewolf-Peeters, C, Oord, J, Clercq, E, Andrei, G (2002) Antimicrob Agents Chemother 46: pp. 3356
    46. Szymanska, A, Szymczak, M, Boryski, J, Stawinski, J, Kraszewski, A, Collu, G, Sanna, G, Giliberti, G, Loddo, R, Collo, P (2006) Bioorg Med Chem 14: pp. 1924
    47. Korshin, EE, Pozdeev, OK (2013) Tetrahedron 69: pp. 11109
    48. Mukhametov, FS, Khorshin, EE, Nekhoroshkov, VM, Efremov, YY (1989) Russ J Gen Chem 59: pp. 1309
    49. Foster, AC, Kemp, JA (2006) Curr Opin Pharmacol 6: pp. 7
    50. Bloom, FE, Iversen, LL (1971) Nature 229: pp. 628
    51. Niswender, CM, Conn, PJ (2010) Annu Rev Pharmacol Toxicol 50: pp. 295
    52. Javitt, DC (1987) J Clin Psychiatry 9: pp. 12
    53. Duty, S (2010) J Pharmacol 161: pp. 271
    54. Selvam, C, Goudet, C, Oueslati, N, Pin, J-P, Acher, F (2007) J Med Chem 50: pp. 4656
    55. Acher FC. Selvam C, Pin J-P, Bertrand HO (2010) Diastereoisomers of hypophosphorous acid derivatives, Patent WO 2010/106526
    56. Beurrier, C, Lopez, S, R茅vy, D, Selvam, C, Goudet, C, Lh茅rondel, M, Gubellini, P, Kerkerie-LeGoff, L, Acher, FC, Pin, J-P, Amalric, M (2010) FASEB J 23: pp. 3619
    57. Selvam, C, Oueslati, N, Lemasson, IA, Brabet, I, Rigault, D, Courtiol, T, Cesarini, S, Triballeau, N, Bertrand, H-O, Goudet, C, Pin, J-P, Acher, FC (2010) J Med Chem 503: pp. 2797
    58. Wieronska, JM, Stachowicz, K, Acher, F, Lech, T, Pilc, A (2012) Psychopharmacology (Berl) 220: pp. 481
    59. Goudet, C, Vilar, B, Courtiol, T, Deltheil, T, Bessiron, T, Brabet, I, Oueslati, N, Rigault, D, Bertrand, H-O, McLean, H, Daniel, H, Amalric, M, Acher, FC, Pin, J-P (2012) FASEB J 26: pp. 1682
    60. Acher F, Busserolles J, Cesarini S, Commare B, Eschalier A, Goudet C, Lemasson I, Pin J-P, Rigault D Hypophosphorous acid derivatives having antihyperalgic activity and biological applications thereof, Patent WO 2012/156931 A1
    61. Paredes, RG, Agmo, A (1992) Neurosci Biobehav Rev 16: pp. 145
    62. O鈥機onnell, AW, Fox, GB, Kjoller, C, Gallagher, HC, Murphy, KJ, Kelly, J, Regan, CM (2001) Eur J Pharmacol 424: pp. 37
    63. Zheng, W, Xie, W, Zhang, J, Strong, JA, Wang, L, Yu, L, Xu, M, Lu, L (2003) J Biol Chem 278: pp. 48321
    64. Sernagor, E, Young, C, Eglen, SJ (2003) J Neurosci 23: pp. 7621
    65. Wisor, JP, DeLorey, TM, Homanics, GE, Edgar, DM (2002) Brain Res 955: pp. 221
    66. Zhang, Q, Lehmann, A, Rigda, R, Den, J, Holloway, RH (2002) Gut 50: pp. 19
    67. Alstermark, C, Amin, K, Dinn, SR, Elebring, T, Fjellstr枚m, O, Fitzpatrick, K, Geiss, WB, Gottfries, J, Guzzo, PR, Harding, JP, Holm茅n, A, Kothare, M, Lehmann, A, Mattsson, JP, Nilsson, K, Sund茅n, G, Swanson, M, Unge, S, Woo, AM, Wyle, MJ, Zheng, X (2008) J Med Chem 51: pp. 4315
    68. Somekh, L, Shanzer, A (1982) J Am Chem Soc 104: pp. 5836
    69. Locock, KES, Yamamoto, I, Tran, P, Hanrahan, JR, Chebib, M, Johnston, GAR, Allan, RD (2013) J Med Chem 56: pp. 5626
    70. Kumar, RJ, Chebib, M, Hibbs, DE, Kim, H-L, Johnston, GAR, Salam, NK, Hanrahan, JR (2008) J Med Chem 51: pp. 3825
    71. Daly, AM, Gilheany, DG (2003) Tetrahedron Asymmetry 14: pp. 127
    72. Hansen HI, Kehler JA (1999) Synthesis 1925
    73. Gavande, G, Yamamoto, I, Salm, NK, Ai, TH, Burden, PM, Johnston, GAR, Hanrahan, JR, Chebib, M (2011) Med Chem Lett 2: pp. 11
    74. Li, X, Cao, JH, Li, Y, Rondard, P, Zhang, Y, Yi, P, Liu, JF, Nan, FJ (2008) J Med Chem 51: pp. 3057
    75. Belley, M, Sullivan, R, Evans, J, O鈥橬eill, G, Ng, GYK (1999) Bioorg Med Chem 7: pp. 2697
    76. Li, ZG, Mintzer, E, Bittman, R (2006) J Org Chem 71: pp. 1718
    77. Hatanaka, Y, Hashimoto, M, Kurihara, H, Nakayama, H, Kanaoka, Y (1994) J Org Chem 59: pp. 383
    78. Kolb, HC, Sharpless, KB (2003) Drug Discov Today 8: pp. 1128
    79. Masharina, A, Reymond, L, Maurel, D, Umezawa, K, Johnsson, K (2012) J Am Chem Soc 134: pp. 19026
    80. Gavande, M, Kim, HL, Doddareddy, MR, Johnston, GAR, Chebib, M, Hanrahan, JR (2013) Med Chem Lett 4: pp. 402
    81. Shane, B (1989) Vitam Horm 45: pp. 263
    82. McBurney, MW, Whitmore, GF (1974) Cell 2: pp. 173
    83. Taylor, RT, Hanna, ML (1975) Arch Biochem Biophys 171: pp. 507
    84. McGuire, JJ, Coward, JK (2003) Drug Future 28: pp. 967
    85. Coward JK, McGuire JJ (2008) In: Litwack G (ed) Vitamins hormones (folic acid and folates). Elsevier, p 347
    86. Tsukamoto, T, Haile, WH, McGuire, JJ, Coward, JK (1998) Arch Biochem Biophys 355: pp. 109
    87. Valiaeva, N, Bartley, D, Konno, T, Coward, JK (2001) J Org Chem 66: pp. 5146
    88. McGuire, JJ, Haile, WH, Valiaeva, N, Bartley, D, Guo, J, Coward, JK (2003) Biochem Pharmacol 65: pp. 315
    89. Bartley, DM, Coward, JK (2005) J Org Chem 70: pp. 6757
    90. McGuire, JJ, Bartley, DM, Tomsho, JW, Haile, WH, Coward, JK (2009) Arch Biochem Biophys 488: pp. 140
    91. Rosowsky, A, Freisheim, JH, Bader, H, Forsch, RA, Susten, SS, Cucchi, CA, Frei, E (1985) J Med Chem 28: pp. 660
    92. Kensler, TW, Cooney, DA (1981) Adv Pharmacol Chemother 18: pp. 273
    93. Christopherson, RI, Lyons, SD (1990) Med Res Rev 10: pp. 505
    94. Collins, KD, Stark, GA (1971) J Biol Chem 246: pp. 6599
    95. Grem, JL, King, SA, O鈥橠wyer, PJ, Leyland-Jones, B (1988) Cancer Res 48: pp. 4441
    96. Fleming, RA, Capizzi, RL, Muss, HB, Smith, S, Fernandes, DJ, Homesley, H, Loggie, BW, Case, LD, Morris, R, Russell, GB, Richards, F (1996) Clin Cancer Res 2: pp. 1107
    97. Chan, TCK, Young, B, King, ME, Taetle, R, Howell, SB (1985) Cancer Treat Rep 69: pp. 425
    98. Coudray, L, Kantrowitz, ER, Montchamp, J-L (2009) Bioorg Med Chem Lett 19: pp. 900
    99. Coudray, L, Pennebaker, AF, Montchamp, J-L (2009) Bioorg Med Chem 17: pp. 7680
    100. Bravo-Altamirano, K, Montchamp, J-L (2006) Org Lett 8: pp. 4169
    101. Bravo-Altamirano, K, Montchamp, JL (2008) Org Synth 85: pp. 96
    102. Cristau, H-J, Herve, A, Virieux, D (2004) Tetrahedron 60: pp. 877
    103. Coudray, L, Bravo-Altamirano, K, Montchamp, J-L (2008) Org Lett 10: pp. 1123
    104. Bravo-Altamirano, K, Abrunhosa-Thomas, I, Montchamp, JL (2008) J Org Chem 73: pp. 2292
    105. Furata, T, Torigai, H, Osawa, T, Iwamura, M (1993) J Chem Soc Perkin Trans 1: pp. 3139
    106. Wade, RH (2009) Mol Biotechnol 43: pp. 177
    107. Verhey, KJ, Gaertig, J (2007) Cell Cycle 17: pp. 2152
    108. Garnham, CP, Roll-Mecak, A (2012) Cytoskeleton 69: pp. 442
    109. Janke, C, Rogowski, K, Wloga, D, Regnard, C, Kajava, AV, Strub, J-M, Temaruk, N, Dijk, J, Boucher, D, Dorsselaer, AV, Suryavanshi, S, Gaertig, J, Edde, B (2005) Science 308: pp. 1758
    110. Ikegami, K, Mukai, M, Tsuchida, J, Heier, RL, MacGregor, GR, Setou, M (2006) J Biol Chem 281: pp. 30707
    111. Ikegami, K, Heier, RL, Taruishi, M, Takagi, H, Mukai, M, Shimma, S, Tairo, S, Hatanaka, K, Morone, N, Yao, I, Campbell, PK, Yuasa, S, Janke, C, MacGregor, GR, Setou, M (2007) Proc Natl Acad Sci U S A 104: pp. 3213
    112. Roll-Mecak, A, McNally, FJ (2010) Curr Opin Cell Biol 22: pp. 96
    113. Zhang, D, Rogers, GC, Buster, DW, Sharp, DJ (2007) J Cell Biol 177: pp. 231
    114. Kashiwaya, K, Nakagawa, H, Hosokawa, M, Mochizuki, Y, Ueda, K, Piao, L, Chung, S, Hamamoto, R, Eguchi, H, Ohigashi, H, Ishikawa, O, Janke, C, Shinomura, Y, Nakamura, Y (2010) Cancer Res 70: pp. 4024
    115. Rogowski, K, Dijk, J, Magiera, MM, Bosc, C, Deloulme, J-C, Bosson, A, Peris, L, Gold, ND, Lacroix, B, Grau, MB, Bec, N, Larroque, C, Desagher, S, Holzer, M, Andrieux, A, Moutin, M-J, Janke, C (2010) Cell 143: pp. 564
    116. Janke, C, Bulinski, JC (2011) Nat Rev Mol Cell Biol 12: pp. 773
    117. Liu, Y, Garnham, CP, Roll-Mecak, A, Tanner, ME (2013) Bioorg Med Chem Lett 23: pp. 4408
    118. Liu, S, Ben, RN (2005) Org Lett 7: pp. 2385
    119. Feng, Y, Coward, JK (2006) J Med Chem 49: pp. 770
    120. Georgiadis, D, Matziari, M, Vassiliou, S, Dive, V, Yiotakis, A (1999) Tetrahedron 55: pp. 14635
    121. Colvin MD (2000) Cancer medicine, 5th edition. Chapter 48 alkylating agents and platinum antitumor compounds
    122. Hudson, HR, Keglevich, G (2008) Phosphorus Sulfur Silicon Relat Elem 183: pp. 2256
    123. Keglevich, G, Brlik, J, Janke, F, Toke, L (1990) Heteroatom Chem 1: pp. 419
    124. Keglevich, G, Toke, L, Kovacs, A, Toth, G, Ujszaszy, K (1993) Heteroatom Chem 4: pp. 61
    125. Keglevich, G, Sipos, M, Szieberth, D, Nyulaszi, L, Imre, T, Ludanyi, K, Toke, L (2004) Tetrahedron 60: pp. 6619
    126. Clarion, L, Jacquard, C, Sainte-Catherine, O, Loiseau, S, Filippini, D, Hirlemann, MH, Volle, JN, Virieux, D, Lecouvey, M, Pirat, JL, Bakalara, N (2012) J Med Chem 55: pp. 2196
    127. Pirat JL, Virieux D, Clarion L, Volle JN, Bakalara N, Mersel M, Montbrun J, Cristau HJ (2009) New phosphorus containing heterocyclic compounds, sugar analogs, and compositions having anticancer activity containing the same. Patent WO 2009/004096 A1
    128. Clarion L, Jacquard C, Sainte-Catherine O, Decoux M, Loiseau S, Rolland M, Lecouvey M, Hugnot JP, Volle JN, Virieux D, Pirat JL, Bakalara N (2014) J Med Chem 57:8293
    129. Tarnowski, GS, Moutain, IM, Stock, CC, Weltzien, HU, Wesphal, O (1978) Cancer Res 38: pp. 339
    130. Eibl, H, Unger, C (1990) Cancer Treat Rev 17: pp. 233
    131. Stekar, J, Hilgard, P, Voegeli, R, Maurer, HR, Engel, J, Kutscher, B, N枚bner, G, Schumacher, W (1993) Cancer Chemother Pharmacol 32: pp. 437
    132. Hilgard, P, Klenner, T, Stekar, J, N枚ssner, G, Kutscher, B, Engel, J (1997) Eur J Cancer 33: pp. 442
    133. Markoulides, MS, Regan, AC (2011) Tetrahedron Lett 52: pp. 2954
    134. Markoulides, MS, Regan, AC (2013) Org Biomol Chem 11: pp. 119
    135. Abdou, WM, Shaddy, AA (2009) ARKIVOC 9: pp. 143
    136. Russell, RGG (2011) Bone 49: pp. 2
    137. Houghton, TJ, Tanaka, KSE, Kang, T, Dietrich, E, Lafontaine, Y, Delorme, D, Ferreira, SS, Viens, F, Arhin, FF, Sarmiento, I, Lehoux, D, Fadhil, I, Laquerre, K, Liu, J, Ostiguy, V, Poirier, H, Moeck, G, Parr, TR, Far, AR (2008) J Med Chem 51: pp. 6955
    138. Luke, GP, Shakespeare, WCA (2002) Synth Commun 32: pp. 2951
    139. Chandraratna RA (1995) US Pat 5399561
    140. Schleifer, KH, Kandler, O (1972) Bacteriol Rev 36: pp. 407
    141. H枚ltje, J-V (1998) Microbiol Mol Biol Rev 62: pp. 181
    142. Heijenoort, J (2001) Nat Prod Rep 18: pp. 503
    143. Pal M, Bearne SL (2014) Bioorg Med Chem Lett 24:1432
    144. Wr贸blewski, AE, Verkade, JG (1996) J Am Chem Soc 118: pp. 10168
    145. Koparir, P, Karaarslan, M, Orek, C, Koparir, M (2011) Phosphorus Sulfur Silicon Relat Elem 186: pp. 2368
    146. Ahmedzade, M, Cukurovali, A, Koparir, M (2003) J Chem Soc Pak 25: pp. 51
    147. Koparir, M, Cansiz, A, Ahmedzade, M, Cetin, A (2004) Heteroatom Chem 15: pp. 26
    148. Koparir, M, Cansiz, A, Ahmedzade, M (2004) Russ J Org Chem 40: pp. 1813
    149. Koparir, M, Cansiz, A, Ahmedzade, M (2006) Chem Heterocycl Comp 3: pp. 424
    150. Nzila, A, Ward, SA, Marsh, K, Sims, PFG, Hyde, JE (2005) Trends Parasitol 21: pp. 334
    151. Nzila, A, Ward, SA, Marsh, K, Sims, PFG, Hyde, JE (2005) Trends Parasitol 21: pp. 292
    152. Yang, Y, Coward, JK (2007) J Org Chem 72: pp. 5748
    153. Wang, P, Wang, Q, Yang, Y, Coward, JK, Nzila, A, Sims, PFG, Hyde, JE (2010) Mol Biochem Parasitol 172: pp. 41
    154. Pastore, EJ, Friedkin, M, Jardetzky, O (1963) J Am Chem Soc 85: pp. 3058
    155. Hillcoat, BL, Blakley, RL (1964) Biochem Biophys Res Commun 15: pp. 303
    156. Evans, JC, Huddler, DP, Jiracek, J, Castro, C, Millian, NS, Garrow, TA, Ludwig, ML (2002) Structure 10: pp. 1159
    157. Obeid, R (2013) Nutrients 5: pp. 3481
    158. Collinsova, M, Castro, C, Garow, TA, Yiotakis, A, Dive, V, Jiracek, J (2003) Chem Biol 10: pp. 113
    159. Jiracek, J, Collinsova, M, Rosenberg, I, Budesinsky, M, Protivinska, E, Netusilova, H, Garrow, TA (2006) J Med Chem 49: pp. 3982
    160. Vanek, V, Budesinsky, M, Kabeleova, P, Sanda, M, Kozisek, M, Hanclova, I, Mladkova, J, Brznda, J, Rosenberg, I, Koutmos, M, Garrow, TA, Jiracek, J (2009) J Med Chem 52: pp. 3652
    161. Picha, J, Vanek, V, Budesinsky, M, Mladkova, J, Garrow, TA, Jiracek, J (2013) Eur J Med Chem 65: pp. 256
    162. Catch JR, Cook AM, Graham AR, Heilbron IJ (1947) J Chem Soc 1609
    163. Zhukov, YN, Khomutov, AR, Osipova, TI, Khomutov, RM (1999) Russ Chem Bull 48: pp. 1348
    164. Liboska, R, Picha, J, Hanclova, I, Budesinsky, M, Sanda, M, Jiracek, J (2008) Tetrahedron Lett 49: pp. 5629
    165. Caughey, GH (1994) Am J Respir Crit Care Med 150: pp. S138
    166. Bank, U, Ansorge, S (2001) J Leukocyte Biol 69: pp. 197
    167. Owen, CA, Campbell, EJ (1999) J Leukocyte Biol 65: pp. 137
    168. Hart, PH (2001) Immunol Cell Biol 79: pp. 149
    169. Caughey, GH (1995) Mast cell proteases in immunology and biology. Marcel-Decker, New-York
    170. Stockley, RA (1999) Am J Respir Crit Care Med 160: pp. S49
    171. Simon, SR (1993) Agents Actions Suppl 42: pp. 27
    172. Greco, MN, Hawkins, MJ, Powell, ET, Almond, HR, Garavilla, L, Hall, J, Minor, LK, Wang, Y, Corcoran, TW, Cera, E, Cantwell, AM, Savvides, SN, Damiano, BP, Maryanoff, BE (2007) J Med Chem 50: pp. 1727
    173. Garavilla, L, Greco, MN, Sukumar, N, Chen, Z-W, Pineda, AO, Mathews, FS, Cera, E, Giardino, EC, Wells, GI, Haertlein, BJ, Kauffman, JA, Corcoran, TW, Derian, CK, Eckardt, AJ, Damiano, BP, Andrade-Gordon, P, Maryanoff, BE (2005) J Biol Chem 280: pp. 18001
    174. Kervinen, J, Crysler, C, Bayoumy, S, Abad, MC, Spurlino, J, Deckman, I, Greco, MN, Maryanoff, BE, Garavilla, L (2010) Biochem Pharmacol 80: pp. 1033
    175. Dunford, JE, Thompson, K, Coxon, FP, Luckman, SP, Hahn, FM, Poulter, CD, Ebetino, FH, Rogers, MJ (2001) J Pharmacol Exp Ther 296: pp. 235
    176. Bergstrom, JD, Bostedor, RG, Masarachia, PJ, Reszka, AA, Rodan, G (2000) Arch Biochem Biophys 373: pp. 231
    177. Dunford, JE, Kwaasi, AA, Rogers, MJ, Barnett, BL, Ebetino, FH, Russell, RGG, Oppermann, U, Kavanagh, KL (2008) J Med Chem 51: pp. 2187
    178. Lieberman, I (1956) J Biol Chem 222: pp. 765
    179. Long, CW, Levitzki, A, Koshland, DE (1970) J Biol Chem 245: pp. 80-87
    180. Verschuur, AC, Gennip, AH, Leen, R, Muller, EJ, Elzinga, L, Vo没te, PA, Kuilenburg, ABP (2000) Eur J Cancer 36: pp. 627
    181. Taylor, SD, Mirzaei, F, Bearne, SL (2006) Org Lett 8: pp. 4243
    182. Taylor, SD, Mirzaei, F, Bearne, SL (2006) J Org Chem 73: pp. 1403
    183. Taylor, SD, Lunn, FA, Bearne, SL (2008) ChemMedChem 3: pp. 1853
    184. Romenko, VD, Kukhar, VP (2006) Chem Rev 106: pp. 3868
    185. Blackburn GM, England DA, Kolkmann FJ (1981) Chem Commun 930
    186. Blackburn, GM, Kent, DE, Koklman, FJ (1984) J Chem Soc Perkin Trans 1: pp. 1119
    187. Davisson, VJ, Woodside, AB, Neal, TR, Stremler, KE, Muehlbacher, M, Poulter, CD (1986) J Org Chem 51: pp. 4768
    188. Chambers RD, O鈥橦agan D, Lamont RB, Jaina SC (1990) Chem Commun 1053
    189. Halazy, S, Ehrhard, A, Danzin, C (1991) J Am Chem Soc 113: pp. 315
    190. Thatcher, GR, Campbell, AS (1993) J Org Chem 58: pp. 2272
    191. Burke, TR, Smyth, MS, Otaka, A, Nomizu, M, Roller, PP, Wolf, G, Case, R, Shoelson, SE (1994) Biochem 33: pp. 6490
    192. Berkowitz, DB, Bose, M (2001) J Fluorine Chem 112: pp. 13
    193. Blackburn, GM, Turkmen, H (2005) Org Biomol Chem 3: pp. 225-226
    194. Surya Prakash, GK, Zibinsky, M, Upton, TG, Kashemirov, BA, McKenna, CE, Oertell, K, Goodman, MF, Batra, VK, Pedersen, LC, Beard, WA, Shock, DD, Wilson, SH, Olah, GA (2010) Proc Natl Acad Sci U S A 107: pp. 15693
    195. McCormack, JG, Westergaard, N, Kristiansen, M, Brand, CL, Lau, J (2001) Curr Pharm Des 7: pp. 1451
    196. Erion, MD, Poelje, VD, Dang, Q, Kasibhatla, SR, Potter, SC, Reddy, MR, Reddy, KR, Jiang, T, Lipscomb, WN (2005) Proc Natl Acad Sci U S A 102: pp. 7970
    197. Dand, Q, Brown, BS, Liu, Y, Rydzewski, RM, Robinson, ED, Poelje, PD, Reddy, MR, Erion, MD (2009) J Med Chem 52: pp. 2880
    198. Froehler, BC, Ng, PG, Matteuci, MD (1986) Nucleic Acids Res 14: pp. 5399
    199. Perish JW, Johns RB (1988) Synthesis 142
    200. Volle, JN, Filippini, D, Krawczy, B, Kaloyanov, N, Lee, A, Maurice, T, Pirat, JL, Virieux, D (2010) Org Biomol Chem 8: pp. 1438
    201. Afarinkia, K, Yu, HW (2003) Tetrahedron Lett 44: pp. 781
    202. Montchamp, JL, Duromnd, YR (2001) J Am Chem Soc 123: pp. 510
    203. Napolitano, LM (2009) Crit Care Clin 25: pp. 279
    204. Squires, JE (2002) Science 295: pp. 1002
    205. Spahn, DR (2000) Adv Drug Deliv Rev 40: pp. 143
    206. Winslow, RM (2007) Semin Hematol 44: pp. 51
    207. Everse, J, Hsia, N (1997) Free Radic Biol Med 22: pp. 1075
    208. Cai, H, Roach, TA, Dabek, M, Somerville, KS, Acharya, S, Hosmane, RS (2010) Bioconjug Chem 21: pp. 1494
    209. Tunaru, S, Kero, J, Schaub, A, Wufka, C, Blaukat, A, Pfeffer, K, Offermanns, S (2003) Nat Med 9: pp. 352
    210. Wise, A, Foord, SM, Fraser, NJ, Barnes, AA, Elshourbagy, N, Eilert, M, Ignar, DM, Murdock, PR, Steplewski, K, Green, A, Brown, AJ, Dowell, SJ, Szekeres, PG, Hassall, DG, Marshall, FH, Wilson, S, Pike, NB (2003) J Biol Chem 278: pp. 9869
    211. Dvorak, CA, Liu, C, Shelton, J, Kuei, C, Sutton, SW, Lovenberg, TW, Carruthers, NI (2012) Med Chem Lett 3: pp. 637
    212. Heyliger, CE, Tahiliani, AG, McNeill, JH (1985) Science 227: pp. 1474
    213. Thomson KH, Orvig C (2000) J Chem Soc Dalton Trans 2885
    214. Kaboudin, B, Moradi, K, Safaei, E, Dehghan, H, Salehi, P (2012) Phosphorus Sulfur Silicon Relat Elem 187: pp. 1521
    215. Perazella, MA (2009) Curr Drug Saf 3: pp. 67
    216. Hermann P, Kubicek V, Lukes I (2008) Dalton Trans 3027
    217. Ramogida, CF, Orvig, C (2013) Chem Commun 49: pp. 4720
    218. Price, EW, Orvig, C (2014) Chem Soc Rev 43: pp. 260
    219. Forsterova M, Svobodova I, Lubal P, Tarborsky, Kotek J, Hermann P, Likes I (2007) Dalton Trans 535
    220. Rudovsky J, Botta M, Hermann P, Lukes I, Maienro V, Aime S (2005) Org Biomol Chem 112
    221. Forsterova, M, Petrik, M, Laznickova, A, Laznicek, M, Hermann, P, Likes, I, Melichar, F (2009) App Rad Isotop 67: pp. 21
    222. Rorudovsky J, Botta M, Hermann P, Koridze A, Aime S (2006) Dalton Trans 2323
    223. Kotkova Z, Helm L, Kotek J, Hermann P, Lukes I (2012) Dalton Trans 13509
    224. Kotkova, Z, Kotek, J, Jirak, D, Jendelova, P, Herynek, V, Berkova, Z, Hermann, P, Lukes, I (2010) Chem Eur J 16: pp. 10094
    225. Mintzer, MA, Grinstaff, MW (2011) Chem Soc Rev 40: pp. 173
    226. Rudovsky, J, Botta, M, Hermann, P, Hardcastle, KI, Lukes, I, Aime, S (2006) Bioconjug Chem 17: pp. 975
    227. Polasek, M, Hermann, P, Peters, JA, Geraldes, CFGC, Lukes, I (2009) Bioconjug Chem 20: pp. 2142
    228. David, T, Prochazkova, S, Havlickova, J, Kotek, J, Kubicek, V, Hermann, P, Lukes, I (2013) Dalton Trans 42: pp. 2414
    229. Pinto-Alphandary, H, Andremont, A, Couvreur, P (2000) J Antimicrob Agents 13: pp. 155
    230. Moses, MA, Brem, H, Langer, R (2003) Cancer Cell 4: pp. 337
    231. Allen, TM, Cullis, PR (2004) Science 303: pp. 1818
    232. Faraji, AH, Wipf, P (2009) Biorg Med Chem 17: pp. 2950
    233. Boudier, A, Castagnos, P, Soussan, E, Beaune, G, Belkhelfa, H, M茅nager, C, Cabuil, V, Haddioui, L, Roques, C, Rico-Lattes, I, Blanzat, M (2011) Int J Pharm 403: pp. 230
    234. Soussan, E, Mille, C, Blanzat, M, Bordat, P, Rico-Lattes, I (2008) Langmuir 24: pp. 2326
    235. Blanzat, M, Perez, E, Rico-Lattes, I, Prom茅, D, Prom茅, JC, Lattes, A (1999) Langmuir 15: pp. 6163
    236. Blanzat, M, Perez, E, Rico-Lattes, I, Lattes, A (1999) New J Chem 23: pp. 1063
    237. Brun, A, Etemad-Moghadam, G (2002) Synthesis 10: pp. 1385
    238. Baillie, AC, Wright, K, Wright, BJ, Earnshaw, CG (1988) Pest Biochem Physiol 30: pp. 103
    239. Wang, T, He, HW (2008) Phosphorus Sulfur Silicon Relat Elem 183: pp. 1884
    240. Deng, X, Liao, G, Long, Q, Gao, Y, Peng, H, He, H (2013) Phosphorus Sulfur Silicon Relat Elem 188: pp. 663
    241. Li, M, Peng, GY, He, H (2013) J Pest Sci 38: pp. 78
    242. He, H-W, Yuan, J-L, Peng, H, Chen, T, Shen, P, Wan, S-Q, Li, Y, Tan, H-L, He, Y-H, He, J-B, Li, Y (2011) J Agric Food Chem 59: pp. 4801
    243. He, H-W, Peng, H, Wang, T, Wang, C, Yuan, J-L, Chen, T, He, J, Tan, X (2013) J Agric Food Chem 61: pp. 2479
    244. Hall, R (2008) Phosphorus Sulfur Silicon Relat Elem 183: pp. 258
    245. Chang, W-C, Mansoorabadi, SO, Liu, H-W (2013) J Am Chem Soc 135: pp. 8153
    246. Lee J-H, Bae B, Kuemin M, Circello BT, Metcalf WW, Nair SK, van der DonK WA (2010) Proc Natl Acad Sci USA 107:17557
    247. Evans, BS, Zhao, C, Gao, J, Evans, CM, Ju, K-S, Doroghazi, JR, Donk, WA, Kelleher, NL, Metcalf, WW (2013) ACS Chem Biol 8: pp. 908
    248. Bryant, DE, Marriott, KER, Macgregor, SA, Kilner, C, Pasek, MA, Kee, TP (2010) Chem Commun 46: pp. 3726
  • 作者单位:Phosphorus Chemistry I
  • 丛书名:978-3-319-15472-5
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Organic Chemistry
    Inorganic Chemistry
    Theoretical and Computational Chemistry
    Medicinal Chemistry
    Biochemistry
    Organometallic Chemistry
  • 出版者:Springer Berlin / Heidelberg
  • ISSN:1436-5049
文摘
This review first outlines general considerations on phosphinic acids and derivatives as bioisosteric groups. The next sections present key aspects of phosphinic acid-based molecules and include a brief description of the biological pathways involved for their activities. The synthetic aspects and the biological activities of such compounds reported in the literature between 2008 and 2013 are also described.

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700