메뉴 건너뛰기




Volumn 56, Issue 10, 2013, Pages 1372-1381

The synthesis of benzoxaboroles and their applications in medicinal chemistry

Author keywords

benzoxaboroles; medicinal chemistry; synthetic methods

Indexed keywords

ANTI-FUNGAL; ANTI-INFLAMMATORY AGENTS; BENZOXABOROLE; BENZOXABOROLES; MEDICINAL CHEMISTRY; ORGANIC SYNTHESIS; PRIVILEGED STRUCTURES; SYNTHETIC METHODS;

EID: 84885627199     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-013-4981-y     Document Type: Review
Times cited : (49)

References (56)
  • 1
    • 79958711382 scopus 로고    scopus 로고
    • Boron-containing inhibitors of synthetases
    • 10.1039/c0cs00131g 1:CAS:528:DC%2BC3MXovVemtbY%3D
    • Baker SJ, Tomsho JW, Benkovic SJ. Boron-containing inhibitors of synthetases. Chem Soc Rev, 2011, 40:4279-4285
    • (2011) Chem Soc Rev , vol.40 , pp. 4279-4285
    • Baker, S.J.1    Tomsho, J.W.2    Benkovic, S.J.3
  • 2
    • 0000008072 scopus 로고
    • Arylboronic acids. III. Bromination of tolylboronic acids according to Wohl-Ziegler
    • 1:CAS:528:DyaG1cXot1Chuw%3D%3D
    • Torssell K. Arylboronic acids. III. Bromination of tolylboronic acids according to Wohl-Ziegler. Ark Kemi, 1957, 10:507-511
    • (1957) Ark Kemi , vol.10 , pp. 507-511
    • Torssell, K.1
  • 4
    • 33746701345 scopus 로고    scopus 로고
    • Discovery of a new boron-containing antifungal agent, 5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (AN2690), for the potential treatment of Onychomycosis
    • 10.1021/jm0603724 1:CAS:528:DC%2BD28Xmt12lsro%3D
    • Baker SJ, Zhang YK, Akama T, Lau A, Zhou HC, Hernandez V, Mao WM, Alley MRK, Sanders V, Plattner JJ. Discovery of a new boron-containing antifungal agent, 5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (AN2690), for the potential treatment of Onychomycosis. J Med Chem, 2006, 49:4447-4450
    • (2006) J Med Chem , vol.49 , pp. 4447-4450
    • Baker, S.J.1    Zhang, Y.K.2    Akama, T.3    Lau, A.4    Zhou, H.C.5    Hernandez, V.6    Mao, W.M.7    Alley, M.R.K.8    Sanders, V.9    Plattner, J.J.10
  • 9
    • 63149123045 scopus 로고    scopus 로고
    • Discovery and structure-activity study of a novel benzoxaborole anti-inflammatory agent (AN2728) for the potential topical treatment of psoriasis and atopic dermatitis
    • 10.1016/j.bmcl.2009.03.007 1:CAS:528:DC%2BD1MXkt1Sjsb4%3D
    • Akama T, Baker SJ, Zhang YK, Hernandez V, Zhou HC, Sanders V, Freund Y, Kimura R, Maples KR, Plattner JJ. Discovery and structure-activity study of a novel benzoxaborole anti-inflammatory agent (AN2728) for the potential topical treatment of psoriasis and atopic dermatitis. Bioorg Med Chem Lett, 2009, 19:2129-2132
    • (2009) Bioorg Med Chem Lett , vol.19 , pp. 2129-2132
    • Akama, T.1    Baker, S.J.2    Zhang, Y.K.3    Hernandez, V.4    Zhou, H.C.5    Sanders, V.6    Freund, Y.7    Kimura, R.8    Maples, K.R.9    Plattner, J.J.10
  • 10
    • 84878910411 scopus 로고    scopus 로고
    • An assessment of the genetic toxicology of novel boron-containing therapeutic agents
    • 10.1002/em.21779 1:CAS:528:DC%2BC3sXms1Cjtb0%3D
    • Ciaravino V, Plattner J, Chanda S. An assessment of the genetic toxicology of novel boron-containing therapeutic agents. Environ Mol Mutagen, 2013, 54:338-346
    • (2013) Environ Mol Mutagen , vol.54 , pp. 338-346
    • Ciaravino, V.1    Plattner, J.2    Chanda, S.3
  • 12
    • 77953084132 scopus 로고    scopus 로고
    • A combined experimental and theoretical study of benzoxaborole derivatives by Raman and IR spectroscopy, static DFT, and first-principle molecular dynamics
    • Jezierska A, Panek JJ, Zukowska GZ, Sporzynski AA. A combined experimental and theoretical study of benzoxaborole derivatives by Raman and IR spectroscopy, static DFT, and first-principle molecular dynamics. J Phys Org Chem, 2010, 3:451-460
    • (2010) J Phys Org Chem , vol.3 , pp. 451-460
    • Jezierska, A.1    Panek, J.J.2    Zukowska, G.Z.3    Sporzynski, A.A.4
  • 13
    • 33947461630 scopus 로고
    • Synthesis of aromatic boronic acids. Aldehydo boronic acids and a boronic acid analog of tyrosine
    • 10.1021/ja01537a021 1:CAS:528:DyaG1cXmtV2lsw%3D%3D
    • Snyder HR, Reedy AJ, Lennarz WJ. Synthesis of aromatic boronic acids. Aldehydo boronic acids and a boronic acid analog of tyrosine. J Am Chem Soc, 1958, 80:835-838
    • (1958) J Am Chem Soc , vol.80 , pp. 835-838
    • Snyder, H.R.1    Reedy, A.J.2    Lennarz, W.J.3
  • 16
    • 84874666253 scopus 로고    scopus 로고
    • Structure-activity relationships of 6-(aminomethylphenoxy)-benzoxaborole derivatives as anti-inflammatory agent
    • 10.1016/j.bmcl.2013.01.072 1:CAS:528:DC%2BC3sXis1SgsLo%3D
    • Akama T, Virtucio C, Dong C, Kimura R, Zhang YK, Nieman JA, Sharma R, Lu XS, Sales M, Singh R. Structure-activity relationships of 6-(aminomethylphenoxy) -benzoxaborole derivatives as anti-inflammatory agent. Bioorg Med Chem Lett, 2013, 23:1680-1683
    • (2013) Bioorg Med Chem Lett , vol.23 , pp. 1680-1683
    • Akama, T.1    Virtucio, C.2    Dong, C.3    Kimura, R.4    Zhang, Y.K.5    Nieman, J.A.6    Sharma, R.7    Lu, X.S.8    Sales, M.9    Singh, R.10
  • 20
    • 79959522795 scopus 로고    scopus 로고
    • An efficient synthesis for a new class antimalarial agent, 7-(2-carboxyethyl)-1, 3-dihydro-1-hydroxy-2, 1-benzoxaborole
    • 10.1016/j.tetlet.2011.05.088 1:CAS:528:DC%2BC3MXnvF2qs70%3D
    • Zhang YK, Plattner JJ, Easom EE, Waterson D, Ge M, Li ZY, Li LC, Jian Y. An efficient synthesis for a new class antimalarial agent, 7-(2-carboxyethyl)-1, 3-dihydro-1-hydroxy-2, 1-benzoxaborole. Tetrahedron Lett, 2011, 52:3909-3911
    • (2011) Tetrahedron Lett , vol.52 , pp. 3909-3911
    • Zhang, Y.K.1    Plattner, J.J.2    Easom, E.E.3    Waterson, D.4    Ge, M.5    Li, Z.Y.6    Li, L.C.7    Jian, Y.8
  • 21
    • 84860416507 scopus 로고    scopus 로고
    • Synthesis of novel benzoxaborole-containing phenylalanine analogues
    • 10.1016/j.tetlet.2011.07.053 1:CAS:528:DC%2BC3MXhtVKjtb3F
    • Li XF, Plattner JJ, Hernandez V, Ding CZ, Wu W, Yang Y, Xu MS. Synthesis of novel benzoxaborole-containing phenylalanine analogues. Tetrahedron Lett, 2011, 52:4924-4926
    • (2011) Tetrahedron Lett , vol.52 , pp. 4924-4926
    • Li, X.F.1    Plattner, J.J.2    Hernandez, V.3    Ding, C.Z.4    Wu, W.5    Yang, Y.6    Xu, M.S.7
  • 24
    • 0033958547 scopus 로고    scopus 로고
    • Palladium-catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates
    • 10.1021/jo991337q 1:CAS:528:DyaK1MXnvFCqs7o%3D
    • Murata M, Oyama T, Watanabe S, Masuda Y. Palladium-catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates. J Org Chem, 2000, 65:164-168
    • (2000) J Org Chem , vol.65 , pp. 164-168
    • Murata, M.1    Oyama, T.2    Watanabe, S.3    Masuda, Y.4
  • 25
    • 0001766644 scopus 로고    scopus 로고
    • Novel palladium (0)-catalyzed coupling reaction of dialkoxyborane with aryl halides: Convenient synthetic route to arylboronates
    • 10.1021/jo970963p 1:CAS:528:DyaK2sXmtVentbY%3D
    • Murata M, Watanabe S, Masuda Y. Novel palladium (0)-catalyzed coupling reaction of dialkoxyborane with aryl halides: Convenient synthetic route to arylboronates. J Org Chem, 1997, 62:6458-6459
    • (1997) J Org Chem , vol.62 , pp. 6458-6459
    • Murata, M.1    Watanabe, S.2    Masuda, Y.3
  • 26
    • 3142514770 scopus 로고
    • Palladium (0)-catalyzed cross-coupling reaction of alkoxydiboron with haloarenes: A direct procedure for arylboronic esters
    • 10.1021/jo00128a024 1:CAS:528:DyaK2MXovFSku7g%3D
    • Ishiyama T, Murata M, Miyaura N. Palladium (0)-catalyzed cross-coupling reaction of alkoxydiboron with haloarenes: A direct procedure for arylboronic esters. J Org Chem, 1995, 60:7508-7510
    • (1995) J Org Chem , vol.60 , pp. 7508-7510
    • Ishiyama, T.1    Murata, M.2    Miyaura, N.3
  • 27
    • 27444439966 scopus 로고    scopus 로고
    • One-pot sequential four-component coupling via Cp RuCl-catalyzed cyclotrimerization and Suzuki-Miyaura coupling
    • 10.1016/j.tet.2005.08.069 1:CAS:528:DC%2BD2MXhtFOrs7vJ
    • Yamamoto Y, Ishii J, Nishiyama H, Itoh K. One-pot sequential four-component coupling via Cp RuCl-catalyzed cyclotrimerization and Suzuki-Miyaura coupling. Tetrahedron, 2005, 61:11501-11510
    • (2005) Tetrahedron , vol.61 , pp. 11501-11510
    • Yamamoto, Y.1    Ishii, J.2    Nishiyama, H.3    Itoh, K.4
  • 28
    • 21644488674 scopus 로고    scopus 로고
    • Cp RuCl-catalyzed formal intermolecular cyclotrimerization of three unsymmetrical alkynes through a boron temporary tether: Regioselective four-component coupling synthesis of phthalides
    • 10.1021/ja051377d 1:CAS:528:DC%2BD2MXkvFSmtLg%3D
    • Yamamoto Y, Ishii J, Nishiyama H, Itoh K. Cp RuCl-catalyzed formal intermolecular cyclotrimerization of three unsymmetrical alkynes through a boron temporary tether: Regioselective four-component coupling synthesis of phthalides. J Am Chem Soc, 2005, 127:9625-9631
    • (2005) J Am Chem Soc , vol.127 , pp. 9625-9631
    • Yamamoto, Y.1    Ishii, J.2    Nishiyama, H.3    Itoh, K.4
  • 29
    • 84985240026 scopus 로고
    • Zum Abbau von 1,2-dihydro-l-hydroxy-2-organo-sulfonyl-2,3,1- benzodiazaborinen und -thieno[3,2-d][1,2,3]diazaborinen in alkalischer wäBriger Lösung
    • Grassberger M. Zum Abbau von 1,2-dihydro-l-hydroxy-2-organo-sulfonyl-2,3, 1-benzodiazaborinen und -thieno[3,2-d][1,2,3]diazaborinen in alkalischer wäBriger Lösung. Liebigs Ann Chem, 1985:683-688
    • (1985) Liebigs Ann Chem , pp. 683-688
    • Grassberger, M.1
  • 30
    • 0009457021 scopus 로고
    • Arylboronic acids. IV. Reactions of borono-phthalide
    • 10.1021/ja01494a021 1:CAS:528:DyaF3MXht1Cmu7Y%3D
    • Lennarz WJ, Snyder HR. Arylboronic acids. IV. reactions of borono-phthalide. J Am Chem Soc, 1960, 82:2172-2175
    • (1960) J Am Chem Soc , vol.82 , pp. 2172-2175
    • Lennarz, W.J.1    Snyder, H.R.2
  • 33
    • 1842266559 scopus 로고
    • Arylboronic acids. VIII. Reactions of boronophthalide
    • 10.1021/jo01034a025 1:CAS:528:DyaF2cXkvFans7Y%3D
    • Haynes RR, Snyder HR. Arylboronic acids. VIII. Reactions of boronophthalide. J Org Chem, 1964, 29:3229-3233
    • (1964) J Org Chem , vol.29 , pp. 3229-3233
    • Haynes, R.R.1    Snyder, H.R.2
  • 34
    • 37849002655 scopus 로고    scopus 로고
    • 3H-2,1-Benzoxaborole-1-spiro-4′-(5-oxa-3a-aza-4-borapyrene)
    • 1:CAS:528:DC%2BD1cXhtFKgsro%3D
    • Robin B, Buell G, Kiprof P, Nemykin VN. 3H-2,1-Benzoxaborole-1-spiro- 4′-(5-oxa-3a-aza-4-borapyrene). Acta Cryst, 2008, 64:o314-o315
    • (2008) Acta Cryst , vol.64
    • Robin, B.1    Buell, G.2    Kiprof, P.3    Nemykin, V.N.4
  • 35
    • 77958481116 scopus 로고    scopus 로고
    • Diverse reactivity of 2-formylphenylboronic acid with secondary amines: Synthesis of 3-amino-substituted benzoxaboroles
    • 10.1016/j.tetlet.2010.09.091 1:CAS:528:DC%2BC3cXhtlentrnK
    • Adamczyk-Wozniak A, Madura I, Velders AH, Sporzynski A. Diverse reactivity of 2-formylphenylboronic acid with secondary amines: synthesis of 3-amino-substituted benzoxaboroles. Tetrahedron Lett, 2010, 51:6181-6185
    • (2010) Tetrahedron Lett , vol.51 , pp. 6181-6185
    • Adamczyk-Wozniak, A.1    Madura, I.2    Velders, A.H.3    Sporzynski, A.4
  • 36
    • 0033543634 scopus 로고    scopus 로고
    • Synthesis and structure of benzoboroxoles: Novel organoboron heterocycles
    • 10.1016/S0040-4039(99)01303-9 1:CAS:528:DyaK1MXls12lt7Y%3D
    • Zhdankin VV, Persichini PJ, Zhang L, Fix S, Kiprof P. Synthesis and structure of benzoboroxoles: Novel organoboron heterocycles. Tetrahedron Lett, 1999, 40:6705-6708
    • (1999) Tetrahedron Lett , vol.40 , pp. 6705-6708
    • Zhdankin, V.V.1    Persichini, P.J.2    Zhang, L.3    Fix, S.4    Kiprof, P.5
  • 37
    • 0010902050 scopus 로고
    • Arylboronic acids. VII. Some reactions of o-formylbenzeneboronic acid
    • 10.1021/jo01031a014 1:CAS:528:DyaF2cXksVOqt7w%3D
    • Tschampel P, Snyder HR. Arylboronic acids. VII. Some reactions of o-formylbenzeneboronic acid. J Org Chem, 1964, 29:2168-2172
    • (1964) J Org Chem , vol.29 , pp. 2168-2172
    • Tschampel, P.1    Snyder, H.R.2
  • 38
    • 27644483869 scopus 로고    scopus 로고
    • 1,3-Dihydro-1-hydroxy-3-morpholin-4-yl-2,1-benzoxaborole: Product of the reaction of o-formylphenylboronic acid with morpholine
    • 10.1002/aoc.991 1:CAS:528:DC%2BD2MXhtFygsLbL
    • Sporzynski A, Lewandowski M, Rogowska P, Cyranski MK. 1,3-Dihydro-1-hydroxy-3-morpholin-4-yl-2,1-benzoxaborole: Product of the reaction of o-formylphenylboronic acid with morpholine. Appl Organometal Chem, 2005, 19:1202-1203
    • (2005) Appl Organometal Chem , vol.19 , pp. 1202-1203
    • Sporzynski, A.1    Lewandowski, M.2    Rogowska, P.3    Cyranski, M.K.4
  • 39
    • 33947538746 scopus 로고    scopus 로고
    • Anortho-lithiated derivative of protected phenylboronic acid: An approach to ortho-functionalized arylboronic acids and 1,3-dihydro-1-hydroxybenzo [c][2,1]oxaboroles
    • 10.1002/aoc.1217
    • Da̧browski M, Kurach P, Luliński S, Serwatowski J. Anortho-lithiated derivative of protected phenylboronic acid: An approach to ortho-functionalized arylboronic acids and 1,3-dihydro-1-hydroxybenzo [c][2,1]oxaboroles. Appl Organometal Chem, 2007, 21:234-238
    • (2007) Appl Organometal Chem , vol.21 , pp. 234-238
    • Da̧browski, M.1    Kurach, P.2    Luliński, S.3    Serwatowski, J.4
  • 40
    • 0032538485 scopus 로고    scopus 로고
    • Total synthesis of vancomycin aglycon-part 1: Synthesis of amino acids 4-7 and construction of the AB-COD ring skeleton
    • 10.1002/(SICI)1521-3773(19981016)37:19<2708: AID-ANIE2708>3.0.CO;2- E 1:CAS:528:DyaK1cXnt1Krurk%3D
    • Nicolaou KC, Natarajan S, Li H, Jain NF, Hughes R, Solomon ME, Ramanjulu JM, Boddy CNC, Takayanagi M. Total synthesis of vancomycin aglycon-part 1: Synthesis of amino acids 4-7 and construction of the AB-COD ring skeleton. Angew Chem Int Ed, 1998, 37:2708-2714
    • (1998) Angew Chem Int Ed , vol.37 , pp. 2708-2714
    • Nicolaou, K.C.1    Natarajan, S.2    Li, H.3    Jain, N.F.4    Hughes, R.5    Solomon, M.E.6    Ramanjulu, J.M.7    Boddy, C.N.C.8    Takayanagi, M.9
  • 42
    • 84861327425 scopus 로고    scopus 로고
    • New therapeutic options for onychomycosis
    • 10.1517/14656566.2012.681779 1:CAS:528:DC%2BC38XntlOmurY%3D
    • Gupta AK, Simpson FC. New therapeutic options for onychomycosis. Expert Opin Pharmacother, 2012, 13:1131-1142
    • (2012) Expert Opin Pharmacother , vol.13 , pp. 1131-1142
    • Gupta, A.K.1    Simpson, F.C.2
  • 43
    • 0031747315 scopus 로고    scopus 로고
    • β-Lactamase-mediated resistance and opportunities for its control
    • 10.1093/jac/41.suppl-4.25 1:CAS:528:DyaK1cXktV2gu7g%3D
    • Livermore DM. β-Lactamase-mediated resistance and opportunities for its control. J Antimicrob Chemother, 1998, 41:25-41
    • (1998) J Antimicrob Chemother , vol.41 , pp. 25-41
    • Livermore, D.M.1
  • 44
    • 0037242882 scopus 로고    scopus 로고
    • Clinical consequences of hepatitis C virus infection
    • 10.1002/rmv.371 1:STN:280:DC%2BD3s%2FgvFymsQ%3D%3D
    • Zoulim F, Chevallier M, Maynard M, Trepo C. Clinical consequences of hepatitis C virus infection. Rev Med Virol, 2003, 13:57-68
    • (2003) Rev Med Virol , vol.13 , pp. 57-68
    • Zoulim, F.1    Chevallier, M.2    Maynard, M.3    Trepo, C.4
  • 45
    • 0036830454 scopus 로고    scopus 로고
    • Side effects of terapy of Hepatitis C and their management
    • 10.1002/hep.1840360730
    • Fried MW. Side effects of terapy of Hepatitis C and their management. Hepatology, 2002, 36:S237
    • (2002) Hepatology , vol.36 , pp. 237
    • Fried, M.W.1
  • 46
    • 68249161340 scopus 로고    scopus 로고
    • Serine protease inhibitors as anti-hepatitis C virus agents
    • 10.1586/eri.09.30 1:CAS:528:DC%2BD1MXms1KksbY%3D
    • Reiser M, Timm J. Serine protease inhibitors as anti-hepatitis C virus agents. Expert Rev Anti Infect Ther, 2009, 7:537-547
    • (2009) Expert Rev Anti Infect Ther , vol.7 , pp. 537-547
    • Reiser, M.1    Timm, J.2
  • 48
    • 84871188045 scopus 로고    scopus 로고
    • Management of trypanosomiasis and leishmaniasis
    • 10.1093/bmb/lds031 1:CAS:528:DC%2BC38XhvVOrsbfO
    • Barrett MP, Croft SL. Management of trypanosomiasis and leishmaniasis. Brit Med Bull, 2012, 104:175-196
    • (2012) Brit Med Bull , vol.104 , pp. 175-196
    • Barrett, M.P.1    Croft, S.L.2
  • 49
    • 80055011837 scopus 로고    scopus 로고
    • Boron-based drugs as antiprotozoals
    • 10.1097/QCO.0b013e32834c630e 1:CAS:528:DC%2BC3MXhtlygsbnF
    • Jacobs RT, Plattner JJ, Keenan M. Boron-based drugs as antiprotozoals. Curr Opin Infect Dis, 2011, 24:586-592
    • (2011) Curr Opin Infect Dis , vol.24 , pp. 586-592
    • Jacobs, R.T.1    Plattner, J.J.2    Keenan, M.3
  • 50
    • 79959790904 scopus 로고    scopus 로고
    • Development of novel drugs for human African trypanosomiasis
    • 10.2217/fmb.11.44 1:CAS:528:DC%2BC3MXotVChtL8%3D
    • Brun R, Don R, Jacobs RT, Wang MZ, Barrett MP. Development of novel drugs for human African trypanosomiasis. Future Microbiol, 2011, 6:677-691
    • (2011) Future Microbiol , vol.6 , pp. 677-691
    • Brun, R.1    Don, R.2    Jacobs, R.T.3    Wang, M.Z.4    Barrett, M.P.5
  • 54
    • 33645810586 scopus 로고    scopus 로고
    • Anticancer agents
    • 1:CAS:528:DC%2BD28XislOktbY%3D
    • Kabalka GW, Yao ML. Anticancer agents. Med Chem, 2006, 6:111-125
    • (2006) Med Chem , vol.6 , pp. 111-125
    • Kabalka, G.W.1    Yao, M.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.