메뉴 건너뛰기




Volumn 6, Issue 5, 2009, Pages 393-396

Bone-targeting anthraquinone-diclofenac prodrugs with hydrolytic and bone affinity characteristics

Author keywords

Anthraquinone; Anti inflammatory; Bone affinity; Bone targeting; Hydrolytic; Prodrug

Indexed keywords

ANTHRAQUINONE; DIACETYLRHEIN; DICLOFENAC; HYDROXYAPATITE; PRODRUG; RHEIN;

EID: 67650552847     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570180810906050393     Document Type: Article
Times cited : (6)

References (33)
  • 2
    • 67650525951 scopus 로고    scopus 로고
    • Effectiveness of complex medication (Glucosamine, Chondroitin Sulphate and Ibuprofen) for treatment of pain syndrome under knee osteoarthritis. Region
    • Povoroznyuk, V.; Dzerovych, N.I. Effectiveness of complex medication (Glucosamine, Chondroitin Sulphate and Ibuprofen) for treatment of pain syndrome under knee osteoarthritis. Region. Anesth. Pain Med., 2008, 33, e213.
    • (2008) Anesth. Pain Med. , vol.33
    • Povoroznyuk, V.1    Dzerovych, N.I.2
  • 3
    • 0013851915 scopus 로고
    • Binding of tetracyclines to bone
    • Perrin, D.D. Binding of tetracyclines to bone. Nature, 1965, 208, 787-788.
    • (1965) Nature , vol.208 , pp. 787-788
    • Perrin, D.D.1
  • 4
    • 0025185407 scopus 로고
    • Diacetylrhein and rhein: In vivo and in vitro effect on lymphocyte membrane fluidity
    • Beccerica, E.; Ferretti, G.; Curatola, G.; Cervini, C. Diacetylrhein and rhein: in vivo and in vitro effect on lymphocyte membrane fluidity. Pharmacol. Res., 1990, 22, 227-285.
    • (1990) Pharmacol. Res. , vol.22 , pp. 227-285
    • Beccerica, E.1    Ferretti, G.2    Curatola, G.3    Cervini, C.4
  • 5
    • 44949201430 scopus 로고    scopus 로고
    • Plant-derived natural product research aimed at new drug discovery
    • Itokawa, H.; Susan, L.; Natschke, M.; Akiyama, T.; Lee, K.H. Plant-derived natural product research aimed at new drug discovery. J Nat. Med., 2008, 62, 263-280.
    • (2008) J Nat. Med. , vol.62 , pp. 263-280
    • Itokawa, H.1    Susan, L.2    Natschke, M.3    Akiyama, T.4    Lee, K.H.5
  • 6
    • 0037067363 scopus 로고    scopus 로고
    • Pharmacological studies of diacerein in animal models of inflammation, arthritis and bone resorption
    • Tamuraa, T.; Shiraia, T.; Kosakaa, N.; Ohmoria, K.; Takafumi. N. Pharmacological studies of diacerein in animal models of inflammation, arthritis and bone resorption. Eur. J. Pharmacol., 2002, 448, 81-87.
    • (2002) Eur. J. Pharmacol. , vol.448 , pp. 81-87
    • Tamuraa, T.1    Shiraia, T.2    Kosakaa, N.3    Ohmoria, K.4    Takafumi, N.5
  • 8
    • 0035027359 scopus 로고    scopus 로고
    • Rhein, an active metabolite of diacerein, down-regulates the production of pro-matrix metalloproteinases- 1,-3,-9 and -13 and up-regulates the production of tissue inhibitor of metalloproteinase-1 in cultured rabbit articular chondrocytes
    • b) Tamura, T.; Kosaka, N.; Ishiwa, J.; Sato, T.; Nagase, H.; Ito, A. Rhein, an active metabolite of diacerein, down-regulates the production of pro-matrix metalloproteinases- 1,-3,-9 and -13 and up-regulates the production of tissue inhibitor of metalloproteinase-1 in cultured rabbit articular chondrocytes. Osteoarthritis and Cart., 2001, 9, 257-263.
    • (2001) Osteoarthritis and Cart. , vol.9 , pp. 257-263
    • Tamura, T.1    Kosaka, N.2    Ishiwa, J.3    Sato, T.4    Nagase, H.5    Ito, A.6
  • 10
    • 34548463859 scopus 로고    scopus 로고
    • Total synthesis of rhein and diacerhein via a directed ortho metalation of an aromatic substrate
    • a) Gonnot, V.; Tisserand, S.; Nicolas, M.; Baati, R.; Mioskowski, C. Total synthesis of rhein and diacerhein via a directed ortho metalation of an aromatic substrate. Tetrahedron Lett., 2007, 48, 7117-7119;
    • (2007) Tetrahedron Lett. , vol.48 , pp. 7117-7119
    • Gonnot, V.1    Tisserand, S.2    Nicolas, M.3    Baati, R.4    Mioskowski, C.5
  • 11
    • 34250377800 scopus 로고    scopus 로고
    • Synthesis and preliminary evaluation of mono- [123I]iodohypericin monocarboxylic acid as a necrosis avid imaging agent. Bioorg
    • b) Fonge, H.; Jin, L.; Wang, H.; Ni, Y.; Bormans, G.; Verbruggen, A. Synthesis and preliminary evaluation of mono- [123I]iodohypericin monocarboxylic acid as a necrosis avid imaging agent. Bioorg. Med. Chem. Lett., 2007, 17, 4001-4005.
    • (2007) Med. Chem. Lett. , vol.17 , pp. 4001-4005
    • Fonge, H.1    Jin, L.2    Wang, H.3    Ni, Y.4    Bormans, G.5    Verbruggen, A.6
  • 13
    • 67650513191 scopus 로고    scopus 로고
    • note
    • The spectra data of compounds 2, A and B.
  • 14
    • 67650537944 scopus 로고    scopus 로고
    • note
    • Compound 2:
  • 15
    • 67650513190 scopus 로고    scopus 로고
    • note
    • Yield: 85%. mp 200∼203 ̊C.
  • 16
    • 67650552332 scopus 로고    scopus 로고
    • note
    • +451.0.
  • 17
    • 67650540665 scopus 로고    scopus 로고
    • note
    • 3), 189.767, 181.225(2C, Ar=O).
  • 18
    • 67650522784 scopus 로고    scopus 로고
    • note
    • IR(cm-1): 3434, 1759, 1724, 1680, 1593, 1372, 1327, 1280, 1254, 1204, 1074, 1025, 745, 701.
  • 19
    • 67650537943 scopus 로고    scopus 로고
    • note
    • 2O (%): C59.86, H 4.07; Found: C 59.37, H 3.838.
  • 20
    • 67650510531 scopus 로고    scopus 로고
    • note
    • Compound A:
  • 21
    • 67650518946 scopus 로고    scopus 로고
    • note
    • Yield: 77%. mp 164∼166 ̊C.
  • 22
    • 67650510532 scopus 로고    scopus 로고
    • note
    • + 606.0.
  • 23
    • 67650518945 scopus 로고    scopus 로고
    • note
    • 2), 6.75(br, 1H, NH), 6.49∼8.37(m, 12H, Ar-H), 11.93, 11.96(s, 1H each, OH).
  • 24
    • 67650546820 scopus 로고    scopus 로고
    • note
    • 2), 180.617(2C, Ar=O).
  • 25
    • 67650540666 scopus 로고    scopus 로고
    • note
    • 1): 3374, 3081, 2905, 2360, 2340, 1723, 1674, 1634, 1451, 1418, 1375, 1291, 1270, 1233, 1199, 1140, 1093, 1020, 777, 749, 666.
  • 26
    • 67650537946 scopus 로고    scopus 로고
    • note
    • 8 (%): C 61.40, H 3.49, N 2.31; Found: C 61.20, H 3.596, N 2.311.
  • 27
    • 67650563780 scopus 로고    scopus 로고
    • note
    • Compound B:
  • 28
    • 67650537947 scopus 로고    scopus 로고
    • note
    • Yield: 46%. mp 149∼151 ̊C.
  • 29
    • 67650534839 scopus 로고    scopus 로고
    • note
    • + 728.3.
  • 30
    • 67650546821 scopus 로고    scopus 로고
    • note
    • 2), 6.47∼8.79(m, 12H, Ar-H).
  • 31
    • 67650516660 scopus 로고    scopus 로고
    • note
    • 2), 180.132, 180.479(2C, Ar=O).
  • 32
    • 67650528672 scopus 로고    scopus 로고
    • note
    • -1): 3444, 3080, 2933, 2360, 1772, 1729, 1675, 1594, 1506, 1456, 1371, 1332, 1280, 1256, 1097, 1021, 921, 881, 770, 747.
  • 33
    • 67650525958 scopus 로고    scopus 로고
    • note
    • 2O (%): C 59.33, H 3.84, N 1.98; Found: C60.81, H4.015, N2.199.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.