메뉴 건너뛰기




Volumn 10, Issue 6, 2012, Pages 471-476

Synthesis of novel furozan-based nitric oxide-releasing derivatives of 1-oxo-oridonin with anti-proliferative activity

Author keywords

1 Oxo oridonin; Activity; Furozan; NO donor; SAR

Indexed keywords

1 OXO ORIDONIN DERIVATIVE; 6BETA,7BETA DIHYDROXY 1,15 DIOXO [14BETA O [2 FORMYL BENZOIC ACID(3 PHENYLSULFONYL 1,2,5 OXADIAZOL 2 OXIDE 4)OXYBUTYL]] 7,20 EPOXY 16 KAURENE; 6BETA,7BETA DIHYDROXY 1,15 DIOXO [14BETA O [2 FORMYL BENZOIC ACID(3 PHENYLSULFONYL 1,2,5 OXADIAZOL 2 OXIDE 4)OXYPROPYL]] 7,20 EPOXY 16 KAURENE; 6BETA,7BETA DIHYDROXY 1,15 DIOXO [14BETA O [4 OXO BUTYRIC ACID(3 PHENYLSULFONYL 1,2,5 OXADIAZOL 2 OXIDE 4)OXYBUTYL]] 7,20 EPOXY 16 KAURENE; 6BETA,7BETA DIHYDROXY 1,15 DIOXO [14BETA O [4 OXO BUTYRIC ACID(3 PHENYLSULFONYL 1,2,5 OXADIAZOL 2 OXIDE 4)OXYETHYL]] 7,20 EPOXY 16 KAURENE; 6BETA,7BETA DIHYDROXY 1,15 DIOXO [14BETA O [4 OXO BUTYRIC ACID(3 PHENYLSULFONYL 1,2,5 OXADIAZOL 2 OXIDE 4)OXYPROPYL]] 7,20 EPOXY 16 KAURENE; 6BETA,7BETA DIHYDROXY 1,15 DIOXO [14BETA O [4 OXO PENTANOIC ACID(3 PHENYLSULFONYL 1,2,5 OXADIAZOL 2 OXIDE 4)OXYBUTYL]] 7,20 EPOXY 16 KAURENE; 6BETA,7BETA DIHYDROXY 1,15 DIOXO [14BETA O [4 OXO PENTANOIC ACID(3 PHENYLSULFONYL 1,2,5 OXADIAZOL 2 OXIDE 4)OXYETHYL]] 7,20 EPOXY 16 KAURENE; 6BETA,7BETA DIHYDROXY 1,15 DIOXO [14BETA O [4 OXO PENTANOIC ACID(3 PHENYLSULFONYL 1,2,5 OXADIAZOL 2 OXIDE 4)OXYPROPYL]] 7,20 EPOXY 16 KAURENE; ANTINEOPLASTIC AGENT; KAURENE DERIVATIVE; NITRIC OXIDE; ORIDONIN; PACLITAXEL; UNCLASSIFIED DRUG;

EID: 84869802122     PISSN: 20956975     EISSN: 18755364     Source Type: Journal    
DOI: 10.1016/S1875-5364(12)60089-2     Document Type: Article
Times cited : (9)

References (22)
  • 1
    • 62549126916 scopus 로고    scopus 로고
    • Nitric oxide: cancer target or anticancer agent [J]
    • Mocellin S Nitric oxide: cancer target or anticancer agent [J]. Curr Cancer Drug Targets 2009, 9(2):214-236.
    • (2009) Curr Cancer Drug Targets , vol.9 , Issue.2 , pp. 214-236
    • Mocellin, S.1
  • 2
    • 0025977048 scopus 로고
    • Signal transduction mechanisms involving nitric oxide [J]
    • Ignarro LJ Signal transduction mechanisms involving nitric oxide [J]. Biochem Pharmacol 1991, 41(4):485-490.
    • (1991) Biochem Pharmacol , vol.41 , Issue.4 , pp. 485-490
    • Ignarro, L.J.1
  • 3
    • 0032612629 scopus 로고    scopus 로고
    • Nitric oxide (NO): formation and biological roles in mammalian systems [J]
    • Fukuto JM, Wink DA Nitric oxide (NO): formation and biological roles in mammalian systems [J]. Met Ions Biol Syst 1999, 36(1):547-595.
    • (1999) Met Ions Biol Syst , vol.36 , Issue.1 , pp. 547-595
    • Fukuto, J.M.1    Wink, D.A.2
  • 4
    • 0036300915 scopus 로고    scopus 로고
    • Influence of the nitric oxide donor glyceryl trinitrate on apoptotic pathways in human colon cancer cells [J]
    • Millet A, Bettaieb A, Renaud F, et al. Influence of the nitric oxide donor glyceryl trinitrate on apoptotic pathways in human colon cancer cells [J]. Gastroenterology 2002, 123(1):235-246.
    • (2002) Gastroenterology , vol.123 , Issue.1 , pp. 235-246
    • Millet, A.1    Bettaieb, A.2    Renaud, F.3
  • 5
    • 0344825132 scopus 로고    scopus 로고
    • Nitric oxide-mediated regulation of hypoxia-induced B16F10 melanoma metastasis [J]
    • Postovit LM, Adams MA, Lash GE, et al. Nitric oxide-mediated regulation of hypoxia-induced B16F10 melanoma metastasis [J]. Int J Cancer 2004, 108(1):47-53.
    • (2004) Int J Cancer , vol.108 , Issue.1 , pp. 47-53
    • Postovit, L.M.1    Adams, M.A.2    Lash, G.E.3
  • 6
    • 2142753987 scopus 로고    scopus 로고
    • Tumor cell responses to a novel glutathione S-transferase-activated nitric oxide-releasing prodrug [J]
    • Findlay VJ, Townsend DM, Saavedra JE, et al. Tumor cell responses to a novel glutathione S-transferase-activated nitric oxide-releasing prodrug [J]. Mol Pharmacol 2004, 65(5):1070-1079.
    • (2004) Mol Pharmacol , vol.65 , Issue.5 , pp. 1070-1079
    • Findlay, V.J.1    Townsend, D.M.2    Saavedra, J.E.3
  • 7
    • 33644838950 scopus 로고    scopus 로고
    • Randomized phase II trial comparing nitroglycerin plus vinorelbine and cisplatin with vinorelbine and cisplatin alone in previously untreated stage IIIB/IV non-small-cell lung cancer [J]
    • Yasuda H, Yamaya M, Nakayama K, et al. Randomized phase II trial comparing nitroglycerin plus vinorelbine and cisplatin with vinorelbine and cisplatin alone in previously untreated stage IIIB/IV non-small-cell lung cancer [J]. J Clin Oncol 2006, 24(4):688-694.
    • (2006) J Clin Oncol , vol.24 , Issue.4 , pp. 688-694
    • Yasuda, H.1    Yamaya, M.2    Nakayama, K.3
  • 8
    • 70349466391 scopus 로고    scopus 로고
    • Phase II study of nitric oxide donor for men with increasing prostate-specific antigen level after surgery or radiotherapy for prostate cancer [J]
    • Siemens DR, Heaton JP, Adams MA, et al. Phase II study of nitric oxide donor for men with increasing prostate-specific antigen level after surgery or radiotherapy for prostate cancer [J]. Urology 2009, 74(4):878-883.
    • (2009) Urology , vol.74 , Issue.4 , pp. 878-883
    • Siemens, D.R.1    Heaton, J.P.2    Adams, M.A.3
  • 9
    • 1642415770 scopus 로고    scopus 로고
    • Design and synthesis of 3'- and 5'-O-(3-benzenesulfonylfuroxan-4-yl)-2'-deoxyuridines: biological evaluation as hybrid nitric oxide donor-nucleoside anticancer agents [J]
    • Moharram S, Zhou A, Wiebe LI, et al. Design and synthesis of 3'- and 5'-O-(3-benzenesulfonylfuroxan-4-yl)-2'-deoxyuridines: biological evaluation as hybrid nitric oxide donor-nucleoside anticancer agents [J]. J Med Chem 2004, 47(7):1840-1846.
    • (2004) J Med Chem , vol.47 , Issue.7 , pp. 1840-1846
    • Moharram, S.1    Zhou, A.2    Wiebe, L.I.3
  • 10
    • 41649090964 scopus 로고    scopus 로고
    • Anticancer properties of the novel nitric oxide-donating compound (S, R)-3-phenyl-4, 5-dihydro-5-isoxazole acetic acid-nitric oxide in vitro and in vivo [J]
    • Maksimovic-Ivanic D, Mijatovic S, Harhaji L, et al. Anticancer properties of the novel nitric oxide-donating compound (S, R)-3-phenyl-4, 5-dihydro-5-isoxazole acetic acid-nitric oxide in vitro and in vivo [J]. Mol Cancer Ther 2008, 7(3):510-520.
    • (2008) Mol Cancer Ther , vol.7 , Issue.3 , pp. 510-520
    • Maksimovic-Ivanic, D.1    Mijatovic, S.2    Harhaji, L.3
  • 11
    • 49449090229 scopus 로고    scopus 로고
    • Design, synthesis, and antihepatocellular carcinoma activity of nitric oxide releasing derivatives of oleanolic acid [J]
    • Chen L, Zhang Y, Kong X, et al. Design, synthesis, and antihepatocellular carcinoma activity of nitric oxide releasing derivatives of oleanolic acid [J]. J Med Chem 2008, 51(15):4834-4838.
    • (2008) J Med Chem , vol.51 , Issue.15 , pp. 4834-4838
    • Chen, L.1    Zhang, Y.2    Kong, X.3
  • 12
    • 77958067172 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of furoxan-based nitric oxide-releasing derivatives of glycyrrhetinic acid as anti-hepatocellular carcinoma agents [J]
    • Lai Y, Shen L, Zhang Z, et al. Synthesis and biological evaluation of furoxan-based nitric oxide-releasing derivatives of glycyrrhetinic acid as anti-hepatocellular carcinoma agents [J]. Bioorg Med Chem Lett 2010, 20(22):6416-6420.
    • (2010) Bioorg Med Chem Lett , vol.20 , Issue.22 , pp. 6416-6420
    • Lai, Y.1    Shen, L.2    Zhang, Z.3
  • 13
    • 77953138517 scopus 로고    scopus 로고
    • Synthesis and evaluation of nitric oxide-releasing derivatives of farnesylthiosalicylic acid as anti-tumor agents [J]
    • Ling Y, Ye X, Ji H, et al. Synthesis and evaluation of nitric oxide-releasing derivatives of farnesylthiosalicylic acid as anti-tumor agents [J]. Bioorg Med Chem 2010, 18(10):3448-3456.
    • (2010) Bioorg Med Chem , vol.18 , Issue.10 , pp. 3448-3456
    • Ling, Y.1    Ye, X.2    Ji, H.3
  • 14
    • 79955868165 scopus 로고    scopus 로고
    • Novel nitric oxide-releasing derivatives of farnesylthiosalicylic acid: synthesis and evaluation of antihepatocellular carcinoma activity [J]
    • Ling Y, Ye X, Zhang Z, et al. Novel nitric oxide-releasing derivatives of farnesylthiosalicylic acid: synthesis and evaluation of antihepatocellular carcinoma activity [J]. J Med Chem 2011, 54(9):3251-3259.
    • (2011) J Med Chem , vol.54 , Issue.9 , pp. 3251-3259
    • Ling, Y.1    Ye, X.2    Zhang, Z.3
  • 15
    • 84855706085 scopus 로고    scopus 로고
    • Synthesis and evaluation of nitric oxide-releasing DDB derivatives as potential Pgp-mediated MDR reversal agents in MCF-7/Adr cells [J]
    • Tang X, Gu X, Ai H, et al. Synthesis and evaluation of nitric oxide-releasing DDB derivatives as potential Pgp-mediated MDR reversal agents in MCF-7/Adr cells [J]. Bioorg Med Chem Lett 2012, 22(2):801-805.
    • (2012) Bioorg Med Chem Lett , vol.22 , Issue.2 , pp. 801-805
    • Tang, X.1    Gu, X.2    Ai, H.3
  • 16
    • 33749026355 scopus 로고    scopus 로고
    • Diterpenoids from Isodon species and their biological activities [J]
    • Sun HD, Huang SX, Han QB Diterpenoids from Isodon species and their biological activities [J]. Nat Prod Rep 2006, 23(5):673-698.
    • (2006) Nat Prod Rep , vol.23 , Issue.5 , pp. 673-698
    • Sun, H.D.1    Huang, S.X.2    Han, Q.B.3
  • 17
    • 78650227978 scopus 로고    scopus 로고
    • Structure and cytotoxicity of diterpenoids from Isodon eriocalyx [J]
    • Li XN, Pu JX, Du X, et al. Structure and cytotoxicity of diterpenoids from Isodon eriocalyx [J]. J Nat Prod 2010, 73(11):1803-1809.
    • (2010) J Nat Prod , vol.73 , Issue.11 , pp. 1803-1809
    • Li, X.N.1    Pu, J.X.2    Du, X.3
  • 18
    • 77954071961 scopus 로고    scopus 로고
    • Induction of G(2)/M phase arrest and apoptosis by oridonin in human laryngeal carcinoma cells [J]
    • Kang N, Zhang JH, Qiu F, et al. Induction of G(2)/M phase arrest and apoptosis by oridonin in human laryngeal carcinoma cells [J]. J Nat Prod 2010, 73(6):1058-1063.
    • (2010) J Nat Prod , vol.73 , Issue.6 , pp. 1058-1063
    • Kang, N.1    Zhang, J.H.2    Qiu, F.3
  • 19
    • 48649094535 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of novel 1-O- and 14-O-derivatives of oridonin as potential anticancer drug candidates [J]
    • Xu J, Yang J, Ran Q, et al. Synthesis and biological evaluation of novel 1-O- and 14-O-derivatives of oridonin as potential anticancer drug candidates [J]. Bioorg Med Chem Lett 2008, 18(16):4741-4744.
    • (2008) Bioorg Med Chem Lett , vol.18 , Issue.16 , pp. 4741-4744
    • Xu, J.1    Yang, J.2    Ran, Q.3
  • 20
    • 79956027640 scopus 로고    scopus 로고
    • Synthesis and anti-tumor activity of 14-O-derivatives of natural oridonin [J]
    • Wang L, Ran Q, Li D, et al. Synthesis and anti-tumor activity of 14-O-derivatives of natural oridonin [J]. Chin J Nat Med 2011, 9(3):194-198.
    • (2011) Chin J Nat Med , vol.9 , Issue.3 , pp. 194-198
    • Wang, L.1    Ran, Q.2    Li, D.3
  • 21
    • 79960988225 scopus 로고    scopus 로고
    • Recent progress in the development of natural ent-kaurane diterpenoids with anti-tumor activity [J]
    • Wang L, Li D, Wang C, et al. Recent progress in the development of natural ent-kaurane diterpenoids with anti-tumor activity [J]. Mini-Rev Med Chem 2011, 11(10):910-919.
    • (2011) Mini-Rev Med Chem , vol.11 , Issue.10 , pp. 910-919
    • Wang, L.1    Li, D.2    Wang, C.3
  • 22
    • 84860351057 scopus 로고    scopus 로고
    • The conversion of oridonin to spirolactone-type or enmein-type diterpenoid: synthesis and biological evaluation of ent-6,7-seco-oridonin derivatives as novel potential anticancer agents [J]
    • Wang L, Li D, Xu S, et al. The conversion of oridonin to spirolactone-type or enmein-type diterpenoid: synthesis and biological evaluation of ent-6,7-seco-oridonin derivatives as novel potential anticancer agents [J]. Eur J Med Chem 2012, 52(1):242-250.
    • (2012) Eur J Med Chem , vol.52 , Issue.1 , pp. 242-250
    • Wang, L.1    Li, D.2    Xu, S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.