메뉴 건너뛰기




Volumn 50, Issue 8, 2007, Pages 1886-1895

Structure-activity relationship study of tricyclic necroptosis inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

2 (HYDROXYACETYL) 3,3A,4,5 TETRAHYDRO 3 (4 METHOXYPHENYL) 8 METHOXY 2H BENZ[G]INDAZOLE; 2 ACETYL 2,3,3A,4 TETRAHYDRO 3 (4 METHOXYPHENYL) 8 METHOXY[1]BENZOTHIOPYRANO[4,3 C]PYRAZOLE; 2 ACETYL 3,3A,4,5 TETRAHYDRO 3 (4 METHOXYPHENYL) 8 FLUORO 2H BENZ[G]INDAZOLE; 2 ACETYL 3,3A,4,5 TETRAHYDRO 3 (4 METHOXYPHENYL) 8 METHOXY 2H BENZ[G]INDAZOLE; 2 PROPIONYL 3,3A,4,5 TETRAHYDRO 3 (4 METHOXYPHENYL) 8 METHOXY 2H BENZ[G]INDAZOLE; AMIDE; BENZOPYRAN DERIVATIVE; CASPASE; HETEROCYCLIC COMPOUND; HYDANTOIN; INDAZOLE DERIVATIVE; INDOLE DERIVATIVE; PYRAZOLE DERIVATIVE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

EID: 34247264421     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm061016o     Document Type: Article
Times cited : (81)

References (35)
  • 2
    • 0034641936 scopus 로고    scopus 로고
    • Apoptosis in the nervous system
    • (a) Yuan, J.; Yankner, B. A. Apoptosis in the nervous system. Nature 2000, 407, 802-809.
    • (2000) Nature , vol.407 , pp. 802-809
    • Yuan, J.1    Yankner, B.A.2
  • 3
    • 2642689658 scopus 로고    scopus 로고
    • Proteases to die for
    • (b) Cryns, V.; Yuan, J. Proteases to die for. Genes Dev. 1998, 12, 1551-1570.
    • (1998) Genes Dev , vol.12 , pp. 1551-1570
    • Cryns, V.1    Yuan, J.2
  • 4
    • 0034618635 scopus 로고    scopus 로고
    • Caspases as targets for anti-inflammatory and anti-apoptotic drug discovery
    • (a) Talanian, R. V.; Brady, K. D.; Cryns, V. L. Caspases as targets for anti-inflammatory and anti-apoptotic drug discovery. J. Med. Chem. 2000, 43, 3351-3371.
    • (2000) J. Med. Chem , vol.43 , pp. 3351-3371
    • Talanian, R.V.1    Brady, K.D.2    Cryns, V.L.3
  • 5
    • 0036186039 scopus 로고    scopus 로고
    • Involvement of caspases and calpains in cerebrocortical neuronal cell death is stimulus-dependent
    • and references therein
    • (b) Moore, J. D.; Rothwell, N. J.; Gibson, R. M. Involvement of caspases and calpains in cerebrocortical neuronal cell death is stimulus-dependent. Br. J. Pharmacol. 2002, 135, 1069-1077 and references therein.
    • (2002) Br. J. Pharmacol , vol.135 , pp. 1069-1077
    • Moore, J.D.1    Rothwell, N.J.2    Gibson, R.M.3
  • 6
    • 1642474148 scopus 로고    scopus 로고
    • Caspases: An ancient cellular sword of Damocle
    • (c) Boyce, M.; Degterev, A.; Yuan, J. Caspases: an ancient cellular sword of Damocle. Cell Death Differ. 2004, 11, 29-37.
    • (2004) Cell Death Differ , vol.11 , pp. 29-37
    • Boyce, M.1    Degterev, A.2    Yuan, J.3
  • 7
    • 0036919717 scopus 로고    scopus 로고
    • Induction of apoptosis in cancer: New therapeutic opportunities
    • (a) Ding, H. F.; Fisher, D. E. Induction of apoptosis in cancer: new therapeutic opportunities. Ann. Med. 2002, 34, 451-469.
    • (2002) Ann. Med , vol.34 , pp. 451-469
    • Ding, H.F.1    Fisher, D.E.2
  • 8
    • 33644832724 scopus 로고    scopus 로고
    • Targeted induction of apoptosis in cancer management: The emerging role of tumor necrosis factor-related apoptosis-inducing ligand receptor activating agents
    • (b) Rowinsky, E. K. Targeted induction of apoptosis in cancer management: the emerging role of tumor necrosis factor-related apoptosis-inducing ligand receptor activating agents. J. Clin. Oncol. 2005, 23, 9394-9407.
    • (2005) J. Clin. Oncol , vol.23 , pp. 9394-9407
    • Rowinsky, E.K.1
  • 9
    • 0032125488 scopus 로고    scopus 로고
    • Neurodegeneration in excitotoxicity, global cerebral ischemia, and target deprivation: A perspective on the contributions of apoptosis and necrosis
    • Martin, L. J.; Al-Abdulla, N. A.; Brambrink, A. M.; Kirsch, J. R.; Sieber, F. E.; Portera-Cailliau, C. Neurodegeneration in excitotoxicity, global cerebral ischemia, and target deprivation: A perspective on the contributions of apoptosis and necrosis. Brain Res. Bull. 1998, 46, 281-309.
    • (1998) Brain Res. Bull , vol.46 , pp. 281-309
    • Martin, L.J.1    Al-Abdulla, N.A.2    Brambrink, A.M.3    Kirsch, J.R.4    Sieber, F.E.5    Portera-Cailliau, C.6
  • 10
    • 84984763363 scopus 로고    scopus 로고
    • Mechanisms, challenges and opportunities in stroke
    • Lo, E. H.; Dalkara, T.; Moskowitz, M. A. Mechanisms, challenges and opportunities in stroke. Nat. Rev. Neurosci. 2003, 4, 399-415.
    • (2003) Nat. Rev. Neurosci , vol.4 , pp. 399-415
    • Lo, E.H.1    Dalkara, T.2    Moskowitz, M.A.3
  • 12
    • 0141884305 scopus 로고    scopus 로고
    • Yuan, J.; Lipinski, M.; Degterev, A. Diversity in the mechanisms of neuronal cell death. Neuron 2003, 40, 401-413.
    • Yuan, J.; Lipinski, M.; Degterev, A. Diversity in the mechanisms of neuronal cell death. Neuron 2003, 40, 401-413.
  • 13
    • 0032971161 scopus 로고    scopus 로고
    • Caspase-independent programmed cell death with necrotic morphology
    • Kitanaka, C.; Kuchino, Y. Caspase-independent programmed cell death with necrotic morphology. Cell Death Differ. 1999, 6, 508-515.
    • (1999) Cell Death Differ , vol.6 , pp. 508-515
    • Kitanaka, C.1    Kuchino, Y.2
  • 14
    • 0033576675 scopus 로고    scopus 로고
    • More than one way to die: Apoptosis, necrosis and reactive oxygen damage
    • Fiers, W.; Beyaert, R.; Declercq, W.; Vandenabeele, P. More than one way to die: apoptosis, necrosis and reactive oxygen damage. Oncogene 1999, 18, 7719-7730.
    • (1999) Oncogene , vol.18 , pp. 7719-7730
    • Fiers, W.1    Beyaert, R.2    Declercq, W.3    Vandenabeele, P.4
  • 15
    • 0033047235 scopus 로고    scopus 로고
    • Apoptosis without caspases: An inefficient molecular guillotine?
    • Borner, C.; Monney, L. Apoptosis without caspases: an inefficient molecular guillotine? Cell Death Differ. 1999, 6, 497-507.
    • (1999) Cell Death Differ , vol.6 , pp. 497-507
    • Borner, C.1    Monney, L.2
  • 16
    • 7744235672 scopus 로고    scopus 로고
    • Death by design: Apoptosis, necrosis and autophagy
    • Edinger, A. L.; Thompson, C. B. Death by design: apoptosis, necrosis and autophagy. Curr. Opin. Cell Biol. 2004, 16, 663-669.
    • (2004) Curr. Opin. Cell Biol , vol.16 , pp. 663-669
    • Edinger, A.L.1    Thompson, C.B.2
  • 17
    • 14644412456 scopus 로고    scopus 로고
    • Do inducers of apoptosis trigger caspase-independent cell death?
    • Chipuk, J. E.; Green, D. R. Do inducers of apoptosis trigger caspase-independent cell death? Nat. Rev. Mol. Cell Biol. 2005, 6, 268-275.
    • (2005) Nat. Rev. Mol. Cell Biol , vol.6 , pp. 268-275
    • Chipuk, J.E.1    Green, D.R.2
  • 18
    • 18244392443 scopus 로고    scopus 로고
    • Cell death independent of caspases: A review
    • Bröker, L. E.; Kruyt, F. A. E.; Giaccone, G. Cell death independent of caspases: a review. Clin. Cancer Res. 2005, 11, 3155-3162.
    • (2005) Clin. Cancer Res , vol.11 , pp. 3155-3162
    • Bröker, L.E.1    Kruyt, F.A.E.2    Giaccone, G.3
  • 19
    • 16244362671 scopus 로고    scopus 로고
    • Apoptosis, pyroptosis, and necrosis: Mechanistic description of dead and dying eukaryotic cells
    • Fink, S. L.; Cookson, B. T. Apoptosis, pyroptosis, and necrosis: mechanistic description of dead and dying eukaryotic cells. Infect. Immun. 2005, 73, 1907-1916.
    • (2005) Infect. Immun , vol.73 , pp. 1907-1916
    • Fink, S.L.1    Cookson, B.T.2
  • 20
    • 22544444514 scopus 로고    scopus 로고
    • Caspase-independent cell death
    • Kroemer, G.; Martin, S. J. Caspase-independent cell death. Nat. Med. 2005, 11, 725-730.
    • (2005) Nat. Med , vol.11 , pp. 725-730
    • Kroemer, G.1    Martin, S.J.2
  • 23
    • 34247181496 scopus 로고    scopus 로고
    • 4, 0°C, 1 h, then switch solvent to toluene, 110°C until 1 h after evolution of nitrogen gas ceases) according to the literature procedure; see: Yoshihama, M.; Nakakoshi, M.; Nakamura, J.; Nakayama, S. WO 9832724, 1998.
    • 4, 0°C, 1 h, then switch solvent to toluene, 110°C until 1 h after evolution of nitrogen gas ceases) according to the literature procedure; see: Yoshihama, M.; Nakakoshi, M.; Nakamura, J.; Nakayama, S. WO 9832724, 1998.
  • 24
    • 34247268020 scopus 로고    scopus 로고
    • Many literature references utilize the cis/trans-isomer nomenclature for the 3,3a,4,5-tetrahydro-2H-benzo[g]indazole ring system. In these references the relative orientation of the C-3 and C-3a protons was used for the assignment of the cis/trans-isomer nomenclature. For example, 5 was referred to as the trans-isomer and 6 as the cis-isomer. However, herein the new naming convention of Chemical Abstracts is used. Isomer 5 is the (3R,3aS)-rel- isomer, and 6 is the (3R,3aR)-rel-isomer.
    • Many literature references utilize the cis/trans-isomer nomenclature for the 3,3a,4,5-tetrahydro-2H-benzo[g]indazole ring system. In these references the relative orientation of the C-3 and C-3a protons was used for the assignment of the cis/trans-isomer nomenclature. For example, 5 was referred to as the trans-isomer and 6 as the cis-isomer. However, herein the new naming convention of Chemical Abstracts is used. Isomer 5 is the (3R,3aS)-rel- isomer, and 6 is the (3R,3aR)-rel-isomer.
  • 25
  • 26
  • 27
    • 0001028918 scopus 로고
    • Synthesis of 3,3a-trans/cis-2-phenyl/acetyl- 3-aryl-tetrahydroindeno/naphtha[1,2-c]- and hexahydrobenzo-[6,7]cyclohepta[1,2- c]pyrazoles as antiimplantation agents
    • Sinha, A. K.; Rastogi, S. N. Synthesis of 3,3a-trans/cis-2-phenyl/acetyl- 3-aryl-tetrahydroindeno/naphtha[1,2-c]- and hexahydrobenzo-[6,7]cyclohepta[1,2- c]pyrazoles as antiimplantation agents. Indian J. Chem. 1991, 30B, 684-692.
    • (1991) Indian J. Chem , vol.30 B , pp. 684-692
    • Sinha, A.K.1    Rastogi, S.N.2
  • 29
    • 0343217451 scopus 로고
    • 1H N.M.R. chemical shifts to differentiate diastereoisomeric [1]benzopyrano-[4,3-c]pyrazoles, pyrazolo[4,3-c]quinolines and related compounds
    • 1H N.M.R. chemical shifts to differentiate diastereoisomeric [1]benzopyrano-[4,3-c]pyrazoles, pyrazolo[4,3-c]quinolines and related compounds. J. Chem. Res., Synop. 1987, 22-23.
    • (1987) J. Chem. Res., Synop , pp. 22-23
    • Sangwan, N.1
  • 30
    • 84986492911 scopus 로고    scopus 로고
    • El-Rayyes, N. R.; Al-Jawhary, A. Heterocycles. Part VIII. Synthesis of new substituted benz[g]indazoles. J. Heterocycl. Chem. 1986, 23, 135-140.
    • El-Rayyes, N. R.; Al-Jawhary, A. Heterocycles. Part VIII. Synthesis of new substituted benz[g]indazoles. J. Heterocycl. Chem. 1986, 23, 135-140.
  • 31
    • 0000866508 scopus 로고
    • Studies in antifertility agents: Part XXXII - synthesis & stereochemistry of 3,3a-trans & cis-2(H)-acetyl-3-aryl-3, 3a-dihydropyrazolo[4,3-c][2H]chromenes, pyrazolo-[3,4-a]benzocycloalk-1-enes & 3,3a-trans- & cis-2-(2H)-acetyl-3-aryl-8-methoxy-5-tosyl-3,3a,4,5- tetrahydropyrazolo[4,3-c]quinolines
    • Sangwan, N.; Rastogi, S. N. Studies in antifertility agents: Part XXXII - synthesis & stereochemistry of 3,3a-trans & cis-2(H)-acetyl-3-aryl-3, 3a-dihydropyrazolo[4,3-c][2H]chromenes, pyrazolo-[3,4-a]benzocycloalk-1-enes & 3,3a-trans- & cis-2-(2H)-acetyl-3-aryl-8-methoxy-5-tosyl-3,3a,4,5- tetrahydropyrazolo[4,3-c]quinolines. Indian J. Chem. 1981, 20B, 135-139.
    • (1981) Indian J. Chem , vol.20 B , pp. 135-139
    • Sangwan, N.1    Rastogi, S.N.2
  • 32
    • 0346984789 scopus 로고
    • A novel and direct alkyl azidation of p-alkylanisoles using phenyl iodine(III) bis(trifluoroacetate) (PIFA) and trimethylsilyl azide
    • Kita, Y.; Tohma, H.; Takada, T.; Mitoh, S.; Fujita, S.; Gyoten, M. A novel and direct alkyl azidation of p-alkylanisoles using phenyl iodine(III) bis(trifluoroacetate) (PIFA) and trimethylsilyl azide. Synlett 1994, 427-428.
    • (1994) Synlett , pp. 427-428
    • Kita, Y.1    Tohma, H.2    Takada, T.3    Mitoh, S.4    Fujita, S.5    Gyoten, M.6
  • 33
  • 34
    • 33947714475 scopus 로고    scopus 로고
    • For examples of zVAD.fmk-induced caspase-independent cell death, see: (a) Vandenabeele, P, Vanden Berghe, T, Festjens, N. Caspase inhibitors promote alternative cell death pathways. Sci. STKE 2006, 358, pe44
    • For examples of zVAD.fmk-induced caspase-independent cell death, see: (a) Vandenabeele, P.; Vanden Berghe, T.; Festjens, N. Caspase inhibitors promote alternative cell death pathways. Sci. STKE 2006, 358, pe44.
  • 35
    • 33748415021 scopus 로고    scopus 로고
    • z-VAD-fmk-induced non-apoptotic cell death of macrophages: Possibilities and limitations for atherosclerotic plaque stabilization
    • (b) Martinet, W.; Schrijvers, D. M.; Herman, A. G.; De Meyer, G. R. z-VAD-fmk-induced non-apoptotic cell death of macrophages: possibilities and limitations for atherosclerotic plaque stabilization. Autophagy 2006, 2, 312-314.
    • (2006) Autophagy , vol.2 , pp. 312-314
    • Martinet, W.1    Schrijvers, D.M.2    Herman, A.G.3    De Meyer, G.R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.