메뉴 건너뛰기




Volumn 52, Issue 4, 2009, Pages 1156-1171

Reactions of functionalized sulfonamides: Application to lowering the lipophilicity of cytosolic phospholipase A 2α inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

(2 FORMYLPHENYL)METHANESULFONYL CHLORIDE; 2 FORMYLPHENYLMETHANE SULFONAMIDE; ALIPHATIC AMINE; AROMATIC COMPOUND; METHYL 4 [2 [1 BENZHYDRYL 5 CHLORO 2 [2 (((CHLOROMETHYL)SULFONYL)AMINO)ETHYL] 1H INDOL 3 YL]ETHOXY]BENZOATE; METHYL 4 [2 [5 CHLORO 1 (DIPHENYLMETHYL) 2 (2 ((VINYLSULFONYL)AMINO)ETHYL) 1H INDOL 3 YL]ETHOXY]BENZOATE; METHYL 4 [3 [5 CHLORO 1 (DIPHENYLMETHYL) 2 (2 (((2 FORMYLBENZYL)SULFONYL)AMINO)ETHYL) 1H INDOL 3 YL]PROPYL]BENZOATE; METHYL 4 [3 [5 CHLORO 1 (DIPHENYLMETHYL) 2 (2 ((VINYLSULFONYL)AMINO)ETHYL) 1H INDOL 3 YL]PROPYL]BENZOATE; PHOSPHOLIPASE A2 INHIBITOR; PHOSPHOLIPASE A2ALPHA INHIBITOR; SULFONAMIDE; UNCLASSIFIED DRUG;

EID: 64349091726     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm8009876     Document Type: Article
Times cited : (17)

References (34)
  • 2
    • 0027212643 scopus 로고
    • 2 enzymes on product-containing vesicles: Application to the determination of substrate preferences
    • 2 enzymes on product-containing vesicles: application to the determination of substrate preferences. Biochemistry 1993, 32, 5949-5958.
    • (1993) Biochemistry , vol.32 , pp. 5949-5958
    • Hanel, A.M.1    Schuttel, S.2    Gelb, M.H.3
  • 3
    • 33744492071 scopus 로고    scopus 로고
    • 2. Anti-Inflammatory Anti-Allergy Agents Med. Chem. 2006, 5 (2), 189-203.
    • 2. Anti-Inflammatory Anti-Allergy Agents Med. Chem. 2006, 5 (2), 189-203.
  • 5
    • 0031445523 scopus 로고    scopus 로고
    • 2 in allergic response and parturition. Nature 1997, 390 (6660), 618-622.
    • 2 in allergic response and parturition. Nature 1997, 390 (6660), 618-622.
  • 9
    • 0031471709 scopus 로고    scopus 로고
    • Reduced fertility and postischemic brain injury in mice deficient in cytosolic phospholipase A2
    • (e) Bonventre, J. V.; Huang, Z.; Taheri, M. R.; O'Leary, E.; Li, E.; Moskowitz, M. A.; Sapirstein, A. Reduced fertility and postischemic brain injury in mice deficient in cytosolic phospholipase A2. Nature (London) 1997, 390 (6660), 622-625.
    • (1997) Nature (London) , vol.390 , Issue.6660 , pp. 622-625
    • Bonventre, J.V.1    Huang, Z.2    Taheri, M.R.3    O'Leary, E.4    Li, E.5    Moskowitz, M.A.6    Sapirstein, A.7
  • 11
    • 45749141743 scopus 로고    scopus 로고
    • McKew, J. C.; Lee, K. L.; Shen, M. W. H.; Thakker, P.; Foley, M. A.; Behnke, M. L.; Hu, B.; Sum, F.-W.; Tam, S.; Hu, Y.; Chen, L.; Kirincich, S. J.; Michalak, R.; Thomason, J.; Ipek, M.; Wu, K.; Wooder, L.; Ramarao, M. K.; Murphy, E. A.; Goodwin, D. G.; Albert, L.; Xu, X.; Donahue, F.; Ku, M. S.; Keith, J.; Nickerson- Nutter, C. L.; Abraham, W. M.; William, C.; Hegen, M.; Clark, J. D. Discovery and in vitro and in vivo characterization of 4-{3- [5-chloro-2-(2-{[(3,4-dichlorobenzyl)sulfonyl]amino}ethyl)-1-(diphe- nylmethyl)-1H-indol-3-yl]propyl}benzoic acid, efipladib. J. Med. Chem. 2008, 51, 3388-3413.
    • (a) McKew, J. C.; Lee, K. L.; Shen, M. W. H.; Thakker, P.; Foley, M. A.; Behnke, M. L.; Hu, B.; Sum, F.-W.; Tam, S.; Hu, Y.; Chen, L.; Kirincich, S. J.; Michalak, R.; Thomason, J.; Ipek, M.; Wu, K.; Wooder, L.; Ramarao, M. K.; Murphy, E. A.; Goodwin, D. G.; Albert, L.; Xu, X.; Donahue, F.; Ku, M. S.; Keith, J.; Nickerson- Nutter, C. L.; Abraham, W. M.; William, C.; Hegen, M.; Clark, J. D. Discovery and in vitro and in vivo characterization of 4-{3- [5-chloro-2-(2-{[(3,4-dichlorobenzyl)sulfonyl]amino}ethyl)-1-(diphe- nylmethyl)-1H-indol-3-yl]propyl}benzoic acid, efipladib. J. Med. Chem. 2008, 51, 3388-3413.
  • 16
    • 0036566182 scopus 로고    scopus 로고
    • Characterization of a novel inhibitor of cytosolic phospholipase A2a, pyrrophenone
    • Ono, T.; Yamada, K.; Chikazawa, Y.; Ueno, M.; Nakamoto, S.; Okuno, T.; Seno, K. Characterization of a novel inhibitor of cytosolic phospholipase A2a, pyrrophenone. Biochem. J. 2002, 363 (3), 727-735.
    • (2002) Biochem. J , vol.363 , Issue.3 , pp. 727-735
    • Ono, T.1    Yamada, K.2    Chikazawa, Y.3    Ueno, M.4    Nakamoto, S.5    Okuno, T.6    Seno, K.7
  • 17
    • 0033617291 scopus 로고    scopus 로고
    • Crystal structure of human cytosolic phospholipase A2 reveals a novel topology and catalytic mechanism
    • Dessen, A.; Tang, J.; Schmidt, H.; Stahl, M.; Clark, J. D.; Seehra, J.; Somers, W. S. Crystal structure of human cytosolic phospholipase A2 reveals a novel topology and catalytic mechanism. Cell 1999, 97, 349-360.
    • (1999) Cell , vol.97 , pp. 349-360
    • Dessen, A.1    Tang, J.2    Schmidt, H.3    Stahl, M.4    Clark, J.D.5    Seehra, J.6    Somers, W.S.7
  • 18
    • 0036663974 scopus 로고    scopus 로고
    • Integration of physicochemical property considerations into the design of combinatorial libraries
    • (a) Lipinski, C. A. Integration of physicochemical property considerations into the design of combinatorial libraries. Pharm. News 2002, 9, 195-202.
    • (2002) Pharm. News , vol.9 , pp. 195-202
    • Lipinski, C.A.1
  • 19
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • (b) Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Delivery Rev. 1997, 23, 3-25.
    • (1997) Adv. Drug Delivery Rev , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 20
    • 64349109989 scopus 로고    scopus 로고
    • Michalak, R. S.; Helom, J. L.; Zeldis, J. Process for the Synthesis of Sulfonyl Halides and Sulfonamides from Sulfonic Acid Salts. U.S. Pat. Appl. Publ. US 2007021614 A1 20070125, 2007; 13 pp.
    • Michalak, R. S.; Helom, J. L.; Zeldis, J. Process for the Synthesis of Sulfonyl Halides and Sulfonamides from Sulfonic Acid Salts. U.S. Pat. Appl. Publ. US 2007021614 A1 20070125, 2007; 13 pp.
  • 21
    • 2442547226 scopus 로고
    • Syntheses of 1,3- dihydro-2,1,4-benzothiadiazepines
    • (a) Hromatka, O.; Knollmueller, M.; Binder, D. Syntheses of 1,3- dihydro-2,1,4-benzothiadiazepines. Monatsh. Chem. 1969, 700, 872-878.
    • (1969) Monatsh. Chem , vol.700 , pp. 872-878
    • Hromatka, O.1    Knollmueller, M.2    Binder, D.3
  • 22
    • 37049102752 scopus 로고
    • The chemistry of o-phenylenediisothiocyanate. Part 3. Studies on the syntheses of heterocyclic compounds
    • (b) Griffiths, D.; Hull, R.; Seden, T. P. The chemistry of o-phenylenediisothiocyanate. Part 3. Studies on the syntheses of heterocyclic compounds. J. Chem. Soc., Perkin Trans 1 1980, (11), 2608-2611.
    • (1980) J. Chem. Soc., Perkin Trans 1 , vol.11 , pp. 2608-2611
    • Griffiths, D.1    Hull, R.2    Seden, T.P.3
  • 23
    • 0001650582 scopus 로고
    • Syntheses of amino alkyl sulphonic acids and their peptide analogues
    • (a) Frankel, M.; Moses, P. Syntheses of amino alkyl sulphonic acids and their peptide analogues. Tetrahedron 1960, 9, 289-294.
    • (1960) Tetrahedron , vol.9 , pp. 289-294
    • Frankel, M.1    Moses, P.2
  • 24
    • 0000063619 scopus 로고
    • An explanation for the failure of aminomethanesulfonic acid to form sulfonamides. Acyl chloride- promoted generation of a-carboxamidoalkylating electrophiles
    • (b) Moe, G. R.; Sayre, L. M.; Portoghese, P. S. An explanation for the failure of aminomethanesulfonic acid to form sulfonamides. Acyl chloride- promoted generation of a-carboxamidoalkylating electrophiles. Tetrahedron Lett. 1981, 22, 537-540.
    • (1981) Tetrahedron Lett , vol.22 , pp. 537-540
    • Moe, G.R.1    Sayre, L.M.2    Portoghese, P.S.3
  • 25
    • 0035936749 scopus 로고    scopus 로고
    • Oxidative cleavage of 1,3-dicarbonyls to carboxylic acids with oxone
    • Ashford, S. W.; Grega, K. C. Oxidative cleavage of 1,3-dicarbonyls to carboxylic acids with oxone. J. Org. Chem. 2001, 66, 1523-1524.
    • (2001) J. Org. Chem , vol.66 , pp. 1523-1524
    • Ashford, S.W.1    Grega, K.C.2
  • 26
    • 0034712156 scopus 로고    scopus 로고
    • Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates
    • (a) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates. J. Org. Chem. 2000, 65, 1158-1174.
    • (2000) J. Org. Chem , vol.65 , pp. 1158-1174
    • Wolfe, J.P.1    Tomori, H.2    Sadighi, J.P.3    Yin, J.4    Buchwald, S.L.5
  • 27
    • 0032541260 scopus 로고    scopus 로고
    • Transition metal catalyzed synthesis of arylamines and aryl ethers from aryl halides and triflates: Scope and mechanism
    • (b) Hartwig, J. F. Transition metal catalyzed synthesis of arylamines and aryl ethers from aryl halides and triflates: scope and mechanism. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
    • (1998) Angew. Chem., Int. Ed , vol.37 , pp. 2046-2067
    • Hartwig, J.F.1
  • 28
  • 29
    • 0026625348 scopus 로고
    • The 5-lipoxygenase inhibitor zileuton blocks antigen-induced late airway responses, inflammation and airway hyperresponsiveness in allergic sheep
    • (a) Abraham, W. M.; Ahmed, A.; Cortes, A.; Sielczak, M. W.; Hinz, W.; Bouska, J.; Lanni, C.; Bell, R. L. The 5-lipoxygenase inhibitor zileuton blocks antigen-induced late airway responses, inflammation and airway hyperresponsiveness in allergic sheep. Eur. J. Pharmacol. 1992, 217 (2-3), 119-126.
    • (1992) Eur. J. Pharmacol , vol.217 , Issue.2-3 , pp. 119-126
    • Abraham, W.M.1    Ahmed, A.2    Cortes, A.3    Sielczak, M.W.4    Hinz, W.5    Bouska, J.6    Lanni, C.7    Bell, R.L.8
  • 30
    • 0005599865 scopus 로고    scopus 로고
    • The development of zileuton (ZYFLO) and the N-hydroxyurea class of 5-lipoxygenase inhibitors
    • (b) Bell, R. L. The development of zileuton (ZYFLO) and the N-hydroxyurea class of 5-lipoxygenase inhibitors. Novel Inhibitors Leukotrienes 1999, 235-249.
    • (1999) Novel Inhibitors Leukotrienes , pp. 235-249
    • Bell, R.L.1
  • 32
    • 13444266910 scopus 로고    scopus 로고
    • Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1- yl]benzenesulfonamide (SC-58635, celecoxib). J. Med. Chem. 1997, 40 (9), 1347-1365.
    • Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1- yl]benzenesulfonamide (SC-58635, celecoxib). J. Med. Chem. 1997, 40 (9), 1347-1365.
  • 33
    • 0029905047 scopus 로고    scopus 로고
    • Predictability of the clinical potency of NSAIDs from the preclinical pharma- codynamics in rats
    • (a) Mukherjee, A.; Hale, V. G.; Borga, O.; Stein, R. Predictability of the clinical potency of NSAIDs from the preclinical pharma- codynamics in rats. Inflammation Res. 1996, 45 (11), 531-540.
    • (1996) Inflammation Res , vol.45 , Issue.11 , pp. 531-540
    • Mukherjee, A.1    Hale, V.G.2    Borga, O.3    Stein, R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.